論文 - 清田　洋正

Synthesis of the A/D/E-ring Core Compounds of Maoecrystal V†. 国際誌

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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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 査読

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年3月

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：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 " 招待 査読

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年1月

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担当区分：責任著者   記述言語：日本語   掲載種別：研究論文（学術雑誌）  

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Chemical Constituents of Plants from the Genus Carpesium 査読

Hui-Min Yan, Hao-Ran Wen, Yu-Fang Wang, Shao-Jing Li, Zhao-Xin Zhang, Yi-Bing Wu, Man-Li Zhang, Yu-Cheng Gu, Mao-Chang Ji, Hiromasa Kiyota

Current Topics in Phytochemistry   18   1 - 10   2023年1月

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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 査読

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年1月

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Machine learning discovery of missing links that mediate alternative branches to plant alkaloids. 国際誌

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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 査読

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年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：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 査読

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

Chemistry Letters   51 ( 1 )   85 - 87   2022年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：The Chemical Society of Japan  

DOI： 10.1246/cl.210613

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Synthesis of the oxazolidinone fragment of thelepamide 査読

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

Natural Product Research   36 ( 7 )   1686 - 1692   2022年

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Informa UK Limited  

Thelepamide, an unique ketide-amino acid isolated from a marine annelid wormThelepus crispus, has a unique oxazolidinone ring derived from cysteine, glycine and valine. Rareness in nature as well as promising bioactive possibility make the oxazolidinone ring an attractive synthetic target. The hydroxy oxazolidinone fragment of thelepamide was prepared by acid-catalysedN,O-acetal formation between a ketoamide and formaldehyde. Lactone-carbonyl selective isopropyl addition to an oxazilidine-dione under Grignard conditions also forms the target compound.

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 査読

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年

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：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 査読

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年

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担当区分：責任著者   記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：Informa UK Limited  

DOI： 10.1080/14786419.2021.1916016

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Influenza A Virus Neuraminidase Inhibitors 招待 国際誌

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

Methods in Molecular Biology   2556   321 - 353   2022年

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記述言語：英語   掲載種別：論文集(書籍)内論文   出版者・発行元：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 招待 国際誌

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

Methods in Molecular Biology   2556   303 - 320   2022年

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担当区分：責任著者   記述言語：英語   掲載種別：論文集(書籍)内論文   出版者・発行元：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 査読

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年1月

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担当区分：責任著者   掲載種別：研究論文（学術雑誌）   出版者・発行元：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 国際誌

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年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：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年

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担当区分：筆頭著者,　最終著者,　責任著者   掲載種別：論文集(書籍)内論文   出版者・発行元：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年8月

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掲載種別：研究論文（学術雑誌）   出版者・発行元：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 招待

Hiromasa Kiyota

Journal of Pesticide Science   45 ( 3 )   177 - 183   2020年8月

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担当区分：筆頭著者,　最終著者,　責任著者   掲載種別：研究論文（学術雑誌）   出版者・発行元：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年8月

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掲載種別：研究論文（学術雑誌）   出版者・発行元：Pesticide Science Society of Japan  

DOI： 10.1584/jpestics.w20-29

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アノマー位置換による不可逆的シアリダーゼ阻害剤の開発

Christopher J. Vavricka, Tatsuma Matsumoto, Hiromasa Kiyota

Trends in Glycoscience and Glycotechnology   32 ( 185 )   E1 - E5   2020年1月

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担当区分：責任著者   掲載種別：研究論文（学術雑誌）  

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 査読

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

J. Pestic. Sci.   44 ( 3 )   171 - 176   2019年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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 査読 国際誌

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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年2月

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掲載種別：研究論文（学術雑誌）   出版者・発行元：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. 査読 国際誌

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

Carbohydr Res.   473   99 - 103   2019年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年2月

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記述言語：日本語   掲載種別：研究論文（大学，研究機関等紀要）  

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

Food Anal. Methods   12 ( 2 )   331 - 337   2019年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

浅田昌古、酒井貴志、清田洋正

岡山大農学報   107   1 - 3   2018年2月

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記述言語：日本語  

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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 査読

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

Heterocycles   96 ( 12 )   2126 - 2134   2018年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.3987/COM-18-14002

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Synthesis of Halogenated-4-nitrophenyl 2-Deoxy-2-halogenopyranosides via N-Halogenosuccinimide Activated Glucal 査読

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

Nat. Prod. Commun.   13 ( 1 )   85 - 87   2018年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Chemical Constituents and Their Activities from Saussurea Genus

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年10月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

DOI： 10.1515/hc-2017-0069

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

Journal of Natural Products   80 ( 9 )   2547 - 2550   2017年9月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1021/acs.jnatprod.7b00305

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Chemical and Pharmacological Research of 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年8月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

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年8月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/s41598-017-07836-y

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その他リンク： 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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：NATURAL PRODUCTS INC  

TMSCl works as an acid catalyst precursor for selective esterification of L-aspartic and L-glutamic acids in the presence of primary, secondary and tertiary alcohols. Although excess TMSCl was required for the completion of esterification, the resulting alkyl TMS ether could be azeotropically removed by simple evaporation with alcohol.

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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

Dong-Gui Yao, Yu-Fang, Wang, Chang-Hong Huo, Yi-Bing Wu, Man-Li Zhang, Li-Geng Li, Qing-Wen Shi, Hiromasa Kiyota, Xiao-Wei Shi

Food Chemistry   214   328 - 338   2017年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

清田洋正

岡山大農学報   106   33 - 38   2017年

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担当区分：筆頭著者   記述言語：日本語   掲載種別：研究論文（学術雑誌）  

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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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ELSEVIER SCIENCE BV  

Alantolactone (AL), an active sesquiterpene originating from Inula helenium, is a potential anticancer and anti-inflammatory agent. However so far, studies on AL metabolism have not been reported. In the present study, we have investigated for the first time the in vivo and in vitro metabolites of AL using ultra performance liquid chromatography combined with time of flight mass spectrometry (UPLC-TOFMS/MS). A unique on-line information-dependent acquisition (IDA) method multiple mass defect filter (MMDF) combined with dynamic background subtraction (DBS) was applied to trace all of the probable metabolites of AL. Five MMDF templates were set according to the core structure of AL and the general metabolite biotransformation patterns, and other five sulfur-containing dimer filter templates were first established on the basis of structural elucidation of AL metabolites obtained from rat intestinal bacteria biotransformation. As a result, 44 metabolites were characterized: 41 metabolites from rat urine, bile and feces after oral administration of AL, and 13 metabolites from AL biotransformation by rat intestinal bacteria. Particularly, 26 metabolites were identified as novel sulfur-containing products. The results indicated that addition of double bond at A(11,13) and oxidization were the main metabolic reactions of AL. A new metabolism pathway to produce addition products of H2S to AL and further generate a series of sulfur-containing dimers of AL was revealed. This study significantly enriched our knowledge about AL metabolism, which will lead to a better understanding of the safety and efficacy of AL. At the same time, the established methodology can be widely applied for the structural determination of the metabolites of other sesquiterpene containing alpha-methylene-gamma-lactone moiety. (C) 2016 Elsevier B.V. All rights reserved.

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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

Dong-Gui Yao, Yu-Fang, Wang, Chang-Hong Huo, Yi-Bing Wu, Man-Li Zhang, Li-Geng Li, Qing-Wen Shi, Hiromasa Kiyota, Xiao-Wei Shi

Bioscience, Biotechnology, and Biochemistry   80 ( 10 )   1883 - 1886   2016年

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

The Journal of General and Applied Microbiology   62 ( 1 )   1 - 6   2016年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

清田洋正

香料   272 ( 272 )   21 - 28   2016年

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担当区分：筆頭著者   記述言語：日本語   掲載種別：研究論文（大学，研究機関等紀要）   出版者・発行元：日本香料協会  

CiNii Article

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Recearch 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年

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

DOI： 10.2174/1570193X13666160614084004

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Synthesis of the Spiroacetal Fragments of Spifofungins A and B, Antibiotics Isolated from Streptomyces violaceusniger Tü 4113

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

Heterocyclic Communications   21 ( 6 )   337 - 343   2015年12月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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 f?r Narurforshung, B   70 ( 11 )   829 - 835   2015年11月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota*

Natural Product Communications   10 ( 4 )   645 - 648   2015年4月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Hydrolysis of octachlorodipropyl ether photolysis in aqueous solution

Yan-Hong Shi, Min Liao, Hiromasa Kiyota, Ri-Mao Hua, Xiang-Wei Wu, Jun Tang, Hai-Qun Cao

Fresenius Environmental Bulletin   24 ( 8 )   2534 - 2539   2015年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1584/jpestics.D14-061

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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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ELSEVIER SCI LTD  

Dieldrin is one of the most persistent organic pollutants, and its oxidative degradation pathways by aerobic microorganisms to 6,7-trans-dihydroxydihydroaldrin (otherwise known as aldrin-trans-diol) and 9-hydroxydieldrin are well documented. The dieldrin-degrading fungus, Mucor racemosus strain DDF, can decrease dieldrin levels with simultaneous production of a small amount of aldrin-trans-diol. A reduction in the levels of aldrin-trans-diol by strain DDF has also been observed. Based on these results, it has been suggested that strain DDF transforms dieldrin to more polar compounds via aldrin-trans-diol. We have conducted a study to identify the metabolites arising from aldrin-trans-diol. The results showed that strain DDF gave reduced levels of aldrin-trans-diol and also produced unknown metabolites. Ultra performance liquid chromatography-electrospray ionization-mass spectroscopy (UPLC-ESI-MS) analysis indicated the metabolites to be either sulfated- or phosphorylated- derivatives of aldrin-trans-diol, but with the metabolites retaining six chlorine atoms. Therefore, the candidate derivatives were synthesized and the retention times of the natural metabolite and the synthetic phosphate were compared. As a result of a co-injection experiment, the metabolites were determined to be aldrin-trans-diol exo- and endo-phosphates. These results were also supported by high-resolution-fast atom bombardment-mass spectrometry (HR-FAB-MS) of the natural metabolite (Delta = 0.63 ppm). Phosphorylation of aldrin-transdiol is the first reported example of phosphate conjugation in microorganisms. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.ibiod.2014.04.005

