Updated on 2025/08/20

写真a

 
KIYOTA Hiromasa
 
Organization
Faculty of Environmental, Life, Natural Science and Technology Professor
Position
Professor
External link

Degree

  • 博士(農学) ( 東京大学 )

Research Interests

  • natural products chemistry

  • organic synthesis

  • 有機合成化学・天然物化学

Research Areas

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Life Science / Pharmaceutical chemistry and drug development sciences

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Life Science / Bioorganic chemistry

Education

  • The University of Tokyo   農学系研究科   農芸化学専攻

    - 1991

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    Country: Japan

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  • The University of Tokyo   農学部   農芸化学科

    - 1989

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    Country: Japan

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Research History

  • - Professor,Graduate School of Environmental and life Science,Okayama University

    2013

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  • - 岡山大学 学術研究院 環境生命自然科学学域 教授

    2013

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  • Tohoku University   Graduate School of Agricultural Science

    2002 - 2013

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  • Associate Professor,Tohoku University

    2002 - 2013

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  • 英国ケンブリッジ大学 化学科 研究員

    2001 - 2002

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  • Research Associate,Tohoku University

    1999 - 2002

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  • Tohoku University   Graduate School of Agricultural Science

    1999 - 2002

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  • Tohoku University   Faculty of Agriculture

    1994 - 1999

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  • Research Associate,Tohoku Univetsity

    1994 - 1999

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  • 東京大学 農学部 助手

    1991 - 1993

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  • Research Associate,The University of Tokyo

    1991 - 1993

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Professional Memberships

Committee Memberships

  • 日本農薬学会   農薬デザイン研究会 委員長  

    2022.1   

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    Committee type:Academic society

    日本農薬学会

  • Novel Compounds Exploration Research Organization   Vice Chairman  

    2023.5 - 2025.3   

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    Committee type:Other

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  • 日本農薬学会   農薬デザイン研究会 委員長  

    2022.2   

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    Committee type:Academic society

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  • Springer   Topics in Heterocyclic Chemistry, Marine Natural Products, Volume Editor  

    2015 - 2022.1   

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    Committee type:Other

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  • Springer   Topics in Heterocyclic Chemistry, Marine Natural Products, Volume Editor  

    2006   

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    Committee type:Other

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  • 日本農芸化学会   創立 100 周年記念記念誌編集分科会第二部委員  

    2022.2   

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    Committee type:Academic society

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  • 日本農芸化学会   創立 100 周年記念記念誌編集分科会第二部委員  

    2022 - 2028.2   

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    Committee type:Academic society

  • 野生桃研究会   顧問  

    2021   

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  • 日本農薬学会   第47回大会 組織委員(総務)  

    2021 - 2022   

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    Committee type:Academic society

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  • 野生桃研究会   第1回研究発表会 実行委員長  

    2020.1   

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  • 日本農芸化学会   創立 100 周年記念記念誌編集分科会第一部分科会委員  

    2020   

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    Committee type:Academic society

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  •   "Bioscience, Biotechnology, and Biochemistry," Special Issue: Natural Product Chemistry: Guest Chief Editor  

    2020 - 2021   

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  • 日本農芸化学会   和文誌「化学と生物」編集長  

    2019 - 2021   

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    Committee type:Academic society

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  • 野生桃研究会   会長  

    2019 - 2021   

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  • 日本農芸化学会   Visionaryシンポジウム「天然物化学」第2回 実行委員長  

    2018 - 2021   

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  • 日本農薬学会   農薬環境科学研究会 委員  

    2017   

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    Committee type:Academic society

    日本農薬学会

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  • 日本農芸化学会   和文誌「化学と生物」編集委員  

    2017 - 2019   

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    Committee type:Academic society

    日本農芸化学会

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  • 日本農芸化学会   学術活動強化委員  

    2015 - 2023.2   

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    Committee type:Academic society

    日本農芸化学会

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  • 日本農芸化学会   英文誌「Bioscience, Biotechnology and Biochemistry」編集委員  

    2015 - 2019   

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    Committee type:Academic society

    日本農芸化学会

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  • 日本農芸化学会   英文誌「Bioscience, Biotechnology and Biochemistry」編集総務委員  

    2015   

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    日本農芸化学会

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  • 日本農芸化学会   中四国支部参与  

    2014.4 - 2018.3   

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    Committee type:Academic society

    日本農芸化学会

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  • 日本農芸化学会   2014年度大会 実行委員  

    2014   

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    Committee type:Academic society

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  • 日本農芸化学会   2014年度岡山大会実行委員  

    2013 - 2015   

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    Committee type:Academic society

    日本農芸化学会

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  • 天然物化学談話会   幹事  

    2013 - 2014   

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    Committee type:Academic society

    天然物化学談話会

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  • 日本農薬学会   評議員  

    2012   

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    Committee type:Academic society

    日本農薬学会

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  • 日本農薬学会   学会誌編集委員  

    2012 - 2025.3   

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    Committee type:Academic society

    日本農薬学会

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  • 日本農芸化学会   第20回農芸化学フロンティアシンポジウム 実行委員長  

    2011 - 2013   

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    Committee type:Academic society

    日本農芸化学会

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  • 日本農芸化学会   2013年度仙台大会実行委員  

    2010 - 2013   

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    Committee type:Academic society

    日本農芸化学会

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  • 有機合成化学協会   編集協力委員  

    2010 - 2011   

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    Committee type:Academic society

    有機合成化学協会

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  • Heterocyclic Communications   Editorial Board  

    2003   

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  • 日本農薬学会   第25回大会 実行委員  

    2001   

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  • 日本農薬学会   農薬デザイン研究会常任幹事  

    1997 - 2022.2   

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    Committee type:Academic society

    日本農薬学会

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  • 日本農芸化学会   東北支部 幹事  

    1997 - 2001   

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    Committee type:Academic society

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  • 日本農芸化学会   関東支部 幹事  

    1993 - 1995   

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Papers

  • Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V†. International journal

    Hiroki Asao, Yasuharu Shimasaki, Ayaka Sasaki, Shunki Katayama, Kousuke Ida, Masaaki Kotake, Eriko Sato, Yuki Sato, Taiki Ishimoto, Minoru Izumi, Christopher J Vavricka, Shigefumi Kuwahara, Hiromasa Kiyota

    Bioscience, biotechnology, and biochemistry   88 ( 7 )   733 - 741   2024.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    Synthesis of the A/D/E-ring core compounds of maoecrystal V was achieved. The key Diels-Alder reactions between tricyclic α-methylene lactones and Kitahara-Danishefsky dienes afforded the spirocyclic core compounds in a regioselective and stereoselective manner.

    DOI: 10.1093/bbb/zbae049

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  • Synthesis of the C/D/E-ring core compound of maoecrystal V Reviewed

    Shunki Katayama, Mitsuki Nishimoto, Tatsuya Ura, Taiki Ishimoto, Kousuke Ida, Yuki Sato, Christopher J. Vavricka, Minoru Izumi, Hiromasa Kiyota

    Synthetic Communications   53 ( 10 )   708 - 712   2023.3

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Informa UK Limited  

    DOI: 10.1080/00397911.2023.2191853

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  • "抗インフルエンザ薬開発を指向したシアル酸誘導体(シアリダーゼ阻害剤)の開発 " Invited Reviewed

    ヴァヴリッカ クリストファー J, 徐超, 桑名晶妃, 森さおり, 清田洋正

    科学と工業   97 ( 1 )   2 - 7   2023.1

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    Authorship:Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)  

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  • Chemical Constituents of Plants from the Genus Carpesium Reviewed

    18   1 - 10   2023.1

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  • Bruceine B-induced Apoptosis of Lung Cancer Cells NCI-H292 through Endoplasmic Reticulum Stress, Death Receptor and Mitochondria-dependent Signaling Pathways Reviewed

    Wen-Zhe Li, Feng Yu, Chuan Wang, Qing-wen Shi, Mei Dong, Zhi- Yu Ni, Mao-Chang Ji, Hiromasa Kiyota

    Current Topics in Phytochemistry   18   11 - 18   2023.1

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

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  • Machine learning discovery of missing links that mediate alternative branches to plant alkaloids. International journal

    Christopher J Vavricka, Shunsuke Takahashi, Naoki Watanabe, Musashi Takenaka, Mami Matsuda, Takanobu Yoshida, Ryo Suzuki, Hiromasa Kiyota, Jianyong Li, Hiromichi Minami, Jun Ishii, Kenji Tsuge, Michihiro Araki, Akihiko Kondo, Tomohisa Hasunuma

    Nature communications   13 ( 1 )   1405 - 1405   2022.3

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    Engineering the microbial production of secondary metabolites is limited by the known reactions of correctly annotated enzymes. Therefore, the machine learning discovery of specialized enzymes offers great potential to expand the range of biosynthesis pathways. Benzylisoquinoline alkaloid production is a model example of metabolic engineering with potential to revolutionize the paradigm of sustainable biomanufacturing. Existing bacterial studies utilize a norlaudanosoline pathway, whereas plants contain a more stable norcoclaurine pathway, which is exploited in yeast. However, committed aromatic precursors are still produced using microbial enzymes that remain elusive in plants, and additional downstream missing links remain hidden within highly duplicated plant gene families. In the current study, machine learning is applied to predict and select plant missing link enzymes from homologous candidate sequences. Metabolomics-based characterization of the selected sequences reveals potential aromatic acetaldehyde synthases and phenylpyruvate decarboxylases in reconstructed plant gene-only benzylisoquinoline alkaloid pathways from tyrosine. Synergistic application of the aryl acetaldehyde producing enzymes results in enhanced benzylisoquinoline alkaloid production through hybrid norcoclaurine and norlaudanosoline pathways.

    DOI: 10.1038/s41467-022-28883-8

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  • Isolation of a Novel Endophytic Bacillus Strain Capable of Transforming Pentachlorophenol and Structure Determination of Pentachlorophenol Phosphate Using Single-Crystal X-ray Diffraction Reviewed

    Koji Ito, Ryota Kataoka, Shunki Katayama, Hiromasa Kiyota, Ahmad Mahmood, Takashi Kikuchi, Takashi Sato, Futa Sakakibara, Kazuhiro Takagi

    Journal of Agricultural and Food Chemistry   70 ( 3 )   770 - 776   2022.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.jafc.1c05987

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  • Structure Analysis of Polyhalogenated Persistent Organic Pollutants by the Crystalline Sponge Method Reviewed

    Jiazhuo Chen, Takashi Kikuchi, Kazuhiro Takagi, Hiromasa Kiyota, Kiyohiro Adachi, Takaaki Mitsuhashi, Makoto Fujita

    Chemistry Letters   51 ( 1 )   85 - 87   2022.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.210613

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  • Synthesis of the oxazolidinone fragment of thelepamide Reviewed

    Naoki Ashida, Kousuke Ida, Yumi Koide, Christopher J. Vavricka, Minoru Izumi, Hiromasa Kiyota

    Natural Product Research   36 ( 7 )   1686 - 1692   2022

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1080/14786419.2020.1809398

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  • Millifolide A, a dimeric ether of degraded sesquiterpene lactones, inhibited the proliferation of human lung cancer cell line A549 Reviewed

    Pan-Pan Yu, Feng Yu, Wen-Zhe Li, Si-Ming Wang, Chuan Wang, Mei Dong, Zhi-Yu Ni, Yong Li, Hiromasa Kiyota

    Natural Product Research   36 ( 11 )   2875 - 2877   2022

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Informa UK Limited  

    DOI: 10.1080/14786419.2021.1922906

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  • Xylomexicanins K-N: limonoids from the leaves and twigs of Xylocarpus granatum Reviewed

    Shao-Jing Li, Li-Kang Zhao, Jin-Jun Chen, Chun-Hua Zhou, Xin-Li Huang, Yi-Bing Wu, Françoise Sauriol, Yu-Cheng Gu, Hiromasa Kiyota

    Natural Product Research   36 ( 19 )   5001 - 5008   2022

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:Informa UK Limited  

    DOI: 10.1080/14786419.2021.1916016

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  • Influenza A Virus Neuraminidase Inhibitors International journal

    Nongluk Sriwilaijaroen, Christopher J. Vavricka, Hiromasa Kiyota, Yasuo Suzuki

    Methods in Molecular Biology   2556   321 - 353   2022

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    Language:English   Publishing type:Part of collection (book)   Publisher:Springer US  

    Depending on the strain, influenza A virus causes animal, zoonotic, pandemic, or seasonal influenza with varying degrees of severity. Two surface glycoprotein spikes, hemagglutinin (HA) and neuraminidase (NA), are the most important influenza A virus antigens. NA plays an important role in the propagation of influenza virus by removing terminal sialic acid from sialyl decoy receptors and thereby facilitating the release of viruses from traps such as in mucus and on infected cells. Some NA inhibitors have become widely used drugs for treatment of influenza. However, attempts to develop effective and safe NA inhibitors that can be used for treatment of anti-NA drugs-resistant influenza viruses have continued. In this chapter, we describe the following updates on influenza A NA inhibitor development: (i) N-acetylneuraminic acid (Neu5Ac)-based derivatives, (ii) covalent NA inhibitors, (iii) sulfo-sialic acid analogs, (iv) N-acetyl-6-sulfo-β-D-glucosaminide-based inhibitors, (v) inhibitors targeting the 150-loop of group 1 NAs, (vi) conjugation inhibitors, (vii) acylhydrazone derivatives, (viii) monoclonal antibodies, (ix) PVP-I, and (x) natural products. Finally, we provide future perspectives on the next-generation anti-NA drugs.

    DOI: 10.1007/978-1-0716-2635-1_21

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  • Synthesis and Neuraminidase Inhibitory Activity of Sialic Acid Analogues with Fluoro, Phosphono, and Sulfo Functionalities International journal

    Christopher J. Vavricka, Nongluk Sriwilaijaroen, Yasuo Suzuki, Hiromasa Kiyota

    Methods in Molecular Biology   2556   303 - 320   2022

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    Authorship:Corresponding author   Language:English   Publishing type:Part of collection (book)   Publisher:Springer US  

    Methods to synthesize influenza virus inhibitors with fluoro, phosphono, and/or sulfo functional groups are described. The resulting sialic acid analogues are produced from the natural substrate N-acetylneuraminic acid as starting material. Fluorescent assay methods for inhibition of influenza neuraminidase and virus proliferation are also provided.

    DOI: 10.1007/978-1-0716-2635-1_20

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  • Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates Reviewed

    Yuta Nagashima, Ayaka Sasaki, Ryoya Hiraoka, Yuko Onoda, Koji Tanaka, Zi-Yi Wang, Atsuki Kuwana, Yuki Sato, Yuji Suzuki, Minoru Izumi, Shigefumi Kuwahara, Manabu Nukina, Hiromasa Kiyota

    Bioscience, Biotechnology, and Biochemistry   85 ( 1 )   134 - 142   2021.1

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    Authorship:Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    <title>Abstract</title>
    Synthesis of assumed natural (12R,13S)-enantiomers of pyriculariol (1) and dihydropyriculariol (2), phytotoxins isolated from rice blast disease fungus, Pyricularia oryzae, was achieved using Wittig reaction or microwave-assisted Stille coupling reaction as the key step. The synthesis revealed that the natural 1 and 2 are racemates. Foliar application test on a rice leaf indicated that both the salicylaldehyde core and side chain were necessary for phytotoxic activity. The fungus is found to produce optically active phytotoxins when incubated with rotary shaker, but racemic ones when cultured using an aerated jar fermenter.

    DOI: 10.1093/bbb/zbaa002

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  • Controlling the production of phytotoxin pyriculol in Pyricularia oryzae by aldehyde reductase International journal

    Yuuki Furuyama, Takayuki Motoyama, Toshihiko Nogawa, Toshiaki Hayashi, Hiroshi Hirota, Hiromasa Kiyota, Takashi Kamakura, Hiroyuki Osada

    Bioscience, Biotechnology, and Biochemistry   85 ( 1 )   126 - 133   2021.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    <title>Abstract</title>
    Pyricularia oryzae is one of the most devastating plant pathogens in the world. This fungus produces several secondary metabolites including the phytotoxin pyriculols, which are classified into 2 types: aldehyde form (pyriculol and pyriculariol) and alcohol form (dihydropyriculol and dihydropyriculariol). Although interconversion between the aldehyde form and alcohol form has been predicted, and the PYC10 gene for the oxidation of alcohol form to aldehyde is known, the gene responsible for the reduction of aldehyde to alcohol form is unknown. Furthermore, previous studies have predicted that alcohol analogs are biosynthesized via aldehyde analogs. Herein, we demonstrated that an aldo/keto reductase PYC7 is responsible for the reduction of aldehyde to alcohol congeners. The results indicate that aldehyde analogs are biosynthesized via alcohol analogs, contradicting the previous prediction. The results suggest that P. oryzae controls the amount of pyriculol analogs using two oxidoreductases, PYC7 and PYC10, thereby controlling the bioactivity of the phytotoxin.

    DOI: 10.1093/bbb/zbaa035

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  • Synthetic Studies of Serinolipids

    Hiromasa Kiyota

    Topics in Heterocyclic Chemistry   2021

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    Authorship:Lead author, Last author, Corresponding author   Publishing type:Part of collection (book)   Publisher:Springer Berlin Heidelberg  

    DOI: 10.1007/7081_2021_52

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  • Biochemical characterization of NADH:FMN oxidoreductase HcbA3 from Nocardioides sp. PD653 in catalyzing aerobic HCB dechlorination

    Koji Ito, Kazuhiro Takagi, Ryota Kataoka, Hiromasa Kiyota

    Journal of Pesticide Science   45 ( 3 )   125 - 131   2020.8

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    Publishing type:Research paper (scientific journal)   Publisher:Pesticide Science Society of Japan  

    DOI: 10.1584/jpestics.d20-23

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  • Synthetic studies of biologically active natural products contributing to pesticide development

    Hiromasa Kiyota

    Journal of Pesticide Science   45 ( 3 )   177 - 183   2020.8

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    Authorship:Lead author, Last author, Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Pesticide Science Society of Japan  

    DOI: 10.1584/jpestics.j20-03

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  • 農薬創製に資する生物活性天然物に関する合成化学的研究

    Japanese Journal of Pesticide Science   45 ( 2 )   85 - 86   2020.8

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    Publishing type:Research paper (scientific journal)   Publisher:Pesticide Science Society of Japan  

    DOI: 10.1584/jpestics.w20-29

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  • Towards Improvement of Covalent Neuraminidase Inhibitors with Anomeric Substitution

    Christopher J. Vavricka, Tatsuma Matsumoto, Hiromasa Kiyota

    Trends in Glycoscience and Glycotechnology   32 ( 185 )   E1 - E5   2020.1

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    Authorship:Corresponding author   Publishing type:Research paper (scientific journal)   Publisher:Forum: Carbohydrates Coming of Age  

    DOI: 10.4052/tigg.1801.1e

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  • Dehalogenation and Dissipation of Chloroaromatic Compounds by Nocardioides sp. PD653: Characterization of the Substrate Specificity Reviewed

    Koji Ito, Kazuhiro Takagi, Ryota Kataoka, Hiromasa Kiyota, Akio Iwasaki

    J. Pestic. Sci.   44 ( 3 )   171 - 176   2019.8

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    DOI: 10.1584/jpestics.D19-024

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  • Mechanism-based tuning of insect 3,4-dihydroxyphenylacetaldehyde synthase for synthetic bioproduction of benzylisoquinoline alkaloids Reviewed International journal

    Christopher John, Vavricka Jr, Takanobu Yoshida, Yuki Kuriya, Shunsuke Takahashi, Teppei Ogawa, Fumie Ono, Kazuko Agari, Hiromasa Kiyota, Jianyong Li, Jun Ishii, Kenji Tsuge, Hiromichi Minami, Michihiro Araki, Tomohisa Hasunuma, Akihiko Kondo

    Nature Communications   10 ( 1 )   2015 - 2015   2019.5

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    Previous studies have utilized monoamine oxidase (MAO) and L-3,4-dihydroxyphenylalanine decarboxylase (DDC) for microbe-based production of tetrahydropapaveroline (THP), a benzylisoquinoline alkaloid (BIA) precursor to opioid analgesics. In the current study, a phylogenetically distinct Bombyx mori 3,4-dihydroxyphenylacetaldehyde synthase (DHPAAS) is identified to bypass MAO and DDC for direct production of 3,4-dihydroxyphenylacetaldehyde (DHPAA) from L-3,4-dihydroxyphenylalanine (L-DOPA). Structure-based enzyme engineering of DHPAAS results in bifunctional switching between aldehyde synthase and decarboxylase activities. Output of dopamine and DHPAA products is fine-tuned by engineered DHPAAS variants with Phe79Tyr, Tyr80Phe and Asn192His catalytic substitutions. Balance of dopamine and DHPAA products enables improved THP biosynthesis via a symmetrical pathway in Escherichia coli. Rationally engineered insect DHPAAS produces (R,S)-THP in a single enzyme system directly from L-DOPA both in vitro and in vivo, at higher yields than that of the wild-type enzyme. However, DHPAAS-mediated downstream BIA production requires further improvement.

    DOI: 10.1038/s41467-019-09610-2

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  • Synthetic Studies of Salicylaldehyde-type Phytotoxins Isolated from Rice Blast Fungus

    Hiromasa Kiyota

    Journal of Synthetic Organic Chemistry, Japan   77 ( 2 )   173 - 180   2019.2

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    Publishing type:Research paper (scientific journal)   Publisher:The Society of Synthetic Organic Chemistry, Japan  

    DOI: 10.5059/yukigoseikyokaishi.77.173

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  • Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan. Reviewed International journal

    Ota R, Okamoto Y, Vavricka CJ, Oka T, Matsunaga E, Takegawa K, Kiyota H, Izumi M

    Carbohydr Res.   473   99 - 103   2019.2

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    β-d-Galactofuranose (Galf) is a component of polysaccharides and glycoconjugates. There are few reports about the involvement of galactofuranosyltransferases and galactofuranosidases (Galf-ases) in the synthesis and degradation of galactofuranose-containing glycans. The cell walls of filamentous fungi in the genus Aspergillus include galactofuranose-containing polysaccharides and glycoconjugates, such as O-glycans, N-glycans, and fungal-type galactomannan, which are important for cell wall integrity. In this study, we investigated the synthesis of p-nitrophenyl β-d-galactofuranoside and its disaccharides by chemo-enzymatic methods including use of galactosidase. The key step was selective removal of the concomitant pyranoside by enzymatic hydrolysis to purify p-nitrophenyl β-d-galactofuranoside, a promising substrate for β-d-galactofuranosidase from Streptomyces species.

