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

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2023-07-14 DOI:10.1021/acs.jnatprod.2c00842

Liping Huang, Mengsha Wei, Lanqin Li, Qin Li, Weiguang Sun, Xiaotan Yu, Fengqing Wang, Zhengxi Hu, Chunmei Chen*, Hucheng Zhu* and Yonghui Zhang*,

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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 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.

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药用植物古蓼根际真菌克宁木霉抗炎活性的聚酮类化合物研究

从药用植物古蓼木霉根际真菌koningiopsis中分离得到12个新的真菌多酮类化合物，koningiopisins I-P(1-8)和trichoketides C-F(9-12)，以及6个已知的同源物(13-18)。通过光谱分析、单晶x射线衍射、改进的Mosher法、化学衍生化、八阶规则、13C NMR和ECD计算，确定了它们的结构和绝对构型。化合物1-5是具有6,8-二恶双环[3.2.1]辛烷核心的八氢铬骨架的三环聚酮。化合物7和8在C-7上含有一个独特的酮羰基，与其他在C-1上含有酮羰基的化合物不同。化合物1、2、13对lps诱导的BV-2细胞产生NO具有抑制作用，IC50值分别为14±1 μM、3.0±0.5 μM和8.9±2.7 μM。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.