Rogersonins C–F, 9H-Imidazo[2,1-i]purine-Incorporating Adenine-Polyketide Hybrids from an Ophiocordyceps-Associated Clonostachys rogersoniana

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL Journal of Natural Products Pub Date : 2024-06-18 DOI:10.1021/acs.jnatprod.4c00266

Xintong Hou, Ruikun Wang, Chunyan Zhang, Yang Xu, Shuaiming Zhu, Yang Zhang*, Xingzhong Liu and Yongsheng Che*,

引用次数: 0

Abstract

Rogersonins C–F (1–4), four unprecedented adenine-polyketide hybrids featuring a rare 9H-imidazo[2,1-i]purine (1,N⁶-ethenoadenine) moiety, were isolated from an Ophiocordyceps-associated fungus, Clonostachys rogersoniana. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1–4 were assigned by a combination of the modified Mosher method, chemical degradation, electronic circular dichroism (ECD) calculations, and X-ray crystallography using Cu Kα radiation. Compound 3 downregulated the expression of PD-L1 protein in MDA-MB-231 and A549 cells, but did not show detectable effect on mRNA transcription of the PD-L1-encoding gene CD274.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Rogersonins C-F，9H-咪唑并[2,1-i]嘌呤内含腺嘌呤-多酮杂交体，来自一种与麦角菌相关的 Clonostachys rogersoniana。

从一种与麦角菌相关的真菌 Clonostachys rogersoniana 中分离出了 Rogersonins C-F（1-4），这是四种前所未有的腺嘌呤-多酮杂交化合物，具有罕见的 9H-咪唑并[2,1-i]嘌呤（1,N6-乙烯腺嘌呤）分子。它们的结构主要是通过核磁共振实验阐明的。通过改良莫舍尔法、化学降解、电子圆二色性（ECD）计算和使用 Cu Kα 辐射的 X 射线晶体学相结合的方法，确定了 1-4 的绝对构型。化合物 3 下调了 MDA-MB-231 和 A549 细胞中 PD-L1 蛋白的表达，但对 PD-L1 编码基因 CD274 的 mRNA 转录没有显示出可检测到的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

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.