    DOI: 10.1016/j.carres.2019.01.005

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  • 抗リーシュマニア原虫活性物質Ancistrocladinium AとBの合成研究

    清田洋正、齋藤昭人、高井桃子、桑原重文

    岡山大農学報   108   1 - 4   2019.2

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  • Analytical Method to Evaluate Gizzerosine in Fishmeal After Diazonium Derivatization Using High-Performance Liquid Chromatography Reviewed

    Food Anal. Methods   12 ( 2 )   331 - 337   2019.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1007/s12161-018-1364-1

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  • 現代のアロマセラピーで使用する乳香とティートリー精油の身体・心への影響について

    岡山大農学報   107   1 - 3   2018.2

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  • Multigram-Scale and Column Chromatography-Free Synthesis of L-Azetidine-2-carboxylic Acid for the Synthesis of Nicotianamine and Its Derivatives Reviewed

    Minoru Izumi, Tomohiro Takaishi, Kyosuke Wakisaka, Christopher J Vavricka, Hiromasa Kiyota

    HETEROCYCLES   96 ( 12 )   2126 - 2134   2018.1

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    DOI: 10.3987/COM-18-14002

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  • Synthesis of Halogenated-4-Nitrophenyl 2-deoxy-2-halogeno-pyranosides via N-Halogenosuccinimide Activated Glucal Reviewed

    Chieri Inoue, Yumi Okamoto, Christopher J. Vavricka, Hiromasa Kiyota, Minoru Izumi

    NATURAL PRODUCT COMMUNICATIONS   13 ( 1 )   85 - 87   2018.1

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  • Chemical constituents from the genus Saussurea and their biological activities

    Ting Zhao, Shao-Jing Li, Zhao-Xin Zhang, Man-Li Zhang, Qing-Wen Shi, Yu-Cheng Gu, Mei Dong, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   23 ( 5 )   331 - 358   2017.10

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    DOI: 10.1515/hc-2017-0069

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  • Xylomexicanins I and J: Limonoids with Unusual B/C Rings from Xylocarpus granatum

    Yi-Bing Wu, Ya-Zhen Wang, Zhi-Yu Ni, Xia Qing, Qing-Wen Shi, Francoise Sauriol, Christopher J. Vavricka, Yu-Cheng Gu, Hiromasa Kiyota

    JOURNAL OF NATURAL PRODUCTS   80 ( 9 )   2547 - 2550   2017.9

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    DOI: 10.1021/acs.jnatprod.7b00305

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  • Chemical and pharmacological research on the plants from genus Ajuga

    Xia Qing, Hui-Min Yan, Zhi-Yu Ni, Christopher J. Vavricka, Man-Li Zhang, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   23 ( 4 )   245 - 268   2017.8

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    DOI: 10.1515/hc-2017-0064

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  • Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality

    Christopher J. Vavricka, Chiaki Muto, Tomohisa Hasunuma, Yoshinobu Kimura, Michihiro Araki, Yan Wu, George F. Gao, Hiroshi Ohrui, Minoru Izumi, Hiromasa Kiyota

    SCIENTIFIC REPORTS   7 ( 1 )   8239   2017.8

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    DOI: 10.1038/s41598-017-07836-y

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    Other Link: https://www.nature.com/srep/

  • Product Selectivity of Esterification of L-Aspartic Acid and L-Glutamic Acid Using Chlorotrimethylsilane

    Tomohiro Takaishi, Minoru Izumi, Ryo Ota, Chieri Inoue, Hiromasa Kiyota, Koichi Fukase

    NATURAL PRODUCT COMMUNICATIONS   12 ( 2 )   247 - 249   2017.2

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  • Study on the metabolites of isoalantolactone in vivo and in vitro by ultra performance liquid chromatography combined with Triple TOF mass spectrometry

    Donggui Yao, Yufang Wang, Changhong Huo, Yibing Wu, Manli Zhang, Ligeng Li, Qingwen Shi, Hiromasa Kiyota, Xiaowei Shi

    FOOD CHEMISTRY   214   328 - 338   2017.1

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    DOI: 10.1016/j.foodchem.2016.07.100

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  • 酵素触媒反応を鍵とする光学活性な香気物質両鏡像体の合成と香気評価

    岡山大農学報   106   33 - 38   2017

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  • Identification of in vitro and in vivo metabolites of alantolactone by UPLC-TOF-MS/MS

    Donggui Yao, Zhe Li, Changhong Huo, Yufang Wang, Yibing Wu, Manli Zhang, Ligeng Li, Qingwen Shi, Hiromasa Kiyota, Xiaowei Shi

    JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES   1033   250 - 260   2016.10

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    DOI: 10.1016/j.jchromb.2016.08.034

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  • Isolation of endosulfan sulfate-degrading Rhodococcus koreensis strain S1-1 from endosulfan contaminated soil and identification of a novel metabolite, endosulfan diol monosulfate

    Koji Ito, Fujimasa Kawashima, Kazuhiro Takagi, Ryota Kataoka, Masaaki Kotake, Hiromasa Kiyota, Kenichi Yamazaki, Futa Sakakibara, Sanae Okada

    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS   473 ( 4 )   1094 - 1099   2016.5

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    DOI: 10.1016/j.bbrc.2016.04.021

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  • Inhibitory effect of 13 taxane diterpenoids from Chinese yew (Taxus chinensis var. mairei) on the proliferation of HeLa cervical cancer cells

    Hai-Sheng Liu, Yu-Huan Gao, Li-Hong Liu, Wei Liu, Qing-Wen Shi, Mei Dong, Toshikazu Suzuki, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   80 ( 10 )   1883 - 1886   2016

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    DOI: 10.1080/09168451.2016.1194182

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  • 12T061A and 12T061C, two new julichrome family compounds, as radical scavengers from Streptomyces sp.

    Toshikazu Komoda, Naoko Saeki, Yoshitaka Koseki, Hiromasa Kiyota

    JOURNAL OF GENERAL AND APPLIED MICROBIOLOGY   62 ( 1 )   1 - 6   2016

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    DOI: 10.2323/jgam.62.1

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  • シクロプロパン環を有する香気物質の創製

    香料   272 ( 272 )   21 - 28   2016

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  • Research Advances on Biological Activities of Tanshinone IIA-A Mini Review

    Yan Zhong, Man-Li Zhang, Jin-Sheng Qi, Qing-Wen Shi, Hiromasa Kiyota

    MINI-REVIEWS IN ORGANIC CHEMISTRY   13 ( 4 )   305 - 311   2016

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    DOI: 10.2174/1570193X13666160614084004

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  • Synthesis of the spiroacetal fragments of spirofungins A and B, antibiotics isolated from Streptomyces violaceusniger Tu 4113

    Hiroyuki Sakauchi, Emi Higashi, Yuko Shimizu, Mikiko Kojima, Yuko Asamitsu, Shigefumi Kuwahara, Minoru Izumi, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   21 ( 6 )   337 - 343   2015.12

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    DOI: 10.1515/hc-2015-0193

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  • Two new taxane-glycosides from the needles of Taxus canadensis

    Nan Li, Jin Wang, Hui-Min Yan, Man-li Zhang, Qing-Wen Shi, Francoise Sauriol, Hiromasa Kiyota, Mei Dong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   70 ( 11 )   829 - 835   2015.11

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    DOI: 10.1515/znb-2015-0074

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  • New Limonoids from the Seeds of Xylocarpus granatum

    Yi-Bing Wu, Dan Liu, Pei-Yu Liu, Xue-Mei Yang, Man Liao, Nan-Nan Lu, Francoise Sauriol, Yu-Cheng Gu, Qing-Wen Shi, Hiromasa Kiyota, Mei Dong

    HELVETICA CHIMICA ACTA   98 ( 5 )   691 - 698   2015.5

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    DOI: 10.1002/hlca.201400290

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  • Synthetic Studies of Enacyloxins: A Series of Antibiotics Isolated from Frateuria sp W-315: C1'-C8' and C9'-C15' Fragments

    Aki Saito, Wataru Igarashi, Hiroyuki Furukawa, Hiroki Hoshikawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    NATURAL PRODUCT COMMUNICATIONS   10 ( 4 )   645 - 648   2015.4

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  • Kinetics of octachlorodipropyl ether photolysis in aqueous solution

    Yan-hong Shi, Min Liao, Hiromasa Kiyota, Hai-qun Cao, Ri-mao Hua, Feng Tang, Yong-de Yue

    JOURNAL OF PESTICIDE SCIENCE   40 ( 2 )   49 - 54   2015

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    DOI: 10.1584/jpestics.D14-061

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  • HYDROLYSIS OF OCTACHLORODIPROPYL ETHER IN AQUEOUS SOLUTIONS

    Yan-hong Shi, Min Liao, Hiromasa Kiyota, Ri-mao Hua, Xiangwei Wu, Jun Tang, Hai-qun Cao

    FRESENIUS ENVIRONMENTAL BULLETIN   24 ( 8 )   2534 - 2539   2015

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  • 12T061C, a new Julichrome family radical scavenger from Streptomyces species

    Toshikazu Komoda, Naoko Saeki, Yoshitaka Koseki, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   20 ( 5 )   271 - 274   2014.10

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    DOI: 10.1515/hc-2014-0126

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  • Novel phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF

    Ken-ichi Yamazaki, Kazuhiro Takagi, Ryota Kataoka, Masaaki Kotake, Teiko Yamada, Hiromasa Kiyota

    INTERNATIONAL BIODETERIORATION & BIODEGRADATION   92   36 - 40   2014.8

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    DOI: 10.1016/j.ibiod.2014.04.005

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  • Xylomexicanins E-H, new limonoids from Xylocarpus granatum

    Yi-Bing Wu, Xia Qing, Chang-Hong Huo, Hui-Min Yan, Qing-Wen Shi, Francoise Sauriol, Yu-Cheng Gu, Hiromasa Kiyota

    TETRAHEDRON   70 ( 30 )   4557 - 4562   2014.7

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    DOI: 10.1016/j.tet.2014.04.062

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  • 5-(2,2-Dimethyl-4H-1,3-benzodioxin) methanol: the synthetic precursor to o-formyl-m-hydroxycinnamic acid, the most oxidized salicylaldehyde-type phytotoxin isolated from rice blast fungus, Magnaporthe grisea

    Akihito Saito, Konosuke Hiramatsu, Hai-Qun Cao, Yuta Nagashima, Koji Tanaka, Ayaka Sasaki, Teiko Yamada, Shigefumi Kuwahara, Manabu Nukina, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   20 ( 3 )   185 - 188   2014.6

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    DOI: 10.1515/hc-2014-0053

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  • Facile synthesis of the cyclohexane fragment of enacloxins, a series of antibiotics isolated from Frateuria sp W-315

    Aki Saito, Wataru Igarashi, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   78 ( 5 )   766 - 769   2014.5

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    DOI: 10.1080/09168451.2014.905192

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  • Structural modification of isoalantolactone and biological activity against the hepatoma cell lines

    Rui-Xia Guo, Li-Geng Li, Man-Li Zhang, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   20 ( 2 )   117 - 121   2014.4

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    DOI: 10.1515/hc-2013-0220

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  • Chemical constituents of plants from the genus Neolitsea

    Xia Qing, Ting Zhao, Rui-Xia Guo, Yi-Bing Wu, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   20 ( 2 )   61 - 75   2014.4

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    DOI: 10.1515/hc-2013-0239

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  • A New Eudesmane Sesquiterpene from Dichrocephala integrifolia Reviewed

    Fang Qin, Yi-Bing Wu, Rui-xia Guo, Mei Dong, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    NATURAL PRODUCT COMMUNICATIONS   9 ( 2 )   149 - 150   2014.2

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  • Arteminal, a New Eudesmane Sesquiterpenolide from Artemisia frigida

    Cun-Fang Li, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Teiko Yamada, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    CHEMISTRY OF NATURAL COMPOUNDS   49 ( 5 )   872 - 874   2013.11

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    DOI: 10.1007/s10600-013-0767-x

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  • A New Taxane with a 4 beta,20-Epoxy Ring from the Rooted Cuttings of Taxus canadensis

    Gen-Dong Yao, Hong-Feng Zhang, Yun Huang, Francoise Sauriol, Qing-Wen Shi, Hiromasa Kiyota, Yu-Cheng Gu

    CHEMISTRY OF NATURAL COMPOUNDS   49 ( 5 )   861 - 863   2013.11

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    DOI: 10.1007/s10600-013-0765-z

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  • Functional and Structural Analysis of Influenza Virus Neuraminidase N3 Offers Further Insight into the Mechanisms of Oseltamivir Resistance

    Qing Li, Jianxun Qi, Yan Wu, Hiromasa Kiyota, Kosuke Tanaka, Yoshitomo Suhara, Hiroshi Ohrui, Yasuo Suzuki, Christopher J. Vavricka, George F. Gao

    JOURNAL OF VIROLOGY   87 ( 18 )   10016 - 10024   2013.9

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    DOI: 10.1128/JVI.01129-13

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  • 11-Hydroxyisocom-2-en-5-one, a new sesquiterpenoid from Echinops spinosissimus

    Zhi-Yu Ni, Yuta Nagashima, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    CHEMISTRY OF NATURAL COMPOUNDS   49 ( 4 )   632 - 634   2013.9

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    DOI: 10.1007/s10600-013-0696-8

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  • A new germacrane sesquiterpenolide isolated from Artemisia frigida

    Manli Zhang, Zhiyu Ni, Cunfang Li, Yufang Wang, Mei Dong, Francoise Sauriol, Changhong Huo, Qingwen Shi, Teiko Yamada, Hiromasa Kiyota, Yucheng Gu, Bin Cong

    CHEMISTRY OF NATURAL COMPOUNDS   49 ( 4 )   626 - 628   2013.9

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    DOI: 10.1007/s10600-013-0694-x

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  • Xylomexicanins C and D, New Mexicanlide-Type Limonoids from Xylocarpus granatum

    Yi-Bing Wu, Zhi-Yu Ni, Chang-Hong Huo, Jian Su, Mei Dong, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   77 ( 4 )   736 - 740   2013.4

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    DOI: 10.1271/bbb.120815

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  • Torreyanoxane, a New 3,4-Secoglutinane Triterpenoid Isolated from the Pulp of Torreya nucifera

    Cong-Mei Cao, Yi-Bing Wu, Rui-Xia Guo, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Teiko Yamada, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    HELVETICA CHIMICA ACTA   96 ( 3 )   375 - 378   2013.3

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    DOI: 10.1002/hlca.201200174

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  • Influenza neuraminidase operates via a nucleophilic mechanism and can be targeted by covalent inhibitors

    Christopher J. Vavricka, Yue Liu, Hiromasa Kiyota, Nongluk Sriwilaijaroen, Jianxun Qi, Kosuke Tanaka, Yan Wu, Qing Li, Yan Li, Jinghua Yan, Yasuo Suzuki, George F. Gao

    NATURE COMMUNICATIONS   4   1491 - 1491   2013.2

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    DOI: 10.1038/ncomms2487

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  • A new alkaloid taxane composed of two N-formyl rotamers from the rooted cuttings of Taxus canadensis

    Hong-Zhen Zhang, Yu-Fang Wang, Man-Li Zhang, Mei Dong, Chang-Hong Huo, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hui-Lan Wang, Hiromasa Kiyota

    Chemistry of Natural Compounds   48 ( 6 )   1035 - 1038   2013.1

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    DOI: 10.1007/s10600-013-0458-7

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  • Cytotoxic flavonoids from the flowers of Achillea millefolium

    Chang-Hong Huo, Yong Li, Man-Li Zhang, Yu-Fang Wang, Qing Zhang, Fang Qin, Qing-Wen Shi, Hiromasa Kiyota

    Chemistry of Natural Compounds   48 ( 6 )   958 - 962   2013.1

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    DOI: 10.1007/s10600-013-0438-y

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  • Constituents from Salvia Species and Their Biological Activities

    Yi-Bing Wu, Zhi-Yu Ni, Qing-Wen Shi, Mei Dong, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    CHEMICAL REVIEWS   112 ( 11 )   5967 - 6026   2012.11

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    DOI: 10.1021/cr200058f

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  • Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations

    Minoru Ueda, Gangqiang Yang, Yasuhiro Ishimaru, Tetsuya Itabashi, Satoru Tamura, Hiromasa Kiyota, Shigefumi Kuwahara, Sho Inomata, Mitsuru Shoji, Takeshi Sugai

    BIOORGANIC & MEDICINAL CHEMISTRY   20 ( 19 )   5832 - 5843   2012.10

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    DOI: 10.1016/j.bmc.2012.08.003

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  • New 6/8/6-Taxanes Isolated from the Heartwood of Taxus cuspidata

    Kai Zhang, Yong Li, Zhi-Yi Ni, Man-Li Zhang, Yu-Fang Wang, Qing-Wen Shi, Chang-Hong Huo, Francoise Sauriol, Hiromasa Kiyota, Yu-Cheng Gu, Mei Dong

    HELVETICA CHIMICA ACTA   95 ( 9 )   1566 - 1572   2012.9

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    DOI: 10.1002/hlca.201200045

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  • Antitumour Activities of Sesquiterpene Lactones from Inula helenium and Inula japonica

    Yong Li, Zhi-Yu Ni, Meng-Chu Zhu, Mei Dong, Si-Ming Wang, Qing-Wen Shi, Man-Li Zhang, Yu-Fang Wang, Chang-hong Huo, Hiromasa Kiyota, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES   67 ( 7-8 )   375 - 380   2012.7

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  • A simple, rapid method for gizzerosine analysis in fish meal by paper electrophoresis

    Zhihua Tao, Minoru Sato, Kegang Wu, Hiromasa Kiyota, Toshiyasu Yamaguchi, Toshiki Nakano

    FISHERIES SCIENCE   78 ( 4 )   923 - 926   2012.7

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    DOI: 10.1007/s12562-012-0507-3

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  • Millifolides A-C. New 1,10-Seco-guaianolides from the Flowers of Achillea millefolium

    Yong Li, Zhi-Yu Ni, Meng-Chu Zhu, Kai Zhang, Yi-Bing Wu, Mei Dong, Qing-Wen Shi, Chang-Hong Huo, Francoise Sauriol, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   67 ( 5 )   438 - 446   2012.5

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    DOI: 10.5560/ZNB.2012-0028

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  • Achillinin B and C, new sesquiterpene dimers isolated from Achillea millefolium

    Yong Li, Meng-Chu Zhu, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Qing-Wen Shi, Chang-Hong Huo, Francoise Sauriol, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    TETRAHEDRON LETTERS   53 ( 21 )   2601 - 2603   2012.5

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    DOI: 10.1016/j.tetlet.2012.03.039

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  • Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis

    Yong Li, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Francoise Sauriol, Qing-Wen Shi, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    HETEROCYCLIC COMMUNICATIONS   18 ( 2 )   57 - 60   2012.4

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    DOI: 10.1515/hc-2012-0035

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  • Relationship between the Structures of Taxane Derivatives and Their Microtubule Polymerization Activity

    Masafumi Hidaka, Tomoe Koga, Hiromasa Kiyota, Tohru Horiguchi, Qing-Wen Shi, Keiko Hirose, Takafumi Uchida

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   76 ( 2 )   349 - 352   2012.2

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    DOI: 10.1271/bbb.110797

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  • Structure-Activity Relationship of 9-Methylstreptimidone, a Compound That Induces Apoptosis Selectively in Adult T-Cell Leukemia Cells

    Masatoshi Takeiri, Eisuke Ota, Shigeru Nishiyama, Hiromasa Kiyota, Kazuo Umezawa

    ONCOLOGY RESEARCH   20 ( 1 )   7 - 14   2012

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    DOI: 10.3727/096504012X13425470196056

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  • Natural Taxanes: Developments Since 1828

    Yu-Fang Wang, Qing-Wen Shi, Mei Dong, Hiromasa Kiyota, Yu-Cheng Gu, Bin Cong

    CHEMICAL REVIEWS   111 ( 12 )   7652 - 7709   2011.12

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    DOI: 10.1021/cr100147u

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  • Synthesis and Biotransformation of Plausible Biosynthetic Intermediates of Salicylaldehyde-Type Phytotoxins of Rice Blast Fungus, Magnaporthe grisea

    Koji Tanaka, Ayaka Sasaki, Hai-Qun Cao, Teiko Yamada, Masahiro Igarashi, Isao Komine, Hirokazu Nakahigashi, Naoko Minami, Shigefumi Kuwahara, Manabu Nukina, Hiromasa Kiyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 31 )   6276 - 6280   2011.11

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    DOI: 10.1002/ejoc.201100771

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  • Synthesis of Both Enantiomers of omega-Trifluorononactic Acid, a New Analogue of Nonactin Monomers

    Kentaro Takai, Tadaatsu Hanadate, Shuichi Oi, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    SYNTHESIS-STUTTGART   ( 22 )   3741 - 3748   2011.11

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    DOI: 10.1055/s-0030-1260234

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  • Diabietane Ether, a New Dimeric Abietane with an Ether Linkage from Taxus cuspidata Needles

    Zhi-Yu Ni, Yi-Bing Wu, Mei Dong, Man-Li Zhang, Yu-Fang Wang, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   66 ( 10 )   1083 - 1086   2011.10

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  • P-60 Synthetic Studies of Salicylaldehyde-type Phytotoxins Isolated from Rice Blast Fungus(Poster Presentation)

    Kiyota Hiromasa, Sasaki Ayaka, Tanaka Koji, Nakamura Yoko, Ueda Rumi, Suzuki Yuji, Kuwahara Shigefumi, Nukina Manabu

    Symposium on the Chemistry of Natural Products, symposium papers   ( 53 )   661 - 666   2011.9

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    Rice blast disease, caused by infection of rice blast fungus Magnaporthe grisea (Hebert) Barr. (perfect stage of Pyricularia oryzae Cabara), has been the most serious pest for rice. The fungus mainly produces several phytotoxic compounds according to fermentation method, i. e., dihydropyriculol (1), pyriculol (2), and pyriculone (3) by a shaking culture; dihydropyriculariol (5) and pyriculariol (6) by an aeration and agitation culture; and tenuazonic acid by a stationary culture in a soy sauce-sucrose medium. Pyricuol (4) together with 2 were produced by a shaking culture with a potato dextrose medium. These salicylaldehyde-type phytotoxins are common metabolites of blast fungi of various host plants except a ginger. To develop novel methods to control the blast disease a better knowledge of the biosynthesis is necessary. Synthesis of both enantiomers of pyricuol (4) from (R)- and (8-lactates was achieved using [2,31-Wittig rearrangement and Stille coupling reactions as the key steps. This revealed that the natural 4 has an R-configuration. Racemic synthesis is also reported. On the other hand, optically active pyriculariol (6) was synthesized from L-rhamnose using microwave assisted Stille coupling reaction of the unprotected substrates as the key step. A comparison of the CD spectra and 1H NMR spectra of the corresponding MTPA esters found that natural pyriculariol (6) existed as a racemate. Biotransformation of the plausible biosynthetic intermediates 7-d2 and 8-d in deuterio forms was also examined. Not diol 7-d2 but aldehyde 8-d was converted by the fungus M. grisea into dihydropyriculariol (1-d) in soy sauce-sucrose medium under a shaking culture. Foliar application test of the synthetic compounds on rice leaves revealed that both a salicylaldehyde and a side chain fragments are necessary for the necrotic activity. In conclusion, the blast fungus M. grisea produced 1, 2, and 4 in optically active forms and 5 and 6 as racemates depending on the culture conditions. Additionally, it is interesting that both oxidation and reduction would be coexist at the later stage of biosynthesis of these phytotoxins.

