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

doi:10.1002/ejoc.201100771

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 journal › Article › peer-review

16 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 language	English
Pages (from-to)	6276-6280
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	31
DOIs	https://doi.org/10.1002/ejoc.201100771
Publication status	Published - Nov 2011
Externally published	Yes

Keywords

Biosynthesis
Isotopic labeling
Phytochemistry
Rice blast disease

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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Tanaka, K., Sasaki, A., Cao, H. Q., Yamada, T., Igarashi, M., Komine, I., Nakahigashi, H., Minami, N., Kuwahara, S., Nukina, M., & Kiyota, H. (2011). Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea. European Journal of Organic Chemistry, (31), 6276-6280. https://doi.org/10.1002/ejoc.201100771

Tanaka, K, Sasaki, A, Cao, HQ, Yamada, T, Igarashi, M, Komine, I, Nakahigashi, H, Minami, N, Kuwahara, S, Nukina, M & Kiyota, H 2011, 'Synthesis and biotransformation of plausible biosynthetic intermediates of salicylaldehyde-type phytotoxins of rice blast fungus, Magnaporthe grisea', European Journal of Organic Chemistry, no. 31, pp. 6276-6280. https://doi.org/10.1002/ejoc.201100771

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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",

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doi = "10.1002/ejoc.201100771",

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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

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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.

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KW - Isotopic labeling

KW - Phytochemistry

KW - Rice blast disease

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

Abstract

Keywords

ASJC Scopus subject areas

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