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

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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. Heptatrienylsalicylaldehyde was converted into dihydropyriculol by the fungus by a shaking culture. A new biosynthetic pathway comprising both oxidation and reduction is proposed.

Original languageEnglish
Pages (from-to)6276-6280
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number31
DOIs
Publication statusPublished - 2011 Nov 1

Keywords

  • Biosynthesis
  • Isotopic labeling
  • Phytochemistry
  • Rice blast disease

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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