    DOI: 10.24496/tennenyuki.53.0_661

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  • Biotransformation of a biosynthetic intermediate mimic of nonactin by Streptomyces griseus

    Tadaatsu Hanadate, Kentaro Takai, Naoki Abe, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   17 ( 3-4 )   93 - 98   2011.9

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    DOI: 10.1515/HC.2011.021

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  • Novel metabolic pathways of organochlorine pesticides dieldrin and aldrin by the white rot fungi of the genus Phlebia

    Pengfei Xiao, Toshio Mori, Ichiro Kamei, Hiromasa Kiyota, Kazuhiro Takagi, Ryuichiro Kondo

    CHEMOSPHERE   85 ( 2 )   218 - 224   2011.9

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    DOI: 10.1016/j.chemosphere.2011.06.028

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  • Novel Taxa-4(20),12-diene and 2(3 -&gt; 20)Abeotaxane from Needles of Taxus canadensis

    Zhi-Yu Ni, Yi-Bing Wu, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   75 ( 9 )   1698 - 1701   2011.9

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    DOI: 10.1271/bbb.110223

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  • Synthesis of macrotetrolide alpha, a designed polynactin analog composed of bishomononactic acids

    Kentaro Takai, Tadaatsu Hanadate, Masaki Abe, Yukie Ono, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    TETRAHEDRON   67 ( 37 )   7066 - 7072   2011.9

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    DOI: 10.1016/j.tet.2011.07.012

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  • Achillinin A, a Cytotoxic Guaianolide from the Flower of Yarrow, Achillea millefolium

    Yong Li, Man-Li Zhang, Bin Cong, Si-Ming Wang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   75 ( 8 )   1554 - 1556   2011.8

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    DOI: 10.1271/bbb.110234

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  • Chemical constituents of plants from the genus caesalpinia

    Ming Wu, Yu-Fang Wang, Man-Li Zhang, Chang-Hong Huo, Mei Dong, Qing-Wen Shi, Hiromasa Kiyota

    Chemistry and Biodiversity   8 ( 8 )   1370 - 1399   2011.8

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    DOI: 10.1002/cbdv.201000176

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  • A Novel Taxatetraene Framework Formed From a New Natural Taxane from Taxus cuspidata

    Yong Li, Yong-Li Wang, Zhi-Yu Ni, Mei Dong, Bin Cong, Francoise Sauriol, Man-Li Zhang, Yu-Fang Wang, Chang-Hong Huo, Yu-Cheng Gu, Qing-Wen Shi, Hiromasa Kiyota

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   66 ( 7 )   759 - 761   2011.7

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  • The first taxane peroxide from the rooted cuttings of Taxus canadensis

    Zhen-Hua Pan, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Chang-Hong Huo, Francoise Sauriol, Qing-Wen Shi, Hiromasa Kiyota, Yong-Jian Zhang

    HETEROCYCLIC COMMUNICATIONS   17 ( 1-2 )   87 - 91   2011.7

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    DOI: 10.1515/HC.2011.019

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  • Stereochemistry of enacyloxins. Part 6: Synthesis of C16 &apos;-C23 &apos; fragments of enacyloxins, a series of antibiotics from Frateuria sp W-315

    Wataru Igarashi, Hiroaki Hoshikawa, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   17 ( 1-2 )   7 - 9   2011.7

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    DOI: 10.1515/HC.2011.008

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  • Stereochemistry of enacyloxins. Part 5: Synthesis of a C9 &apos;-C15 &apos; fragment of enacyloxins, a series of antibiotics from Frateuria sp W-315

    Hiroyuki Furukawa, Hiroaki Hoshikawa, Wataru Igarashi, Manabu Yaosaka, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    HETEROCYCLIC COMMUNICATIONS   17 ( 1-2 )   3 - 5   2011.7

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    DOI: 10.1515/HC.2011.007

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  • Isolation and identification of dieldrin-degrading Pseudonocardia sp strain KSF27 using a soil-charcoal perfusion method with aldrin trans-diol as a structural analog of dieldrin

    Futa Sakakibara, Kazuhiro Takagi, Ryota Kataoka, Hiromasa Kiyota, Yuuki Sato, Sanae Okada

    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS   411 ( 1 )   76 - 81   2011.7

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    DOI: 10.1016/j.bbrc.2011.06.096

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  • Improved Method for Antinematodal Assay by Using Extraction Thimble and Antinematodal Activity of 4-Methylumbelliferyl Glycosides Synthesized by Mitsunobu Reaction Reviewed

    Minoru Izumi, Kentaro Nakamura, Ayuko Ishizaka, Hiromasa Kiyota, Shuhei Nakajima

    51 ( 2 )   33 - 36   2011.3

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  • A Novel Taxane 13-Glucoside and Other Taxanes from the Leaves of Taxus cuspidata

    Zhi-Yu Ni, Mei Dong, Bin Cong, Francoise Sauriol, Man-Li Zhang, Yu-Fang Wang, Chang-Hong Huo, Qing-Wen Shi, Hiromasa Kiyota

    PLANTA MEDICA   77 ( 3 )   281 - 283   2011.2

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    DOI: 10.1055/s-0030-1250333

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  • Oxepinamides: Novel Liver X Receptor Agonists from Aspergillus puniceus

    Xin-Hua Lu, Qing-Wen Shi, Zhi-Hui Zheng, Ai-Bing Ke, Hua Zhang, Chang-Hong Huo, Ying Ma, Xiao Ren, Ye-Ying Li, Jie Lin, Qin Jiang, Yu-Cheng Gu, Hiromasa Kiyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 4 )   802 - 807   2011.2

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    DOI: 10.1002/ejoc.201000812

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  • Chemical and Pharmacological Research on Plants from the Genus Senecio

    Yan Yang, Lei Zhao, Yu-Fang Wang, Man-Li Chang, Chang-Hong Huo, Yu-Cheng Gu, Qing-Wen Shi, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   8 ( 1 )   13 - 72   2011

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    DOI: 10.1002/cbdv.201000027

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  • Two New Phytoecdysteroids from the Needles of Taxus canadensis

    Yu Fang, Zhi-Yu Ni, Teiko Yamada, Yu-Fang Wang, Man-Li Zhang, Mei Dong, Bin Cong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Hiromasa Kiyota

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   65 ( 11 )   1401 - 1405   2010.11

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  • Biodegradation of Dieldrin by a Soil Fungus Isolated from a Soil with Annual Endosulfan Applications

    Ryota Kataoka, Kazuhiro Takagi, Ichiro Kamei, Hiromasa Kiyota, Yuuki Sato

    ENVIRONMENTAL SCIENCE & TECHNOLOGY   44 ( 16 )   6343 - 6349   2010.8

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    DOI: 10.1021/es1000227

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  • Chemical Constituents of Plants from the Genus Valeriana

    Yufang Wang, Liqing Jin, Shuhong Yu, Qingwen Shi, Yucheng Gu, Hiromasa Kiyota

    MINI-REVIEWS IN ORGANIC CHEMISTRY   7 ( 2 )   161 - 172   2010.5

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    DOI: 10.2174/157019310791065537

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  • Xylocarpanoids A and B, unique C-28 skeleton limonoids from Xylocarpus granatum

    Chang-Hong Huo, Dong Guo, Li-Ru Shen, Bao-Wei Yin, Francoise Sauriol, Li-Geng Li, Man-Li Zhang, Qing-Wen Shi, Hiromasa Kiyota

    TETRAHEDRON LETTERS   51 ( 4 )   754 - 757   2010.1

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    DOI: 10.1016/j.tetlet.2009.11.123

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  • Identification of the Mesorhizobium loti gene responsible for glycerophosphorylation of periplasmic cyclic beta-1,2-glucans Reviewed

    Yasuyuki Kawaharada, Hiromasa Kiyota, Shima Eda, Kiwamu Minamisawa, Hisayuki Mitsui*

    FEMS Microb. Lett.   302 ( 2 )   131 - 137   2010.1

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    DOI: 10.1111/j.1574-6968.2009.01843.x

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  • Secondary Metabolites of Plants from the Genus Saussurea: Chemistry and Biological Activity

    Yu-Fang Wang, Zhi-Yu Ni, Mei Dong, Bin Cong, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   7 ( 11 )   2623 - 2659   2010

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    DOI: 10.1002/cbdv.20090

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  • Synthesis of Pteroenone and Its Stereoisomers, a Defensive Metabolite of the Abducted Antarctic Pteropod Clione antarctica

    Hiroki Asao, Yoko Nakamura, Yukito Furuya, Shigefumi Kuwahara, Bill J. Baker, Hiromasa Kiyota

    HELVETICA CHIMICA ACTA   93 ( 10 )   1933 - 1944   2010

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    DOI: 10.1002/hlca.201000258

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  • Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity

    Toshiro Noshita, Yumi Kidachi, Hirokazu Funayama, Hiromasa Kiyota, Hideaki Yamaguchi, Kazuo Ryoyama

    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY   44 ( 12 )   4931 - 4936   2009.12

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    DOI: 10.1016/j.ejmech.2009.08.005

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  • Synthetic Studies on procyanidins, (-)-epicatechin 3-(3"-Ο-methylgallate), and resveratrol

    Iijima Takashi, Mohri Yoshihiro, Sagehashi Masayoshi, Yamada Taiji, Hattori Yasunao, Hamauzu Yasunori, Kamo Tsunashi, Hirota Mitsuru, Kiyota Hiromasa, Makabe Hidefumi

    Symposium on the Chemistry of Natural Products, symposium papers   ( 51 )   289 - 294   2009.9

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    1. Synthesis of procyanidin B1-B4(1-4). Stereoselective synthesis of catechin and epocatechin under intermolecular condensation of equimolar amount of catechin derivatives catalyzed by Yb(OTf)_3. The coupled products were successfully converted to procyanidin B1 (1), B2 (2), B3 (3), and B4 (4), respectively. 2. synthetic of (-)-epicatechin 3-(3"-O-methylgallate) (13) and (+)-catechin 3-(3"-O-methylgallate) (14) A concise synthesis of (-)-epicatechin 3-(3"-O-methylgallate)(13, ECG3"Me), which is a minor constituent of tea, and (+)-catechin 3-(3"-O-methylgallate)(14, CG3"Me) via condensation of equimolar amount of catechin and gallate derivatives has been achieved. The anti-inflammatory effect of the synthetic compounds on TPA-induced inflammation of mouse ears was examined. Compounds 13 and 14 suppressed the TPA-induced inflammation of mouse ears by 50% and 43%, respectively, at a dose of 200μg. 3. Short step synthesis of resveratrol derivative. An efficient synthesis of trimethoxylated resveratrol (20) is presented using advanced Heck reaction promoted by Pd(dba)_2 in the presence of P(t-Bu)_3.

    DOI: 10.24496/tennenyuki.51.0_289

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  • First synthesis and absolute configuration of (-)-pyriculariol, a phytotoxin isolated from rice blast fungus, Magnaporthe grisea. Use of microwave irradiation to control Stille coupling reaction products

    Ayaka Sasaki, Koji Tanaka, Yuuki Sato, Shigefumi Kuwahara, Hiromasa Kiyota

    TETRAHEDRON LETTERS   50 ( 32 )   4637 - 4638   2009.8

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    DOI: 10.1016/j.tetlet.2009.05.109

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  • Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

    Koji Tanaka, Yoko Nakamura, Ayaka Sasaki, Rumi Ueda, Yuji Suzuki, Shigefumi Kuwahara, Hiromasa Kiyota

    TETRAHEDRON   65 ( 31 )   6115 - 6122   2009.8

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    DOI: 10.1016/j.tet.2009.05.052

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  • Gene expression profiles in differentiating leukemia cells induced by methyl jasmonate are similar to those of cytokinins and methyl jasmonate analogs induce the differentiation of human leukemia cells in primary culture

    H. Tsumura, M. Akimoto, H. Kiyota, Y. Ishii, H. Ishikura, Y. Honma

    LEUKEMIA   23 ( 4 )   753 - 760   2009.4

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    DOI: 10.1038/leu.2008.347

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  • New Cytotoxic Phenolic Derivatives from Matured Fruits of Magnolia denudata

    Toshiro Noshita, Hiromasa Kiyota, Yumi Kidachi, Kazuo Ryoyama, Shinji Funayama, Ken Hanada, Tetsuya Murayama

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   73 ( 3 )   726 - 728   2009.3

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    DOI: 10.1271/bbb.80597

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  • Taxusecone, a Novel Taxane with an Unprecedented 11,12-Secotaxane Skeleton, from Taxus cuspidata Needles

    Shu-Hong Yu, Zhi-Yu Ni, Jing Zhang, Mei Dong, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   73 ( 3 )   756 - 758   2009.3

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    DOI: 10.1271/bbb.80698

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  • Xylomexicanins A and B, New Delta(14,15)-Mexicanolides from Seeds of the Chinese Mangrove Xylocarpus granatum

    Li-Ru Shen, Mei Dong, Dong Guo, Bao-Wei Yin, Man-Li Zhang, Qing-Wen Sha, Chang-Hong Huo, Hiromasa Kiyota, Nobuo Suzuki, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES   64 ( 1-2 )   37 - 42   2009.1

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  • Two New 11(15 -&gt; 1)Abeotaxanes with a 2,20-Epoxy Ring from the Needles of Taxus canadensis

    Man-Li Zhang, Jing Zhang, Mei Dong, Shu-Hua Feng, Chang-Hong Huo, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES   64 ( 1-2 )   43 - 48   2009.1

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  • Synthesis of (-)-Epicatechin 3-(3-O-Methylgailate) and (+)-Catechin 3-(3-O- Methylgallate), and Their Anti-Inflammatory Activity

    Takashi Iijima, Yoshihiro Mohri, Yasunao Hattori, Atsushi Kashima, Tsunashi Kamo, Mitsuru Hirota, Hiromasa Kiyota, Hidefumi Makabe

    CHEMISTRY & BIODIVERSITY   6 ( 4 )   520 - 526   2009

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    DOI: 10.1002/cbdv.200800224

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  • Chemical and Pharmacological Studies of the Plants from Genus Celastrus

    Xiao-Hui Su, Man-Li Zhang, Wen-Hong Zhan, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   6 ( 2 )   146 - 161   2009

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    DOI: 10.1002/cbdv.200700403

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  • The Daphniphyllum alkaloids

    Mei Dong, Man-Li Zhang, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota

    Current Organic Chemistry   13 ( 6 )   646 - 682   2009

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    DOI: 10.2174/138527209787847345

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  • Enzymatic Resolution of (+/-)-2-Exo-7-syn-7-(1-propynyl)norbornan-2-ol, a Key Synthetic Intermediate for Jasmonoids

    Hiromasa Kiyota, Daisuke Nakashima, Shigefumi Kuwahara, Takayuki Oritani

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   63 ( 12 )   1441 - 1442   2008.12

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  • Synthesis and Anti-Angiogenic Activity of Cortistatin Analogs

    Yuuki Sato, Hiroshi Kamiyama, Takeo Usui, Tamio Saito, Hiroyuki Osada, Shigefumi Kuwahara, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   72 ( 11 )   2992 - 2997   2008.11

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    DOI: 10.1271/bbb.80562

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  • Taxpropellane: A Novel Taxane with an Unprecedented Polycyclic Skeleton from the Needles of Taxus canadensis

    Man-Li Zhang, Mei Dong, Chang-Hong Huo, Li-Geng Li, Francoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hidefumi Makabe, Hiromasa Kiyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 32 )   5414 - 5417   2008.11

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    DOI: 10.1002/ejoc.200800587

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  • Chemical and pharmacological research of the plants in genus Euphorbia

    Qing-Wen Shi, Xiao-Hui Su, Hiromasa Kiyota

    CHEMICAL REVIEWS   108 ( 10 )   4295 - 4327   2008.10

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    DOI: 10.1021/cr078350s

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  • Synthesis of the L-Acid (C1-C18) Fragment of Pamamycin-593 and De-N-methylpamamycin-579

    Ayako Miura, Shin-ya Takigawa, Yukito Furuya, Yusuke Yokoo, Shigefumi Kuwahara, Hiromasa Kiyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 29 )   4955 - 4962   2008.10

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    DOI: 10.1002/ejoc.200800600

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  • Structural characterization of neutral and anionic glucans from Mesorhizobium loti

    Yasuyuki Kawaharada, Hiromasa Kiyota, Shima Eda, Kiwamu Minamisawa, Hisayuki Mitsui

    CARBOHYDRATE RESEARCH   343 ( 14 )   2422 - 2427   2008.9

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    DOI: 10.1016/j.carres.2008.07.007

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  • A new pseudo-alkaloid taxane and a new rearranged taxane from the needles of Taxus canadensis

    Manti Zhang, Changhong Huo, Mei Dong, Ligeng Li, Franqoise Sauriol, Qingwen Shi, Yucheng Gu, Hiromasa Kiyota, Bin Cong

    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES   63 ( 8 )   1005 - 1011   2008.8

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  • A new taxane composed of two N-formyl rotamers from Taxus canadensis

    Man-Li Zhang, Mei Dong, Xiao-Ning Li, Li-Geng Li, Fancoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

    TETRAHEDRON LETTERS   49 ( 21 )   3405 - 3408   2008.5

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    DOI: 10.1016/j.tetlet.2008.03.115

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  • Echinopines A and B: Sesquiterpenoids possessing an unprecedented skeleton from Echinops spinosus

    Mei Dong, Bin Cong, Shu-Hong Yu, Francoise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Lolita O. Zamir, Hiromasa Kiyota

    ORGANIC LETTERS   10 ( 5 )   701 - 704   2008.3

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    DOI: 10.1021/ol702629z

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  • A taxane with a novel 9 alpha,13 alpha-oxygen bridge from Taxus cuspidata needles

    Man-Li Zhang, Qing-Wen Shi, Mel Dong, Yu-Fang Wang, Chang-Hong Huo, Yu-Cheng Gu, Bin Cong, Hiromasa Kiyota

    TETRAHEDRON LETTERS   49 ( 7 )   1180 - 1183   2008.2

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    DOI: 10.1016/j.tetlet.2007.12.045

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  • Total Synthesis of Natural Products of Microbial Origins

    Tohoku Journal of Agricultural Research   58 ( 3-4 )   167 - 173   2008

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  • Two new taxanes from Taxus canadensis

    Changhong Huo, Yongming Zhao, Xiaotang Si, Ligeng Li, Manli Zhang, Qingwen Shi, Hiromasa Kiyota

    BIOCHEMICAL SYSTEMATICS AND ECOLOGY   35 ( 12 )   909 - 913   2007.12

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    DOI: 10.1016/j.bse.2007.05.006

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  • A new taxol analogue from the leaves of Taxus cuspidata

    Changhong Huo, Xiping Zhang, Cunfang Li, Wang Wang, Qingwen Shi, Hiromasa Kiyota

    BIOCHEMICAL SYSTEMATICS AND ECOLOGY   35 ( 10 )   704 - 708   2007.10

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    DOI: 10.1016/j.bse.2007.03.005

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  • 12 Enantio-Differential Approach to the Receptor Protein of glucosylated Jasmonate-type leaf-closing factor

    Nakamura Yoko, Miyatake Ryoji, Inomata Sho, Kiyota Hiromasa, Ueda Minoru

    Symposium on the Chemistry of Natural Products, symposium papers   ( 49 )   67 - 72   2007.8

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    Albizzia plants close their leaves in the evening, as if to sleep, and open them in the morning according to the circadian rhythum. Potassium β-D-glucopyranosyl-12-hydroxyjasmonate was isolated as leaf-closing factor (LCF) of Albizzia saman. We developed molecular probes consisting of modified LCF in order to identify its mode of action. However, it is often discussed whether molecular probes containing a larger and less polar functional unit such as fluorescence dye can bind to genuine binding protein of a natural product in living organisms. So, we need appropriate negative control. And an enantiomer of a biologically active natural product can be used as an ideal control because all physical propaties except for optical rotation and affinity to binding proteins are identical between a pair of enantiomers. Thus, enantio-differential approach that compares the results using a pair of probes that was prepared from a pair of enantiomers would be an ideal method in the bioorganic study using molecular probes. We synthesized probe 11 and biologically inactive enantiomer-type probe 12. And carried out fluorescence labeling study using 11 and 12. The results was clearly shown that the motor cells contain some specific binding protein that can differentiate the stereochemistry of the ligands. Similarly, we synthesized enantio pair-type photoaffinity-labeling probes 20 and 21, and used them for photoaffinity labeling of receptor for LCF. By using protoplast of motor cell, we found 35kDa membrane protein strictly recognizes the stereochemistry of LCF, and it is highly likely that the protein is the specific receptor for LCF.

    DOI: 10.24496/tennenyuki.49.0_67

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  • Synthesis of (-)-tabtoxinine-beta-lactam, the phytotoxin of tobacco wildfire disease

    Hiromasa Kiyota, Takafumi Takai, Yasuharu Shimasaki, Masatoshi Saitoh, Osamu Nakayama, Tomoko Takada, Shigefumi Kuwahara

    SYNTHESIS-STUTTGART   2007 ( 16 )   2471 - 2480   2007.8

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    DOI: 10.1055/s-2007-983785

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  • Three new taxanes with the 10-alkoxy group from the heartwood of Taxas cuspidata

    Mei Dong, Man-Li Zhang, Yu-Fang Wang, Xi-Ping Zhang, Cun-Fang Li, Qln-Wen Shi, Bin Cong, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   71 ( 8 )   2087 - 2090   2007.8

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    DOI: 10.1271/bbb.70210

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  • New 14-hydroxy-taxane and 2 alpha,20-epoxy-11(15 -&gt; 1)abeotaxane from the needles of Taxus canadensis

    Qing-Wen Shi, Mei Dong, Chang-Hong Huo, Xiao-Hui Su, Cun-Fang Li, Xi-Ping Zhang, Yu-Fang Wang, Hiromasa Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   71 ( 7 )   1777 - 1780   2007.7

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    DOI: 10.1271/bbb.70063

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  • Structural determination of a new 2(3 -&gt; 20)abeotaxane with an unusual 13 beta-substitution pattern and a new 6/8/6-ring taxane from Taxus cuspidata

    Changhong Huo, Xiaohui Su, Xing Li, Xiping Zhang, Cunfang Li, Yufang Wang, Qingwen Shi, Hiromasa Kiyota

    MAGNETIC RESONANCE IN CHEMISTRY   45 ( 6 )   527 - 530   2007.6

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    DOI: 10.1002/mrc.2001

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  • Chemical Constituents in the Genus Wedelia and their Bioactivity Reviewed

    Chemistry and Biodiversity   4 ( 4 )   823 - 836   2007.4

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  • Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

    Chang-Hong Huo, Xiao-Hui Su, Yu-Fang Wang, Xi-Ping Zhang, Qing-Wen Shi, Hiromasa Kiyota

    TETRAHEDRON LETTERS   48 ( 15 )   2721 - 2724   2007.4

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    DOI: 10.1016/j.tetlet.2007.02.063

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  • Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

    Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara, Hiromasa Kiyota

    TETRAHEDRON-ASYMMETRY   18 ( 4 )   537 - 541   2007.3

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    DOI: 10.1016/j.tetasy.2007.02.007

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  • Chemical constituents of the plants from the genus Laggera

    Xing-Cui Li, Chang-Hong Huo, Qing-Wen Shi, Hiromasa Kiyota

    Chemistry and Biodiversity   4 ( 2 )   105 - 111   2007

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    DOI: 10.1002/cbdv.200790014

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  • A new metabolite with a new substitution pattern from the seeds of the Chinese yew, Taxus mairei

    Chang-Hong Huo, Yu-Fang Wang, Xi-Ping Zhang, Cun-Fang Li, Qing-Wen Shi, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   4 ( 1 )   84 - 88   2007

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    DOI: 10.1002/cbdv.200790009

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  • Structures and biological properties of the chemical constituents from the genus Wedelia

    Xing Li, Mei Dong, Yong Liu, Qing-Wen Shi, Hiromasa Kiyota

    Chemistry and Biodiversity   4 ( 5 )   823 - 836   2007

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  • Stereochemistry of enacyloxins - Part 4 - Complete structural and configurational assignment of the enacyloxin family, a series of antibiotics from Frateuria sp W-315 Reviewed

    Hiroyuki Furukawa, Hiromasa Kiyota, Teiko Yamada, Manabu Yaosaka, Ryo Takeuchi, Toshihiko Watanabe, Shigefumi Kuwahara

    CHEMISTRY & BIODIVERSITY   4 ( 7 )   1601 - 1604   2007

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  • 7,8 beta-dihydroponasterone A, a new phytoecdysteroid from the needles of the Japanese yew, Taxus cuspidata

    Qing-Wen Shi, Mei Dong, Chang-Hong Huo, Xiao-Hui Su, Xing Li, Teiko Yamada, Hiromasa Kiyota

    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY   18 ( 5 )   1081 - 1084   2007

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  • Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B

    Akira Morita, Hiromasa Kiyota, Shigefumi Kuwahara

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   70 ( 10 )   2564 - 2566   2006.10

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    DOI: 10.1271/bbb.60253

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  • Synthesis of (S)-gizzerosine, a potent inducer of gizzard erosion in chicks

    Yasuharu Shimasaki, Hiromasa Kiyota, Minoru Sato, Shigefumi Kuwahara

    TETRAHEDRON   62 ( 41 )   9628 - 9634   2006.10

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    DOI: 10.1016/j.tet.2006.07.080

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  • P-41 New Synthetic Analogs of Macrotetraolide Antibiotics Polynactins

    Takai K., Hanadate T., Oi S., Kuwahara S., Kiyota H.

