Bipoladisins A-G, Uncommon Sesterterpenoids with Three Types of Carbon Skeletons from Bipolaris maydis and Their Reversal Activity on Paclitaxel Resistance.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-05-21 DOI:10.1021/acs.jnatprod.5c00024

Yong Shen, Qin Li, Nanjin Ding, Mengru Yu, Xiaoxia Gu, Weiguang Sun, Ying Tang, Chunmei Chen, Yonghui Zhang, Hucheng Zhu

引用次数: 0

Abstract

Bipoladisins A-G (1-7), seven sesterterpenoids featuring three distinct carbon skeletons, were isolated from the fungus Bipolaris maydis. Their structures were elucidated by spectroscopic data, HRESIMS, ECD/ORD calculations, and single-crystal X-ray diffraction analyses. Bipoladisin C (3) contained a unique C-5-C-14 oxygen bridge that formed a complex caged structure. Bipoladisins D (4) and E (5) were a pair of C-17 stereoisomers, both decorated by an oxygen bridge. Bipoladisins F (6) and G (7), possessing a 4/9 bicyclic ring system, were first reported from the genus Bipolaris. Compound 4 could reverse the resistance of cancer cells to paclitaxel (PTX) with the reverse fold of 24 and inhibit the efflux function of P-gp.

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双极甾烷类化合物A-G及其对紫杉醇抗性的逆转作用。

Bipoladisins A-G（1-7）是从真菌Bipolaris maydis中分离得到的具有三个不同碳骨架的7个酯萜类化合物。它们的结构通过光谱数据、hresms、ECD/ORD计算和单晶x射线衍射分析得以阐明。Bipoladisin C(3)含有独特的C-5-C-14氧桥，形成复杂的笼状结构。双极素D(4)和E(5)是一对C-17立体异构体，都有氧桥修饰。双极素F(6)和G(7)具有4/9双环系统，首次从双极草属植物中报道。化合物4能逆转癌细胞对紫杉醇（PTX）的耐药，并能抑制P-gp的外排功能。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.