{"title":"Anti-Bredt-Like Triterpenoids from Mycelial Cultures of the Edible Mushroom Oudemansiella cf. canarii","authors":"Malipan Sappan, Panida Chinthanom, Vanicha Vichai, Thitiya Boonpratuang, Teera Chantarojsiri* and Masahiko Isaka*, ","doi":"10.1021/acs.orglett.5c03296","DOIUrl":null,"url":null,"abstract":"<p >Sixteen undescribed triterpene glycosides, oudecanarins A–P (<b>1</b>–<b>16</b>), were isolated from cultures of basidiomycete <i>Oudemansiella</i> cf. <i>canarii</i> TBRC-BCC 85371. Oudecanarins A–G (<b>1</b>–<b>7</b>) contain a bicyclo[4.3.1]decene system bearing the bridgehead double bond as a DE ring of pentacyclic triterpene. The unique carbon skeleton was confirmed by the X-ray crystallographic analysis of oudecanarin B (<b>2</b>). The proposed plausible late-stage biosynthetic pathway for oudecanarin A (<b>1</b>) was supported by chemical conversion experiments.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 37","pages":"10429–10434"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03296","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
Sixteen undescribed triterpene glycosides, oudecanarins A–P (1–16), were isolated from cultures of basidiomycete Oudemansiella cf. canarii TBRC-BCC 85371. Oudecanarins A–G (1–7) contain a bicyclo[4.3.1]decene system bearing the bridgehead double bond as a DE ring of pentacyclic triterpene. The unique carbon skeleton was confirmed by the X-ray crystallographic analysis of oudecanarin B (2). The proposed plausible late-stage biosynthetic pathway for oudecanarin A (1) was supported by chemical conversion experiments.
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.