    Symposium on the Chemistry of Natural Products, symposium papers   ( 48 )   361 - 365   2006.9

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    DOI: 10.24496/tennenyuki.48.0_361

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  • Enantio-diffferential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

    Yoko Nakamura, Ryoji Miyatake, Akira Matsubara, Hiromasa Kiyota, Minoru Ueda

    TETRAHEDRON   62 ( 37 )   8805 - 8813   2006.9

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    DOI: 10.1016/j.tet.2006.06.092

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  • P-37 Fluorescence Studies on the Nyctinasty of Albizzia Plants, An enantio-differential approach Using Enantio-pair of Fluorescence-labeled leaf closing factors

    Nakamura Yoko, Miyatake Ryoji, Kiyota Hiromasa, Ueda Minoru

    International Symposium on the Chemistry of Natural Products   2006   "P - 37"   2006.7

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    DOI: 10.24496/intnaturalprod.2006.0__P-37_

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  • New taxanes from the seeds of Taxus mairei

    Q. -W. Shi, Z. -P. Li, C. -L. Wang, M. -L. Zhang, N. Choony, H. Kiyota

    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH   8 ( 5 )   431 - 437   2006.7

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    DOI: 10.1080/10286020500172848

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  • Spirofungins A and B: a reassignment of Kiyota's spiroketals

    LG de Oliveira, LC Dias, H Sakauchi, H Kiyota

    TETRAHEDRON LETTERS   47 ( 14 )   2413 - 2418   2006.4

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    DOI: 10.1016/j.tetlet.2006.01.153

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  • Direct observation of the target cell for jasmonate-type leaf-closing factor: genus-specific binding of leaf-movement factors to the plant motor cell

    Y Nakamura, H Kiyota, T Kumagai, M Ueda

    TETRAHEDRON LETTERS   47 ( 17 )   2893 - 2897   2006.4

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  • Two new alkaloidal taxoids from the needles of Taxus canadensis

    QW Shi, XT Si, YM Zhao, XH Su, Li, X, LO Zamir, T Yamada, H Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   70 ( 3 )   732 - 736   2006.3

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    DOI: 10.1271/bbb.70.732

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  • Four new epoxy taxanes from needles of Taxus cuspidata (Taxaceae)

    QW Shi, CM Cao, JS Gu, H Kiyota

    NATURAL PRODUCT RESEARCH   20 ( 2 )   173 - 179   2006.2

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    DOI: 10.1080/14786410500049426

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  • Synthesis of naturally derived bioactive compounds of agricultural interest

    H Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   70 ( 2 )   317 - 324   2006.2

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    DOI: 10.1271/bbb.70.317

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  • 1-deoxypaclitaxel and abeo-taxoids from the seeds of Taxus mairei

    QW Shi, YM Zhao, XT Si, ZP Li, T Yamada, H Kiyota

    JOURNAL OF NATURAL PRODUCTS   69 ( 2 )   280 - 283   2006.2

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    DOI: 10.1021/np0503451

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  • Isolation and structure revision of 10-deacetyltaxinine from the seeds of the Chinese yew, Taxus mairei

    QW Shi, ZP Li, D Zhao, JS Gu, H Kiyota

    NATURAL PRODUCT RESEARCH   20 ( 1 )   47 - 51   2006.1

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    DOI: 10.1080/14786410500111184

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  • A new abeotaxane diterpenoid from the seeds of Taxus mairei

    ML Zhang, LG Li, CM Cao, ZP Li, QW Shi, H Kiyota

    CHINESE CHEMICAL LETTERS   17 ( 1 )   27 - 30   2006.1

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  • Effects of Highly Volatile Organochlorine Solvents on Soil Respiration and Microbial Biomass

    Hiromasa Kiyota,* Shinjiro Kanazawa, Akihito Yokoyama, Hidenori Wada

    International Journal of Soil Science   1 ( 3 )   235 - 242   2006

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  • Synthesis and odor description of both enantiomers of methyl 4,5-didehydrojasmonate, a component of jasmin absolute

    Yuko Asamitsu, Yoko Nakamura, Minoru Ueda, Shigefumi Kuwahara, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   3 ( 6 )   654 - 659   2006

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    DOI: 10.1002/cbdv.200690068

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  • Syntheses and odor descriptions of cyclopropanated compounds part 6. Analogs of aliphatic monoterpene dienols and non-branched alcohols

    Hiroyuki Sakauchi, Hiroki Asao, Tsutomu Hasaba, Shigefumi Kuwahara, Hiromasa Kiyota

    Chemistry and Biodiversity   3 ( 5 )   544 - 552   2006

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    DOI: 10.1002/cbdv.200690058

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  • Two new taxanes from the needles and branches bark of Taxus cuspidata

    Cong-Mei Cao, Man-Li Zhang, Yu-Fang Wang, Qing-Wen Shi, Teiko Yamada, Hiromasa Kiyota

    CHEMISTRY & BIODIVERSITY   3 ( 10 )   1153 - 1161   2006

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    DOI: 10.1002/cbdv.200690117

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  • Chemical constituents of the plants in the genus Achillea

    Xiao-Tang Si, Man-Li Zhang, Qing-Wen Shi, Hiromasa Kiyota

    Chemistry and Biodiversity   3 ( 11 )   1163 - 1180   2006

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    DOI: 10.1002/cbdv.200690119

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  • Chemical constituents of plants from the genus Inula

    YM Zhao, ML Zhang, OW Shi, H Kiyota

    CHEMISTRY & BIODIVERSITY   3 ( 4 )   371 - 384   2006

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    DOI: 10.1002/cbdv.200690041

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  • Facile synthesis of (S)-gizzerosine - A potent inducer of gizzard erosion in chicks - Using successive zinc-mediated and palladium-catalyzed coupling reactions

    Y Shimasaki, H Kiyota, M Sato, SN Kuwahara

    SYNTHESIS-STUTTGART   2005 ( 19 )   3191 - 3192   2005.12

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    DOI: 10.1055/s-2005.918447

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  • Synthesis to determine the absolute configuration of (-)-pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

    Y Nakamura, H Kiyota, R Ueda, S Kuwahara

    TETRAHEDRON LETTERS   46 ( 42 )   7107 - 7109   2005.10

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    DOI: 10.1016/j.tetlet.2005.08.099

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  • A novel 3,8-seco-taxane metabolite from the seeds of the Chinese yew, Taxus mairei

    QW Shi, LG Li, ZP Li, CM Cao, H Kiyota

    TETRAHEDRON LETTERS   46 ( 37 )   6301 - 6303   2005.9

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    DOI: 10.1016/j.tetlet.2005.07.040

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  • Intramolecular migration of long chain acyl group of Enacyloxin IIa methyl ester

    Y Sugiyama, H Kiyota, T Watanabe, T Oritani

    NATURAL PRODUCT RESEARCH   19 ( 6 )   581 - 584   2005.9

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    DOI: 10.1080/14786410412331271997

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  • Structure elucidation and complete NMR spectral assignments of a new taxane glycoside from the needles of Taxus cuspidata - Note

    LG Li, CM Cao, CH Huo, ML Zhang, QW Shi, H Kiyota

    MAGNETIC RESONANCE IN CHEMISTRY   43 ( 6 )   475 - 478   2005.6

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    DOI: 10.1002/mrc.1579

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  • First synthesis of (+)-pteroenone: A defensive metabolite of the abducted antarctic pteropod Clione antarctica Reviewed

    Yoko Nakamura, Hiromasa Kiyota, Bill J. Baker, Shigefumi Kuwahara

    Synlett   ( 4 )   635 - 636   2005.3

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    DOI: 10.1055/s-2005-862389

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  • Synthesis of southern (C1 '-C11 ') fragment of pamamycin-635A

    A Miura, H Kiyota, S Kuwahara

    TETRAHEDRON   61 ( 5 )   1061 - 1067   2005.1

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    DOI: 10.1016/j.tet.2004.11.067

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  • New natural taxane diterpenoids from Taxus species since 1999

    QW Shi, H Kiyota

    CHEMISTRY & BIODIVERSITY   2 ( 12 )   1597 - 1623   2005

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    DOI: 10.1002/cbdv.200590131

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  • First example of 11,12-epoxytaxane-glucoside from the needles of taxus cuspidata

    CL Wang, ML Zhang, CM Cao, QW Shi, H Kiyota

    HETEROCYCLIC COMMUNICATIONS   11 ( 3-4 )   211 - 214   2005

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  • Enzymatic resolution and odor description of both enantiomers of lavandulol, a fragrance of lavender oil

    H Sakauchi, H Kiyota, S Takigawa, T Oritani, S Kuwahara

    CHEMISTRY & BIODIVERSITY   2 ( 9 )   1183 - 1186   2005

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    DOI: 10.1002/cbdv.200590088

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  • Facile synthesis of (-)-tabtoxinine-beta-lactam and its (3 ' R)-isomer

    H Kiyota, T Takai, M Saitoh, O Nakayama, T Oritani, S Kuwahara

    TETRAHEDRON LETTERS   45 ( 44 )   8191 - 8194   2004.10

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    DOI: 10.1016/j.tetlet.2004.09.033

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  • Induction of differentiation of human myeloid leukemia cells by jasmonates, plant hormones

    Y Ishii, H Kiyota, S Sakai, Y Honma

    LEUKEMIA   18 ( 8 )   1413 - 1419   2004.8

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    DOI: 10.1038/sj.leu.2403421

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  • New 2(3 -&gt; 20)Abeotaxane and 3,11-cyclotaxane from needles of Taxus cuspidata

    QW Shi, ZP Li, D Zhao, JS Gu, T Oritani, H Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   68 ( 7 )   1584 - 1587   2004.7

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    DOI: 10.1271/bbb.68.1584

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  • Syntheses and odor descriptions of cyclopropanated compounds Part 5 Analogs of methyl jasmonate to fix the relative configuration of the two side chains

    H Kiyota, S Takigawa, S Kuwahara

    HELVETICA CHIMICA ACTA   87 ( 7 )   1854 - 1859   2004

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    DOI: 10.1002/hlca.200490164

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  • 88(P-12) Synthesis of Non-Selective Phytotoxin, Tabtoxinine-β-Lactam

    Kiyota Hiromasa, Takai Takafumi, Saitoh Masatoshi, Nakayama Osamu, Oritani Takayuki, Kuwahara Shigefumi

    Symposium on the Chemistry of Natural Products, symposium papers   ( 45 )   521 - 526   2003.9

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    Tobacco wildfire disease, caused by infection of tobacco wildfire disease fungus Pseudomonas tabaci, has been the most serious pest for tobacco, and tabtoxin (1) was isolated from the fungus as a phytopathogenic toxin. 1 is converted by host plant peptidases to tabtoxinine-β-lactam (2), which inactivates glutamine synthetase irreversibly. 1 can be a selective pesticide when crops resistant to 1 are developed. We began the synthetic studies of 2 to supply samples to its biological tests and to develop an efficient synthetic route. Zinc mediated coupling of iodide 4b with ester 6 and silyl ether 9 gave 10b and 13b, respectively. Sharpless asymmetric dihydroxylation of the double bonds of each compound afforded 19b (20-30%de) and 21b (81-91%de), respectively. The primary hydroxy group of the diol 19b was converted to amino group, and magnesium mediated β-lactam formation and deprotection gave 2. However, the diastereomeric selectivity of the dihydroxylation of 19b had not improved. So, we tried the conversion of 21b. Oxidation of the primary hydroxy group of 21b gave acid 32b. The corresponding benzyloxy amide 33b was converted to mesylate 35b. The key β-lactam formation using NaH afforded 36b. The last deprotection steps are now in progress.

    DOI: 10.24496/tennenyuki.45.0_521

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  • Biosynthesis and metabolism of abscisic acid and related compounds

    T Oritani, H Kiyota

    NATURAL PRODUCT REPORTS   20 ( 4 )   414 - 425   2003.8

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    DOI: 10.1039/b109859b

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  • Synthesis and biological evaluation of 4-deacetoxy-1,7-dideoxy azetidine paclitaxel analogues

    Q Cheng, H Kiyota, M Yamaguchi, T Horiguchi, T Oritani

    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS   13 ( 6 )   1075 - 1077   2003.3

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    DOI: 10.1016/S0960-894X(03)00054-4

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  • Syntheses and odour descriptions of cyclopropanated compounds: 4. Modification of aliphatic dienols

    H Kiyota, T Takai, S Kuwahara

    FLAVOUR AND FRAGRANCE JOURNAL   18 ( 2 )   100 - 105   2003.3

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    DOI: 10.1002/ffj.1171

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  • First synthesis of (+/-)-pyricuol, a plant pathogen isolated from rice blast disease fungus Magnaporthe grisea

    H Kiyota, R Ueda, T Oritani, S Kuwahara

    SYNLETT   2003 ( 2 )   219 - 220   2003.2

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  • Synthesis and antitumor activity of 2-(m-substituted-benzoyl)baccatin III analogs from taxinine

    T Horiguchi, T Oritani, H Kiyota

    TETRAHEDRON   59 ( 9 )   1529 - 1538   2003.2

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    DOI: 10.1016/S0040-4020(03)00048-6

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  • 6 Synthesis, Structure Revision and Absolute Configuration of (+)-Didemniserinolipid B, a Serinol Marine Natural Product from a Tunicate Didemnum sp.

    Kiyota Hiromasa, Dixon Darren J., Luscombe Christine K., Hettstedt Stephen, Ley Steven. V.

    Symposium on the Chemistry of Natural Products, symposium papers   ( 44 )   31 - 36   2002.9

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    Synthesis of two possible diastereomers of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., were studied. The known butanediacetal (BDA) protected aldehyde 2 was converted to the core coupling component 8. The serinol fragments (S)-13 and (R)-13 were prepared from D-serine and L-serine, respectively. Wittig-Horner reaction of 8 and (S)-13 gave (4"S)-14, which was converted to ester (4"S)-18. Finally, removal of all the protecting group was achieved in acidic EtOH to afford (30S)-1. Similarly, (30R)-1 was synthesized from (R)-13. However, the ^1H and ^<13>C NMR spectra of the synthetic 1 were different from those of natural 1. In view of the fact that related natural products were sulfated on the serinol unit we therefore believed the 31 position of the natural 1 should be sulfated. Based on this assumption, we investigated further derivatization of the synthetic compounds. We studied sulfation of N-Fmoc derivative (30R)-19, however, with the usual reagents and conditions resulted in only recovery of the starting material. Finally we developed new microwave-assisted sulfation conditions which gave the desired monosulfate, followed by the Fmoc deprotection affording 31-monosulfate (30R)-20. As the ^1H and ^<13>C NMR data and the value of the specific optical rotation of (30R)-20 coincided with those of the natural product, we concluded that the real structure of (+)-didemniserinolipid B corresponded to a 31-sulfate and the absolute configuration was 8R,9R,10R,13S,30S. The microwave-assisted sulfation developed in this process are effective for unreactive hydroxyl groups.

    DOI: 10.24496/tennenyuki.44.0_31

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  • Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.

    H Kiyota, DJ Dixon, CK Luscombe, S Hettstedt, SV Ley

    ORGANIC LETTERS   4 ( 19 )   3223 - 3226   2002.9

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  • Syntheses and odour descriptions of cyclopropanated compounds 2. Analogues of methyl jasmonate

    H Kiyota, T Koike, E Higashi, T Oritani

    FLAVOUR AND FRAGRANCE JOURNAL   17 ( 4 )   267 - 271   2002.7

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    DOI: 10.1002/ffj.1094

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  • A new drimane from the heartwood of the Japanese yew, Taxus cuspidata

    H Kiyota, QW Shi, T Oritani

    NATURAL PRODUCT LETTERS   16 ( 1 )   21 - 24   2002.2

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    DOI: 10.1080/1057563029001/4791

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  • Syntheses and odour descriptions of cyclopropanated compounds 3.1 Analogues of leaf alcohol, its esters and leaf acetal Reviewed

    Hiromasa Kiyota, Emi Higashi, Takafumi Takai, Takayuki Oritani, Shigefumi Kuwahara

    Flavour and Fragrance Journal   17 ( 3 )   227 - 231   2002

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    DOI: 10.1002/ffj.1092

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  • Synthesis of southern (C1 '-C11 ') and eastern (C8-C18) fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger

    H Kiyota, Y Furuya, S Kuwahara, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   65 ( 12 )   2630 - 2637   2001.12

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    DOI: 10.1271/bbb.65.2630

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  • Stereochemistry of enacyloxins. Part 3. (12 ' S,17 ' R,18 ' S,19 ' R)-absolute configuration of enacyloxins, a series of antibiotics from Frateuria sp W-315

    R Takeuchi, H Kiyota, M Yaosaka, T Watanabe, K Enari, T Sugiyama, T Oritani

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   2001 ( 20 )   2676 - 2681   2001.10

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    DOI: 10.1039/b104341m

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  • 88(P-45) Synthetic Studies of Pamamycin-607

    FURUYA Yukito, KIYOTA Hiromasa, KUWAHARA Shigefumi

    Symposium on the Chemistry of Natural Products, symposium papers   ( 43 )   521 - 526   2001.9

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    Pamamycins are a series of antibiotic macrodiolides isolated from various Streptomyces species. Among them, pamamycin-607 (1) exhibited aerial mycelium-inducing activity for an aerial mycelium-negative mutant strain and showed antibiotic activity against Gram positive bacteria and fungi. Several synthetic studies including the northern and the southern fragment have been reported to date. In our preliminary communication, we reported the synthesis of the southern fragment (2). In addition, we have also achieved the synthesis of the eastern fragment. Herein we describe the synthetic pathways of these two fragments including experimental details. Synthesis of the southern C1'-C11' and eastern C8-C18 fragments of pamamycin-607, an aerial mycelium-inducing substance of Streptomyces alboniger, was achieved. The southern fragment was synthesized by using Evans aldol reaction and cis-selective iodoetherification as the key steps in 9.6% overall yield (7 steps). The eastern fragment was also constructed via Julia coupling reaction and cis-selective iodoetherification in 3.0% overall yield (8 steps from the known epoxide).

    DOI: 10.24496/tennenyuki.43.0_521

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  • Synthesis of macrotetrolide alpha, a designed polynactin analog composed of (+)- and (-)-bishomononactic acids

    T Hanadate, H Kiyota, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   65 ( 9 )   2118 - 2120   2001.9

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  • Synthesis of (-)-methyl shikimate via enzymatic resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one

    T Oritani, R Ueda, H Kiyota

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   65 ( 9 )   2106 - 2109   2001.9

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    DOI: 10.1271/bbb.65.2106

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  • Syntheses and odour descriptions of jasmine lactone and cis-jasmone analogues bearing cyclopropane moieties

    H Kiyota, E Higashi, T Koike, T Oritani

    FLAVOUR AND FRAGRANCE JOURNAL   16 ( 3 )   175 - 179   2001.5

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    DOI: 10.1002/ffj.974

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  • Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

    H Kiyota, E Higashi, T Koike, T Oritani

    TETRAHEDRON-ASYMMETRY   12 ( 7 )   1035 - 1038   2001.5

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    DOI: 10.1016/S0957-4166(01)00169-0

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  • New 11(15 -&gt; 1)abeotaxane, 11(15 -&gt; 1),11(10 -&gt; 9) bisabeotaxane and 3,11-cyclotaxanes from Taxus yunnanensis

    H Kiyota, QW Shi, T Oritani, LG Li

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   65 ( 1 )   35 - 40   2001.1

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    DOI: 10.1271/bbb.65.35

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  • Synthesis of actiketal, a unique benzofuran type glutarimide antibiotic isolated from Streptomyces pulveraceus subsp epiderstagenes

    H Kiyota, Y Shimizu, T Oritani

    JOURNAL OF PESTICIDE SCIENCE   26 ( 1 )   93 - 95   2001

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    DOI: 10.1584/jpestics.26.93

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  • (+/-)-Methyl 11-fluorojasmonate as a designed antimetabolite of methyl jasmonate: Synthesis and plant growth regulatory activity

    H Kiyota, T Koike, E Higashi, Y Satoh, T Oritani

    JOURNAL OF PESTICIDE SCIENCE   26 ( 1 )   96 - 99   2001

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    DOI: 10.1584/jpestics.26.96

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  • Stereochemistry of enacyloxins 1. Absolute configuration of the cyclohexane ring part of enacyloxins, a series of antibiotics from Frateuria sp W-315

    T Fujimori, O Nakayama, H Kiyota, Y Kamijima, T Watanabe, T Oritani

    HETEROCYCLIC COMMUNICATIONS   7 ( 4 )   327 - 330   2001

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  • Stereochemistry of enacyloxins 2. Structure elucidation of decarbamoyl enacyloxin IIa and IVa, new members of enacyloxin antibiotics from Frateuria sp W-315

    T Watanabe, H Kiyota, R Takeuchi, K Enari, T Oritani

    HETEROCYCLIC COMMUNICATIONS   7 ( 4 )   313 - 316   2001

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  • Synthesis of (-)-ent-altholactone, (+)-7a-epi-altholactone, (-)-ent-isoaltholactone and (-)-7a-epi-Isoaltholactone from 2,3-O-cyclohexylidene-D-glyceraldehyde

    A Hiratate, H Kiyota, T Oritani

    JOURNAL OF PESTICIDE SCIENCE   26 ( 4 )   361 - 365   2001

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    DOI: 10.1584/jpestics.26.361

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  • Synthesis of both enantiomers of altholactone, isoaltholactone and 5-hydroxygoniothalamin from tri-O-acetyl-D-glucal, and their biological activities

    A Hiratate, H Kiyota, T Noshita, R Takeuchi, T Oritani

    JOURNAL OF PESTICIDE SCIENCE   26 ( 4 )   366 - 370   2001

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    DOI: 10.1584/jpestics.26.366

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  • Three new taxoids from the leaves of the Japanese yew, Taxus cuspidata

    QW Shi, T Oritani, H Kiyota, R Murakami

    NATURAL PRODUCT LETTERS   15 ( 1 )   55 - 62   2001

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  • 125(P-66) Conversion of Taxinine to Taxol analogs : Chemical reactivity of Taxinine derivatives

    Horiguchi Tohru, Kiyota Hiromasa, Cheng Qian, Oritani Takayuki

    Symposium on the Chemistry of Natural Products, symposium papers   ( 42 )   745 - 750   2000.10

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    Currently, diterpenoid paclitaxel (faxol^[○!R] 1) is regarded as a powerful therapeutic drug for cancer chemotherapy. 1 exhibits potent antitumor activity against various cancers that have been ineffectively treated by existing chemotherapeutic drugs, and 1 have been approved by the FDA for the treatment of advanced ovarian cancer and breast cancer. Recent studies have shown that treatment for various types of advanced solid cancers with paclitaxel and docetaxel often insults in the emergence of multi-drug resistance (MDR). Thus, it is important to explore new taxoids either with improved activity against various classes of tumors, especially against drug-resistant human cancers. Here we report the methods to convert taxinine, abundantly available from the Japanese yew leaves, to a new 2-m-azido-1,7-deoxybaccatin III analog,which would be an active substrate for the tublin depolymerization test as well as 1. We also report that the biomimetic hydroxylation of C-1 position of 2-deacetoxy-taxinine J derivative (2d) had been successfully achieved by a simple chemical oxidation using dimethyl-dioxirane (DMDO), leading to the 1β-hydroxy-4α, 20-epoxide (26) and its 4β-isomer (27). This method could not be applied for 2-acetoxy-taxoids. In addition, it was found that the change of reaction temperature could control the regioselectivity of the epoxidation between the endo- and exo-double bonds of 2-deacetoxytaxinine J (2d) with m-CPBA. Attempts of biomimetic construction of the D-ring of taxol from the 4 β, 20-epoxy-5-mesyl taxoids (17) with Lewis acid mediated reaction were unsuccessful. While the same condition could convert 22-bromo-4 β, 5β-epoxy taxoid (20) to 4, 22-spirotaxoids (21) as a sole product. These result suggest that the nucleophilic trap of carbocation (III) at 5-position by water would be prior to that at 4-position, that is, it is difficult to demonstrate the proposed biosynthetic pathway of D-ring by a synthetic method.