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Xylomexicanin 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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tet.2014.04.062

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Synthesis of o-Formyl-m-hydroxycinnamic Acid, the Most Oxidized Salicylaldehyde-type Phytotoxin Isolated from Rice Blast Fungus, Magnaporthe grisea, from 5-(2,2-Dimethyl-4H-1,3-benzdioxin)methanol

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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1515/hc-2014-0053

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Facile Synthesis of the Cyclohexane Fragment of Enacyloxins, a Series of Antibiotics Isolated from Frateruria sp. W-315

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

Bioscience, Biotechnology, and Biochemistry   78 ( 5 )   766 - 769   2014年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1080/09168451.2014.905192

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Structural Modification of Isoalantolactone and Biological Activity Against the Hepatoma Cell Line

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

Heterocyclic Communications   20 ( 2 )   117 - 121   2014年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1515/hc-2013-0220

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Chemical Constituents of Plants from the Genus Neolitsea

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

Heterocyclic Communications   20 ( 2 )   61 - 75   2014年4月

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記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

DOI： 10.1515/hc-2013-0239

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A New Eudesmane Sesquiterpene from Dichrocephala integrifolia 査読

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：NATURAL PRODUCTS INC  

A new sesquiterpene, eudesm-11-ene-4 alpha,7 beta,9 beta-triol, was isolated from the EtOH extract of aerial parts of Dichrocephala integrifolia. Its structure was determined on the basis of spectral analysis of ID and 2D NMR data.

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

Geng-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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1007/s10600-013-0765-z

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Arteminal, a New Eudesmane Sesquiterpenolide Isolated from Artemisia frigida

Cun-Fang Li, Man-Li Zhang, Yu-Fang Wang, Mei Dong, Fran?oise 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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1007/s10600-013-0767-x

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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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER SOC MICROBIOLOGY  

The influenza virus neuraminidase H274Y substitution is a highly prevalent amino acid substitution associated with resistance to the most heavily used influenza drug, oseltamivir. Previous structural studies suggest that the group specific 252 residue ( Y252 in group 1 and T252 in group 2) might be a key factor underlying H274Y resistance. However, H274Y has only been reported in N1 subtypes, which indicates that there must be additional key residues that determine H274Y resistance. Furthermore, we found that members of NA serotype N3 also possess Y252, raising the key question as to whether or not H274Y resistance may also be possible for some group 2 NAs. Here, we demonstrate that the H274Y substitution results in mild oseltamivir resistance for N3. Comparative structural analysis of N3, N1, and their 274Y variants indicates that the interaction of residue 296 ( H in N1 and nonaromatic for other serotypes) with conserved W295 is another important determinant of oseltamivir resistance.

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, Fran?oise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Chemistry of Natural Compounds   49 ( 4 )   632 - 634   2013年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：SPRINGER  

A novel germacrane sesquiterpenolide was isolated from the whole plant of Artemisia frigida. The structure was characterized as 1 alpha,3 alpha-dihydroxy-7 beta,11 alpha H-germacra-4Z,10(14)-dien-12,6 alpha-olide (1) on the basis of spectroscopic methods.

DOI： 10.1007/s10600-013-0694-x

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

YI-BING WU, ZHI-YU NI, CHANG-HONG HUO, JIAN SU, MEI DONG, FRAN?OISE SAURIOL, QING-WEN SHI, YU-CHENG GU, and HIROMASA KIYOTA*

Bioscience, Biotechnology, and Biochemistry   77 ( 4 )   736 - 740   2013年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1271/bbb.120815

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Torreyanoxane, a New 3,4-Seco-glutinane Triterpenoid Isolated from Torreya nucifera

Cong-Mei Cao, Man-Li Zhang, Mei Dong, Fran?oise Sauriol, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*, Bin Cong

Helvetica Chimica Acta   96 ( 3 )   375 - 378   2013年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1038/ncomms2487

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Cytotoxic Flavonoids from the Flowers of Achillea millefolium

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

Chemistry of Natural Compounds   48 ( 6 )   958 - 962   2013年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1007/s10600-013-0438-y

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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年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

A taxane with an amino-side chain on C-5 was identified for the first time from rooted cuttings of the Canadian yew, Taxus canadensis. The structure was characterized as 2α,10β,13α-triacetoxy-5α-[3'-(N-formyl- Nmethylamino)-3'-phenylpropanoyloxy]taxa-4(20),12-dien-9α-ol (1) on the basis of 1D and 2D NMR data and HR-FAB-MS analyses. The spectra revealed that in CDCl3 solution 1 was composed of two rotamers (1a and 1b) in a ratio of approximately 1:1. © 2013 Springer Science+Business Media New York.

DOI： 10.1007/s10600-013-0458-7

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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年11月

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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, Gangquiang Yang, Yasuhiro Ishimaru, Tetsuya Itabashi, Satoru Tamura, Hiromasa Kiyota, Shigefumi Kuwahara, Sho Inomata, Mitsuru Shoji, and Takeshi Sugai

Bioorganic and Medicinal Chemistry   20 ( 19 )   5832 - 5843   2012年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.bmc.2012.08.003

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New 686-Taxanes Isolated from the Heartwood of Taxus cuspidata

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

Helvetica Chimica Acta   95 ( 9 )   1566 - 1572   2012年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VERLAG Z NATURFORSCH  

Eight sesquiterpene lactones were isolated from the roots of Inula helenium and flowers of I. japonica. Among them, isoalantolactone (3) and santamarine (6) exhibited significant growth inhibitory activities against gynecologic cancer cell lines, while others weakly inhibited the growth of the cell lines (IC50 &lt;= 100 mu m). In addition, 3 significantly inhibited the tumour growth of S180 tumour-bearing mice. Compounds 3 and 6 were not toxic to human embryonic lung fibroblast cells in vitro. These results demonstrated that the antitumour activities are closely related to the structures of the compounds, that is, an alpha-exomethylene-gamma-lactone ring is necessary for these activities.

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A Simple, Rapid Method for Gizzerosine Analysis in Fish Meal by Pper Electrophoresis

Zhi-Hua Tao, Minoru Sato, Ke-Gang Wu, Hiromasa Kiyota, Toshiyasu Yamaguchi, Toshiki Nakano

Fisheries Science   78 ( 4 )   923 - 926   2012年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1007/s12562-012-0507-3

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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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Two novel sesquiterpene dimers, achillinin B and C, were isolated from the flowers of Achillea millefolium. The structures were elucidated by extensive spectroscopic analysis. A plausible biosynthetic pathway of achillinin B and C by Diels-Alder reaction of the corresponding guaiane sesquiterpenoids is also discussed. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2012.03.039

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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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VERLAG Z NATURFORSCH  

Ten 1,10-secoguaianolides were isolated from the flowers of Achillea millefolium. Their structures were determined on the basis of spectroscopic methods. Three of them (millifolides A-C) including two dimeric sesquiterpenoids exhibit new skeletons. Seco-tanapartholide A exhibited moderate cell growth inhibitory activity against the human cancer cell line MCF7WT (IC50 = 5.51 mu m) in vitro.

DOI： 10.5560/ZNB.2012-0028

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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, Fran?oise Sauriol, Qing-Wen Shi, Hiromasa Kiyota*, Yu-Cheng Gu, Bin Cong,

Heterocyclic Communications   18 ( 2 )   57 - 60   2012年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1515/hc-2012-0035

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Relationship between Structure and Microtubule Polymerization Activity of Taxane Derivatives

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

Biosci. Biotechnol. Biochem.   76 ( 2 )   349 - 352   2012年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1271/bbb.110797

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Structure-activity relationship of 9-methylstreptimidone that induces selective apoptosis in adult T-cell leukemia cells

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

Oncology Research   20 ( 1 )   7 - 14   2012年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年12月

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-BLACKWELL  

Rice blast fungus, Magnaporthe grisea, produces a series of salicylaldehyde-type phytotoxins such as pyriculol, pyricuol, and pyriculariol. Plausible biosynthetic intermediates of these phytotoxins were synthesized in deuterium labeled forms using the Stille coupling reaction as the key step, and subjected to biotransformation by the fungus. Heptatrienyl-salicylaldehyde was converted into dihydropyriculol by the fungus by a shaking culture. A new biosynthetic pathway comprising both oxidation and reduction is proposed.

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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：GEORG THIEME VERLAG KG  

Both (+)- and (-)-omega-trifluorononactic acid, a designed analogue of nonactic acid, were synthesized. The racemic acid, prepared by using cis-selective iodoetherification, was resolved as the corresponding (S)-O-acetylmandelates. The structure was determined by X-ray crystallographic analysis.

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VERLAG Z NATURFORSCH  

Diabietane ether (1), a new abietane dimer connected by an ether linkage, and two known abietane diterpenoids (2 and 3) were isolated from the needles of Taxus cuspidata.

