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

6 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 - Nov 2011
Externally publishedYes

Fingerprint

fungi
rice
blasts
Fungi
synthesis
shaking
Deuterium
deuterium
Oxidation
oxidation
salicylaldehyde
Biotransformation

Keywords

  • Biosynthesis
  • Isotopic labeling
  • Phytochemistry
  • Rice blast disease

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea. / Tanaka, Koji; Sasaki, Ayaka; Cao, Hai Qun; Yamada, Teiko; Igarashi, Masahiro; Komine, Isao; Nakahigashi, Hirokazu; Minami, Naoko; Kuwahara, Shigefumi; Nukina, Manabu; Kiyota, Hiromasa.

In: European Journal of Organic Chemistry, No. 31, 11.2011, p. 6276-6280.

Research output: Contribution to journalArticle

Tanaka, Koji ; Sasaki, Ayaka ; Cao, Hai Qun ; Yamada, Teiko ; Igarashi, Masahiro ; Komine, Isao ; Nakahigashi, Hirokazu ; Minami, Naoko ; Kuwahara, Shigefumi ; Nukina, Manabu ; Kiyota, Hiromasa. / Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea. In: European Journal of Organic Chemistry. 2011 ; No. 31. pp. 6276-6280.
@article{c77f9ac8174c4a198d0e1eff84b128e6,
title = "Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea",
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.",
keywords = "Biosynthesis, Isotopic labeling, Phytochemistry, Rice blast disease",
author = "Koji Tanaka and Ayaka Sasaki and Cao, {Hai Qun} and Teiko Yamada and Masahiro Igarashi and Isao Komine and Hirokazu Nakahigashi and Naoko Minami and Shigefumi Kuwahara and Manabu Nukina and Hiromasa Kiyota",
year = "2011",
month = "11",
doi = "10.1002/ejoc.201100771",
language = "English",
pages = "6276--6280",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "31",

}

TY - JOUR

T1 - Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea

AU - Tanaka, Koji

AU - Sasaki, Ayaka

AU - Cao, Hai Qun

AU - Yamada, Teiko

AU - Igarashi, Masahiro

AU - Komine, Isao

AU - Nakahigashi, Hirokazu

AU - Minami, Naoko

AU - Kuwahara, Shigefumi

AU - Nukina, Manabu

AU - Kiyota, Hiromasa

PY - 2011/11

Y1 - 2011/11

N2 - 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.

AB - 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.

KW - Biosynthesis

KW - Isotopic labeling

KW - Phytochemistry

KW - Rice blast disease

UR - http://www.scopus.com/inward/record.url?scp=80054886922&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80054886922&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201100771

DO - 10.1002/ejoc.201100771

M3 - Article

AN - SCOPUS:80054886922

SP - 6276

EP - 6280

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 31

ER -