Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

Koji Tanaka; Yoko Nakamura; Ayaka Sasaki; Rumi Ueda; Yuji Suzuki; Shigefumi Kuwahara; Hiromasa Kiyota

doi:10.1016/j.tet.2009.05.052

Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

Koji Tanaka, Yoko Nakamura, Ayaka Sasaki, Rumi Ueda, Yuji Suzuki, Shigefumi Kuwahara, Hiromasa Kiyota

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce.

Original language	English
Pages (from-to)	6115-6122
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2009.05.052
Publication status	Published - 2009 Aug 1

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.05.052

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title = "Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea",

abstract = "Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce.",

author = "Koji Tanaka and Yoko Nakamura and Ayaka Sasaki and Rumi Ueda and Yuji Suzuki and Shigefumi Kuwahara and Hiromasa Kiyota",

note = "Funding Information: We thank Prof. Jin-Keol Kim (KRICT, Korea) for providing the natural sample of pyricuol, and Prof. Manabu Nukina (Yamagata University, Japan) for giving the useful information about foliar application assay. We also appreciate the assistance of Mrs. Teiko Yamada (Tohoku Univ.) for measuring NMR and mass spectra. Financial supports by grant-in-aid from Japan Society for the Promotion of Science (No. 17580092 and 19580120), The Agricultural Chemical Research Foundation, Intelligent Cosmos Foundation, and The Naito Foundation is gratefully acknowledged.",

year = "2009",

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doi = "10.1016/j.tet.2009.05.052",

language = "English",

volume = "65",

pages = "6115--6122",

journal = "Tetrahedron",

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T1 - Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

AU - Tanaka, Koji

AU - Nakamura, Yoko

AU - Sasaki, Ayaka

AU - Ueda, Rumi

AU - Suzuki, Yuji

AU - Kuwahara, Shigefumi

AU - Kiyota, Hiromasa

N1 - Funding Information: We thank Prof. Jin-Keol Kim (KRICT, Korea) for providing the natural sample of pyricuol, and Prof. Manabu Nukina (Yamagata University, Japan) for giving the useful information about foliar application assay. We also appreciate the assistance of Mrs. Teiko Yamada (Tohoku Univ.) for measuring NMR and mass spectra. Financial supports by grant-in-aid from Japan Society for the Promotion of Science (No. 17580092 and 19580120), The Agricultural Chemical Research Foundation, Intelligent Cosmos Foundation, and The Naito Foundation is gratefully acknowledged.

PY - 2009/8/1

Y1 - 2009/8/1

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AB - Both enantiomers and racemate of pyricuol, a phytotoxin isolated from the rice blast disease fungus, Magnaporthe grisea, have been synthesized by using Stille coupling and [2,3]-Wittig rearrangement reactions as the key steps. Both enantiomers induced dark necrotic lesions on rice leaves almost equally, but did not affect the growth of rice second leaf sheath and the germination of lettuce. Only natural enantiomer promoted the root growth of rice and lettuce.

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ER -

Synthesis and plant growth inhibitory activity of both enantiomers of pyricuol, a phytotoxin isolated from rice blast disease fungus Magnaporthe grisea

Abstract

ASJC Scopus subject areas

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