    DOI: 10.24496/tennenyuki.42.0_745

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  • Synthesis and antifungal activity of the four stereoisomers of streptimidone, a glutarimide antibiotic from Streptomyces rimosus forma paromomycinus

    H Kondo, T Oritani, H Kiyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2000 ( 20 )   3459 - 3462   2000.10

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    DOI: 10.1002/1099-0690(200010)2000:20<3459::AID-EJOC3459>3.0.CO;2-F

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  • Synthesis of both enantiomers of cis-alpha-irone and cis-gamma-irone, principal constituents of iris oil, via resolution of (+/-)-2,2,4-trimethyl-3-cyclohexene-1-carboxylic acid

    T Inoue, H Kiyota, T Oritani

    TETRAHEDRON-ASYMMETRY   11 ( 18 )   3807 - 3818   2000.9

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    DOI: 10.1016/S0957-4166(00)00345-1

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  • Effect of fertilizer and manure application on L-glutaminase and L-asparaginase activities in soils

    S Kanazawa, H Kiyota

    SOIL SCIENCE AND PLANT NUTRITION   46 ( 3 )   741 - 744   2000.9

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  • Synthesis of (+/-)-methyl bishomononactate, a monomeric component of polynactin antibiotics

    T Hanadate, H Kiyota, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   64 ( 8 )   1671 - 1674   2000.8

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    DOI: 10.1271/bbb.64.1671

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  • Taxane diterpenoids from Taxus yunnanensis and Taxus cuspidata

    QW Shi, T Oritani, H Kiyota, D Zhao

    PHYTOCHEMISTRY   54 ( 8 )   829 - 834   2000.8

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    DOI: 10.1016/S0031-9422(00)00186-2

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  • Synthesis of actiketal, a glutarimide antibiotic

    H Kiyota, Y Shimizu, T Oritani

    TETRAHEDRON LETTERS   41 ( 31 )   5887 - 5890   2000.7

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    DOI: 10.1016/S0040-4039(00)00928-X

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  • Enzymatic resolution of (+/-)-epoxy-beta-cyclogeraniol, a synthetic precursor for abscisic acid analogs

    R Okazaki, H Kiyota, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   64 ( 7 )   1444 - 1447   2000.7

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    DOI: 10.1271/bbb.64.1444

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  • Synthesis of the spiroacetal parts of spirofungin A and B

    Y Shimizu, H Kiyota, T Oritani

    TETRAHEDRON LETTERS   41 ( 17 )   3141 - 3144   2000.4

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    DOI: 10.1016/S0040-4039(00)00371-3

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  • Synthesis and antimicrobial activity of unnatural (-)-antimycin A(3) and its analog

    H Kondo, T Oritani, H Kiyota

    HETEROCYCLIC COMMUNICATIONS   6 ( 3 )   211 - 214   2000

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  • Synthesis of the southern part of pamamycin-607, an aerial mycelium-inducing substance of streptomyces alboniger

    Y Furuya, H Kiyota, T Oritani

    HETEROCYCLIC COMMUNICATIONS   6 ( 5 )   427 - 430   2000

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  • Synthesis of (+/-)-methyl tuberonate, a potato tuber-forming substance, and its epimer

    H Kiyota, D Nakashima, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   63 ( 12 )   2110 - 2117   1999.12

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    DOI: 10.1271/bbb.63.2110

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  • Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

    H Kiyota, M Nakabayashi, T Oritani

    TETRAHEDRON-ASYMMETRY   10 ( 19 )   3811 - 3817   1999.9

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    DOI: 10.1016/S0957-4166(99)00391-2

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  • Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

    H Akao, H Kiyota, T Nakajima, T Kitahara

    TETRAHEDRON   55 ( 25 )   7757 - 7770   1999.6

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    DOI: 10.1016/S0040-4020(99)00407-X

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  • Three new rearranged taxane diterpenoids from the bark of Taxus chinensis var. mairei and the needles of Taxus cuspidata

    QW Shi, T Oritani, T Sugiyama, H Kiyota, T Horiguchi

    HETEROCYCLES   51 ( 4 )   841 - 850   1999.4

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  • New taxane diterpenoids isolated from yew trees

    SHI Q. W.

    Natural Product Research and Development   11 ( 6 )   62 - 78   1999

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  • Two new taxanes from Taxus chinensis var. Mairei

    QW Shi, T Oritani, T Sugiyama, H Kiyota

    PLANTA MEDICA   64 ( 8 )   766 - 769   1998.12

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  • Three novel bicyclic 3,8-secotaxane diterpenoids from the needles of the Chinese yew, Taxus chinensis var. mairei

    QW Shi, T Oritani, T Sugiyama, H Kiyota

    JOURNAL OF NATURAL PRODUCTS   61 ( 11 )   1437 - 1440   1998.11

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    DOI: 10.1021/np980213q

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  • Isolation and structure elucidation of a new 11 (15 -&gt; 1)-abeotaxane from the Chinese yew, Taxus mairei

    QW Shi, T Oritani, H Kiyota, T Horiguchi

    NATURAL PRODUCT LETTERS   12 ( 1 )   67 - 74   1998

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    DOI: 10.1080/10575639808048873

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  • 14 beta-hydroxytaxusin, a new taxane from Taxus mairei

    QW Shi, T Oritani, H Kiyota

    NATURAL PRODUCT LETTERS   12 ( 2 )   85 - 90   1998

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    DOI: 10.1080/10575639808048274

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  • Synthesis and biological activities of methyl 3,7- and 4,5-didehydrojasmonates

    H Kiyota, Y Yoneta, T Oritani

    PHYTOCHEMISTRY   46 ( 6 )   983 - 986   1997.11

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    DOI: 10.1016/S0031-9422(97)00374-9

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  • Synthesis of (+)-homononactic acid via iodoetherification

    H Kiyota, M Abe, Y Ono, T Oritani

    SYNLETT   1997 ( 9 )   1093 - 1095   1997.9

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  • Stereochemistry of a unique tricarbocyclic compound prepared by superacid-catalyzed cyclization

    H Tanimoto, H Kiyota, T Oritani, K Matsumoto

    SYNLETT   1997 ( 1 )   121 - &   1997.1

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  • Synthesis of (+/-)-homononactic acid by using cis-selective iodoetherification

    M Abe, H Kiyota, M Adachi, T Oritani

    SYNLETT   1996 ( 8 )   777 - &   1996.8

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    DOI: 10.1055/s-1996-5536

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  • Synthesis and potato tuber-inducing activity of methyl 5',5',5'-trifluorojasmonate

    H Kiyota, M Saitoh, T Oritani, T Yoshihara

    PHYTOCHEMISTRY   42 ( 5 )   1259 - 1262   1996.7

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    DOI: 10.1016/0031-9422(96)00145-8

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  • 2-fluoro and 2-methoxycarbonyl epoxy-beta-ionylideneacetic acids as abscisic acid analogs

    H Kiyota, T Masuda, J Chiba, T Oritani

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   60 ( 7 )   1076 - 1080   1996.7

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    DOI: 10.1271/bbb.60.1076

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  • ESTIMATION OF L-GLUTAMINASE AND L-ASPARAGINASE ACTIVITIES IN SOILS BY THE INDOPHENOL METHOD

    S KANAZAWA, H KIYOTA

    SOIL SCIENCE AND PLANT NUTRITION   41 ( 2 )   305 - 311   1995.6

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    DOI: 10.1080/00380768.1995.10419587

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  • PHEROMONE SYNTHESIS .165. A NEW SYNTHESIS OF (3S,7R,8E,10E)-3,7,9-TRIMETHYL-8,10-DODECADIEN-6-ONE, THE MAJOR COMPONENT OF THE SEX-PHEROMONE OF THE MARITIME PINE SCALE

    K MORI, T FURUUCHI, H KIYOTA

    LIEBIGS ANNALEN DER CHEMIE   1994 ( 10 )   971 - 974   1994.10

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    DOI: 10.1002/jlac.199419941003

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  • FACILE PREPARATION OF CONJUGATED DIENES FROM ALLYLIC ALCOHOLS

    T KITAHARA, T MATSUOKA, H KIYOTA, Y WARITA, H KURATA, A HORIGUCHI, K MORI

    SYNTHESIS-STUTTGART   1994 ( 7 )   692 - 694   1994.7

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  • SYNTHESIS OF (2S,4R,5S)-2,4,6-TRIMETHYL-5-HEPTANOLIDE, A SEX-PHEROMONE COMPONENT FOR MACROCENTRUS-GRANDII

    H KIYOTA, K MORI

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   58 ( 6 )   1120 - 1122   1994.6

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    DOI: 10.1271/bbb.58.1120

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  • Synthesis of the Enantiomers of syn-4-Methyl-5-nonanol to Determine the Absolute Configuration of the Naturally Occurring (4S,5S) Isomer Isolated as the Male-Produced Pheromone Compound of Rhynchophorus vulneratus and Metamasius hemipterus Reviewed

    Kenji Mori, Hiromasa Kiyota, Christian Malosse, Didier Rochat

    Liebigs Annalen der Chemie   1993   1201 - 1204   1993.10

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  • Synthesis of the Stereoisomers of 3-Methyl-4-octanol to Determine the Absolute Configuration of the Naturally Occurring (3S.4S)-Isomer Isolated as the Male-Produced Aggregation Pheromone of the African Palm Weevil, Rhynchophorus phoenicis Reviewed

    Kenji Mori, Hiromasa Kiyota, Didier Rochat

    Liebigs Annalender Chemie   1993   865 - 870   1993.7

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  • A New Synthesis of (3S,4R)-8-Nonene-3,4-diol, the key Intermediate for the Synthesis of (+)-endo-Brevicomin Reviewed

    Kenji Mori, Hiromasa Kiyota

    Liebigs Annalen der Chemie   1992   989 - 992   1992.8

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  • Synthesis of Oxygenated Eremophilanes, Gigantenone, Phomenone and Phaseolinone, Phytotoxins from Pathogenic Fungi Reviewed

    Takeshi Kitahara, Hiromasa Kiyota, Hitoshi Kurata, Kenji Mori

    Tetrahedron   47 ( 9 )   1649 - 1654   1991.3

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  • 創農薬の事例 : 分子設計を中心に = Case studies of pesticide development : focusing on molecular design

    清田, 洋正, 日本農薬学会50周年記念出版編集委員会 (農薬デザイン研究会), 日本農薬学会( Role: Edit)

    日本農薬学会  2025.4  ( ISBN:9784990141721

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    Total pages:iii, 139p   Language:Japanese

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  • Glycobiology/Methods in Molecular Biology

    Christopher J. Vavricka, Nongluk Sriwilaijaroen, Yasuo Suzuki, Hiromasa Kiyota( Role: Joint author ,  Synthesis and Neuraminidase Inhibitory Activity of Sialic Acid Analogs with Fluoro, Phosphono, or Sulfo Functionality)

    SpringerNature  2022  ( ISBN:9781071626351

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  • Glycobiology/Methods in Molecular Biology

    Nongluk Sriwilaijaroen, Christopher J. Vavricka, Hiromasa Kiyota, Yasuo Suzuki( Role: Joint author ,  Influenza A Virus Neuraminidase Inhibitors - Recent Progresses -)

    SpringerNature  2022  ( ISBN:9781071626351

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  • Marine natural products

    Kiyota, H.( Role: Edit)

    Springer  2021  ( ISBN:9789811646362

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  • Marine natural products

    Kiyota, H( Role: Joint author ,  Synthetic Studies of Serinolipids)

    Springer  2021  ( ISBN:9789811646362

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  • 生物有機化学がわかる講義

    清田洋正*( Role: Sole author)

    講談社サイエンティフィク  2010  ( ISBN:9784061501515

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  • Chemical and Pharmacological Research of the Plants from Genus Celastrus

    Xiao-Hui Su, Mei Dong, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*( Role: Joint author)

    Research Signpost  2008  ( ISBN:813080140X

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  • Chemical Constituents in Taxus canadensis

    Mei Dong, Man-Li Zhang, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*( Role: Joint author)

    Research Signpost  2008  ( ISBN:813080140X

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  • Phytochemical Studies of Taxane Diterpenoids from Yew Trees

    Qing-Wen Shi, Hiromasa Kiyota*( Role: Joint author)

    Narosa  2006  ( ISBN:9788173198861

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  • Preface

    Hiromasa Kiyota*( Role: Edit)

    Springer  2006  ( ISBN:9783642070280

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  • Synthesis of Marine Natural Products with Spiro and/or Bicyclic Acetals

    Hiromasa Kiyota*( Role: Edit)

    Springer  2006  ( ISBN:9783642070280

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  • Synthesis of Antibiotics Containing Nitrogen Atoms

    Hiromasa Kiyota*( Role: Edit)

    Springer  2006  ( ISBN:9783642070280

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  • Synthesis and Biological Evaluation of Abscisic Acid, Jasmonic Acid and their Analogs

    Hiromasa Kiyota,* Takayuki Oritani, Shigefumi Kuwahara( Role: Joint author)

    American Chemical Society  2005  ( ISBN:0841239037

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MISC

  • Synthetic studies of phytotoxins of rice blast fungus

    Hiromasa Kiyota

    54 ( 5 )   20 - 29   2025.5

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  • いもち病菌毒素の生物有機化学~合成と生合成研究が解き明かす二次代謝産物の不思議~ Invited

    清田洋正

    化学   79 ( 12 )   72 - 73   2024.12

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  • 農薬デザインのイノベーション Invited

    清田洋正, 山内千明

    日本農薬学会誌   49 ( 1 )   32 - 34   2024.1

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    DOI: 10.1584/jpestics.W24-07

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  • 農薬のニューモダリティー Invited

    清田洋正, 幸堀伸哉

    日本農薬学会誌   48 ( 1 )   72 - 75   2023.2

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    DOI: 10.1584/jpestics.W23-04

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  • 第35回農薬デザイン研究会—新技術が拓く次世代の農薬デザイン—

    浩郷 滝川, 岳 小森

    Japanese Journal of Pesticide Science   47 ( 1 )   27 - 29   2022.2

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    DOI: 10.1584/jpestics.w22-06

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  • 脂質の化学構造が紐解く生理機能の多様性 Invited

    安部真人, 清田洋正

    化学と生物   59 ( 11 )   557 - 557   2021.11

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  • ストリゴラクトン研究の最先端

    林謙一郎, 石崎公庸, 清田洋正

    化学と生物   58 ( 10 )   572 - 572   2020.10

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  • 第37回農薬環境科学研究会「グリーンケミストリー—有機化合物の合成と分解に学ぶSustainability—」

    Japanese Journal of Pesticide Science   45 ( 1 )   36 - 39   2020.2

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    DOI: 10.1584/jpestics.w20-07

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  • 高校教科書ノススメ

    化学と生物   57 ( 7 )   389 - 389   2019.7

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  • 日本の創農薬力強化

    農薬誌   44 ( 1 )   78 - 81   2019.2

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    DOI: 10.1584/jpestics.W19-13

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  • 未来型創農薬〜既成概念からの脱却〜

    農薬誌   43 ( 1 )   73 - 75   2018.2

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    DOI: 10.1584/jpestics.W18-15

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  • 天然物化学と構造活性相関・・・分子設計の今

    日本農薬学会誌   42 ( 1 )   248 - 251   2017

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    DOI: 10.1584/jpestics.W17-42

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  • C315 Identification of a metabolite of endosulfansulfate by Rhodococcus koreensis strain S1 -1 using UPLC-MS

    Kawashima Fujimasa, Kataoka Ryota, Kotake Masaaki, Kiyota Hiromasa, Yamazaki Kenichi, Sakakibara Futa, Okada Sanae, Takagi Kazuhiro

    ( 38 )   150 - 150   2013.3

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  • C316 Phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF

    Yamazaki Kenichi, Takagi Kazuhiro, Kataoka Ryota, Kotake Masaaki, Yamada Teiko, Kiyota Hiromasa

    ( 38 )   151 - 151   2013.3

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  • B208 Synthetic Studies of JBIR-23

    KIYOTA Hiromasa, OKADA Koji, AMI Toshiyuki, SAITO Aki, YAMADA Teiko, KUWAHARA Shigefumi

    ( 38 )   76 - 76   2013.3

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  • C209 Novel metabolic pathway of dieldrin by Pseudonocardia sp. KSF27

    Sakakibara Futa, Kataoka Ryota, Ito Koji, Yamazaki Kenichi, Hatakeyama Takashi, Kawashima Fujimasa, Sato Yuuki, Kiyota Hiromasa, Okada Sanae, Takagi Kazuhiro

    ( 38 )   101 - 101   2013.3

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  • ディルドリン分解糸状菌によるディルドリン残留土壌の浄化法

    生産・流通・加工工程における体系的な危害要因の特性解明とリスク低減技術の開発 技術情報集   50   2013

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  • C307 Synthetic studies of salycylaldehyde-type phytotoxins produced by rice blast fungus

    Sasaki Ayaka, Nagashima Yuta, Tanaka Koji, Nakamura Yoko, kuwahara Shigefumi, Nukina Manabu, Kiyota Hiromasa

    ( 37 )   144 - 144   2012.3

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  • 研究室(有機化学系)の被災状況と対策

    化学と生物   50 ( 1 )   67 - 68   2012

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    DOI: 10.1271/kagakutoseibutsu.50.67

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  • BIT's 2nd Annual World Congress of Catalytic Asymmetric Synthesis-2011

    財団法人農芸化学研究奨励会 事業報告書   H23   19 - 20   2012

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  • A208 Rice Blast Fungus Magnaporthe grisea Produces Phytotoxin Pyriculariol as a Racemate !

    Sasaki Ayaka, Tanaka Koji, Hyodo Takatsugu, Kuwahara Shigefumi, Suzuki Yuji, Nukina Manabu, Kiyota Hiromasa

    ( 36 )   52 - 52   2011.2

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  • 新しい合成:エステル類 開裂

    有機合成化学協会誌   69   2011

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  • 新しい合成:β-アミノエステル類 マンニッヒ反応

    有機合成化学協会誌   69   2011

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  • 植物病原菌毒素(イネいもち病、タバコ野火病)の合成化学的研究

    東北大学研究シーズ集   46   2011

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  • 新しい合成:フェニルアセチレン類 脱炭酸カップリング

    有機合成化学協会誌   69   2011

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  • 2C19 Simplification and enrichment of aldrin -trans- diol degrading bacteria using the charcoal perfusion method

    Sakakibara Futa, Kataoka Ryota, Kiyota Hiromasa, Utimura Tai, Takagi Kazuhiro

    ( 35 )   104 - 104   2010.4

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  • フッ素化学入門<2010> 基礎の応用の最前線

    有機合成化学協会誌   68 ( 10 )   1093 - 1093   2010

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  • 9A02 Exploration of Dieldrin-dechlorinating bacteria using the soil-charcoal perfusion method

    Sakakibara Futa, Kataoka Ryota, Kiyota Hiromasa, Sato Yuki, Utimura Tai, Takagi Kazuhiro

    ( 34 )   76 - 76   2009.2

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  • 9C02 Synthetic studies of ehinopines.

    Tanaka Koji, Shi Qing-Wen, Kuwahara Shigefumi, Kiyota Hiromasa

    ( 34 )   98 - 98   2009.2

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  • 大量合成を指向した有機触媒を用いる不斉触媒反応

    日本農薬学会誌   34 ( 2 )   153 - 153   2009

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  • メタミドホス・マチルパラチオンと安全な農薬

    東北大学大学院農学研究科・農学部 農学部広報   3   1 - 2   2009

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  • 有機化学<有機合成化学と生命現象の解明>

    バイオサイエンスとインダストリー   35 ( 6 )   300 - 301   2007

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  • New Technologies for Lead Generation and Drug Design

    日本農薬学会誌   増刊   2007

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  • 2. New Technologies for Lead Generation and Drug Design(Poster Session Category I) :

    Journal of pesticide science   32   S94 - S97   2007

  • 含フッ素アルキンの化学ーヒドロメタル化反応およびカルボメタル化反応を基盤とした新規有機合成ー

    日本農薬学会誌   31 ( 2 )   232 - 232   2006

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  • 有機化学<天然物と誘導体合成>

    バイオサイエンスとインダストリー   32 ( 6 )   395 - 396   2004

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  • 氷を使って身近になった高圧反応

    化学   58 ( 3 )   59 - 60   2004

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  • 生態相関物質の合成研究-昆虫フェロモンを中心として-

    化学と生物   42 ( 4 )   265 - 272   2004

  • ものつくりという研究

    内藤財団時報   74   51   2004

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  • Synthetic Study of Non-selective Phytopathogenic Toxin Tabtoxinine-β-lactam

    TAKAI Takafumi, KIYOTA Hiromasa, SAITO Masatoshi, NAKAYAMA Osamu, ITO Yoshifumi, ORITANI Takayuki, KUWAHARA Shigefumi

    28   53 - 53   2003.3

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  • 地球環境に優しい農薬事業と啓蒙活動

    日本農薬学会誌   28 ( 4 )   500 - 501   2003

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  • Synthetic studies of natural products for investigation of biological activities and application

    Hiromasa Kiyota

    Nippon Nogeikagaku Kaishi   77 ( 11 )   1086 - 1093   2003

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    Authorship:Lead author   Language:Japanese   Publisher:Japan Society for Bioscience Biotechnology and Agrochemistry  

    DOI: 10.1271/nogeikagaku1924.77.1086

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  • Synthesis of analogs of abscisic acid and jasmonic acid with a cyclopropane ring

    KIYOTA Hiromasa, TAKIGAWA Shin-ya, NAKABAYASHI Miho, ORITANI Takayuki, KUWAHARA Shigefumi

    27   57 - 57   2002.2

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  • Synthetic studies of phytopathogenic toxins to develop novel pesticides

    日本農芸化学会誌   76 ( 8 )   105   2002

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  • Synthetic Study of Polynactin

    HANADATE T., KIYOTA H., ORITANI T.

