Synthesis and biological evaluation of burnettiene A derivatives enabling discovery of novel fungicide candidates.

IF 1.5 4区农林科学 Q2 ENTOMOLOGY

Journal of Pesticide Science Pub Date : 2024-08-20 DOI:10.1584/jpestics.D24-014

Aoi Kimishima, Atsuka Nishitomi, Iori Tsuruoka, Masako Honsho, Sota Negami, Sota Honma, Katsuyuki Sakai, Toshiyuki Tokiwa, Hiroki Kojima, Kenichi Nonaka, Shin-Ichi Fuji, Takumi Chinen, Takeo Usui, Yukihiro Asami

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引用次数: 0

Abstract

An antifungal polyene-decalin polyketide natural product, burnettiene A (1) has been re-discovered from the culture broth of Lecanicillium primulinum (current name: Flavocillium primulinum) FKI-6715 strain utilizing our original multidrug-sensitive yeast system. This polyene-decalin polyketide natural product was originally isolated from Aspergillus burnettii. The antifungal activity of 1 against Candida albicans has been reported. However, only one fungal species for the antifungal activity of 1 has been revealed, and details of the antifungal activity against other pathogenic fungus remain unknown. After extensive screening for antifungal activity, we found that 1 exhibits broad antifungal activity against pathogenic plant fungi, including Colletotrichum gloeosporioides, Botrytis cinerea, Pyricularia oryzae, Leptosphaeria maculans, and Rhizoctonia solani. Furthermore, we synthesized 12 derivatives from 1 and evaluated their antifungal activity to reveal the detailed structure-activity relationship. The methyl ester derivative showed antifungal activity against Saccharomyces cerevisiae 12geneΔ0HSR-iERG6 100-fold more potent than that of 1. Our research indicates that 1 would be a promising natural product as a new fungicidal candidate and the methyl ester derivative especially has great potential.

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合成灼烧烯 A 衍生物并对其进行生物学评价，从而发现新型候选杀真菌剂。

利用我们独创的多药敏感酵母系统，我们从原毛黄腐霉菌（Lecanicillium primulinum，现名：Flavocillium primulinum）FKI-6715 菌株的培养液中重新发现了一种抗真菌多烯萘多酮苷天然产物 Burnettiene A (1)。这种多烯癸醛多酮天然产物最初是从燃烧曲霉（Aspergillus burnettii）中分离出来的。据报道，1 对白色念珠菌具有抗真菌活性。然而，1 的抗真菌活性只针对一种真菌，对其他致病真菌的抗真菌活性仍不清楚。经过广泛的抗真菌活性筛选，我们发现 1 对病原植物真菌具有广泛的抗真菌活性，包括球孢子菌（Colletotrichum gloeosporioides）、灰霉病菌（Botrytis cinerea）、Pyricularia oryzae、Leptosphaeria maculans 和根瘤菌（Rhizoctonia solani）。此外，我们还从 1 中合成了 12 种衍生物，并评估了它们的抗真菌活性，以揭示详细的结构-活性关系。我们的研究表明，1 是一种很有前途的天然产物，可作为一种新的杀真菌候选物，尤其是其甲酯衍生物具有很大的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Pesticide Science 农林科学-昆虫学

CiteScore

4.30

自引率

4.20%

发文量

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.