Cytotoxic Ergosteroids from a Strain of the Fungus Talaromyces adpressus

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2023-09-07 DOI:10.1021/acs.jnatprod.3c00089

Meijia Zheng, Yang Xiao, Qin Li, Yixin Lai, Bingbing Dai, Mi Zhang, Xin Kang, Qingyi Tong, Jianping Wang, Chunmei Chen*, Hucheng Zhu* and Yonghui Zhang*,

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引用次数: 1

Abstract

Nine new ergosteroids (1–9) and seven known ones (10–16) were isolated from Talaromyces adpressus. Their structures and absolute configurations were determined by the interpretation of NMR spectroscopic data, HRESIMS, ECD calculations, and single-crystal X-ray diffraction analyses. Structurally, compound 1 was an ergosteroid with two epoxy and a 3α-OH group at ring A, while compounds 8 and 9 had a contracted ring A with a peroxy bridge between C-3 and C-9, which were reported for the first time. Compounds 2–6, 9, 11, and 15 displayed cytotoxic activities with IC₅₀ values ranging from 0.4 to 32 μM, and compound 7 exhibited an immunosuppressive effect against LPS-induced B lymphocyte proliferation with an IC₅₀ value of 8.6 μM. The structure–activity relationships of these compounds are briefly discussed.

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一株真菌Talaromyces adpressus的细胞毒性Ergosteroids

从阿氏Talaromyces adpressus中分离到9种新的麦角甾体（1-9）和7种已知的麦角甾醇（10-16）。通过NMR光谱数据的解释、HRESIMS、ECD计算和单晶X射线衍射分析确定了它们的结构和绝对构型。在结构上，化合物1是一种麦角甾体，在环a上有两个环氧基和一个3α-OH基团，而化合物8和9有一个收缩环a，在C-3和C-9之间有一个过氧桥，这是首次报道。化合物2-6、9、11和15表现出细胞毒性活性，IC50值范围为0.4-32μM，化合物7对LPS诱导的B淋巴细胞增殖表现出免疫抑制作用，IC50为8.6μM。简要讨论了这些化合物的结构-活性关系。

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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.