    26   58 - 58   2001.2

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  • Synthetic Study of Salicylaldehyde-Type Phytotoxins

    KIYOTA H., KOMINE I., NAKAHIGASHI H., MINAMI N., SUGIYAMA T., NUKINA M., SASSA T., ORITANI T.

    26   57 - 57   2001.2

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  • 最近の農薬的天然生理活性物質に関する新展開

    日本農薬学会誌   25 ( 4 )   435 - 437   2001

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  • Synthesis of (-)-ent-Altholactone, (+)-7a-epi-Altholactone, (-)-ent-Isoaltholactone and (-)-7a-epi-Isoaltholactone from 2, 3-O-Cyclohexylidene-D-glyceraldehyde

    HIRATATE Akira, KIYOTA Hiromasa, ORITANI Takayuki

    Journal of pesticide science   26 ( 4 )   361 - 365   2001

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    Synthesis of the diastereomers of (+)-altholactone, an antitumor acetogenin from various Goniothalamus species, was achieved. Four isomers including 3a, 7a-trans-fused analogs were synthesized from 2, 3-O-cyclohexylidene-D-glyceraldehyde via twice separation of diastereomers.

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  • Synthesis of Both Enantiomers of Altholactone, Isoaltholactone and 5-Hydroxygoniothalamin from Tri-O-acetyl-D-glucal, and Their Biological Activities

    HIRATATE Akira, KIYOTA Hiromasa, NOSHITA Toshiro, TAKEUCHI Ryo, ORITANI Takayuki

    Journal of pesticide science   26 ( 4 )   366 - 370   2001

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    Both enantiomers of altholactone, isoaltholactone and 5-hydroxygoniothalamin were synthesized from tri-O-acetyl-D-glucal, and biological activities of altholactones were examined. For brine shrimp, the configuration of 3-hydroxy group at convex site was important for lethal activity, while (2S, 3S)-configuration was inhibitory to lettuce germination.

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    Other Link: http://dl.ndl.go.jp/info:ndljp/pid/10877185

  • Synthesis and plant growth regulatory activity of jasmonic acid analogs

    KIYOTA Hiromasa, KOIKE Takanori, HIGASHI Emi, ORITANI Takayuki

    Chemical Regulation of Plants   35 ( 2 )   222 - 223   2000.12

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  • Synthesis and Plant Growth Regulatory Activity of Jasmonic Acid Analogs

    Kiyota Hiromasa, Koike Takanori, Higashi Emi, Oritani Takayuki

    ( 35 )   25 - 25   2000.11

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    The growth inhibitory activity on rice seedlings of (±)-methyl 11-fluorojasmonate, a designed antimetabolic analog of methyl jasmonate, was 10 times weaker than that of methyl jasmonate. The C-F bond of this analog would be recognized not as C-H bond mimic but as C-OH bond mimic.

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  • Synthetic study of spirofungin A, B.

    SHIMIZU Yuko, KIYOTA Hiromasa, ORITANI Takayuki

    25   33 - 33   2000.3

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  • Synthetic Study of Pamamycin-607

    FURUYA Yukito, KIYOTA Hiromasa, ORITANI Takayuki

    25   35 - 35   2000.3

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  • Synthetic study of non-selective phytotoxin tabtoxinite-β-lactam.

    SAITO Masatoshi, KIYOTA Hiromasa, NAKAYAMA Osamu, SUGIYAMA Takeyoshi, ITO Yoshifumi, ORITANI Takayuki

    25   41 - 41   2000.3

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  • Synthesis of jasmonic acid analogs.

    KOIKE Takanori, KIYOTA Hiromasa, ORITANI Takayuki

    25   44 - 44   2000.3

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  • Synthetic study on Polynactin

    HANADATE Tadaatsu, KIYOTA Hiromasa, ORITANI Takayuki

    25   34 - 34   2000.3

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  • Study on the Stereochemistry of Polyenic Antibiotics Enacyloxin.

    YAOSAKA M., TAKEUCHI R., HUZIMORI T., KIYOTA H., SUGIYAMA T., ORITANI T., WATANABE T.

    25   36 - 36   2000.3

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  • Obligado! Brazil(第22回IUPAC天然物国際会議)

    翠生農学振興会ニュース   12   6   2000

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  • ジャスモン酸関連化合物の合成と生物活性 : 有機化学・天然物化学

    清田 洋正, 米田 靖, 折谷 隆之

    日本農藝化學會誌   70   56 - 56   1996.3

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  • フッ素置換したジャスモン酸メチルの合成と生物活性 : 有機化学・天然物化学

    清田 洋正, 斎藤 真帆, 山田 てい子, 折谷 隆之, 吉原 照彦

    日本農藝化學會誌   69   219 - 219   1995.7

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  • 系内基質再生システムを用いたオリゴ糖のシアロLexの酵素的合成

    化学と工業   47 ( 1 )   54 - 55   1994

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Presentations

  • 農薬創製に資する生物活性天然物に関する合成化学的研究 Invited

    清田洋正*

    日本農薬学会第46回大会(東京)  2021 

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    Event date: 2021.3.8

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    Venue:東京WEB  

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  • サリチルアルデヒド型イネいもち病菌毒素の合成化学的研究 Invited

    清田洋正*

    日本農芸化学会2020年度大会(福岡)  2020 

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    Event date: 2020.3.27

    Language:Japanese  

    Venue:福岡  

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  • サリチルアルデヒド型イネいもち病菌毒素類の合成研究 Invited

    清田洋正*

    東京大学有機化学研究室創立70周年シンポジウム  2023 

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    Event date: 2023.9.16

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    Venue:東京  

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  • 単結晶X線構造解析法を用いた水田土壌細菌によるイミダクロプリド分解物の直接構造決定

    菊池貴*、伊藤虹児、榊原風太、佐藤孝、清田洋正、髙木和宏

    第40回農薬環境科学研究会  2023 

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    Event date: 2023.9.14

    Language:Japanese  

    Venue:愛媛  

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  • Enacyloxin IIa の合成研究

    芦田直樹*、三木由崇、梁晗、泉実、清田洋正

    日本農芸化学会2023年度大会  2023 

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    Event date: 2023.3.15

    Language:Japanese  

    Venue:広島  

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  • Machine learning discovery of specialized enzymes for the biosynthesis of plant alkaloids International conference

    ヴァヴリッカ クリストファー、高橋俊介、渡邉直暉、清田洋正、荒木通啓、近藤昭彦、蓮沼誠久

    日本農薬学会第48回大会(東京)  2023 

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    Event date: 2023.3.10

    Language:Japanese  

    Venue:東京  

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  • Maoecrystal Vの合成研究

    片山峻樹*、石本泰輝、西本光希、浦達哉、清田洋正

    日本農薬学会第48回大会(東京)  2023 

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    Event date: 2023.3.10

    Language:Japanese  

    Venue:東京  

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  • Synthetic studies of the Heterocyclic Moiety of Maoecrystal V

    Shunki Katayama*, Hiromasa Kiyota

    International Symposium on Environmental and Life Science  2023 

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    Event date: 2023.1.24

    Language:Japanese  

    Venue:Okayama  

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  • サリチルアルデヒド型イネいもち病菌毒素類の合成研究

    温皓然*、王子依、平岡諒也、泉実、清田洋正

    日本農芸化学会中四国支部第64回講演会  2023 

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    Event date: 2023.1.21

    Language:Japanese  

    Venue:岡山  

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  • ハーブIsodon eriocalyxから単離されたMaoecrystal VのCDE環モデル合成

    浦達哉*、石本泰輝、西本光希、片山峻樹、井田浩介、泉実、清田洋正

    日本農芸化学会中四国支部第64回講演会  2023 

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    Event date: 2023.1.21

    Language:Japanese  

    Venue:岡山  

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  • 抗生物質Enacyloxin類の合成研究

    三木由崇*、梁晗、芦田直樹、泉実、清田洋正

    日本農芸化学会中四国支部第64回講演会  2023 

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    Event date: 2023.1.21

    Language:Japanese  

    Venue:岡山  

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  • 藍藻Oscillatoria sancta由来のマクロラクトン抗生物質Sanctolide Aのモデル合成研究

    香山健太郎*、岩崎聡美、田中善將、坂口愛、平田智大、長尾実佳、泉実、清田洋正

    日本農芸化学会中四国支部第64回講演会  2023 

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    Event date: 2023.1.21

    Language:Japanese  

    Venue:岡山  

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  • マオエクリスタルVの合成研究

    片山 峻樹*、浦達哉、井田浩介、佐藤勇気、泉実、清田洋正

    日本農芸化学会2021年度大会(仙台)  2021 

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    Event date: 2021.3.20

    Language:Japanese  

    Venue:仙台WEB  

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  • 土壌・木炭還流法を用いた水田土壌からのイミダクロプリド分解菌の集積と分解代 謝物の構造推定

    _木和広*、伊藤虹児、清田洋正

    日本農薬学会第46回大会(東京)  2021 

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    Event date: 2021.3.10

    Language:Japanese  

    Venue:東京WEB  

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  • 海洋環形動物から単離された Thelepamide のオキサゾリジン環の合成研究

    芦田直樹*、井田浩介、泉実、清田洋正

    日本農薬学会第46回大会(東京)  2021 

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    Event date: 2021.3.9

    Language:Japanese  

    Venue:東京WEB  

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  • Synthetic studies of maoecystal V International conference

    Shunki Katayama, Tatsuya Ura, Kousuke Ida, Yuki Sato, Minoru Izumi, Hiromasa Kiyota

    International Symposium on Environmental and Life Science  2021 

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    Event date: 2021.1.25

    Language:English  

    Venue:Okayama  

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  • 中国産ハーブから単離されたマオエクリスタルVのモデルおよび全合成研究

    片山峻樹*、佐藤勇気、浦達哉、井田浩介、泉実、清田洋正

    日本農芸化学会中四国支部第57回講演会  2020 

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    Event date: 2020.9.18

    Language:Japanese  

    Venue:徳島WEB  

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  • イネいもち病菌毒素ピリキュラリオールおよび生合成中間体の合成研究

    王子依*,桑名晶妃、平岡諒也、小野田祐子、泉実、清田洋正

    日本農芸化学会中四国支部第57回講演会  2020 

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    Event date: 2020.9.18

    Language:Japanese  

    Venue:徳島WEB  

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  • 好気的HCB脱塩反応に関与するフラビンレダクターゼHcbA3の生化学的解析

    伊藤虹児*、_木和広、片岡良太、清田洋正

    日本農薬学会第45回大会  2020 

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    Event date: 2020.3.9

    Language:Japanese  

    Venue:大阪  

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  • 海洋環形動物から単離された Thelepamide のオキサゾリジン環モデルの合成研究

    芦田直樹*、井田浩介、泉実、清田洋正

    日本農薬学会第45回大会  2020 

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    Event date: 2020.3.9

    Language:Japanese  

    Venue:大阪  

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  • 抗腫瘍物質 Maoecrystal Vのラクトン環モデルの合成研究

    片山峻樹*、井田浩介、泉実、清田洋正

    日本農薬学会第45回大会  2020 

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    Event date: 2020.3.9

    Language:Japanese  

    Venue:大阪  

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  • 農薬創製に資する生物活性天然物に関する合成化学的研究 Invited

    清田洋正*

    日本農薬学会第45回大会  2020 

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    Event date: 2020.3.8

    Language:Japanese  

    Venue:大阪  

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  • Application of the design, build, test and learn paradigm to the discovery and engineering of specialized aromatic aldehyde synthases

    Christopher J. Vavricka、清田洋正、 荒木通啓、近藤昭彦、蓮沼誠久_

    第37回農薬環境科学研究会(倉敷)  2019 

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    Event date: 2019.11.21

    Language:English  

    Venue:倉敷  

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  • 海洋環形動物Thelepus clispusより単離されたThelepamideのモデル合成研究_

    芦田直樹*、井田浩介、泉実、清田洋正

    第37回農薬環境科学研究会(倉敷)  2019 

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    Event date: 2019.11.21

    Language:Japanese  

    Venue:倉敷  

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  • 抗腫瘍物質 Maoecrystal V の合成研究

    片山峻樹、井田浩介、泉実、清田洋正*

    第37回農薬環境科学研究会(倉敷)  2019 

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    Event date: 2019.11.21

    Language:Japanese  

    Venue:倉敷  

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  • 抗腫瘍物質 Maoecrystal V の合成研究〜6員環ラクトンの構築

    片山峻樹*、井田浩介、泉実、清田洋正

    第34回農薬デザイン研究会(東京)  2019 

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    Event date: 2019.11.8

    Language:Japanese  

    Venue:東京  

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  • Re-design, synthesis, and bio-analysis of sulfosialic acids as covalent inhibitors of neuraminidase

    Christopher J. Vavricka*、松本達磨、荒木通啓、蓮沼誠久、泉実、清田洋正

    第61回天然有機化合物討論会(広島)  2019 

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    Event date: 2019.9.12

    Language:Japanese  

    Venue:広島  

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  • 海洋環形動物から単離された Thelepamide のオキサゾリジン環モデルの合成研究

    芦田直樹*、井田浩介、泉実、清田洋正

    日本農芸化学会中四国支部第54回講演会  2019 

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    Event date: 2019.6.1

    Language:Japanese  

    Venue:岡山  

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  • 抗腫瘍物質 Sanctolide A の 14 員環モデルの合成研究

    岩崎聡美*、田中善將、平田智大、長尾実佳、林 建太、泉 実、清田洋正

    日本農芸化学会中四国支部第54回講演会  2019 

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    Event date: 2019.6.1

    Language:Japanese  

    Venue:岡山  

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  • 抗腫瘍物質 Maoecrystal Vのラクトン環モデルの合成研究

    片山峻樹*、井田浩介、佐藤勇気、泉実、清田洋正

    日本農芸化学会中四国支部第54回講演会  2019 

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    Event date: 2019.6.1

    Language:Japanese  

    Venue:岡山  

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  • 生物活性物質の合成研究 生命現象解明と創薬を目指して Invited

    清田洋正*

    クミアイ化学研究所講演会  2019 

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    Event date: 2019.5.23

    Language:Japanese  

    Venue:磐田  

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  • Pyricularia oryzae における pyriculol 類生合成に関わる NADPH-dependent aldo/keto reductase (PYR7) の研究_

    古山祐貴*、本山高幸、野川俊彦、清田洋正、鎌倉 高志、長田 裕之

    日本農芸化学会2019年度大会(東京)  2019 

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    Event date: 2019.3.27

    Language:Japanese  

    Venue:東京  

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  • 好気的HCB脱塩素分解菌Nocardioides sp. PD653の基質特異性に関する研究

    伊藤虹児*、_木和広、片岡良太、清田洋正、岩崎昭夫

    日本農薬学会第44回大会(名古屋)  2019 

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    Event date: 2019.3.12

    Language:Japanese  

    Venue:名古屋  

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  • NAADPアンタゴニストNed-19が有する植物生長阻害活性

    小出祐実*、小岩美月、清田洋正、泉実

    日本農芸化学会中四国支部第53回講演会  2019 

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    Event date: 2019.1.26

    Language:Japanese  

    Venue:高知  

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  • 食用花に含まれる色素aureusidinの合成と生体内抗酸化作用

    中島清花*、清田洋正、中村俊之、宗正晋太郎、村田芳行、中村宜督

    日本農芸化学会中四国支部第53回講演会  2019 

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    Event date: 2019.1.26

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    Venue:高知  

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  • Aspergillus属真菌型ガラクトマンナンに存在するガラクトフラノース含有糖鎖の化学酵素的合成

    岡本有未*、太田涼、清田洋正、泉実

    2018度日本化学会中国四国支部大会(愛媛)  2018 

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    Event date: 2018.11.17

    Language:Japanese  

    Venue:愛媛  

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  • 化合物ライブラリーの構築を指向した含フッ素天然化合物Nucleocidinの合成研究

    井上千枝李*、造田みな美、松本恵、清田洋正、泉実

    2018度日本化学会中国四国支部大会(愛媛)  2018 

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    Event date: 2018.11.17

    Language:Japanese  

    Venue:愛媛  

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  • グルタルイミド抗生物質2,6-diepi-Streptovitacin Aの合成研究

    川上翔大*、泉実、清田洋正

    第33回農薬デザイン研究会(静岡)  2018 

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    Event date: 2018.11.8

    Language:Japanese  

    Venue:焼津  

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  • イネいもち病菌の生産する植物毒素(±)-Dihydropyriculariolの合成研究

    平岡諒也*、小野田祐子、泉実、清田洋正

    第33回農薬デザイン研究会(静岡)  2018 

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    Event date: 2018.11.8

    Language:Japanese  

    Venue:焼津  

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  • 新規迅速構造解析法ー結晶スポンジ法ーの農薬デザインへの応用の提唱

    足立精宏、横山利彦、清田洋正*

    第33回農薬デザイン研究会(静岡)  2018 

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    Event date: 2018.11.8

    Language:Japanese  

    Venue:焼津  

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  • 植物が生産する金属輸送物質 Nicotianamine のプロセス化学研究

    脇坂暁介*、高石茂宏、清田洋正、泉実

    日本農芸化学会中四国支部第52回講演会(島根)  2018 

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    Event date: 2018.9.21

    Language:Japanese  

    Venue:島根  

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  • シアル酸1位置換誘導体の合成研究

    松本達磨*、武藤千明、森さおり、Chiristopher J. Vavricka、蓮沼誠久、泉実、清田洋正

    日本農芸化学会中四国支部第52回講演会(島根)  2018 

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    Event date: 2018.9.21

    Language:Japanese  

    Venue:島根  

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  • 海洋環形動物から単離されたThelepamideの合成研究

    小出祐実、井田浩介、泉実、清田洋正*

    日本農芸化学会2018年度大会(名古屋)  2018 

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    Event date: 2018.3.17

    Language:Japanese  

    Venue:名古屋  

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  • イネいもち病菌におけるpyriculol類生合成関連aldo/keto reductase遺伝子の機能解析

    古山祐貴*、本山高幸、野川俊彦、清田洋正、鎌倉高志、長田裕之

    日本農芸化学会2018年度大会(名古屋)  2018 

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    Event date: 2018.3.17

    Language:Japanese  

    Venue:名古屋  

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  • 抗腫瘍活性物質Sanctolide Aの合成研究

    清田洋正*、田中善將、平田智大、長尾実佳、泉実

    日本農芸化学会2018年度大会(名古屋)  2018 

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    Event date: 2018.3.17

    Language:Japanese  

    Venue:名古屋  

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  • 抗腫瘍活性物質Sanctolide Aの合成研究

    田中善將*、平田智大、長尾実佳、泉実、清田洋正

    第32回農薬デザイン研究会  2017 

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    Event date: 2017.11.17

    Language:Japanese  

    Venue:東京  

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  • 糖加水分解酵素阻害剤を指向した 2-デオキシ-2-ハロゲン化糖の合成

    井上千枝李*、岡本有未、清田洋正、泉実

    2017年日本化学会中国四国支部大会  2017 

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    Event date: 2017.11.11

    Language:Japanese  

    Venue:鳥取  

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  • 植物が生産する金属輸送物質 Nicotianamine のプロセス化学研究

    高石茂宏*、泉実、清田洋正

    2017年日本化学会中国四国支部大会  2017 

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    Event date: 2017.11.11

    Language:Japanese  

    Venue:鳥取  

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  • NAADP アンタゴニストNed-19のプロセス化学研究と生物活性評価_

    小岩美月、花木瑞穂、小林教代、清田洋正、中島修平、泉実*

    2017年日本化学会中国四国支部大会  2017 

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    Event date: 2017.11.11

    Language:Japanese  

    Venue:鳥取  

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  • 農芸化学のビジョン Invited

    清田洋正*

    日本農芸化学会東北支部若手の会(秋田)  2017 

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    Event date: 2017.11.4

    Language:Japanese  

    Venue:秋田  

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  • 次世代の抗インフルエンザ薬を目指して〜シアリダーゼ阻害剤の設計〜 Invited

    清田洋正*

    日本農芸化学会中四国支部支部第26回若手研究者シンポジウム(東広島)  2017 

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    Event date: 2017.10.7

    Language:Japanese  

    Venue:東広島  

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  • 糖加水分解阻害剤を志向した2-デオキシ-2-ハロゲン化糖の合成

    井上千枝李*、岡本有未、清田洋正、泉実

    日本農芸化学会関西・中四国・西日本支部2017年度合同大阪大会  2017 

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    Event date: 2017.9.22

    Language:Japanese  

    Venue:大阪  

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  • NAADPアンタゴニストNed-19のプロセス化学研究とその生物活性評価

    小岩美月*、佐藤瑞穂、小林教代、清田洋正、中島修平、泉実

    日本農芸化学会関西・中四国・西日本支部2017年度合同大阪大会  2017 

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    Event date: 2017.9.22

    Language:Japanese  

    Venue:大阪  

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  • 農芸化学の将来展望 Invited

    清田洋正*

    日本農芸化学会Visonary農芸化学100シンポジウム  2017 

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    Event date: 2017.9.9

    Language:Japanese  

    Venue:名古屋  

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  • 次世代型抗インフルエンザ薬を指向したシアリダーゼ阻害剤の設計 Invited

    清田洋正*

    日本農芸化学会中部支部第179回例会(伊那)  2017 

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    Event date: 2017.6.24

    Language:Japanese  

    Venue:伊那  

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  • 抗生物質エナシロキシン類の合成研究

    清田洋正*、五十嵐渉、齋藤亜紀、古川博之、星川浩輝、桑原重文、泉実

    第111回有機合成シンポジウム(岡山)  2017 

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    Event date: 2017.6.8 - 2017.6.9

    Language:Japanese  

    Venue:岡山  

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  • スルホシアル酸の創製:シアリダーゼ阻害剤開発の次世代型戦略

    Christopher J. Vavricka、武藤千明、泉実、清田洋正*

    日本農芸化学会2017年度大会(京都)  2017 

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    Event date: 2017.3.19

    Language:Japanese  

    Venue:京都  

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  • 農芸化学VISIONARY100〜天然物化学領域 Invited

    清田洋正*

    日本農芸化学会2017年度大会(京都)  2017 

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    Event date: 2017.3.17

    Language:Japanese  

    Venue:京都  

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  • 抗インフルエンザ薬を指向したシアリダーゼ阻害剤の設計 Invited

    清田洋正*

    日本化学会中国四国支部 岡山地区化学講演会  2016 

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    Event date: 2016.12.10

    Language:Japanese  

    Venue:岡山  

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  • Sulfo-sialic acids: synthesis and sialidase inhibitory activity

    Christopher J. Vavricka, Chiaki Muto*, Minoru Izumi, Hiromasa Kiyota

    第44回構造活性相関シンポジウム&第31回農薬デザイン研究会(京都)  2016 

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    Event date: 2016.11.16

    Language:Japanese  

    Venue:京都  

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  • 植物キレーターNicotianamineのプロセス化学研究

    高石茂宏*、井上千枝李、清田洋正、泉実

    2016年日本化学会中国四国支部大会(香川)  2016 

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    Event date: 2016.11.5

    Language:Japanese  

    Venue:香川  

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  • 酵素法と化学合成法を用いたガラクトフラノシド誘導体の合成(第二報)