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P-60 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(ポスター発表の部)

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講演要旨集   ( 53 )   661 - 666   2011年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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

CiNii Article

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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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WALTER DE GRUYTER GMBH  

A mimic of a plausible biosynthetic intermediate of bishomononactic acid, one of the monomers of macrotetrolide antibiotics (polynactin), was synthesized as a thiol ester. FAB-MS analysis showed that fermentation of polynactin producing Streptomyces griseus with the compound, afforded the unnatural polynactins containing bishomononactic acid(s).

DOI： 10.1515/HC.2011.021

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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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2011.07.012

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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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

White rot fungi can degrade a wide spectrum of recalcitrant organic pollutants, including polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated biphenyls (PCBs). In this experiment, 20 white rot fungi, belonging to genus Phlebia, were investigated for their ability to degrade dieldrin. Based on the screening results, we further investigated Phlebia acanthocystis, Phiebia brevispora, and Phlebia aurea to determine their degradation capacity and metabolic products towards dieldrin and aldrin. The three fungi were able to remove over 50% of dieldrin in a low nitrogen medium, after 42 d of incubation. Three hydroxylated products were detected as metabolites of dieldrin, suggesting that in Phlebia strains, hydroxylation reactions might play an important role in the metabolism of dieldrin. In contrast to dieldrin, aldrin exhibited higher levels of degradation activity. Over 90% of aldrin was removed after 28 d of incubation, and several new metabolites of aldrin in microorganisms, including 9-hydroxyaldrin and two carboxylic acid products, were detected in fungal cultures. These results indicate that the methylene moiety of aldrin and dieldrin molecules might be prone to enzymatic attack by white rot fungi. In this study, we describe for the first time a new metabolic pathway of both compounds by fungi of genus Phlebia. (C) 2011 Elsevier Ltd. All rights reserved.

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3 -&gt; 20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7 beta,9 alpha,10 beta-triacetoxy-taxa-4(20),12-diene-2 alpha,5 alpha,11 beta-triol (1) and 2 alpha,7 beta,10 beta-triacetoxy-5 alpha-hydroxy-2 (3 -&gt; 20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.

DOI： 10.1271/bbb.110223

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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, Fran?oise Sauriol, Chang-Hong Huo,Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Biosci. Biotechnol. Biochem.   75 ( 8 )   1554 - 1556   2011年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1271/bbb.110234

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Chemical and Pharmacological Research of the Plants of Genus Caesalpinia

Yan Yanga, Lei Zhaoa, Changhong Huoa, Yucheng Gua, Qingwen Shi, Hiromasa Kiyota*

Chemistry and Biodiversity   8 ( 8 )   1370 - 1399   2011年8月

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.201000176

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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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ACADEMIC PRESS INC ELSEVIER SCIENCE  

We isolated a novel aerobic dieldrin-degrading bacterium from an enrichment culture in a soil-charcoal perfusion system. Enrichment culture using a soil-charcoal perfusion system was an effective way to obtain microorganisms that degrade recalcitrant compounds. The soil-charcoal perfusion was performed using aldrin trans-diol, which was a metabolite of dieldrin. Aldrin trans-diol had higher bioavailability (2.5 mg/l) than dieldrin (0.1-0.25 mg/l), therefore it is possible for microorganisms to utilize it as a substrate in soil. After 100 days of circulation and three exchanges of the medium, the enriched charcoal was harvested and a bacterium isolated. The isolate was designated as strain KSF27 and was found to be closely related to Pseudonocardia spp. as determined by 16S rRNA sequencing analysis. Strain KSF27 degraded aldrin trans-diol by 0.05 mu mol/l from an initial concentration of 25.5 mu mol/l. The metabolite of aldrin trans-diol was detected by HPLC/MS and determined to be aldrindicarboxylic acid based on retention time and the MS fragment. Moreover, strain KSF27 degraded dieldrin from 14.06 mu mol/l to 2.01 mu mol/l over a 10-day incubation at 30 degrees C. This strain degraded dieldrin and other persistent organo-chlorine pesticides, such as alpha-endosulfan, beta-endosulfan, endosulfan sulfate, heptachlor, heptachlor epoxide and chlordecone. (C) 2011 Elsevier Inc. All rights reserved.

DOI： 10.1016/j.bbrc.2011.06.096

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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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VERLAG Z NATURFORSCH  

Sinenxan H [2 alpha,14 beta-diacetoxytaxa-4(20),11-diene-5 alpha, 10 beta-diol, 1] was isolated from the heartwood of Taxus cuspidata, for the first time from natural sources. Compound 1 was found to be readily converted into 2 alpha-acetoxytaxa-4(20),10,12(18),13-tetraen-5 alpha-ol (2), the first example of a taxane with 10,11- and/or 13,14-double bond(s) and a conjugated triene system, in CDCl(3).

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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, Fran?oise Sauriol, Qing-Wen Shi, Hiromasa Kiyota*, Yong-Jian Zhang

Heterocyclic Communications   17 ( 1-2 )   87 - 91   2011年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1515/HC.2011.019

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Stereochemistry of enacyloxins 6. Synthesis of a C16'-C17' fragment of Enacyloxins, A Series of Antibiotics from Frateuria sp. W-315

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

Heterocyclic Communications   17 ( 1-2 )   7 - 9   2011年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WALTER DE GRUYTER & CO  

The C9&apos;-C15&apos; fragment of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, was synthesized from diethyl D-tartrate.

DOI： 10.1515/HC.2011.007

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

Nematological Research   51 ( 2 )   33 - 36   2011年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：GEORG THIEME VERLAG KG  

Three new taxanes, 2 alpha, 9 alpha, 10 beta-triacetoxy-13 alpha-(beta-D-glucopyranosyloxy)taxa-4(20), 11-dien-5 alpha-ol (1), 5 alpha, 10 beta, 13 alpha-triacetoxytax-11-ene-2 alpha,7 beta,9 alpha,20-tetraol (2), and 5 alpha, 10 beta, 13 beta-triacetoxy-2 alpha, 7 beta-dihydroxy-2(3 -&gt; 20)abeotaxa-4(20), 11-dien-9-one (3), were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-BLACKWELL  

Four novel oxepin-containing pyrimidines, namely oxepinamides D-G (1-4), were isolated from cultures of Aspergillus puniceus F02Z-1744. The structures of 1-4 were elucidated by analyzing their spectroscopic data generated by 1D and 2D NMR and MS methods. The configurations of 1 and 2 were established based on single-crystal X-ray crystallographic analysis. All four compounds 1-4 showed transcriptional activation on Liver X Receptor alpha (LXR alpha) with EC(50) values of 10.6, 12.8, 13.6, and 12.1 mu M, respectively.

DOI： 10.1002/ejoc.201000812

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Chemical and Pharmacological Research of the Plants of Genus Senecio

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

Chemistry and Biodiversity   8 ( 1 )   13 - 72   2011年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VERLAG Z NATURFORSCH  

Two new phytoecdysteroids with a 20,22-acetal group were identified for the first time from the needles of the Canadian yew, Taws canadensis. Their structures were characterized as ponasterone A 20,22-p-hydroxybenzylidene acetal (1) and ponasterone A 20,22-acetonide (2) on the basis of 1D, 2D NMR evidence and high-resolution FABMS analysis.

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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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

An aerobic dieldrin-degrading fungus, Mucor racemosus strain DDF, was isolated from a soil to which endosulfan had been annually applied for more than 10 years until 2008 Strain DDF degraded dieldrin to 1 01 mu M from 143 mu M during a 10-day incubation at 25 degrees C Approximately 0 15 mu M (9%) of aldrin transdiol was generated from the dieldrin degradation after a 1-day incubation The degradation of dieldrin by strain DDF was detected over a broad range of pH and concentrations of glucose and nitrogen sources. Extracellular fluid without mycelia also degraded dieldrin Strain DDF degraded not only dieldrin but also heptachlor, heptachlor epoxide, endosulfan, endosulfan sulfate, DDT, and ODE Endosulfan sulfate and heptachlor were degraded by 0.64 mu M (95%) and 0.75 mu M (94%), respectively, whereas endosulfan and DDE were degraded by 2 42 mu M (80%) and 3 29 mu M (79%), respectively, and DDT and heptachlor epoxide were degraded by 695 mu M (49 3%) and 5 36 mu M (67 5%), respectively, compared with the control, which had a concentration of approximately 14 mu M. These results suggest that strain DDF could be a candidate for the bioremediation of sites contaminated with various persistent organochlorine pesticides including POPs

DOI： 10.1021/es1000227

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Chemical Constituents of Plants from Genus Valeriana

Yu-Fang Wang, Li-Qing Jin, Chang-Hong Huo, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Mini-Reviews in Organic Chemistry   7 ( 2 )   161 - 172   2010年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.2174/157019310791065537

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Xylocarponoids A and B, Unique C28 Skeleton Limonoids from Xylocarpus granatum

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

Tetrahedron Letters   51 ( 4 )   754 - 757   2010年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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 査読

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

FEMS Microb. Lett.   302 ( 2 )   131 - 137   2010年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1111/j.1574-6968.2009.01843.x

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

Yu-Fang Wang, Zhi-Yu NI, Mei Dong, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota*

Chemistry and Biodiversity   7 ( 11 )   2623 - 2659   2010年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.20090

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Synthesis of Pteroenone and its Diastereomers, 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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER  

There is increasing demand for novel anti-inflammatory drugs with different mechanisms of action. We synthesized a series of isothiocyanates 2b-h based on 6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) found in the pungent spice Wasabia japonica. Inhibitory activities against in-vitro growth of tumor cells and production of nitric oxide (NO) using the mouse macrophage-like cell line J774.1 were noted. All isothiocyanates were optimized by Hartree-Fock/3-21G model, and the log P values and the polar surface area (PSA) values were calculated. Substitution of the methylsulfinyl group (CH(3)S(=O)-R) in 6-MITC with a formyl (CHO-R), a methylsulfanyl (CH(2)S-R) or a methyl (CH(3)-R) group reduced the activities of the parent isothiocyanate. Substitution with a formyl group resulted in lower lipophilicity (log P value) whereas substitution with a methylsulfanyl or methyl group resulted in a lower PSA value. The inhibitory activity of isothiocyanates showed better correlation with their PSA values rather than their partition coefficient (log P) values. Isothiocyanates with higher PSA values and some degree of log P value may have potent biological activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

DOI： 10.1016/j.ejmech.2009.08.005

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P-17 プロシアニジン,メチル化カテキン類縁体,レスベラトロールの合成研究(ポスター発表の部)

飯島 崇士, 毛利 圭宏, 提箸 正義, 山田 大士, 服部 恭尚, 濱渦 康範, 加茂 綱嗣, 廣田 満, 清田 洋正, 真壁 秀文

天然有機化合物討論会講演要旨集   ( 51 )   289 - 294   2009年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce. (C) 2009 Elsevier Ltd. All rights reserved.

