Yan Xue, Da Song, Shi-Rong Liu, Chuan-Wen Lei, Hui Shi, Ying Zhou, Ting-Ting Feng, Xin Wei
{"title":"Discovery, Characterization, and Anti-XOD Activity of Calcium Metallophore from Coix lacryma-jobi","authors":"Yan Xue, Da Song, Shi-Rong Liu, Chuan-Wen Lei, Hui Shi, Ying Zhou, Ting-Ting Feng, Xin Wei","doi":"10.1021/acs.orglett.4c04391","DOIUrl":null,"url":null,"abstract":"In this work, coixalkyne A (<b>1</b>), a natural polynuclear calcium complex with a novel cross-shaped molecular architecture, was isolated from <i>Coix lacryma-jobi</i> L. along with the undescribed analogue coixalkyne B (<b>2</b>). 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 <b>1</b> as well as compound <b>2</b> possess rare terminal alkynes and a <i>nor</i>-carbon sesquiterpene (C14) framework. The antihyperuricemic activity of <i>C. lacryma-jobi</i> and xanthine oxidase (XOD) inhibitory effects of <b>1</b>–<b>2</b> were elucidated by <i>in vivo</i> and <i>in vitro</i> 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 <b>1</b> and <b>2</b> provided new proof for the natural calcium metallophore in plants with xanthine oxidase inhibitory activity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"162 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04391","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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.
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.