We report on the chemical analysis of a mud dauber wasp nest-associated fungus, Penicillium sp. CMB-MD22, leading to the discovery and structure elucidation of three known (1–3) and two new (4 and 5) anthrones, and a family of new and known bianthrones, neobulgarones 6–23. Detection and structure elucidation of 1–23 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 anti from syn bianthrone isomers, while a facile thermal equilibration was shown to favor anti over syn isomers. The neobulgarones 6–23 are natural products, and a crude extract rich in 6–23 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.

中文翻译：

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重新审视 Neobulgarones：来自澳大利亚泥浆 Dauber 黄蜂巢相关真菌 Penicillium sp. 的 Anti and Syn Bianthrones。CMB-MD22

我们报告了泥涂器黄蜂巢相关真菌Penicillium sp.的化学分析。CMB-MD22，导致三个已知（发现和结构鉴定1 - 3）和两个新的（4和5）anthrones，和一个家族的新的和已知的bianthrones，neobulgarones 6 - 23。检测和结构鉴定1 - 23用详细的光谱分析，以及化学（热）的转换，以及全球天然产品的社会（大亚湾核电站）的分子网络的支持。使用 HPLC 保留时间的经验方法可有效区分anti和Syn二蒽酮的异构体，而一个浅显的热平衡被证明有利于抗过顺式异构体。Neobulgarones 6 – 23是天然产物，富含6 – 23的粗提取物对共同分离的泥鳅蜂巢相关真菌表现出选择性抗真菌活性，暗示可能作为抗真菌化学防御的生态作用。