Syntheses of natural 1,3-polyol/alpha-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi

Yamauchi Satoshi; Isozaki Yasuyoshi; Nishiwaki Hisashi; Akiyama Koichi

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Syntheses of natural 1,3-polyol/alpha-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi

机译：合成天然1,3-多元醇/α-吡喃酮及其所有立体异构体，以评估其对植物病原真菌的抗真菌活性

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All stereoisomers of 1,3-polyol/alpha-pyrone 1-8 with more than 99% ee were synthesized to estimate the effect of stereochemistry on the antifungal activity. The absolute configuration of natural compound was determined as (6R,2'S,4'R)-2. The eight stereoisomers showed the antifungal activity against plant pathogenic Alternaria alternata Japanese pear pathotype and Colletotrichum lagenarium. The large difference of activity level was not observed between stereoisomers, showing 43-72% of growth ratio against control at 0.5 mM. The most potent stereoisomer was (6S,2'S,4'S)-8 and the activity of ( 6R,2'S,4'S)-1 was weakest against both fungi. (C) 2015 Elsevier Ltd. All rights reserved.

机译：合成了具有超过99％ee的1,3-多元醇/α-吡喃酮1-8的所有立体异构体，以评估立体化学对抗真菌活性的影响。天然化合物的绝对构型确定为（6R，2'S，4'R）-2。八种立体异构体均显示出对植物病原体链格孢日本梨病原体和炭疽菌的抗真菌活性。在立体异构体之间未观察到活性水平的大差异，显示出在0.5mM下相对于对照的生长率的43-72％。最有效的立体异构体是（6S，2'S，4'S）-8，而（6R，2'S，4'S）-1对两种真菌的活性最弱。（C）2015 Elsevier Ltd.保留所有权利。

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《Bioorganic and Medicinal Chemistry Letters》 |2015年第10期|共4页
作者
Yamauchi Satoshi; Isozaki Yasuyoshi; Nishiwaki Hisashi; Akiyama Koichi;
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正文语种 eng
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5; 6-Dihydro-alpha-pyrone; 1; 3-Polyol/alpha-pyrone; Antifungal activity;

机译：5;6-二氢-α-吡喃酮;1;3-多元醇/α-吡喃酮;抗真菌活性;

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1. Syntheses of natural 1,3-polyol/alpha-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi [J] . Yamauchi Satoshi, Isozaki Yasuyoshi, Nishiwaki Hisashi, Bioorganic and Medicinal Chemistry Letters . 2015,第10期

机译：合成天然1,3-多元醇/α-吡喃酮及其所有立体异构体，以评估其对植物病原真菌的抗真菌活性
2. Strategy for Enantio- and Diastereoselective Syntheses of All Possible Stereoisomers of 1,3-Polyol Arrays Based on a Highly Catalyst-Controlled Epoxidation of alpha,beta-Unsaturated Morpholinyl Amides: Application to Natural Product Synthesis [J] . Shin-ya Tosaki, Yoshihiro Horiuchi, Tetsuhiro Nemoto, Chemistry: A European journal . 2004,第6期

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5. Variability in the antifungal activity of wetland plants and implications to natural products research. [D] . Kuhajek, Jeanne Marie. 2001

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Syntheses of natural 1,3-polyol/alpha-pyrone and its all stereoisomers to estimate antifungal activities against plant pathogenic fungi

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