Asperinamide A, an anti-inflammatory prenylated indole alkaloid possessing an unprecedented bicyclo[2.2.2]diazaoctane fused with substituted piperidine scaffold from Aspergillus sp. TE-65L

文献类型： 外文期刊

第一作者： Zhao, Dong-Lin

作者： Zhao, Dong-Lin;Yuan, Xiao-Long;Zhang, Peng;Huo, Xue-Yan;Huang, Li-Jun;Huo, Xue-Yan;Li, Pan-Pan;Li, Sheng-Ying;Du, Lei

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关键词： Prenylated indole alkaloids; bicyclo[2.2.2]diazaoctane fused with; substituted piperidine scaffold; Structure elucidation; Radical-mediated rearrangement; Anti-inflammatory activity; TLR4/NF; kappa B signaling pathway

期刊名称：TETRAHEDRON （ 影响因子：2.1； 五年影响因子：1.9 ）

ISSN： 0040-4020

年卷期： 2023 年 149 卷

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收录情况： SCI

摘要： Prenylated indole alkaloids (PIAs) containing a bicyclo[2.2.2]diazaoctane ring have gained extensive attention due to their chemical (especially stereochemical), biosynthetic/synthetic, and bioactive interests. In the present study, An unprecedented PIA (namely asperinamide A, 1), featuring a 6/6/5/6/6/6/5 heptacyclic scaffold fused with bicyclo[2.2.2]diazaoctane and substituted piperidine, hitherto unknown among this family of PIAs, along with its biosynthetic-related analogues sclerotiamide (2) and (+)-stephacidin A (3), were isolated from the Nicotiana tabacum-derived endophytic fungus Aspergillus sp. TE-65L. Their structures were unambiguously determined by detailed NMR, mass spectra, and X-ray crystallographic analysis. A detailed plausible biosynthetic analysis for compounds 1-3 was proposed, which revealed that the unique substituted piperidine ring may be formed through a radical-mediated rearrangement. Compound 1 showed significant anti-inflammatory activity targeting the TLR4-MD2 site in the TLR4/NF-kappa B signaling pathway.

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