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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：NATURE PUBLISHING GROUP  

Jasmonates are potent lipid regulators in plants that play pivotal roles in their biological activities. Methyl jasmonate (MJ) is very effective at inducing the myelomonocytic differentiation of human myeloid leukemia HL-60 cells. We examined the gene expression profiles associated with exposure to MJ using cDNA microarrays, and compared the results with those obtained with other inducers of differentiation, such as all-trans retinoic acid (ATRA), 1 alpha,25-dihydroxyvitamin D(3) (VD(3)), isopentenyladenine (IPA) and cotylenin A (CN-A). Many genes were upregulated, and only a small fraction was downregulated, upon exposure to the inducers. MJ, IPA and CN-A, but not ATRA or VD3, immediately induced the expression of mRNA for the calcium-binding protein S100P. The gene expression profile induced by MJ resembled that induced by IPA, suggesting that these inducers share many common signal transduction systems for inducing the differentiation of leukemia cells. Methyl 4,5-didehydrojasmonate was about 30 times more potent than MJ and the natural form of the stereoisomer was more effective than the unnatural isomer. It significantly stimulated both the functional and morphological differentiation of leukemia cells that had been freshly isolated from patients with hematological malignancies. Jasmonate derivatives may be promising therapeutic agents for differentiation therapy of leukemia.

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Magnolia species are widely cultivated in Japan as garden plants, and have been found to contain various compounds, including alkaloids, terpenoids, lignans, and neolignans. The constituents of the mature fruits of M. denudata were investigated, and two new phenolic derivatives, named denudalide and denudaquinol, were isolated and characterized, together with a known neolignan compound (denudatin A). Denudalide and denudaquinol showed cytotoxicity against the SFME and r/mHM-SFME-1 cell lines.

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Taxusecone, 2 alpha,7 beta,9 alpha,10 beta-tetraacetoxy-5 alpha,12-dihydroxy-11,12-secotax-4(20)-ene-11,13-dione (1), a novel taxane with an unprecedented skeleton, was isolated from the needles of Taxus cuspidata.

DOI： 10.1271/bbb.80698

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Xylomexicanins A and B, New Δ14,15-Mexicanolides from the Seeds of the Chinese Mangrove Xylocarpus granatum

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

Zeitshrift fuer Naturforschung, C   64 ( 1-2 )   37 - 42   2009年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Two New 11(15→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, Françoise Sauriol, Qing-Wen Shi, Yu-Cheng Gu, Hiromasa Kiyota, Bin Cong

Zeitshrift fuer Naturforschung, C   64 ( 1-2 )   43 - 48   2009年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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The Daphyniphyllum Alkaloids

Xiao-Hui Su, Su-Zhen Gong, Qing-Wen Shi, Hiromasa Kiyota*

Current Organic Chemistry   13 ( 6 )   646 - 682   2009年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.2174/138527209787847345

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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 and Biodiversity   6 ( 2 )   146 - 161   2009年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.200700403

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Synthesis and Anti-inflammatory Activity of (–)-Epicatechin-3-(3-O-methylgallate) and (+)-Catechin-3-(3-O-methylgallate)

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

Chemistry and Biodiversity   6 ( 4 )   520 - 526   2009年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/cbdv.200800224

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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

Zeitshrift fuer Naturforschung, B   63 ( 12 )   1441 - 1442   2008年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Analogs of cortistatins, a series of anti-angiogenic compounds isolated from the Indonesian marine sponge Cortisium simplex, were synthesized from estrone by using the Suzuki-Miyaura coupling reaction as the key step. The estrone-isoquinoline hybridized compound showed selective inhibitory activity against the proliferation and VEGF-induced migration of HUVEC.

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, Fran?oise Sauriol, Qing-Wen Shi, Yu-Cheng, Gu, Hidefumi Makabe, Hiromasa Kiyota*

European Journal of Organic Chemistry   ( 32 )   5414 - 5417   2008年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年10月

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

The L-acid (C1-C18) fragment of pamamycin-593 and de-N-methylpamamycin-579, strong aerial mycelium-inducers of Streptomyces alboniger, was synthesized using a cis-selecfive iodoetherification and a nucleophilic addition of a cerium acetylide to an aldehyde as the key steps. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ELSEVIER SCI LTD  

The periplasmic glucans of Mesorhizobium loti were isolated and separated into fractions according to their acidity. NMR spectroscopy confirmed their backbone structure to be a cyclic beta-(1--&gt;2)-D-glucan as in the case of other rhizobia, and revealed no non-glycosidic substituents in the neutral fraction, and glycerophosphoryl and succinyl residues as major and minor substituents, respectively, in the anionic fractions. MALDI-TOF mass spectrometry showed that the anionic glucans contain one, two, or three such substituents per molecule according to their acidity, and, in contrast, that all the anionic subfractions have a similar size distribution to that of the neutral glucans, where molecules composed of 20-24 glucosyl residues are predominant. These results clarify the periplasmic glucan composition in terms of charge-to-mass ratios in M. loti cells. (C) 2008 Elsevier Ltd. All rights reserved.

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WALTER DE GRUYTER GMBH  

A new taxane with an amino side chain on C-5 and a new 11(15 -&gt; 1)abeotaxane having a tetrahydrofuran ring along carbon atoms C-2, C-3, C-4, C-20 identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 2 alpha,7 beta,9 alpha, 10 beta, 13-pentaacetoxy-11 beta-hydroxy-5a-(2'-hydroxy,3'-N,N-dimethylamino-3'-phenyl)-propionyloxytaxa-4(20), 12-diene (1) and 13 alpha,20 beta-diacetoxy- 5 alpha,7 beta,9 alpha,10 beta-tetrahydroxy-2 alpha,20-epoxy-11(15 -&gt; 1)abeotaxa-11, 15-diene (2) on the basis of 1D, 2D NMR spectroscopy and high-resolution FABMS analysis. Taxane 1 contains a rare C-12, C-13 double bond and a basic side chain, while taxane 2 bears a rare isopropenyl group at C-1.

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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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A taxane with an amino-side chain on C-5 was identified for the first time from rooted cuttings of the Canadian yew, Taxus camadensis. The structure was characterized as 7 beta,9 alpha,10 beta,13 alpha-tetraacetoxy-5 alpha-[3&apos;-(N-formyl-N-methylamino)-3&apos;-phenylpropanoyl]oxytaxa-4(20),12-diene (1) on the basis of 1D-, 2D-NMR data, and HR-FABMS analyses. The spectra revealed that in CDCl(3) solution 1 was composed of two rotamers (1a and 1b) in a ratio of approximately 2:1. (C) 2008 Elsevier Ltd. All rights reserved.

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Echinopines A (1) and B (2), novel sesquiterpenoids with an unprecedented rearranged skeleton named echinopane, were isolated from the roots of Echinops spinosus. The structures were elucidated by extensive spectroscopic analysis. The relative configuration of 1 was assigned by a combination of NOESY correlations and a simulation analysis. A plausible biosynthetic pathway for echinopane was discussed.

DOI： 10.1021/ol702629z

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A Novel Taxane with a Rare 9α,13α-Oxygen Bridge from Taxus cuspidata Needles

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

Tetrahedron Letters   49 ( 7 )   1180 - 1183   2008年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/j.tetlet.2007.12.045

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Total Synthesis of Natural Products of Microbial Origins

Hiromasa Kiyota, Shigefumi Kuwahara

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

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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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年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

DOI： 10.1016/j.bse.2007.03.005

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12 エナンチオ・ディファレンシャル法によるジャスモン酸配糖体型就眠物質受容体タンパク質の生物有機化学(口頭発表の部)

中村 葉子, 宮武 良至, 猪俣 翔, 清田 洋正, 上田 実

天然有機化合物討論会講演要旨集   ( 49 )   67 - 72   2007年8月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：GEORG THIEME VERLAG KG  

Synthesis of (-)-tabtoxinine-p-lactam and its (3R)-isomer, the cause of tobacco wildfire disease, was achieved from Lserine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactainization of beta-mesyloxy benzylhydroxamate amide as the key steps.

DOI： 10.1055/s-2007-983785

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Three New Taxanes with 10-Alkoxy Group from the Heartwood of Taxus cuspidata

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

Bioscience, Biotechnology, and Biochemistry   71 ( 8 )   2087 - 2090   2007年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Two new taxanes were isolated from the needles of Taxus canadensis. Their structures were established as 10 beta,13 alpha-diacetoxytaxa-4(20),11-diene-5 alpha,9 alpha,14 beta-triol (1) and 4 alpha,13 alpha-diacetoxy-2 alpha,20-epoxy-11(15 -&gt; 1)abeotaxa-11,15-diene-5 alpha,7 beta,9 alpha,10 beta-tetraol (2) on the basis of a spectroscopic analysis.

