Synthesis and antifungal activity of the proposed structure of a volatile compound isolated from the edible mushroom Hypsizygus marmoreus

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Journal of Pesticide Science Pub Date : 2022-02-20 DOI:10.1584/jpestics.D21-061
Nguyen Thi Ngoc Anh, Daisuke Miyaji, Kumiko Osaki-Oka, Tatsuo Saito, A. Ishihara, A. Yajima
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Abstract

We synthesized the proposed structure of an antifungal compound detected in the culture broth of the edible mushroom Hypsizygus marmoreus. Using the Evans aldol and Abiko–Masamune aldol reactions as the key steps, we synthesized all of the stereoisomers of the compound with high stereoselectivity. The GC retention times and the fragmentation patterns in the mass spectra of the synthesized isomers did not match those of the natural product. Therefore, this result may imply that it is necessary to reisolate the natural product and reconsider its structure. All of the synthesized isomers were found to exhibit antifungal activity against the phytopathogenic fungus Alternaria brassicicola. Due to their simple structures, the obtained isomers could be lead compounds for new pesticides.
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一种从食用菌Hypsizygus marmoreus中分离的挥发性化合物的合成及其抗真菌活性
我们合成了一种在食用菌海绵菌培养液中检测到的抗真菌化合物的拟议结构。以Evans羟醛和Abiko–Masamune羟醛反应为关键步骤,合成了该化合物所有具有高立体选择性的立体异构体。合成异构体的GC保留时间和质谱中的碎片模式与天然产物的不匹配。因此,这一结果可能意味着有必要重新分离天然产物并重新考虑其结构。所有合成的异构体都对植物病原真菌油菜链格孢具有抗真菌活性。由于其结构简单,所获得的异构体可能是新农药的先导化合物。
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来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
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