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

Liping Huang, Mengsha Wei, Lanqin Li, Qin Li, Weiguang Sun, Xiaotan Yu, Feng‐Qing Wang, Zhengxi Hu, Chunmei Chen, Hucheng Zhu, Yonghui Zhang

2023Journal of Natural Products13 citationsDOI

Abstract

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 13 C 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 IC 50 values of 14 ± 1, 3.0 ± 0.5, and 8.9 ± 2.7 μM, respectively.

Topics & Concepts

DerivatizationKetoneRhizosphereStereochemistryChemistryPolygonumGliotoxinPolygonaceaeBotanyOrganic chemistryBiologyBacteriaHigh-performance liquid chromatographyGeneticsEcologyAspergillus fumigatusMicrobial Natural Products and BiosynthesisPhytochemical compounds biological activitiesMarine Sponges and Natural Products
Polyketides with Anti-Inflammatory Activity from <i>Trichoderma koningiopsis</i>, a Rhizosphere Fungus from the Medicinal Plant <i>Polygonum paleaceum</i> | Litcius