DOI： 10.1271/bbb.70063

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Structural Determination of a New 2(3->20)Abeotaxane with an Unusual13b-Substitution and a New 6/8/6-Ring Taxane from Taxus cuspidata

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

Magnetic Resonance in Chemistry   45 ( 6 )   527 - 530   2007年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/mrc.2001

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Chemical Constituents in the Genus Wedelia and their Bioactivity 査読

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

Chemistry and Biodiversity   4 ( 4 )   823 - 836   2007年4月

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2 alpha,10 beta-diaectoxy-5 alpha,9 alpha,20 alpha-trihydroxy-3 alpha- 11 alpha;4 alpha, 12 alpha;14 alpha,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition. (c) 2007 Elsevier Ltd. All rights reserved.

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Both enantiomers of cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol were synthesized and their odor properties evaluated. Odor characters in enantiomeric pairs were similar in the geraniol series. The (+)-(2R,3S)-nerol derivative showed various odor aspects. From the results of nor-leaf alcohol derivatives, an interaction between the (2-re,3-re)-face of nor-leaf alcohol and the human olfactory receptor was suggested. The odor of (3R)-matsutake alcohol derivative was superior to the enantiomer. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetasy.2007.02.007

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

A new taxoid metabolite with a new substitution pattern was isolated from the methanol extract of the seeds of Taxus mairei, and its structure was established as 5 alpha,15-dihydroxy-7 beta 9 alpha-diacetoxy-11(15 -&gt; 1)abeo-taxa-4(20),11-dien-13-one (1) on the basis of spectral analysis including H-1- and C-13-NMR, HMQC, HMBC, NOESY, and confirmed by HR-FAB mass spectrometry.

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年

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記述言語：英語  

DOI： 10.1002/cbdv.200790070

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Chemical Constituents from Genus Laggera

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

Chemistry and Biodiversity   4 ( 2 )   105 - 111   2007年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.200790014

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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 査読

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

CHEMISTRY & BIODIVERSITY   4 ( 7 )   1601 - 1604   2007年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

The absolute configurations of the enacyloxins, a series of polyhydroxylated polyene antibiotics from Frateuria species, were determined. The so far elusive (13'R,14'R,15'S)-configuration was assigned to enacycloxin IVa (1) by means of 'J-resolved HMBC-1' and NOESY NMR methods.

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：SOC BRASILEIRA QUIMICA  

A new plant ecdysteroid 7,8 beta-dihydroponasterone A, together with ponasterone A, were isolated from the methanol extract of the needles of the Japanese yew, Taxus cuspidata. Their structures were elucidated on the basis of spectroscopic analysis including H-1 NMR, C-13 NMR, H-1-H-1 COSY, NOESY, HMQC and HMBC and confirmed by high-resolution FABMS data.

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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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

(S)-Gizzerosine, a potent inducer of gizzard erosion in chicks, was synthesized using successive zinc-mediated and palladium-catalyzed coupling reactions as the key steps. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2006.07.080

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P-41 マクロテトラオリド抗生物質polynactin類のアナログ創製研究(ポスター発表の部)

高井 健太郎, 花舘 忠篤, 大井 秀一, 桑原 重文, 清田 洋正

天然有機化合物討論会講演要旨集   ( 48 )   361 - 365   2006年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.

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年7月

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記述言語：英語   出版者・発行元：天然有機化合物討論会  

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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Two new taxoid metabolites were isolated from the methanol extract of the Taxus mairei seeds. Their structures were established as 2 alpha-hydroxy-9 alpha,10 beta,13 alpha-triacetoxy-5 alpha-cinnamoyloxytaxa-11-en-4 beta,20-epoxide (1) and 2'-acetyl taxol (2) on the basis of spectral analysis.

DOI： 10.1080/10286020500172848

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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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

We report the synthesis of the novel fluorescence-labeled jasmonate glycoside 2 based on beta-D-glucopyranosyl 12-hydroxy-jasmonate 1, which is a leaf-closing substance of Albizzia Durazz. The fluorescence study using 2 revealed that the target cell for 1 is a motor cell. Probe 2 bound to the motor cells of two plants belonging to genus Albizzia. This result suggested that a receptor for 2, which is common among genus Albizzia would be involved in the nyctinastic leaf movement. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.02.123

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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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

In this letter, we present our results obtained in attempts to synthesize the initially proposed structure of the spiroketal core of spirofungin B. Based on these results, we propose a reassignment for the structures of the spiroketals obtained by Kiyota's group. (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.01.153

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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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Two new taxanes with a dimethylamino group on the C-5 side chain were identified for the first time in the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 7 beta,10 beta,13 alpha-triacetoxy-5 alpha-(3'-dimethylamino-3'-phenylpropanoyl)- oxy-2 alpha-hydroxy-2(3 -&gt; 20)abeotaxa-4(20),11-dien-9-one (1) and 2 alpha,10 beta-diacetoxy-9 alpha-hydroxy-5 alpha-(3'-dimethylamino-3'-phenylpropanoyl)oxy-3,11-cyclotax-4(20)-en- 13-one (2).

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Four new epoxy taxoids were isolated from the needles of Taxus cuspidata. Their structures were established as 2 alpha,9 alpha-diacetoxy-5 alpha-cinnamoyloxy-11,12-epoxy-10 beta-hydroxytax-4(20)-en-13-one (1), 2 alpha,10 beta-diacetoxy-5 alpha-cinnamoyloxy-11,12-epoxy-9 alpha-hydroxytax-4(20)-en-13-one (2), 2 alpha,9 alpha-diacetoxy-11,12-epoxy-10 beta,20-dihydroxytax-4-en-13-one (3) and 2 alpha,10 beta-diacetoxy-11,12-epoxy-9 alpha,20-dihydroxytax-4-en-13-one (4) on the basis of spectral analysis including H-1-NMR, C-13-NMR, H-1-H-1- COSY, HSQC, HMBC and HRFABMS. Compounds 3 and 4 are the first example of 11,12-epoxy taxoids with C-4 double bond found in T. cuspidata.

DOI： 10.1080/14786410500049426

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Synthetic Studies of Naturally Derived Bioactive Compounds of Agricultural Interest

Hiromasa Kiyota*

Bioscience, Biotechnology, and Biochemistry   70 ( 2 )   317 - 324   2006年2月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

A new paclitaxel derivative and two new 2(3 -&gt; 20)-abeo-taxoids were isolated from a methanol extract of the seeds of Taxus mairei, and their structures were established as 1-deoxypaclitaxel (1), 7 beta,10 beta-diacetoxy-2 alpha,5 alpha,13 alpha-trihydroxy2(3-20)-abeo-taxa-4(20),11-dien-9-one (2), and 2 alpha,13 alpha-diacetoxy-10 beta-hydroxy-2(3 -&gt; 20)-abeo-taxa-4(20),6,11-triene-5,9-dione (3) on the basis of spectroscopic data analysis. Taxane I is the first example of a paclitaxel analogue with a C-1 beta hydrogen substituent. Taxane 3 is an 2(3 -&gt; 20)-abeo-taxane with a rare C-5 ketone and C-6 double bond.

DOI： 10.1021/np0503451

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Isolation and Structure Revision of 10-Deacetyltaxinine from the Seeds of the Chinese Yew, Taxus mairei

Qing-Wen Shi, Zuo-Ping Li, Ding Zhao, Ji-Shun Gu, Hiromasa Kiyota*

Natural Product Research   20 ( 1 )   47 - 51   2006年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1080/14786410500111184

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A New Abeotaxane from the sseds of Taxus mairei

Man-Li Zhang, Li-Geng LI, Cong-Mei Cao, Zuo-PIng Li, Qing-Wen Shi, Hiromasa Kiyota

Chinese Chemical Letters   17 ( 1 )   27 - 30   2006年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Chemical Constituents from Genus Achillea

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

Chemistry and Biodiversity   3 ( 11 )   1163 - 1180   2006年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.200690119

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Chemical Constituents from Genus Inula

Yong-Min Zhao, Man-Li Zhang, Qing-Wen Shi, Hiromasa Kiyota*

Chemistry and Biodiversity   3 ( 4 )   371 - 384   2006年

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

DOI： 10.1002/cbdv.200690041

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Two New Taxanes from the Branches Bark and Needles of Taxus cuspidata

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

Chemistry and Biodiversity   3 ( 10 )   1153 - 1161   2006年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/cbdv.200690117

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

Synthesis of both enantionters of methyl 4,5-didehydrojasmonate (1, Delta(4,5)-MJA; &gt; 99.8% ee), a constituent of jasmin absolute, established the absolute configuration of the natural product, and their odor quality was evaluated. The fragrance of the natural (3S,7R)-enantiomer (a fresh natural, sweet floral fruity odor, reminiscent of Jasmin and Ylang Ylang flower, more intensive and tenacious) was superior to that of the unnatural (3R,7S)-enantiomer (a floral green odor with slight metallic green aspect, less intensive than the natural form) and the racemate (green-floral note, having weak and less volume than methyl jasmonate). Odor difference between natural and unnatural enantiomers of methyl jasmonate (2) is also reported.

