重新审视新保加利亚酮类化合物：来自澳大利亚泥蜂巢穴相关真菌CMB - MD22的双蒽酮类化合物。

Neobulgarones Revisited: and Bianthrones from an Australian Mud Dauber Wasp Nest-Associated Fungus, sp. CMB-MD22.

作者信息

Elbanna Ahmed H, Khalil Zeinab G, Bernhardt Paul V, Capon Robert J

机构信息

Institute for Molecular Bioscience, The University of Queensland, Brisbane, QLD 4072, Australia.

School of Chemistry and Molecular Bioscience, The University of Queensland, Brisbane, QLD 4072, Australia.

出版信息

J Nat Prod. 2021 Mar 26;84(3):762-770. doi: 10.1021/acs.jnatprod.0c01035. Epub 2021 Feb 3.

DOI:10.1021/acs.jnatprod.0c01035

PMID:33534571

Abstract

We report on the chemical analysis of a mud dauber wasp nest-associated fungus, sp. CMB-MD22, leading to the discovery and structure elucidation of three known (-) and two new ( and ) anthrones, and a family of new and known bianthrones, neobulgarones -. Detection and structure elucidation of - was supported by detailed spectroscopic analysis, as well as chemical (thermal) transformations, and global natural products social (GNPS) molecular networking. An empirical approach using HPLC retention times was effective at differentiating from bianthrone isomers, while a facile thermal equilibration was shown to favor over isomers. The neobulgarones - are natural products, and a crude extract rich in - exhibits selective antifungal activity against a co-isolated mud dauber wasp nest-associated fungus, suggestive of a possible ecological role as an antifungal chemical defense.

摘要

我们报告了一种与泥蜂巢穴相关的真菌（种CMB - MD22）的化学分析，结果发现并阐明了三种已知的（-）蒽酮和两种新的（和）蒽酮，以及一个新的和已知的联蒽酮家族，新保加利亚酮 - 。 - 的检测和结构阐明得到了详细的光谱分析、化学（热）转化以及全球天然产物社会（GNPS）分子网络的支持。使用高效液相色谱保留时间的经验方法有效地区分了联蒽酮异构体，同时表明一种简便的热平衡有利于 - 异构体而非 - 异构体。新保加利亚酮 - 是天然产物，富含 - 的粗提物对一种共同分离出的与泥蜂巢穴相关的真菌表现出选择性抗真菌活性，这表明其可能作为一种抗真菌化学防御发挥生态作用。