Periconiastone A, an Antibacterial Ergosterol with a Pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane System from Periconia sp. TJ403-rc01

Periconiastone A (1), an ergosterol with an unprecedented pentacyclo­[8.7.0.01,5.02,14.010,15]­heptadecane system, was isolated from Periconia sp. TJ403-rc01. Its structure was assigned by extensive spectroscopic analyses and quantum-chemical 13C NMR and ECD calculations. A vinylogous α-ketol rearra...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8469-8472
Main Authors: Gao, Weixi, Chai, Chenwei, He, Yan, Li, Fengli, Hao, Xincai, Cao, Fei, Gu, Lianghu, Liu, Junjun, Hu, Zhengxi, Zhang, Yonghui
Format: Article
Language:English
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Summary:Periconiastone A (1), an ergosterol with an unprecedented pentacyclo­[8.7.0.01,5.02,14.010,15]­heptadecane system, was isolated from Periconia sp. TJ403-rc01. Its structure was assigned by extensive spectroscopic analyses and quantum-chemical 13C NMR and ECD calculations. A vinylogous α-ketol rearrangement and an aldol condensation reaction during biosynthesis were proposed as key steps for the formation of 1. Compound 1 showed antibacterial activity against Gram-positive S. aureus and E. faecalis with MIC values of 4 and 32 μg/mL, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03270