DOI： 10.1002/cbdv.200690068

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Syntheses and Odour Descriptions of Cyclopropanated Compounds 5. Analogs of Nor-leaf Alcohol and Monoterpene Dienols

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

Chemistry and Biodiversity   3 ( 5 )   544 - 552   2006年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/cbdv.200690058

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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年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：GEORG THIEME VERLAG KG  

Gizzerosine, a potent inducer of gizzard erosion in C chicks, was synthesized using successive zinc-mediated and palladium-catalyzed Coupling reactions as the key steps. The piperonyl inoiety was used as a novel N-protecting-1-group.

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The absolute configuration of (-)-pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea, was determined to be R by synthetic studies. (c) 2005 Elsevier Ltd. All rights reserved.

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The structure of a novel 3,8-seco-bicyclic taxanoid metabolite, isolated from the methanol extract of seeds of the Chinese yew, Taxus mairei, was established as (11 alpha H)-3,8-seco-taxa-3E,7E, 12(18)-triene-2 alpha,6 alpha,9 beta-triol (1) on the basis of spectral analysis including H-1 NMR, C-13 NMR, HMQC, HMBC, NOESY and HR-FABMS. (c) 2005 Elsevier Ltd. All rights reserved.

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Enacyloxin IIa methyl ester in non-protic solvent gave rearranged product in acidic conditions such as surface of TLC plate of silica gel or by treatment with a catalytic amount of p-toluenesulfonic acid. On the other hand, such a rearrangement did not occur in polar protic solvent. The structure of the rearranged product was elucidated as 4-acyl analog of the cyclohexane ring.

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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY  

Anew taxane glycoside was isolated from a methanol extract of the needles of Taxus cuspidata. The structure was established as 2 alpha,9 alpha,10 beta-triacetoxytaxa-4(20),11-dien-13-one-5 alpha-O-beta-D-glucopyranoside (1) on the basis of 1D and 2D NMR and high-resolution fast atom bombardment mass spectral analyses. Copyright (c) 2005 John Wiley & Sons, Ltd.

DOI： 10.1002/mrc.1579

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

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

Synlett   ( 4 )   635 - 636   2005年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

(+)-Pteroenone, a defensive metabolite of the abducted antarctic pteropod Clione antarctica, was firstly and efficiently synthesized by employing anti-selective aldol reaction as the key step.

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年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The synthesis of the southern (C1'-C11') fragment of pamamycin-635A, isolated from Streptomyces alboniger, was achieved via an Evans aldol reaction, a cis-selective iodoetherification and a stereospecific deiodination as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2004.11.067

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New natural taxane diterpenoids from Taxus species since 1999

Qing-Wen Shi, Hiromasa Kiyota*

Chemistry and Biodiversity   2 ( 12 )   1597 - 1623   2005年

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：FREUND PUBLISHING HOUSE LTD  

A new taxane-glucoside was isolated from the needles of Taxus cuspidata. The structure was established as 2 alpha,9 alpha,10 beta-triacetoxy-11,12-epoxytax-4(20)-en-13-one-5 alpha-O-beta-D-glucopyranoside (1) on the basis of 1D- and 2D spectral analyses.

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Enzymatic Resolution and Odor Descriptions of Both Enantiomers of Lavandulol, a Fragrance of Lavender Oil

Hiroyuki Sakauchi, Hiromasa Kiyota,* Shin-ya Takigawa, Takayuki Oritani, Shigefumi Kuwahara

Chemistry and Biodiversity   2 ( 9 )   1183 - 1186   2005年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

A concise and high yielding synthesis of (-)-tabtoxinine-beta-lactam 1, the cause of tobacco wildfire disease, was achieved from L-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of N-OBn amide as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：NATURE PUBLISHING GROUP  

Some regulators of plant growth and differentiation have been shown to induce the differentiation of several human myeloid leukemia cells, and might be effective as differentiation inducers to control acute myelogenous leukemia cells. In this study, the growth-inhibiting and differentiation-inducing effects of jasmonates on human myeloid leukemia cells were examined. Several myeloid leukemia cells were cultured with methyl jasmonate (MJ) and its derivatives. Cell differentiation was determined by nitroblue tetrazolium-reducing activity, morphological changes, alpha-naphthyl acetate esterase activity and expression of differentiation-associated surface antigens. MJ induced both monocytic and granulocytic differentiation of HL-60 cells. MJ activated mitogen-activated protein kinase (MAPK) in the cells before causing myelomonocytic differentiation. MAPK activation was necessary for MJ-induced differentiation, since PD98059, an inhibitor of MAPK kinase, suppressed the differentiation induced by MJ. MJ also induced the differentiation of other human leukemia cell lines. Introduction of a double bond at the 4,5-position greatly enhanced the differentiation-inducing activity of MJ. MJ and its derivatives potently induce the differentiation of some myelomonocytic leukemia cells. One novel derivative is a particularly promising therapeutic agent for the treatment of leukemia.

DOI： 10.1038/sj.leu.2403421

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New 2(3->20)Abeotaxane and 3,11-Cyclotaxane from Needles of Taxus cuspidata

Qing-Wen Shi, Zuo-Ping Li, Ding Zhao Ji-Shun Gu, Takayuki Oritani, Hiromasa Kiyota*

Bioscience, Biotechnology, and Biochemistry   68 ( 7 )   1584 - 1587   2004年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1271/bbb.68.1584

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Syntheses and Odour Descriptions of Cyclopropanated Compounds 5. Analogues of Methyl Jasmonate to Fix the Relative Stereochemistry of the Two Side Chains.

Hiromasa Kiyota,* Shin-ya Takigawa, Shigefumi Kuwahara

Helvetica Chimica Acta   87 ( 7 )   1854 - 1859   2004年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1002/hlca.200490164

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88(P-12) タバコ野火病原因菌由来の非選択的植物毒素tabtoxinine-β-lactamの合成研究(ポスター発表の部)

清田 洋正, 高井 隆文, 齋藤 正年, 中山 修, 折谷 隆之, 桑原 重文

天然有機化合物討論会講演要旨集   ( 45 )   521 - 526   2003年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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

Takayuki Oritani, Hiromasa Kiyota

Natural Product Reports   20 ( 4 )   414 - 425   2003年8月

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担当区分：筆頭著者   記述言語：英語   掲載種別：研究論文（大学，研究機関等紀要）  

DOI： 10.1039/b109859b

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Synthesis and Biological Evaluation of 1-Deoxy-4,7-dideacetoxy Azetidine Paclitaxel Analogs

Qian Cheng, Hiromasa Kiyota,* Marina Yamaguchi, Tohru Horiguchi, Takayuki Oritani

Bioorganic and Medicinal Chemistry Letters   13 ( 6 )   1075 - 1077   2003年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JOHN WILEY & SONS LTD  

Several long-chain aliphatic dienols used as commercial odourants were modified with cyclopropane rings, and their characteristics were examined. We used commercially available (2E, 4E)-2, 4-decadien-l-ol, (3Z, 6Z)-3, 6-nonadien-1-ol, and (2E, 6Z)-2, 6-nonadien-1-ol as parent compounds. Monocyclopropanation of the two double bonds in each compound resulted in a significant increase of odour quality. However, dicyclopropanated analogues lost their original odour quality and intensity. Copyright (C) 2003 John Wiley Sons, Ltd.

DOI： 10.1002/ffj.1171

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First Synthesis of (±)-Pyricuol, a Plant Pathogen Isolated from Rice Blast Disease Fungus Magnaporthe grisea

Hiromasa Kiyota, Rumi Ueda, Takayuki Oritani, Shigefumi Kuwahara

Synlett   2003 ( 2 )   219 - 220   2003年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

2-m-Azidobenzoyl and 2-m-chlorobenzoyl baccatin III analogs were prepared from taxinine, a major component in Japanese yew leaves. In this study, a novel acetyl migration from 13- to 4-hydroxyl group was observed. The antitumor activity of these compounds was evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(03)00048-6

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6 Didemniserinolipid Bの全合成と構造の改定(口頭発表の部)

清田 洋正, Dixon Darren J., Luscombe Christine K., Hettstedt Stephen, Ley Steven. V.

天然有機化合物討論会講演要旨集   ( 44 )   31 - 36   2002年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

En route to proving the absolute and relative stereochemistry, through synthesis, of (+)-didemniserinolipid B (1), the first natural serinolipid isolated from a tunicate Didemnum sp., it was discovered that the isolated natural product was in fact the 31-sulfate configured 8R,9R,10R,13S,30S. This structural reassignment was only possible after the development of a microwave-assisted method for the sulfation of unreactive hydroxyl groups.

DOI： 10.1021/ol026421y

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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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JOHN WILEY & SONS LTD  

Analogues of methyl jasmonate bearing a cyclopropane ring were synthesized and their odour characteristics were examined. Cyclopropanation of the pentenyl side chains not only increased the odour intensity, but also gave a mossy mushroom characteristic when compared with the original odour. Modification of the cyclopentanone to fix the cis ring geometry reduced both the quality and intensity of the original odour. Copyright (C) 2002 John Wiley Sons, Ltd.

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年2月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

A new drimane sesquiterpenoid was isolated from the heartwood of the Japanese yew, Taxus cuspidata Sieb. et Zucc. Its structure was established as 1beta-acetoxyisodrimeninol (1beta-acetoxy-11,12-epoxy-7-drimen-11-ol, 1). This compound was gradually oxidized to give gamma-lactone (1beta-acetoxy-8-drimeno-11,12-lactone, 4).

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 査読

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

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

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

Analogues of leaf alcohol and related compounds, bearing a cyclopropane ring in place of the double bond, were synthesized and their odour characteristics were examined. cis-(Ethylcyclopropyl)ethanol was prepared using the Simmons-Smith reaction with leaf alcohol. Ethoxyethyl ether and some alkyl and aryl esters were also prepared. Cyclopropanation of the double bond modified their original odour characteristic without losing the key green note. Copyright © 2002 John Wiley &amp
Sons, Ltd.

