Discovery, Characterization, and Anti-XOD Activity of Calcium Metallophore from Coix lacryma-jobi

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-30 DOI:10.1021/acs.orglett.4c04391

Yan Xue, Da Song, Shi-Rong Liu, Chuan-Wen Lei, Hui Shi, Ying Zhou, Ting-Ting Feng, Xin Wei

引用次数: 0

Abstract

In this work, coixalkyne A (1), a natural polynuclear calcium complex with a novel cross-shaped molecular architecture, was isolated from Coix lacryma-jobi L. along with the undescribed analogue coixalkyne B (2). Their structures were identified by means of NMR spectroscopy, ECD calculations, and single-crystal X-ray diffraction. It is noteworthy that the calcium ligands of 1 as well as compound 2 possess rare terminal alkynes and a nor-carbon sesquiterpene (C14) framework. The antihyperuricemic activity of C. lacryma-jobi and xanthine oxidase (XOD) inhibitory effects of 1–2 were elucidated by in vivo and in vitro assays, while the possible mechanism of action was suggested by molecular docking. Different from the reported chemical synthesis and protein calcium carriers, the discovery of compounds 1 and 2 provided new proof for the natural calcium metallophore in plants with xanthine oxidase inhibitory activity.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.