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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)134-142
Number of pages9
JournalBioscience, biotechnology, and biochemistry
Volume85
Issue number1
DOIs
Publication statusPublished - Jan 7 2021

Keywords

  • Pyricularia oryzae
  • rice blast disease
  • structure revision
  • total synthesis

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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