このエントリーをはてなブックマークに追加
ID 62024
Author
Nagashima, Yuta Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Sasaki, Ayaka Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Hiraoka, Ryoya Graduate School of Environmental and Life Science, Okayama University
Onoda, Yuko Graduate School of Environmental and Life Science, Okayama University
Tanaka, Koji Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Wang, Zi-Yi Graduate School of Environmental and Life Science, Okayama University
Kuwana, Atsuki Graduate School of Environmental and Life Science, Okayama University
Sato, Yuki Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Suzuki, Yuji Laboratory of Plant Nutrition and Function, Graduate School of Agricultural Science, Tohoku University
Izumi, Minoru Graduate School of Environmental and Life Science, Okayama University Kaken ID publons researchmap
Kuwahara, Shigefumi Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University
Nukina, Manabu Professor Emeritus, Yamagata University
Kiyota, Hiromasa Graduate School of Environmental and Life Science, Okayama University ORCID Kaken ID publons researchmap
Abstract
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.
Keywords
Pyricularia oryzae
rice blast disease
structure revision
total synthesis
Note
This is an Accepted Manuscript of an article published by Oxford University Press
This fulltext is available in January 2022
Published Date
2021-01-21
Publication Title
Bioscience, Biotechnology, and Biochemistry
Volume
volume85
Issue
issue1
Publisher
Oxford University Press (OUP)
Start Page
134
End Page
142
ISSN
1347-6947
NCID
AA12018610
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
File Version
author
PubMed ID
DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.1093/bbb/zbaa002
Funder Name
Japan Society for the Promotion of Science
Agricultural Chemical Research Foundation
Intelligent Cosmos Foundation
Naito Memorial Foundation
Sumitomo Chem Co. Ltd.
助成番号
17580092
19580120