Polyketides with Anti-Inflammatory Activity from Trichoderma koningiopsis, a Rhizosphere Fungus from the Medicinal Plant Polygonum paleaceum

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2023-07, Vol.86 (7), p.1643-1653
• Main Authors: Huang, Liping, Wei, Mengsha, Li, Lanqin, Li, Qin, Sun, Weiguang, Yu, Xiaotan, Wang, Fengqing, Hu, Zhengxi, Chen, Chunmei, Zhu, Hucheng, Zhang, Yonghui
• Format: Article
• Language: English
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.2c00842

Twelve new fungal polyketides, koningiopisins I–P (1–8) and trichoketides C–F (9–12), together with six known congeners (13–18), were isolated from Trichoderma koningiopsis, a rhizosphere fungus obtained from the medicinal plant Polygonum paleaceum. Their structures and absolute configurations were established by spectroscopic analysis, single-crystal X-ray diffraction, the modified Mosher’s method, chemical derivatization, the octant rule, and 13C NMR and ECD calculations. Compounds 1–5 are tricyclic polyketides possessing an octahydrochromene framework with a 6,8-dioxabicyclo[3.2.1]­octane core. Compounds 7 and 8 contain a unique ketone carbonyl group at C-7 and differ from other members of this group of compounds with the ketone carbonyl group at C-1. Compounds 1, 2, and 13 showed inhibitory activity on LPS-induced BV-2 cells on NO production with IC50 values of 14 ± 1, 3.0 ± 0.5, and 8.9 ± 2.7 μM, respectively.