Herpotriquinones A and B, two dimeric naphthoquinone-epoxycyclohexenone adducts with anti-neuroinflammatory activity from the isopod-associated fungus Herpotrichia sp. SF09

文献类型： 外文期刊

第一作者： Zhai, Yi-Jie

作者： Zhai, Yi-Jie;Wang, Wen-Ji;Wang, Xin-Yu;Wang, Zi-Jue;Li, Wen-Li;Gao, Jin-Ming;Han, Wen-Bo;Zhou, Zhen-Zhen;Zhou, Zhen-Zhen;Lei, Xinxiang;Zhai, Yi-Jie;Li, Wen-Li;Dai, Guang-Zhi

作者机构：

期刊名称：ORGANIC CHEMISTRY FRONTIERS （ 影响因子：4.7； 五年影响因子：4.5 ）

ISSN： 2052-4129

年卷期： 2024 年 11 卷 21 期

页码：

收录情况： SCI

摘要： Herpotriquinones A and B (1 and 2), two pyran-bridged naphthoquinone-epoxycyclohexenone dimers with an unprecedented 6/6/6/6/6-fused pentacyclic ring skeleton, along with two known precursors (3 and 4) were isolated from the isopod-associated fungus Herpotrichia sp. SF09. Their structures were elucidated by means of spectroscopic data, single-crystal X-ray diffraction, and quantum chemical calculations of C-13 NMR and electronic circular dichroism (ECD). Herpotriquinones A and B (1 and 2) represent the first examples of polyketide heterodimers biogenetically constructed by a molecule of epoxycyclohexenone with a naphthoquinone unit via a rare formal oxa-[3 + 3] cycloaddition. The density functional theory (DFT) calculations and intermediate-trapping experiment facilitated the proposal of the biosynthetic pathway for these polyketides. In addition, compounds 1 and 2 were found to be potent anti-neuroinflammatory agents in CuSO4-induced zebrafish and lipopolysaccharide (LPS)-stimulated BV-2 microglial cells. Meanwhile, western blot analysis suggested that 1 and 2 could ameliorate the neuroinflammation by suppressing the activation of the NF-kappa B and MAPK signaling pathways.

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