Cadinane- and drimane-type sesquiterpenoids produced by Paecilomyces sp. TE-540, an endophyte from Nicotiana tabacum L., are acetylcholinesterase inhibitors

文献类型： 外文期刊

第一作者： Xu, Kuo

作者： Xu, Kuo;Li, Xiu-Qi;Luo, Tian;Yuan, Xiao-Long;Zhang, Zhong-Feng;Zhang, Peng;Zhou, Qi;Li, Xiu-Qi

作者机构：

关键词： Paecilomyces; Nicotiana tabacum; Cadinane; Drimane; Acetylcholinesterase

期刊名称：BIOORGANIC CHEMISTRY （ 影响因子：5.275； 五年影响因子：5.252 ）

ISSN： 0045-2068

年卷期： 2020 年 104 卷

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收录情况： SCI

摘要： Sesquiterpenoids with diverse skeleton types are regarded as potential lead compounds in pharmacological and other applications. Herein, we report the discovery of two new cadinane-type sesquiterpenoids, paecilacadinol A (1) and B (2); two new drimane-type sesquiterpenoids, ustusol D (3) and ustusol E (4); and six known analogs (5-10) from the endophytic fungus Paecilomyces sp. TE-540, enriching the structural diversity of naturally occurring sesquiterpenoids. Their planar structures were determined on the basis of detailed interpretation of 1D and 2D NMR spectroscopy and HRESIMS data, while their stereochemical structures were established by X-ray crystallographic analyses for 1 and 3-8 and theoretical calculations for 2. Notably, compounds 1 and 2 represent novel examples of cadinane-type sesquiterpenoids with ether bonds formed by intramolecular dehydration. Compounds 5 and 6 showed moderate activities against acetylcholinesterase (AChE), with IC50 values of 43.02 +/- 6.01 and 35.97 +/- 2.12 mu M, respectively. Docking analysis predicted that 5 bound well in the catalytic pocket of AChE via hydrophobic interactions with Trp84, Gly117, Ser122, and Tyr121 residues, while 6 was located with Asp72 and Ser122 residues.

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