{"title":"Tinocrinoids A-D, clerodane diterpenoids from Tinospora crispa and structural revision of related diterpenoid","authors":"Ming-Jie Huang, Yi-Ke Yin, Yi-Fei Zhang, Jie Bao, Jun-Sheng Zhang, Hua Zhang","doi":"10.1016/j.tet.2025.134851","DOIUrl":null,"url":null,"abstract":"<div><div>Four new clerodane diterpenoids, tinocrinoids A−D (<strong>2</strong>−<strong>5</strong>), were isolated from the leaves of <em>Tinospora crispa</em>. Compounds <strong>3</strong>−<strong>5</strong> represents rare clerodane diterpenoids with a C-8-<em>O</em>-C-12 ether bridge. The structures of the new diterpenoids were elucidated using spectral analysis in conjunction with NMR/ECD calculations and X-ray crystallography. The application of computational methods, enhanced by the DP4+ probability approach, made it possible to propose a structural revision for the known diterpenoid, tinobakisin. Evaluation of their immune modulatory effects revealed that <strong>2</strong> could enhance the proliferation of Jurkat T cells in a dose-dependent manner.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"185 ","pages":"Article 134851"},"PeriodicalIF":2.2000,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025004077","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Four new clerodane diterpenoids, tinocrinoids A−D (2−5), were isolated from the leaves of Tinospora crispa. Compounds 3−5 represents rare clerodane diterpenoids with a C-8-O-C-12 ether bridge. The structures of the new diterpenoids were elucidated using spectral analysis in conjunction with NMR/ECD calculations and X-ray crystallography. The application of computational methods, enhanced by the DP4+ probability approach, made it possible to propose a structural revision for the known diterpenoid, tinobakisin. Evaluation of their immune modulatory effects revealed that 2 could enhance the proliferation of Jurkat T cells in a dose-dependent manner.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.