文献类型： 外文期刊

作者： Zhai, Yi-Jie ¹ ; Zhou, Zhen-Zhen ² ; Wang, Wen-Ji ¹ ; Wang, Xin-Yu ¹ ; Wang, Zi-Jue ¹ ; Dai, Guang-Zhi ⁶ ; Lei, Xinxiang ⁴ ; Li, Wen-Li ¹ ; Gao, Jin-Ming ¹ ; Han, Wen-Bo ¹ ;

作者机构： 1.Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Xianyang 712100, Peoples R China

2.Jiangsu Acad Agr Sci, Prov Key Lab Agrobiol, Nanjing 210014, Jiangsu, Peoples R China

3.Jiangsu Acad Agr Sci, Inst Germplasm Resources & Biotechnol, Nanjing 210014, Jiangsu, Peoples R China

4.Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou Magnet Resonance Ctr, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

5.Northwest A&F Univ, Coll Plant Protect, Yangling 712100, Shaanxi, Peoples R China

6.Shandong Univ, State Key Lab Microbial Technol, Helmholtz Inst Biotechnol, Helmholtz Int Lab for Antiinfect, Qingdao 266237, Shandong, Peoples R China

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.