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

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

研究成果: Article査読

抄録

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.

本文言語English
ページ(範囲)134-142
ページ数9
ジャーナルBioscience, Biotechnology, and Biochemistry
85
1
DOI
出版ステータスPublished - 2021 1 7

ASJC Scopus subject areas

  • バイオテクノロジー
  • 分析化学
  • 生化学
  • 応用微生物学とバイオテクノロジー
  • 分子生物学
  • 有機化学

フィンガープリント

「Synthesis of (12R,13S)-pyriculariol and (12R,13S)-dihydropyriculariol revealed that the rice blast fungus, Pyricularia oryzae, produces these phytotoxins as racemates」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル