抗真菌 Pseuboyenes A-J, Bergamotene-Derived Sesquiterpenoids from a Cold-Seep-Derived Pseudallescheria boydii

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-05-03 DOI:10.1021/acs.jnatprod.3c01175
Zhen Ying, Xiao-Ming Li, Sui-Qun Yang, Hong-Lei Li, Xin Li, Bin-Gui Wang and Ling-Hong Meng*, 
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摘要

通过对一种源自冷沉积物的真菌 Pseudallescheria boydii CS-793 进行化学研究,发现了 10 种新型佛手柑烯类倍半萜化合物,即 pseuboyenes A-J (1-10)。通过光谱和 X 射线晶体学分析以及使用改进的莫舍尔法,这些化合物的结构得以阐明。化合物 1 代表了第一个含有 6-氧代双环[3.2.1]辛烷核与乳酸甲酯单元加成的 β-佛手柑烯的实例,而化合物 8-10 则涉及佛手柑烯的骨架重排。化合物 2-5 对 Colletotrichum gloeosporioides Penz.和 Fusarium oxysporum 具有显著的抗真菌活性,其 MICs 为 0.5 至 8 μg/mL。化合物 4 具有体外抗 F. proliferatum 的效果,EC50 值为 1.0 μg/mL。
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Antifungal Pseuboyenes A–J, Bergamotene-Derived Sesquiterpenoids from a Cold-Seep-Derived Pseudallescheria boydii

A chemical investigation of a cold-seep-sediment-derived fungus, Pseudallescheria boydii CS-793, resulted in characterization of 10 novel bergamotene-derived sesquiterpenoids, pseuboyenes A–J (110). Their structures were elucidated by spectroscopic and X-ray crystallographic analyses as well as using the modified Mosher’s method. Compound 1 represents the first example of a β-bergamotene containing a 6-oxobicyclo[3.2.1]octane nucleus adducted with a methyl lactate unit, while 810 involve a skeletal rearrangement from bergamotene. Compounds 25 showed significant antifungal activities against Colletotrichum gloeosporioides Penz. and Fusarium oxysporum with MICs ranging from 0.5 to 8 μg/mL. Compound 4 exhibited an in vitro anti-F. proliferatum effect with an EC50 value of 1.0 μg/mL.

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来源期刊
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.
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