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 journalArticlepeer-review

    13 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

    Keywords

    • Biosynthesis
    • Isotopic labeling
    • Phytochemistry
    • Rice blast disease

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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