Acremosides A–G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-04-01 DOI:10.1021/acs.jnatprod.4c00015

Xiaomeng Hao, Shasha Li, Jianrui Li, Guiyang Wang, Jiao Li, Zonggen Peng* and Maoluo Gan*,

引用次数: 0

Abstract

Seven new sugar alcohol-conjugated acyclic sesquiterpenes, acremosides A–G (1–7), were isolated from the cultures of the sponge-associated fungus Acremonium sp. IMB18-086 cultivated with heat-killed Pseudomonas aeruginosa. The structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data. The relative configurations were established by J-based configuration analysis and acetonide derivatization. The absolute configurations were elucidated by the Mosher ester method and ECD calculations. The structures of acremosides E–G (5–7) featured the linear sesquiterpene skeleton with a tetrahydrofuran moiety attached to a sugar alcohol. Acremosides A (1) and C–E (3–5) showed significant inhibitory activities against hepatitis C virus (EC₅₀ values of 4.8–8.8 μM) with no cytotoxicity (CC₅₀ of >200 μM).

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Acremosides A-G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species.

从用热处理铜绿假单胞菌培养的海绵相关真菌 Acremonium sp.通过对一维和二维核磁共振光谱数据进行综合分析，确定了这些化合物的结构。通过基于 J 的构型分析和丙酮衍生化确定了相对构型。绝对构型是通过 Mosher 酯法和 ECD 计算阐明的。阿克瑞木苷 E-G（5-7）的结构以线性倍半萜骨架为特征，四氢呋喃分子与糖醇相连。Acremosides A (1) 和 C-E (3-5) 对丙型肝炎病毒具有显著的抑制活性（EC50 值为 4.8-8.8 μM），且无细胞毒性（CC50 >200 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.