研究者詳細 - 清田　洋正

論文 - 清田　洋正

分割表示 235 件中 1 - 20 件目／全件表示 >>

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

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

"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

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

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

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

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

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

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

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

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

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

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

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

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

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