Lanostanoid triterpenes from the fungus Rigidoporus microporus. Issue 21 (2nd November 2021)

• Record Type: Journal Article
• Authors: Rincón, Yuliet A.; Siless, Gastón E.; Amado, Lucía Daniela; Dansey, María Virginia; Grassi, Emanuel; Schenone, Nahuel; Cabrera, Gabriela M.
• Is Part Of: Natural product research. Volume 35:Issue 21(2021)
• Page Start: 3945
• Page End: 3954
• Publication Date: 2021-11-02
• Subjects: Rigidoporus microporus -- 3-ketolanostanes -- 1-methyl-19-nor-lanostane -- liver X receptors -- antifungal activity; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2020.1752205
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Five new lanostanoid triterpenes were isolated from the extract of R. microporus . Three of the metabolites (1–3 ) present a Δ 8, 9 skeleton with an uncommon keto functionality at C–1. Another compound (4 ) has an unprecedented rearranged skeleton in which methyl-19 was transposed to C–1, with conjugated double bonds at Δ 1–10 and Δ 8–9 . All of the compounds have hydroxylated or furane-cyclized side-chains. The structures were elucidated by spectroscopic methods, and the absolute configuration of the hydroxyl-bearing carbon in the side chain of compound 5 was established in silico . The metabolites were evaluated for their antifungal activity and the bioactivity as agonist/antagonists of the liver X receptors (LXRs). Compound 4 presents antifungal activity and compounds 3 and 5 are the agonists of LXRs. Graphical Abstract: