Two New Ergosterol Derivatives from the Basidiomycete Cortinarius glaucopus. Issue 5 (13th April 2017)

• Record Type: Journal Article
• Authors: Aung, Hnin Thanda; Porta, Alessio; Clericuzio, Marco; Takaya, Yoshiaki; Vidari, Giovanni
• Is Part Of: Chemistry & biodiversity. Volume 14:Issue 5(2017)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-04-13
• Subjects: Cortinarius glaucopus -- Basidiomycota -- Ergosterol derivatives -- Strophastane derivatives -- Glaucoposterols; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201600421
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract : Two new sterols1 and2 and five known ones3 –7 were isolated for the first time from the fruiting bodies of Cortinarius glaucopus . Their structures were established by 1‐ and 2D‐NMR spectra and HR‐FABS‐MS. The relative configuration of1 was firmly determined by comparison of the observed 1 H– 1 H couplings and NOESY correlations, with those predicted for the computed geometries of the conformers. Calculations were performed by means of DFT with the B3LYP functional at 6‐31 + G(d, p) level of theory, in CHCl3 as the solvent. The structures of the new ergosterol derivatives, called glaucoposterol A (1 ) and B (2 ), were thus established as (3 S, 5 R, 7 R, 10 R, 13 R, 17 R, 20 S, 22 R, 23 R, 24 R )‐5, 6‐epoxy‐3, 7, 23‐trihydroxystrophast‐8‐en‐14‐one and (22 E, 3 S, 5 S, 9 S, 10 R, 13 R, 17 R, 20 R, 24 R )‐3, 5‐dihydroxyergosta‐6, 8(14), 22‐trien‐15‐one, respectively. Moreover, the configuration of known strophasterol C (3 ) was determined as (3 S, 5 R, 6 S, 7 R, 10 R, 13 R, 17 R, 20 S, 22 S, 24 R ). Glaucoposterol A (1 ) and strophasterol C (3 ) represent the second finding in nature of steroids with the rare strophastane skeleton. Abstract :