{"title":"Synthesis and biological evaluation of burnettiene A derivatives enabling discovery of novel fungicide candidates.","authors":"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","doi":"10.1584/jpestics.D24-014","DOIUrl":null,"url":null,"abstract":"<p><p>An antifungal polyene-decalin polyketide natural product, burnettiene A (<b>1</b>) has been re-discovered from the culture broth of <i>Lecanicillium primulinum</i> (current name: <i>Flavocillium primulinum</i>) FKI-6715 strain utilizing our original multidrug-sensitive yeast system. This polyene-decalin polyketide natural product was originally isolated from <i>Aspergillus burnettii</i>. The antifungal activity of <b>1</b> against <i>Candida albicans</i> has been reported. However, only one fungal species for the antifungal activity of <b>1</b> has been revealed, and details of the antifungal activity against other pathogenic fungus remain unknown. After extensive screening for antifungal activity, we found that <b>1</b> exhibits broad antifungal activity against pathogenic plant fungi, including <i>Colletotrichum gloeosporioides</i>, <i>Botrytis cinerea</i>, <i>Pyricularia oryzae</i>, <i>Leptosphaeria maculans</i>, and <i>Rhizoctonia solani</i>. Furthermore, we synthesized 12 derivatives from <b>1</b> and evaluated their antifungal activity to reveal the detailed structure-activity relationship. The methyl ester derivative showed antifungal activity against <i>Saccharomyces cerevisiae</i> 12geneΔ0HSR-iERG6 100-fold more potent than that of <b>1</b>. Our research indicates that <b>1</b> would be a promising natural product as a new fungicidal candidate and the methyl ester derivative especially has great potential.</p>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"49 3","pages":"159-167"},"PeriodicalIF":1.5000,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11464271/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Pesticide Science","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1584/jpestics.D24-014","RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENTOMOLOGY","Score":null,"Total":0}
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.
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.