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年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

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 the Evans aldol reaction and cis-selective iodoetherification as the key steps in a 9.6% overall yield (7 steps). The eastern fragment was constructed via the Julia coupling reaction and cis-selective iodoetherification in a 3.0% overall yield (8 steps from the known epoxide).

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：ROYAL SOC CHEMISTRY  

The absolute configuration of the 12',17',18',19'-positions of enacyloxins (ENXs), a series of polyhydroxy-polyenic antibiotics from Frateuria sp. W-315, was determined. As degradation of decarbamoyl (dec) ENX IIa gave (5R,6S,1'E)-6-(but-1'-enyl)-5-chloro-5,6-dihydro-2H-pyran-2-one, which corresponded to the 15'-23' skeleton of dec ENX IIa, its enantiomers were synthesized from tri-O-acetyl-D-glucal. Comparison of the HPLC retention time of these naturally derived and synthetic compounds revealed the 17'R,18'S,19'R-configuration of ENXs; Hydrogenation and oxidation of ENX IIa gave methyl 13-hydroxy-6,12-dimethyltridecanoate, which was converted to the 13-MTPA ester. Comparison of the H-1 NMR chemical shifts and the coupling constants with the model compounds revealed the 12' S-configuration. This absolute stereochemistry is necessarily applicable to other enacyloxins.

DOI： 10.1039/b104341m

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88(P-45) Pamamycin-607の合成研究(ポスター発表の部)

古屋 幸人, 清田 洋正, 桑原 重文

天然有機化合物討論会講演要旨集   ( 43 )   521 - 526   2001年9月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

Macrotetrolide alpha, a designed analog of polynactin composed of (+)- and (-)-bishomononactic acids, was synthesized. These monomers were prepared via optical resolution of the corresponding (S)-O-acetylmandelates. Assembly of the monomers to macrotetrolide alpha took seven steps without any loss of the intermediates.

DOI： 10.1271/bbb.65.2118

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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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

The synthesis of methyl (-)-shikimate [(-)-2] was achieved via lipase-catalyzed optical resolution of (1S*, 4R*, 5R*)-4-hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one (3). Transesterification of (+/-)-3 and vinyl acetate with lipase MY and subsequent hydrolysis gave optically pure (-)-3. This compound was converted to (-)-2 in two steps.

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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JOHN WILEY & SONS LTD  

Analogues of jasmine lactone and cis-jasmone, bearing cyclopropane rings instead of double bonds, were synthesized and their odour characteristics were examined. Modification of the cyclopentenone ring of cis-jasmone reduced both the quality and the intensity of the original odour. Cyclopropanation of the pentenyl side chains did not increase the odour intensity, but it gave a fruity characteristic to the original odours of cis-jasmone and jasmine lactone. Copyright (C) 2001 John Wiley & Sons, Ltd.

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年5月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (+/-)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (+/-)-3 (E=370) and hydrolysis of the corresponding acetate (E=41). Resolution of (+/-)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0957-4166(01)00169-0

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New 11(15->10)Abeotaxane, 11(15->1),11(10->9)Bisabeotaxane and 3,11-Cyclotaxanes from Taxus yunnanensis

Hiromasa Kiyota,* Qing-Wen Shi, Takayuki Oritani, Ligeng Li

Bioscience, Biotechnology, and Biochemistry   65 ( 1 )   35 - 40   2001年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1271/bbb.65.35

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Synthesis of Actiketal, an Unique Benzofuran Glutarimide Antibiotic from Streptomyces pulveraceus subsp. epiderstagenes

Hiromasa Kiyota,* Yuko Shimizu, Takayuki Oritani

Journal of Pesticide Science   26 ( 1 )   93 - 95   2001年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

Hiromasa Kiyota, Takanori Koike, Emi Higashi, Yasushi Satoh, Takayuki Oritani

Journal of Pesticide Science   26 ( 1 )   96 - 99   2001年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：FREUND PUBLISHING HOUSE LTD  

The stereochemical study of the cyclohexane ring part of enacyloxins (ENXs), a series of antibiotics isolated from Frateuria sp. W-315, was examined. The relative configuration was elucidated by the coupling constant values of the H-1 NMR spectrum. The absolute structure was determined to be 1S, 3R, 4S, because the CD spectrum of the corresponding 3,4-dibenzoate derivative showed negative chirality. This conclusion was confirmed by the synthesis of the dibenzoate from tri-O-acetyl-D-glucal.

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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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：FREUND PUBLISHING HOUSE LTD  

Two new members of enacyloxins (ENXs) were isolated from the culture extract of Frateuria sp. W-315. Spectrometric analyses revealed their structures as decarbamoyl enacyloxin IVa and IIa, the latter preferentially existed in the hemiacetal form. Formation of these compounds were catalyzed by enzymes produced by the fungus. From the coupling constant values of the hemiacetal part of dec ENX IIa, the (17'R*, 18'S*, 19'R*) relative configuration of ENXs was also elucidated.

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

Akira Hiratate, Hiromasa Kiyota, Takayuki Oritani

Journal of Pesticide Science   26 ( 4 )   361 - 365   2001年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PESTICIDE SCI SOC JAPAN  

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 or 3-hydroxy group at convex site was important for lethal activity. while (2S,3S)-configuration was inhibitory to lettuce germination.

DOI： 10.1584/jpestics.26.366

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Three New Taxoids from the Leaves of the Japanese Yew, Taxus cuspidata

Qing-Wen Shi, Takayuki Oritani, Hiromasa Kiyota, Ryo Murakami

Natural Product Letters   15 ( 1 )   55 - 62   2001年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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125(P-66) TaxinineからTaxol analogsへの変換 : Taxinine誘導体の化学反応性(ポスター発表の部)

堀口 透, 清田 洋正, 程 潜, 折谷 隆之

天然有機化合物討論会講演要旨集   ( 42 )   745 - 750   2000年10月

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記述言語：日本語   出版者・発行元：天然有機化合物討論会  

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：WILEY-V C H VERLAG GMBH  

Four stereoisomers of streptimidone (1), an antibiotic from Streptomyces rimosus forma paromomycinus, were synthesized from methyl (S)-3-hydroxy-2-methylpropanoate. The natural diastereomer 1 shows the strongest antimicrobial activity.

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-α-Irone and cis-g-Irone, Principal Constituents of Irish oil, via Optical Resolution of (±)-2,2,4-trimethyl-3-cyclohexene Carboxylic Acid

Takahiro Inoue, Hiromasa Kiyota, Takayuki Oritani

Tetrahedron: Asymmetry   11 ( 18 )   3807 - 3818   2000年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JAPANESE SOC SOIL SCIENCE PLANT NUTRITION  

Effects of fertilizer and manure application on L-glutaminase and L-asparaginase activities on volcanic ash soil and gray lowland soil mere examined. The activities were estimated by using the indophenol method. This involved the colorimetric estimation of NH4+ released from L-glutamine or L-asparagine catalyzed by the enzymes, when the soils were incubated with 0.25 M L-glutamine or L-asparagine in 0.1 M phosphate buffer (pH 7.6) and toluene used as a germicide, Both L-glutaminase and L-asparagine activities were the largest in the farmyard manure plot (OM), followed by the chemical fertilizer plot (CF) and the plot without fertilizer application, hereafter referred to as "no fertilizer plot" (NF).

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Synthesis of (+-)-Methyl Bishomononactate, a Monomeric Component of Macrotetrolides

Tadaatsu Hanadate, Hiromasa Kiyota,* Takayuki Oritani

Bioscience, Biotechnology, and Biochemistry   64 ( 8 )   1671 - 1674   2000年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Chemical examination of the seeds of the Chinese yew, Taxus yunnanensis Cheng et L. K. Fu and the Japanese yew, Taxus cuspidata Sieb et Zucc, resulted in the isolation of four taxane diterpenoids. The structures of these taxoids were established as (12 alpha)-2 alpha-acetoxy-5 alpha,9 alpha,10 beta-trihydroxy-3,11-cyclotax-4(20)-en-13-one; 2 alpha,7 beta,13 alpha-triacetoxy-5 alpha,9 alpha-dihydroxy-2(3 --&gt; 20)abeotaxa-4(20),11-dien-10-one; 9 alpha,10 beta-diacetoxy-5 alpha-cinnamoyloxytaxa-4(20),11-dien-13 alpha-ol and the known 2 alpha,7 beta,9 alpha,10 beta,13-pentaacetoxytaxa-4(20),12-diene-5 alpha,11 beta-diol on the basis of spectral analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0031-9422(00)00186-2

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Synthesis of Actiketal, a Glutarimide Antibiotic

Hiromasa Kiyota,* Yuko Shimizu, Takayuki Oritani

Tetrahedron Letters   41 ( 31 )   5887 - 5890   2000年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1016/S0040-4039(00)00928-X

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Enzymatic Resolution of (±)-Epoxy-β-cyclogeraniol, a Synthetic Precursor for Abscisic Acid Analog

Ryou Okazaki, Hiromasa Kiyota, Takayuki Oritani

Bioscience, Biotechnology, and Biochemistry   64 ( 7 )   1444 - 1447   2000年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

The C9-C20 spiroacetal parts of spirofungin A and B, antifungal antibiotics from Strephomyces violaceusniger Tu 4113, were synthesized simultaneously from (S)-citronellyl bromide and (+/-)-epoxy alcohol via alkyne-lactone coupling reaction and diastereomeric separation. (C) 2000 Elsevier Science Ltd. All rights reserved.

