Antiviral Chlorinated Drimane Meroterpenoids from the Fungus Talaromyces pinophilus LD-7 and Their Biosynthetic Pathway.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-08-23 Epub Date: 2024-08-10 DOI:10.1021/acs.jnatprod.4c00539

Meng Ren, Zhuang Li, Zixuan Wang, Wenjie Han, Fengxiao Wang, Yu Li, Wenrong Zhang, Xingjian Liu, Jun Zhang, Du-Qiang Luo

引用次数: 0

Abstract

Ten new drimane meroterpenoids talarines A-J (1-10), along with six known analogues (11-16), were isolated from desert soil-derived fungus Talaromyces pinophilus LD-7. Their 2D structures were elucidated by comprehensive interpretation of NMR and HRESIMS data. Electronic circular dichroism calculation was used to establish their absolute configurations. Compounds 2, 10, and 11 showed antiviral activities toward vesicular stomatitis virus with IC₅₀ values of 18, 15, and 23 nM, respectively. The structure-bioactivity relationship indicated that chlorine substitution at C-5 contributed greatly to their antiviral activities. Finally, we identified a new halogenase outside the biosynthetic gene cluster, which was responsible for C-5 halogenation of the precursor isocoumarin 17 as a tailoring step in chlorinated meroterpenoids assembly.

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来自真菌 Talaromyces pinophilus LD-7 的抗病毒氯化二烷基 Meroterpenoids 及其生物合成途径。

从源自沙漠土壤的真菌 Talaromyces pinophilus LD-7 中分离出了 10 种新的 drimane meroterpenoids talarines A-J（1-10）以及 6 种已知的类似物（11-16）。通过全面解读核磁共振和 HRESIMS 数据，阐明了它们的二维结构。电子圆二色性计算用于确定它们的绝对构型。化合物 2、10 和 11 对水泡性口炎病毒具有抗病毒活性，IC50 值分别为 18、15 和 23 nM。结构-生物活性关系表明，C-5 处的氯取代在很大程度上促进了它们的抗病毒活性。最后，我们在生物合成基因簇之外发现了一种新的卤化酶，它负责前体异香豆素 17 的 C-5 卤化，这是氯化美拉德珀类组装的一个剪裁步骤。

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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.