    太田涼*、小岩美月、清田洋正、岡拓二、竹川薫、泉実

    2016年日本化学会中国四国支部大会(香川)  2016 

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    Event date: 2016.11.5

    Language:Japanese  

    Venue:香川  

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  • 植物病原菌毒素の合成研究 Invited

    清田洋正*

    岡山大学 農学部植物研研究交流会  2016 

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    Event date: 2016.11.4

    Language:Japanese  

    Venue:岡山・倉敷  

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  • 生物活性物質の合成研究 全合成と創薬を目指して Invited

    清田洋正*

    住友化学健康・農業関連事業研究所講演会  2016 

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    Event date: 2016.10.7

    Language:Japanese  

    Venue:大阪  

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  • 抗リーシュマニア原虫活性物質ancistrocladinium 類の合成研究

    清田洋正*、齋藤昭人、高井桃子、桑原重文

    日本農芸化学会中四国支部第45回講演会(香川)  2016 

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    Event date: 2016.6.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:香川・木田  

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  • 抗生物質スピロファンジンA、Bの合成研究

    阪内啓之、東栄美、清水由布子、小嶋美紀子、朝光優子、桑原重文、泉実、清田洋正*

    日本農薬学会第41回講演会(島根)  2016 

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    Event date: 2016.3.19

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:島根  

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  • 海洋環形動物から単離されたThelepamideの合成研究 〜oxazolinone環モデルの合成〜

    井田浩介*、泉実、清田洋正

    日本農芸化学会中四国支部第44回講演会(岡山)  2016 

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    Event date: 2016.1.23

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:岡山  

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  • 天然有機化合物の合成:構造の誤りと訂正 〜自らを省みて Invited

    清田洋正*

    関学フォーラム「化学と倫理」  2015 

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    Event date: 2015.11.21

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:三田  

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  • 酵素法と化学合成法を用いたガラクトフラノシド誘導体の合成

    太田涼*、篠塚早紀、竹川薫、岡拓二、清田洋正、泉実

    2015年日本化学会中四国支部大会(岡山)  2015 

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    Event date: 2015.11.15

    Language:Japanese   Presentation type:Poster presentation  

    Venue:岡山  

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  • 植物鉄輸送体ニコチアナミンの合成および蛍光プローブ作製

    高石茂宏*、平田智大、清田洋正、泉実

    2015年日本化学会中四国支部大会(岡山)  2015 

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    Event date: 2015.11.15

    Language:Japanese   Presentation type:Poster presentation  

    Venue:岡山  

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  • 抗腫瘍物質maoecrystal Vの合成研究

    清田洋正*、小竹正晃、佐藤勇気、佐々木郁香、浅尾洋樹、島崎泰治、桑原重文

    2015年日本化学会中四国支部大会(岡山)  2015 

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    Event date: 2015.11.15

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:岡山  

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  • 抗マツノザイセンチュウ薬剤の開発及び新規アッセイ法の探索

    平田智大*、中村健太郎、清田洋正、中島修平、泉実

    第30回農薬デザイン研究会(京都)  2015 

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    Event date: 2015.11.12

    Language:Japanese   Presentation type:Poster presentation  

    Venue:京都  

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  • 有機合成化学が生物学で果たす役割

    清田洋正*

    県立広島大学・生命システム科学特別講義(広島)  2015 

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    Event date: 2015.9.30

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:庄原  

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  • サリチルアルデヒド型イネいもち病菌毒素の合成研究〜o-Formyl-m-hydroxycinnamic Acidの合成

    清田洋正*、齋藤昭人、平松幸之助、操海群、長島優太、田中功二、佐々木郁香、桑原重文

    日本農芸化学会中四国支部第43回講演会(愛媛)  2015 

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    Event date: 2015.9.18

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗生物質エナシロキシン類の合成研究

    清田洋正*、五十嵐渉、齋藤亜紀、古川博之、星川浩輝、桑原重文

    第57回天然有機化合物討論会  2015 

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    Event date: 2015.9.9 - 2015.9.11

    Language:Japanese   Presentation type:Poster presentation  

    Venue:横浜  

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  • Discovery and improvement of covalent influenza neuraminidase inhibitors International conference

    Christopher J. Vavricka,* Chiaki Muto, Minoru Izumi, Hiromasa Kiyota

    250th ACS National Meeting in Boston  2015 

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    Event date: 2015.8.16 - 2015.8.20

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 脂肪酸合成経路阻害物質platensimycinの合成研究

    清田洋正*、佐藤恵里子、桑原重文

    日本農芸化学会中四国支部第42回講演会(鳥取)  2015 

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    Event date: 2015.6.13

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗生物質Enacyloxin類の全合成研究

    清田洋正*、五十嵐渉、齋藤亜紀、古川博之、星川浩輝、山田てい子、桑原重文

    日本農芸化学会2015年度大会(岡山)  2015 

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    Event date: 2015.3.26 - 2015.3.29

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • インフルエンザ・シアリダーゼ阻害剤の開発:二フッ化シアル酸

    清田洋正*、Christopher J. Vavricka、田中皓祐、桑原重文、鈴木康夫、大類洋、George F. Gao

    日本農芸化学会中四国支部第41回講演会  2015 

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    Event date: 2015.3.26 - 2015.3.29

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:下関  

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  • Total Synthesis of Nicotianamine and Non-natural Analogues International conference

    Tomohiro Hirata*, Yuki Kido, Minoru Izumi, Hiromasa Kiyota

    Okayama University Campus Asia Pilot Program  2015 

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    Event date: 2015.2.12

    Language:English   Presentation type:Oral presentation (general)  

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  • におい物質の化学 Invited

    清田洋正*

    日本農芸化学会東北支部平成25年度市民フォーラム(山形大学工学部)  2013 

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    Event date: 2014.11.30

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 二フッ化シアル酸:インフルエンザ・シアリダーゼの機構解明と共有結合阻害剤の開発

    清田洋正*、Christopher J. Vavricka、田中皓祐、Nongluk Sriwilaijaroen、佐藤宏樹、鈴木康夫、桑原重文、須原義智、大類洋、George F. Gao

    第56回天然有機化合物討論会  2014 

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    Event date: 2014.10.14 - 2014.10.16

    Language:Japanese   Presentation type:Poster presentation  

    Venue:高知  

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  • 抗腫瘍物質マオエクリスタルVの合成研究

    清田洋正*、佐藤恵理子、小竹正晃、佐々木郁香、浅尾洋樹、島崎泰治、山田てい子、桑原重文

    日本農芸化学会2014年度大会(川崎)  2014 

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    Event date: 2014.9.26 - 2014.9.27

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗腫瘍物質マオエクリスタルVの合成研究

    清田洋正*、佐藤恵理子、小竹正晃、佐々木郁香、浅尾洋樹、島崎泰治、山田てい子、桑原重文

    日本農芸化学会中四国支部第40回講演会(福山)  2014 

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    Event date: 2014.9.26 - 2014.9.27

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Synthetic Studies of Enacyloxin IIa International conference

    Wataru Igarashi, Aki Saito*, Hiroyuki Furukawa, HIroaki Hoshikawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    Tohoku University Campus Asia Summer School 2013  2014 

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    Event date: 2014.8.25 - 2014.8.26

    Language:English   Presentation type:Poster presentation  

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  • Synthetic Studies of Maoecrystal V International conference

    Hiromasa Kiyota, Eriko Sato*, Masaaki Kotake, Hiroki Asao, Ayaka Sasaki, Masaharu Shimasaki, Shigefumi Kuwahara

    Tohoku University Campus Asia Summer School 2013  2014 

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    Event date: 2014.8.25 - 2014.8.26

    Language:English   Presentation type:Poster presentation  

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  • 抗生物質Enacyloxin IIaの合成研究

    清田洋正*、五十嵐渉、齋藤亜紀、古川博之、星川浩輝、山田てい子、桑原重文

    日本農芸化学会中四国支部第39回講演会(福山)  2014 

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    Event date: 2014.5.31

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 生物活性物質の合成化学的研究〜農芸化学における合成化学の役割〜

    清田洋正*

    日本農芸化学会創立90周年記念第17回中四国支部若手シンポジウム  2014 

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    Event date: 2014.5.16 - 2014.5.17

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 抗生物質Enacyloxin類の合成研究

    清田洋正*

    第4回有機分子構築法夏の勉強会  2014 

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    Event date: 2014.5.10 - 2014.5.11

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 放線菌の生産するDPPHラジカル捕捉物質13T030Aの単離と化学構造

    佐伯奈央子、杉浦舞*、越野広雪、清田洋正、菰田俊一

    日本農芸化学会2014年度大会(川崎)  2014 

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    Event date: 2014.3.27 - 2014.3.30

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 放線菌の生産するDPPHラジカル捕捉物質12T061Aの単離と化学構造

    菰田俊一*、佐伯奈央子、越野広雪、清田洋正

    日本農芸化学会2014年度大会(川崎)  2014 

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    Event date: 2014.3.27 - 2014.3.30

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • ディルドリン微生物分解産物の合成化学的手法を用いた同定

    清田洋正*、小竹正晃、高木和広、山崎健一、榊原風太、伊藤虹児、片岡良太、近藤隆一郎、亀井一郎

    日本農芸化学会2014年度大会(川崎)  2014 

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    Event date: 2014.3.27 - 2014.3.30

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • タミフル代替薬の候補化合物を開発

    清田洋正*

    岡山大学 定例記者発表  2014 

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    Event date: 2014.3.18

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 新規ディルドリン分解菌Rhodanobacter spathipyhlli DRE株によるディルドリン分解代謝物の探索

    伊藤虹児*、榊原風太、畠山誉史、山崎健一、清田洋正、岡田早苗、高木和広

    日本農薬学会第39回大会(京都)  2014 

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    Event date: 2014.3.13 - 2014.3.15

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • LC-Orbitrap MSを用いたディルドリン分解代謝物の探索

    榊原風太*、伊藤虹児、松尾洋輔、清田洋正、中川博之、高木和広

    日本農薬学会第39回大会(京都)  2014 

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    Event date: 2014.3.13 - 2014.3.15

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗生物質エナシロキシン類の合成研究

    清田洋正*、五十嵐渉、齋藤亜紀、古川博之、星川浩輝、八尾坂学、山田てい子、桑原重文

    日本農薬学会第39回大会(京都)  2014 

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    Event date: 2014.3.13 - 2014.3.15

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 生物活性を有する天然低分子有機化合物の合成化学的研究

    清田洋正*

    第21回大阪電気通信大学エレクトロニクス基礎研究所シンポジウム「バイオマテリアルの新展開」  2013 

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    Event date: 2013.12.20

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  • 土壌・木炭還流法を用いた新規ディルドリン分解菌の集積・単離及び同定 -ピルビン酸(C源)濃度がディルドリン分解能に与える影響-

    伊藤虹児*、榊原風太、畠山誉史、山崎健一、清田洋正、岡田早苗、高木和広

    第31回農薬環境科学研究会  2013 

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    Event date: 2013.11.21 - 2013.11.22

    Language:Japanese   Presentation type:Poster presentation  

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  • 抗生物質Enacyloxin IIaの合成研究

    五十嵐渉*、齋藤亜紀、古川博之、山田てい子、桑原重文、清田洋正

    第28回農薬デザイン研究会(京都)  2013 

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    Event date: 2013.11.8

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  • 生物活性物質の合成化学的研究

    清田洋正*

    第138回農芸化学特別セミナー(岡山大学)  2013 

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    Event date: 2013.10.3

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  • Detection of novel transformation products from dieldrin by Pseudonocardia sp. KSF27 using a high-resolution LC-Orbitrap MS International conference

    Futa Sakakibara*,Koji Ito, Y. Matsuo, Kenichi Yamazaki, T. Hatakeyama, Ryota Kataoka, Hiromasa Kiyota, H. Nakagawa, Kazuhiro Takagi,

    The 5th International Conference on Environmental, Industrial and Applied Microbiology - BioMicroWorld2013  2013 

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    Event date: 2013.10.2 - 2013.10.4

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  • Synthetic Studies of Maoecrystal V International conference

    Hiromasa Kiyota,* Masaaki Kotake, Hiroki Asao, Ayaka Sasaki, Masaharu Shimasaki, Shigefumi Kuwahara

    International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan  2013 

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    Event date: 2013.9.28 - 2013.9.30

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  • Synthetic studies of clionamines, autophgy-modulating amino steroids isolated from Cliona celata International conference

    Akiyuki Yoshida*, Yuuki Sato, Konosuke Hiramatsu, Teiko Yamada, Shigefumi Kuwahara, and Hiromasa Kiyota

    International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan  2013 

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    Event date: 2013.9.28 - 2013.9.30

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  • Synthetic studies of enacyloxins (2): C1-C6 and C1'-C15' fragments International conference

    Aki Saito*, Wataru Igarashi, Osamu Nakayama, Hiroyuki Furukawa, Hiroaki Hoshikawa, Teiko Yamada, Shigefumi Kuwahara and Hiromasa Kiyota

    International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan  2013 

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    Event date: 2013.9.28 - 2013.9.30

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  • Synthetic studies of enacyloxins (1): C9'-C23' fragment International conference

    Wataru Igarashi*, Hiroyuki Furukawa, Hiroaki Hoshikawa, Aki Saito, Manabu Yaosaka, Teiko Yamada, Shigefumi Kuwahara and Hiromasa Kiyota

    International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan  2013 

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    Event date: 2013.9.28 - 2013.9.30

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  • Synthetic studies of clionamines, autophagy-modulating amino steroids isolated from Cliona celata International conference

    Akiyuki Yoshida*, Yuuki Sato, Konosuke Hiramatsu, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

    Tohoku University Campus Asia Summer School 2013  2013 

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    Event date: 2013.8.29 - 2013.8.30

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  • 鉄資材を用いたディルドリン分解における分解生成物の解析

    上田祐子*、榊原風太、清田洋正、長島優太、高木和広、本田克久

    第22回環境化学討論会  2013 

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    Event date: 2013.7.31

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  • フッ化シアル酸類の合成とシアリダーゼ阻害活性

    田中皓祐、ノングラック・スリウィライジャロエン、佐藤宏樹、桑原重文、大類洋、須原義智、鈴木康夫、清田洋正

    日本農芸化学会2013年度大会  2013 

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    Event date: 2013.3.26 - 2013.3.30

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  • オートファジー促進物質Clionamine A-Dの合成研究

    吉田晃之*、平松幸之助、佐藤勇気、山田てい子、桑原重文、清田洋正

    日本農芸化学会2013年度大会  2013 

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    Event date: 2013.3.26 - 2013.3.30

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  • 血管新生阻害物質cortistatin A類の合成研究

    柴田要*、佐藤勇気、山田てい子、桑原重文、清田洋正

    日本農芸化学会2013年度大会  2013 

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    Event date: 2013.3.26 - 2013.3.30

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  • 抗腫瘍物質Maoecrystal Vの合成研究

    小竹正晃*、浅尾洋樹、佐々木郁香、島崎泰治、桑原重文、清田洋正

    日本農芸化学会2013年度大会  2013 

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    Event date: 2013.3.26 - 2013.3.30

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  • Rhodococcus属によるエンドスルファンスルフェートの分解と代謝物の同定

    川島藤正*、片岡良太、小竹正晃、清田洋正、山崎健一、榊原風太、岡田早苗、高木和広

    日本農薬学会第38回大会(筑波)  2013 

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    Event date: 2013.3.14 - 2013.3.16

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  • 抗ガン物質JBIR-23の合成研究

    清田洋正*、岡田弘二、阿美利幸、齋藤亜紀、山田てい子、桑原重文

    日本農薬学会第38回大会(筑波)  2013 

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    Event date: 2013.3.14 - 2013.3.16

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  • ディルドリン分解糸状菌Mucor racemosus DDF株によるアルドリントランスジオールのリン酸化

    山崎健一*、高木和広、片岡良太、小竹正晃、山田てい子、清田洋正

    日本農薬学会第38回大会(筑波)  2013 

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    Event date: 2013.3.14 - 2013.3.16

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  • シュードノカルジア属細菌KSF27株によるディルドリンの新規代謝経路

    榊原風太*、片岡良太、伊藤虹児、山崎健一、畠山誉史、川島藤正、佐藤勇気、清田洋正、岡田早苗、高木和広

    日本農薬学会第38回大会(筑波)  2013 

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    Event date: 2013.3.14 - 2013.3.16

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  • 中国産薬用ハーブから単離されたMaoecrystal Vの合成研究

    小竹正晃、佐々木郁香、浅尾洋樹、島崎泰治、桑原重文、清田洋正*

    第27回農薬デザイン研究会(東京)  2012 

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    Event date: 2012.11.8

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  • KSF27株による新規ディルドリン分解代謝物の同定

    榊原風太*、片岡良太、伊藤虹児、山崎健一、畠山誉史、川島藤正、佐藤勇気、清田洋正、岡田早苗、高木和広

    第30回農薬環境科学研究会  2012 

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    Event date: 2012.10.18

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • フッ素化シアル酸誘導体とシアリダーゼ阻害活性

    田中皓祐、ノングラック・スリウィライジャロエン、佐藤宏樹、桑原重文、大類洋、須原義智、鈴木康夫、清田洋正*

    日本農芸化学会東北支部若手の会(第13回・弘前)  2012 

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    Event date: 2012.10.6

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Bioconversion from aldrin trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF International conference

    Kenichi Yamazaki*, Ryota Kataoka, Kazuhiro Takagi, Hiromasa Kiyota, Masaaki Kotake

    The 4th International Conference on Soil Pollution and Remediation (Soilrem 2012)  2012 

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    Event date: 2012.9.23 - 2012.9.26

    Language:English   Presentation type:Poster presentation  

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  • Isolation and charactarization of endosulfansulfate-degrading Rhodococcus koreensis strain S1-1 International conference

    Fujimasa Kawashima*, Ryota Kataoka, Kenichi Yamazaki, Kazuhiro Takagi, Hiromasa Kiyota, Masaaki Kotake

    The 4th International Conference on Soil Pollution and Remediation (Soilrem 2012)  2012 

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    Event date: 2012.9.23 - 2012.9.26

    Language:English   Presentation type:Poster presentation  

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  • Novel metabolic pathways of dieldrin by Pseudonocardia sp. KSF27 International conference

    Futa Sakakibara*, Ryota Kataoka, Kenichi Yamazaki, Hiromasa Kiyota, Kazuhiro Takagi, Masaaki Kotake

    The 4th International Conference on Soil Pollution and Remediation (Soilrem 2012)  2012 

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    Event date: 2012.9.23 - 2012.9.26

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  • 抗腫瘍物質Maoecrystal Vの合成研究

    小竹正晃*、佐々木郁香、浅尾洋樹、島崎泰治、桑原重文、清田洋正*

    第3回山形生命科学セミナー(米沢)  2012 

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    Event date: 2012.9.21

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • β-D-アスパルチルグリシンの生物活性

    高津戸敬祐*、中野俊樹、山口敏康、清田洋正、佐藤実

    平成24年度日本水産学会秋季大会(下関)  2012 

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    Event date: 2012.9.14

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • イネいもち病菌の生産する毒素に関する合成化学的研究

    清田洋正*、佐々木郁香、長島優太、田中功二、平松幸之助、斉藤昭人、桑原重文、貫名学

    第8回化学生態学研究会(函館)  2013 

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    Event date: 2012.6.28

    Language:Japanese   Presentation type:Poster presentation  

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  • 海洋生物(クリオネ・アメフラシ)の防御物質に関する合成化学的研究

    清田洋正*、浅尾洋樹、中村葉子、古屋幸人、桑原重文、高津戸敬祐、中野俊樹、山口俊康、佐藤實

    第8回化学生態学研究会(函館)  2013 

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    Event date: 2012.6.28

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  • 環状ジエン殺虫剤(ドリン剤)誘導体の合成

    清田洋正*、小竹正晃、田中皓祐、高木和広

    「POPsの汚染除去技術の開発」プロジェクト研究発表会  2012 

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    Event date: 2012.6.13

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • イネいもち病菌の生産する毒素ピリキュラリオールはラセミ体であった

    清田洋正*、佐々木郁香、長島優太、田中功二、兵藤孝次、貫名学、桑原重文

    日本農芸化学会2012年度大会(京都)  2012 

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    Event date: 2012.3.26

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  • Maoecrystal Vの合成研究

    小竹正晃*、浅尾洋樹、佐々木郁香、島崎泰治、桑原重文、清田洋正

    日本農芸化学会2012年度大会(京都)  2012 

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    Event date: 2012.3.26

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  • イネいもち病菌の生産するサリチルアルデヒド型毒素類の合成研究

    佐々木郁香、長島優太、田中功二、中村葉子、桑原重文、貫名学、清田洋正*

    日本農薬学会第37回大会(岡山)  2012 

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    Event date: 2012.3.15

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 環状ジエン殺虫剤の探索と汚染現場への適用

    高木和広*、片岡良太、清田洋正、長島優太

    「野菜等におけるPOPsのリスク低減技術の開発」成績検討会  2012 

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    Event date: 2012.1.12

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 生体触媒反応を利用した生物活性天然有機化合物の合成研究

    清田洋正*

    第15回生体触媒化学シンポジウム  2011 

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    Event date: 2011.12.21

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 糸状菌による汚染土壌中の環状ジエン殺虫剤の分解除去技術の開発

    高木和広*、片岡良太、清田洋正

    「生産・流通・加工工程における体系的な危害要因の特性解明とリスク低減技術の開発」化学物質チーム研究成果報告会  2011 

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    Event date: 2011.11.7

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗ガン物質cortistatin類のアナログ及びモデル合成研究

    柴田要*、佐藤勇気、桑原重文、清田洋正

    日本農芸化学会東北支部若手の会(第12回・山形)  2011 

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    Event date: 2011.10.8

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • Isolation and identification of a novel dieldrin-degrading Pseudonocardia sp. using a soil-charcoal perfusion method with aldrin trans-diol as a structural analog of dieldrin International conference

    Futa Sakakibara*, Ryota Kataoka, Yuuki Sato, Hiromasa Kiyota, Sanae Okada, Kazuhiro Takagi

    International Symposium on Environmental Biogeochmistry 2011  2011 

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    Event date: 2011.9.27 - 2011.9.30

    Language:English   Presentation type:Poster presentation  

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  • サリチルアルデヒド型イネいもち病菌毒素の合成化学的研究

    清田洋正*、佐々木郁香、田中功二、中村葉子、上田留美、鈴木雄二、桑原重文、貫名学

    天然有機化合物討論会(第53回・大阪)  2011 

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    Event date: 2011.9.27 - 2011.9.30

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 血管新生阻害物質cortistatin A類の合成研究

    柴田要*、佐藤勇気、桑原重文、清田洋正

    第3回山形生命科学セミナー(米沢)  2012 

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    Event date: 2011.9.21

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 呉茱萸に含まれるラジカル捕捉成分に関する研究

    江國仁美*、野下俊朗、大内秀一、清田洋正、山田てい子

    日本農芸化学会西日本支部・中四国支部合同大会  2011 

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    Event date: 2011.9.16 - 2011.9.17

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗腫瘍物質Maoecrtystal Vの合成研究

    清田洋正*、佐々木郁香、浅尾洋樹、島崎泰治、小竹正晃、桑原重文

    有機合成化学セミナー(第28回)  2011 

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    Event date: 2011.8.31 - 2011.9.2

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  • Asymmetric Total Synthesis of Phytotoxins International conference

