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

IF 5 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
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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 12 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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薏米中钙金属蛋白的发现、表征及抗xod活性研究
在这项工作中,coixalkyne A(1)是一种天然多核钙配合物,具有新颖的十字形分子结构,从Coix lacryma-jobi L.中分离出来,与未描述的类似物coixalkyne B(2)一起。它们的结构通过NMR波谱,ECD计算和单晶x射线衍射进行了鉴定。值得注意的是,化合物1和化合物2的钙配体具有罕见的末端炔和无碳倍半萜(C14)框架。通过体内和体外实验,阐明了丙烯丙酸的抗高尿酸活性和黄嘌呤氧化酶(XOD)抑制作用,并通过分子对接提出了其可能的作用机制。与文献报道的化学合成和蛋白质钙载体不同,化合物1和2的发现为植物中天然钙金属蛋白具有黄嘌呤氧化酶抑制活性提供了新的证据。
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来源期刊
Organic Letters
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.
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