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

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

Regular Articles

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

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

Author information

Aoi Kimishima
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University
Atsuka Nishitomi
Graduate School of Infection Control Sciences, Kitasato University
Iori Tsuruoka
Graduate School of Infection Control Sciences, Kitasato University
Masako Honsho
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University
Sota Negami
Graduate School of Infection Control Sciences, Kitasato University
Sota Honma
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University
Katsuyuki Sakai
Graduate School of Infection Control Sciences, Kitasato University
Toshiyuki Tokiwa
Ōmura Satoshi Memorial Institute, Kitasato University
Hiroki Kojima
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University
Kenichi Nonaka
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University
Shin-ichi Fuji
Faculty of Bioresource Sciences, Akita Prefectural University
Takumi Chinen
Graduate School of Life and Environmental Sciences, University of Tsukuba
Takeo Usui
Graduate School of Life and Environmental Sciences, University of Tsukuba
Yukihiro Asami Corresponding author
Graduate School of Infection Control Sciences, Kitasato University
Ōmura Satoshi Memorial Institute, Kitasato University

Keywords: multidrug-sensitive budding yeast, natural product, derivatization, pathogenic plant fungi

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Supplementary material

2024 Volume 49 Issue 3 Pages 159-167

DOI https://doi.org/10.1584/jpestics.D24-014

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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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