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年

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：FREUND PUBLISHING HOUSE LTD  

Unnatural enantiomer of a dilactone antibiotic (-)-antimycin A(3) and its deformylamidodehydroxy analog were synthesized using chelation controlled alkylation as a key step. (-)-Antimycin A(3) and its analog hardly showed antimicrobial activity compared with natural antimycin A complex. The formal synthesis of natural (+)-antimycin A(3) is also achieved.

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Synthesis of the Southern Part of Pamamycin-607, an Aerial Mycelium-Inducing Substance of Streptomyces alboniger

Yukito Furuya, Hiromasa Kiyota,* Takayuki Oritani

Heterocyclic Communications   6 ( 5 )   427 - 430   2000年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Synthesis of (±)-Methyl Tuberonate, a Potato Tuber Forming Substance, and its Epimer

Hiromasa Kiyota, Daisuke Nakashima, Takayuki Oritani

Bioscience, Biotechnology, and Biochemistry   63 ( 12 )   2110 - 2117   1999年12月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)-ester. (C) 1999 Elsevier Science Ltd. All rights reserved.

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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

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年4月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Three new rearranged taxane diterpenoids with 5/7/6-membered ring system were isolated from the bark of Taxus chinensis var, mairei (1 and 2) and the needles of T. cuspidata (3). The structures of them were established as 2 alpha,7 beta-diacetoxy-5 alpha, 10 beta, 13 alpha, 15-tetrahydroxy-4 beta (20)-epoxy-9 alpha-benzoyloxy 11(15--&gt;1)abeotax-11-ene (1), 2 alpha,4 alpha-diacetoxy-7 beta-benzoyloxy-5 beta,20-epox 10 beta, 13 alpha,15-tetrahydroxy-11 (15--&gt;1)abeotax-11-ene (2), and 4 alpha, 7 beta-diacetoxy-2 alpha-benzoyloxy-5 beta,20-epoxy-9 alpha, 10 beta, 13 alpha, 15-tetrahydroxy-11(15--&gt;1)abeotax-11-ene (3) on the basis of spectral data including 2D NMR spectroscopies.

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New taxane diterpenoids isolated from yew trees

Qing-Wen Shi, Hiromasa Kiyota, Takayuki Oritani

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

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記述言語：英語   掲載種別：研究論文（国際会議プロシーディングス）  

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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年12月

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記述言語：英語   出版者・発行元：GEORG THIEME VERLAG  

Two bicyclic taxanes and two abeotaxanes were isolated from the bark and the needles of the Chinese yew, Taxus chinensis var. mairei. Thestructures of the two new compounds, 5-(N,N-dimethyl-3'-phenylisoseryl)taxachitriene A and 13-acetyl-9-deacetyl-9-benzoyl-10-debenzoyltaxchinin A, were established by spectral methods.

DOI： 10.1055/s-2006-957580

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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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：AMER CHEMICAL SOC  

Three novel (1-3) and five known bicyclic 3,8-secotaxane diterpenoids were isolated from the needles of the Chinese yew, Taxus chinensis var, mairei. The structures of the new compounds were established, respectively, as (3E,7E)-2 alpha,10 beta,13 alpha-triacetoxy-5 alpha,20-dihydroxy-3,8-11-trien-9-one (1), (3E,7E)-2 alpha, 10 beta-diacetoxy-5 alpha,13 alpha,20-trihydroxy-3,8-secotaxa-3,7,11-trien-9-one (2), and (3E,8E)-7 beta,9,10 beta,13 alpha,20-pentaacetoxy-3,8-secotaxa-3,8,11-triene-2 alpha,5 alpha-diol (2-deacetyltaxachitriene A) (3), on the basis of spectral analysis. The other five bicyclic taxane diterpenoids were determined as canadensene, 6-deacetyltaxachitriene B, taxachitriene B, taxuspine U, and taxuspine X by comparison of their physical properties and spectral data with those previously reported.

DOI： 10.1021/np980213q

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Isolation and Structure Elucidation of a New 11(15→1)-Abeotaxane from the Chinese Yew, Taxus mairei

Qing-Wen Shi, Takayuki Oritani, Hiromasa Kiyota, Tohru Horiguchi

Natural Product Letters   12 ( 1 )   67 - 74   1998年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

DOI： 10.1080/10575639808048873

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14β-Hydroxytaxusin, a New Taxane from Taxus mairei

Qing-Wen Shi, Takayuki Oritani, Hiromasa Kiyota

Natural Product Letters   12 ( 2 )   85 - 90   1998年

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年11月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Methyl 3,7-didehydrojasmonate was synthesized as an analogue of methyl epijasmonate. This analogue inhibited the germination of lettuce seed more strongly than methyl jasmonate. Methyl 4,5-didehydrojasmonate was also synthesized and its biological activities were comparable to those of methyl jasmonate. (C) 1997 Elsevier Science Ltd.

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年9月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：GEORG THIEME VERLAG  

(+)-Homononactic acid, one of the monomers of polynactin, and its 8-epimer were synthesized. The key step was cis-selective iodoetherification of the enone or the alpha-silyloxyolefin intermediates constructed with Wittig-Horner or Julia coupling reactions, respectively.

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Stereochemistry of a Unique Tricarbocyclic Compound Prepared by Superacid-Catalyzed Cyclization

Hisahide Tanimoto, Hiromasa Kiyota, Takayuki Oritani, Keita Matsumoto

Synlett   1997 ( 1 )   121 - &   1997年1月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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Synthesis of (±)-Homononactic Acid by Using cis-Selective Iodoetherification

Masaki Abe, Hiromasa Kiyota, Takayuki Oritani

Synlett   1996 ( 8 )   777 - &   1996年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD  

Methyl 5',5',5'-trifluorojasmonate was synthesized as an antimetabolic analogue of methyl jasmonate. It induced potato tuber formation more effectively than methyl jasmonate and inhibited the growth of rice seedlings and the germination of lettuce and radish seeds. These results suggest that epijasmonic acid itself has potato tuber-inducing activity and that the hydroxyl group of tuberonic acid is not necessary for this activity.

DOI： 10.1016/0031-9422(96)00145-8

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2-Fluoro and 2-Methoxycarbonyl Epoxy-β-ionylideneacetic Acids as Abscisic Acid Analogs

Hiromasa Kiyota, Tadateru Masuda, Jun Chiba, Takayuki Oritani

Bioscience, Biotechnology and Biochemistry   60 ( 7 )   1076 - 1080   1996年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：JAPANESE SOC SOIL SCIENCE PLANT NUTRITION  

A simple and rapid method was developed for determining L-glutaminase and L-asparaginase activities in soils. It involved colorimetric estimation of NH4+ released by the activity of L-glutaminase and L-asparaginase when soil was incubated with 0.25 M L-glutamine or L-asparagine in 0.1 M phosphate buffer (pH 7.6) and toluene used as a germicide.
The indophenol method was applied to the assay of NH4+ for soil L-glutaminase and L-asparaginase activities. Color development in the indophenol method required one hour. The color development was stable for 2 d and was not appreciably affected by the presence of L-glutamine, L-glutamic acid, L-asparagine, and L-aspartic acid. In addition, no turbidity nor precipitate appeared in the presence of a high concentration (10 mu g) of NH4+-N. The L-glutaminase activity was estimated in three soil samples differing in pH, organic-C content, and land use. The L-glutaminase activity in the three soils ranged from 28 to 1,470 mU (10(-9) mol min(-1) g(-1) of dry soil at 30 degrees C). The optimum pH for the L-glutaminase activity in soils was about 7.5 in phosphate buffer.
The incubation time of L-glutaminase and L-asparaginase can be shortened, because the sensitivity of the indophenol method is about 24 times as high as that of the Nessler method.

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年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：VCH PUBLISHERS INC  

(3S,7R,8E,10E)-3,7,9-Trimethyl-8,10-dodecadien-6-one (1), the major component of the female-produced sex pheromone of the maritime pine scale (Matsucoccus feytaudi), was synthesized by starting from epoxide 2, which was obtained from meso-epoxy diacetate (F) by employing enzyme-catalyzed asymmetric hydrolysis as the key step.

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年7月

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記述言語：英語   出版者・発行元：GEORG THIEME VERLAG  

An efficient two-step procedure to prepare conjugated dienes from allylic alcohols is developed without the formation of regioisomers and rearranged products.

DOI： 10.1055/s-1994-25548

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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年6月

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記述言語：英語   掲載種別：研究論文（学術雑誌）   出版者・発行元：TAYLOR & FRANCIS LTD  

(2S,4R,5S)-2,4,6-Trimethyl-5-heptanolide (1), a ses pheromone component for Macrocentrus grandii, aas synthesized by starting from methyl (R)-citronellate (2) and employing bromolactonization (10--&gt;11) as the key reaction.

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 査読

Kenji Mori, Hiromasa Kiyota, Christian Malosse, Didier Rochat

Liebigs Annalen der Chemie   1993   1201 - 1204   1993年10月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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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 査読

Kenji Mori, Hiromasa Kiyota, Didier Rochat

Liebigs Annalender Chemie   1993   865 - 870   1993年7月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

Kenji Mori, Hiromasa Kiyota

Liebigs Annalen der Chemie   1992   989 - 992   1992年8月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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

Takeshi Kitahara, Hiromasa Kiyota, Hitoshi Kurata, Kenji Mori

Tetrahedron   47 ( 9 )   1649 - 1654   1991年3月

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記述言語：英語   掲載種別：研究論文（学術雑誌）  

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