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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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。
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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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