    Hiromasa Kiyota*

    BIT's 2nd Annual World Congress of Catalytic Asymmetric Synthesis-2011  2011 

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    Event date: 2011.8.9 - 2011.8.11

    Language:English   Presentation type:Oral presentation (invited, special)  

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  • Brassica rapaにおける高圧誘導生合成

    上野茂昭*、新井祥生、小柳梓、宮崎達雄、鰺坂勝美、林真由美、重松亮、中島裕希、小西徹也、山田てい子、清田洋正、藤井智幸

    日本農芸化学会2011年度大会(京都)  2011 

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    Event date: 2011.3.26 - 2011.3.30

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  • Maoecrystal Vの合成研究

    佐々木郁香*、浅尾洋樹、島崎泰治、桑原重文、清田洋正

    日本農芸化学会2011年度大会(京都)  2011 

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    Event date: 2011.3.26 - 2011.3.30

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  • イネいもち病菌の生産する毒素ピリキュラリオールはラセミ体であった

    佐々木郁香*、田中功二、兵藤孝次、桑原重文、鈴木雄二、貫名学、清田洋正

    日本農薬学会第36回大会(東京)  2011 

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    Event date: 2011.3.16 - 2011.3.18

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  • 環状ジエン殺虫剤及びHCH分解菌の探索と汚染現場への適用

    高木和広*、片岡良太、清田洋正、長島優太

    「野菜等におけるPOPsのリスク低減技術の開発」成績検討会  2011 

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    Event date: 2011.1.11

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  • 環状ジエン殺虫剤(ドリン剤)誘導体の合成

    清田洋正*、長島優太

    「POPsの汚染除去技術の開発」プロジェクト研究発表会  2010 

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    Event date: 2010.12.3

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  • 特異な四環性セスキテルペノイドechinopine類の合成研究

    長島優太*、田中功二、桑原重文、史清文、清田洋正

    日本農薬学会農薬デザイン研究会(25回・磐田)  2010 

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    Event date: 2010.11.5

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  • 植物病原菌毒素の合成研究

    清田洋正*

    第13回先端農学セミナー(仙台)  2010 

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    Event date: 2010.8.27

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 生命現象解明と創薬を指向した生物活性物質の合成化学的研究

    清田洋正*

    第4回バイオセミナー(山形)  2010 

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    Event date: 2010.7.4

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 木炭環流法を用いたアルドリントランスジオール分解菌の純化・集積

    榊原風太*、片岡良太、清田洋正、内村泰、高木和広

    日本農薬学会第35回大会(札幌)  2010 

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    Event date: 2010.5.29

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  • 血管新生阻害物質cortistatin類の合成化学的研究

    佐藤勇気、山田てい子、桑原重文、清田洋正*

    日本農芸化学会2010年度大会(東京)  2010 

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    Event date: 2010.3.26 - 2010.3.29

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 抗生物質enacyloxin類のC9'-C23'部分の合成研究

    五十嵐渉*、星川浩輝、古川博之、八尾坂学、山田てい子、桑原重文、清田洋正*

    日本農芸化学会2010年度大会(東京)  2010 

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    Event date: 2010.3.26 - 2010.3.29

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • サリチルアルデヒド型イネいもち病菌毒素類の全合成研究

    佐々木郁香*、田中功二、中村葉子、上田留美、貫名学、桑原重文、鈴木雄二、清田洋正

    香料・テルペンおよび精油化学に関する討論会(第53回・奈良)  2009 

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    Event date: 2009.11.7

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  • シクロプロパン環を有する香気物質の創製

    清田洋正*、浅尾洋樹、阪内啓之、高井隆文、滝川真弥、東栄美、小池貴徳、枷場努、桑原重文

    香料・テルペンおよび精油化学に関する討論会(第53回・奈良)  2009 

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    Event date: 2009.11.7

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  • 血管新生阻害物質cortistatin類モデル化合物の合成研究

    佐藤勇気*、桑原重文、清田洋正

    日本農芸化学会東北支部大会(144回・岩手)  2009 

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    Event date: 2009.10.31

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  • 新規四環性セスキテルペノイドechinopine類の合成研究

    長島優太*、田中功二、桑原重文、史清文、清田洋正

    日本農芸化学会東北支部大会(144回・岩手)  2009 

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    Event date: 2009.10.31

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  • 医薬・農薬リード開発を指向した海洋及び植物起源生理活性物質の合成とその機能解明に向けた新手法の開発

    清田洋正*、此木敬一

    東北大学農学部オープンキャンパス(仙台)  2009 

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    Event date: 2009.7.28 - 2009.7.29

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  • Ancistrocladinium Aの合成研究

    高井桃子*、桑原重文、清田洋正

    日本農芸化学会2009年度大会(福岡)  2009 

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    Event date: 2009.3.27 - 2009.3.30

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  • 根粒菌の環状グルカンに存在する酸性置換基が共生窒素固定に果たす役割

    川原田泰之、清田洋正、江田志磨、三井久幸*、南澤究

    日本農芸化学会2009年度大会(福岡)  2009 

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    Event date: 2009.3.27 - 2009.3.30

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  • 抗腫瘍活性物質maoecrystal Vの合成研究

    浅尾洋樹、島崎泰治、佐々木郁香、桑原重文、清田洋正*

    日本農芸化学会2009年度大会(福岡)  2009 

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    Event date: 2009.3.27 - 2009.3.30

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  • イネいもち病菌毒素pyriculariol及び生合成関連物質の合成研究

    佐々木郁香*、田中功二、貫名学、桑原重文、清田洋正

    日本農芸化学会2009年度大会(福岡)  2009 

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    Event date: 2009.3.27 - 2009.3.30

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  • 土壌・木炭環流法を用いたディルドリン脱塩素分解細菌の探索

    榊原風太*、片岡良太、清田洋正、佐藤勇気、内村泰、高木和広

    日本農薬学会第34回大会(東京)  2009 

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    Event date: 2009.3.18 - 2009.3.20

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • 新規骨格植物成分echinopine類の合成研究

    田中功二*、史清文、桑原重文、清田洋正

    日本農薬学会第34回大会(東京)  2009 

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    Event date: 2009.3.18 - 2009.3.20

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  • 緑膿菌における新規のスペルミジン、スペルミン代謝経路に関する研究

    東方和也*、清田洋正、船田剛玄、伊藤義文、阿部直樹

    日本ポリアミン研究会 第23回研究発表会  2009 

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    Event date: 2009.1.22

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  • 抗インフルエンザ薬を目指して 〜シアリダーゼ阻害剤の設計〜 Invited

    清田洋正

    熊本大学大学院先端科学研究部特別講演  2022.11.30 

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  • 抗腫瘍物質Maoecrystal Vの複素環部分の合成研究

    片山峻樹, 石本泰輝, 西本光希, 浦達哉, 清田洋正

    第36回農薬デザイン研究会(小田原)  2022.11.11 

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  • 抗インフルエンザ薬を指向したシアル酸の1位置換誘導体の合成研究

    桑名晶妃, 松本達磨, 森さおり, 武藤千明, Chritopher J. Vavricka, 泉実, 清田洋正

    日本農薬学会第47回大会(岡山)  2022.3.8 

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  • グルタルイミド系抗生物質(±)-2,6-diepi -Streptovitacin A の合成研究

    馬場健司, 川上翔大, 泉実, 清田洋正

    日本農薬学会第47回大会(岡山)  2022.3.8 

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  • 抗腫瘍物質 Maoecrystal V の合成研究

    片山峻樹, 西本光希, 浦達哉, 井田浩介, 佐藤勇気, 泉実, 清田洋正

    日本農薬学会第47回大会(岡山)  2022.3.8 

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  • 単結晶 X 線構造解析法を用いた水田土壌細菌によるイミダクロプリド分解代謝物 の直接構造決定

    髙木和広, 菊池貴史, 佐藤孝, 榊原風太, 伊藤虹児, 清田洋正

    日本農薬学会第47回大会(岡山)  2022.3.8 

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  • Enacyloxin IIa の合成研究

    芦田直樹, 三木由崇, 泉実, 清田洋正

    日本農薬学会第47回大会(岡山)  2022.3.8 

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  • Synthetic studies of enacyloxin IIa

    Naoki Ashida, Hiromasa Kiyota

    International Symposium on Environmental and Life Science  2022.1.24 

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  • Design & Synthesis of Next-generation Sialidase Inihibitors Invited

    清田洋正

    東京農業大学 特別講演  2021.11.9 

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    Language:Japanese  

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  • Machine learning-based discovery of aryl acetaldehyde producing enzymes for the biosynthesis of benzylisoquinoline alkaloids

    Christopher J. Vavricka, 高橋俊介, 渡邉直暉, 清田洋正, 荒木通啓, 近藤昭彦, 蓮沼誠久

    第38回農薬環境科学研究会(神戸)  2021.10.28 

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  • 領域紹介:天然物化学 Invited

    清田洋正

    Visionary100農芸化学シンポジウム 天然物化学第2回  2021.1.9 

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  • インフルエンザ・シアリダーゼ阻害剤の開発:二フッ化シアル酸

    日本農芸化学会2015年度大会(岡山)  2015 

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  • におい物質の化学

    日本農芸化学会東北支部平成25年度市民フォーラム(山形大学工学部)  2014 

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  • 二フッ化シアル酸:インフルエンザ・シアリダーゼの機構解明と共有結合阻害剤の開発

    第29回農薬デザイン研究会  2014 

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  • Synthetic Studies of Maoecrystal V

    13th International Coference on the Chemistry of Antibiotics and Other Bioactive Compounds (ICCA-13)  2013 

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  • 海洋生物(クリオネ・アメフラシ)の防御物質に関する合成化学的研究

    第8回化学生態学研究会(函館)  2012 

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  • イネいもち病菌の生産する毒素に関する合成化学的研究

    第8回化学生態学研究会(函館)  2012 

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  • フッ素化シアル酸誘導体とシアリダーゼ阻害活性

    日本農芸化学会東北支部大会(第147回・弘前)  2012 

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  • 血管新生阻害物質cortistatin A類の合成研究

    第3回山形生命科学セミナー(米沢)  2011 

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  • 抗ガン物質cortistatin類のアナログ及びモデル合成研究

    日本農芸化学会東北支部大会(第146回・山形)  2011 

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  • 特異な四環性セスキテルペノイドechinopine類の合成研究

    日本農芸化学会東北支部大会(145回・仙台)  2010 

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Industrial property rights

  • Preparation of sialic acid derivatives, and sialidase inhibitors, antibacterial agents and antiviral agents using them

    Hiromasa Kiyota, Christopher J. Vavricka

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    Application no:特願2016-162979  Date applied:2016.8.23

    Announcement no:特開2018-30801 

    Patent/Registration no:特許6871587 

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  • 光学活性1,2-エポキシ-2,6,6-トリメチルシクロヘキサンメタノールの製造法

    清田洋正, 岡崎亮, 折谷隆之

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    Application no:特願2000-36546 

    Announcement no:特開2001-226363 

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  • Processes for Producing Optically Active 1,2-Epoxy2,6,6-trimethylcyclohexanemethanol

    Hiromasa Kiyota, Ryo Okazaki, Takayuki Oritani

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    Application no:PCT/JP01/00882 

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  • 光学活性4-ヒドロキシ-6-オキサビシクロ[3.2.1]オクト-2-エン-7-オンの製造方法

    清田洋正, 上田留美, 折谷隆之

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    Application no:特願2001-153762 

    Announcement no:特開2002-335992 

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  • (-)-(1S,4R,5R)-4-ヒドロキシ-6-オキサビシクロ[3.2.1]オクト-2-エン-7-オンの製造方法

    清田洋正, 上田留美, 折谷隆之

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    Application no:特願2001-153763 

    Announcement no:特開2002-335990 

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  • シクロプロパン化合物および香料組成物

    清田洋正

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    Application no:特願2001-193752 

    Patent/Registration no:特許3991625 

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  • シクロプロパン化合物および香料組成物

    清田洋正

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    Application no:特願2002-054300 

    Announcement no:特開2003-252812 

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  • シクロプロパン化合物及び香料組成物

    清田洋正

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    Application no:特願2005-301066 

    Announcement no:特開2007-106721 

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  • 光学活性なホモノナクチン酸誘導体およびその製造方法

    清田洋正, 折谷隆之

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    Application no:特願1997-48901 

    Announcement no:特開平10-245381 

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  • 光学活性4-ヒドロキシ-2,6,6-トリメチル-2-シクロヘキセン-1-オンの製造方法

    清田洋正, 中林美穂, 折谷隆之

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    Application no:特願1999-201184 

    Announcement no:特開2001-25395 

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  • 光学活性4-ヒドロキシ-2,6,6-トリメチル-2-シクロヘキセン-1-オンの製造法

    清田洋正, 中林美穂, 折谷隆之

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    Application no:特願1999-201185 

    Announcement no:特開2001-025396 

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  • 光学活性1,2-エポキシ-2,6,6-トリメチルシクロヘキサンメタノールの製造方法

    清田洋正, 岡崎亮, 折谷隆之

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    Application no:特願2000-36545 

    Announcement no:特開2001-224396 

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Awards

  • Society Awards 2020 (on high prospectiveness/prominent achievement)

    2020.3   Pesticide Science Sociery of Japan   Synthetic studies of biologically active natural products contributing to pesticide development

    Hiromasa Kiyota

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  • JSBBA Award for Young Scientists

    2003.3   Japan Society for Bioscience, Biotechnology, and Agrochemistry  

    Hiromasa Kiyota

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  • 2nd Intelligent Cosmos Award

    2003.3  

    Hiromasa Kiyota

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Research Projects

  • Creation of novel plant-microbe hybrid remediation system by a POPs-degrading endophytic bacteria and Cucurbitaceae plant.

    Grant number:18H02319  2018.04 - 2021.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    Takagi Kazuhiro

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    Grant amount:\17290000 ( Direct expense: \13300000 、 Indirect expense:\3990000 )

    We tried the approach from the academic question, “Does it possible for remediation by constructing a plant-microbial complex system?” Cucurbitaceae plants that specifically uptake POPs were used in this study, and we revealed endophytic bacterial community in Cucurbitaceae plants. On the other hand, although we explored DDT and PCP-degrading bacteria from the endophytic bacteria living in Cucurbitaceae plants, unfortunately we could not find any DDT-degrading bacteria. However, we succeeded in identifying PCP-degrading bacteria, and it was clarified that PCP was converted to more hydrophilic unknown metabolite. We identified the unknown metabolite as PCP-phosphate using an advanced single crystal X-ray diffraction measurement. PCP phosphate is a novel metabolite and terminal compound. There have been no reports of POPs degradation by endophytic bacteria to date, and this is the first achievement all over the world.

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  • Development of Sulfo-Sialic Acids into Next-Generation Antimicrobial Agents

    Grant number:18K06577  2018.04 - 2021.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Vavricka Christopher

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    Grant amount:\4420000 ( Direct expense: \3400000 、 Indirect expense:\1020000 )

    Fluorinated sulfonates and phosphonates were designed as inhibitors of sialic acid binding viruses. Three milestones were reached to produce target sialic acid analogues: 1) C-2 fluorine introduction into pyranose analogues, 2) introduction of fluorine and hydroxy groups into C-1 and C-2 positions of open-chain analogues, and 3) substitution of the sialic acid anomeric carboxy with a sulfonamide group.

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  • Synthetic studies of biologically active natural products with unique structures ~ developments of new drug leads

    Grant number:17K07772  2017.04 - 2020.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Kiyota Hiromasa

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    Grant amount:\4810000 ( Direct expense: \3700000 、 Indirect expense:\1110000 )

    Natural organic compounds and derivatives having a unique structure and biological activity have been used as pesticides, medicines, or prototypes thereof. In this study, we succeeded in isolating novel structures of terpenoids with antitumor activity etc. form the Chinese yew, mangrove, and herb. Furthermore, we conducted synthetic studies on the plant component maoecrystal V, the antibiotic enacyloxins, the marine substances telepamide, clionnamines, greensporones, sanctolide A, cortistatin A, etc., and achieved total synthesis or the synthesis of key intermediates. We have also succeeded in synthesizing sulfosialic acids, which are lead candidates for antiinfluenza drugs.

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  • シアリダーゼの共有結合阻害を指向した抗インフルエンザ薬の開発

    Grant number:14F04392  2014.04 - 2017.03

    日本学術振興会  科学研究費助成事業  特別研究員奨励費

    清田 洋正, VAVRICKA CHRISTOPHER, VAVRICKA Christopher

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    Grant amount:\2900000 ( Direct expense: \2900000 )

    インフルエンザウィルスが宿主細胞から放出される段階で働くシアリダーゼの阻害剤は、抗ウィルス薬として有効である。これまでタミフルやリレンザなどが上市されてきたが、耐性ウィルスの出現や副作用などの問題から新規薬剤の開発が望まれている。我々は、2,3-ジフルオロシアル酸がシアリダーゼを不可逆的に阻害することを明らかにした。この結果に基づき、より強固な結合能を求めて、全てのシアリダーゼ活性中心にある三つのアルギニン残基と結合する、アノマー位カルボキシ基の代替を検討した。カルボキシ基の代替としてホスホノ基が有効であるとの知見を参考に、より電子吸引性の大きいスルホ基の導入を試みた。
    シアル酸誘導体のアノマー位をSAc基で置換しO,S-アセタール及びそのグリカールに導いた。各々を Oxoneで酸化してスルホン酸塩に導き、脱保護によりスルホシアル酸類を得た。
    スルホシアル酸類のインフルエンザウィルス (H2N2)、ウェルシュ菌 (Clostridium)、連鎖球菌 (Streptococcus) のシアリダーゼ阻害活性試験を行った。エクアトリアル型スルホシアル酸はN2に対してエクアトリアル型ホスホン酸より40倍強力であり、アキシアル型スルホシアル酸とグルカール型スルホシアル酸も強い活性を示した。エクアトリアル型スルホシアル酸はウェルシュ菌と連鎖球菌にも効果があった。
    スルホ基は、アノマー位官能基として最強の活性を示すというこれら結果は、スルホシアル酸を基盤とする次世代型不可逆的阻害剤の開発に繋がる成果である。

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  • Roles of chromatin and nuclear structure in DNA repair: approaches from actin family proteins

    Grant number:24380183  2012.04 - 2016.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)  Grant-in-Aid for Scientific Research (B)

    Harata Masahiko, OHTA KUNIHIRO, TASHIRO SATOSHI, KIYOTA HIROMASA

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    Grant amount:\18330000 ( Direct expense: \14100000 、 Indirect expense:\4230000 )

    We analyzed the contribution of the SWR chromatin remodeling complex, containing Arp4 and Arp6, and of the INO80 chromatin remodeling complex, containing Arp4, Arp5, and Arp8 to DNA damage repair. We showed that these nuclear actin-related proteins contribute to DNA damage repair through relocation of double strand break sites to nuclear periphery. We also performed screening of peptides which bind to these nuclear actin-related proteins, and got some candidates.

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  • Bioorganic Research on Biologically Active Natural Products towards Development of Agrochemical and Medicinal Lead Compounds

    Grant number:19580120  2007 - 2009

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    KIYOTA Hiromasa

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    Grant amount:\4680000 ( Direct expense: \3600000 、 Indirect expense:\1080000 )

    Bioorganic research on biologically active natural products have been achieved. Total synthesis : analogs of polynactin antibiotics, phytotoxin T-beta-L and pyricuols, marine antifeedant pteroenone, plant hormone jasmonic acids, and gizzerosine. Patial synthesis : antibiotics pamamycis, spirofungins and enacyloxins, and anti-angiogenetic cortistatins. Isolation and structure elucidation : enacyloxins, taxanes, limonoids and echinopines.

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  • Synthetic studies on bioactive natural products directed toward the creation of new insecticides and herbicides.

    Grant number:19380065  2007 - 2009

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    KUWAHARA Shigefumi, KIYOTA Hiromasa

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    Grant amount:\16380000 ( Direct expense: \12600000 、 Indirect expense:\3780000 )

    Total syntheses of natural products possessing such biological properties as insecticidal, herbicidal, and antimicrobial activities have been accomplished. Most of the target molecules were synthesized for the first time and the absolute configuration of some of the natural products were elucidated by this synthetic studies.

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  • SYNTHETIC STUDIES OF NATURAL PRODUCTS TO ELUCIDATE BIOLOGICAL ACTIVITIES AND DEVELOP NEWLY FUNCTIONAL COMPOUNDS

    Grant number:17580092  2005 - 2006

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    KIYOTA Hiromasa

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    Grant amount:\3700000 ( Direct expense: \3700000 )

    ・Total synthesis of macrotetrolide a and β was achieved. β showed immnosuppressive nor cytotoxic activity. Biotransformation of the biosynthetic intemediate analog of a was examined. Synthesis of northern and southern hemispheres of pamamycin 597, and southern hemisphere of 635A was achieved.
    ・13'S,14'R,15'S-Absolute configuration of enacyloxin IVa was elucidated using 2D NMR such as J- resolved HMBC and NOESY methods. Synthesis of the cyclohexane moiety was achieved.
    ・Reassignment of the stereochemistry of spiroacetal cores of spirofungin A and B was done. Formal synthesis of spirofungin was achieve.
    ・Absolute configuration of pyricuol was elucidated by the synthesis of unnatural enantiomer. Presumed biosynthetic intermediated of dechloromonilidiol was synthesized
    ・Total synthesis of tabtoxinine-β-lactam was achieved.
    ・Synthesis of all four diastereomers of pteroenone was achieved.
    ・Absolute configuration of methyl 4,5-didehydrojasmonate was determined by the synthesis of both enantiomers. Odor of the natural enantiomer was superior to the unnatural one. Probe derivative of tuberonic acid was prepared.
    ・Total synthesis of gizzerosine was achieved.

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  • Analysis and biological Activity of Taxane diterpenoids contained in Yew Trees

    Grant number:09556020  1997 - 1999

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    ORITANI Takayuki, ORITANI Takashi, KIYOTA Hiromasa

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    Grant amount:\12400000 ( Direct expense: \12400000 )

    1. Three kinds of yew trees, Japanese yew Taxus cuspidata (needles and seeds) and Chinese yews T. mairei (sees, bark, and needles) and T. yunnanensis (seeds), were investigated, and about 200 compounds including taxoids, flavonoids, ligananes, ecdysteroids, abietanes, 9(10→20)-abeo abietanes, vomifoliol and its derivatives were isolated.
    2. More than 70 new taxoids including almost all the structural types were isolated form above three kinds of yew trees, and their structures were established through spectroscopic methods including 1D and 2D NMR techniques.
    3. 2(3→20)-Abeotaxanes and bicyclic taxoids were rare in the nature. Among more than 300 taxoids only eight 2(3→20)-abeotaxanes and six bicyclic taxoids were reported in the past researching. In this work, besides six known bicyclic taxoids and six out of eight known 2(3→20)-abeotaxanes, nineteen new bicyclic taxoids and ten new 2(3→20)-abeotaxanes were added to these two smaller groups.
    4. Several crucial intermediates were isolated from yew trees for the first time, especially taxoid with 4(5),11-diene and bicyclic taxoid with a 7-en-9-one structural unit (a verticillene skeleton) has never been isolated from Taxus species in the past studies. Accordingly, the isolation of these two kinds of compounds from yew trees may shed light on the biosynthesis of taxane diterpenoids, and also afford new clues for the total synthesis of paclitaxel and related compounds.
    5. It was found that T. cuspidata distributed in Shikoku area contained a relatively high level of taxol in the leaves, and that a bicyclic taxane diterpenoids showed the anticancer activity.

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