Sesquiterpenes from Cultures of the Basidiomycete Clitocybe conglobata and Their 11.BETA.-Hydroxysteroid Dehydrogenase Inhibitory Activity

Abstract

A new drimane sesquiterpenoid, 3-keto-drimenol (1), were isolated from cultures of the basidiomycete Clitocybe conglobata together with 3b b-hydroxy-11-acetyldrimene (2), 3b b-hydroxydrimenol (3), 11,12-dihydroxydrimene (4), 3b b-hydroxy-11,12-O-isopropyldrimene (5), and 3b b,11,12-trihydroxydrimene (6). Their structures were established from MS and NMR experiments. Compounds 1, 3, and 6 showed inhibitory activities against two isozymes of 11b b-hydroxysteroid dehydrogenases with IC 50 1.7-8.0 m mg/ml (human 11b b-HSD1), 10.7-24.1 m mg/ml (mouse 11b b-HSD1); 177.0-220.0 m mg/ml (human 11b b-HSD2), 250.5-500.2 m mg/ml (mouse 11b b-HSD2), respectively, which catalyze the interconversion of active cortisol and inactive cortisone.

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria

“…Compound 1 was obtained as a colorless oil and had a molecular formula C 21 15.0 (q) in 1 indicated an aglycone of sesquiterpene, and these 13 C NMR spectral data were similar to a known drimane sesquiterpene, 3b-hydroxydrimenol [18,19]. The obvious differences were the significant down-fielded shift of C-3 from d C 79.6 to 90.8, as well as the presence of six sugar carbons in compound 1.…”

Seven new drimane-type sesquiterpenoids from cultures of fungus Laetiporus sulphureus

“…LH-20, silica gel and reversed-phased C 18 column to afford seven new drimane-type sesquiterpenoids, sulphureuines B-H (1-7) (Fig. 1), together with four known compounds, agripilol A (8) [7], 3β-hydroxy-11,12-O-isopropyldrimene (9) [8], eburicoic acid (10) [9], and sulphurenic acid (11) 3H, s, H-15), 1.10 (3H, s, H-13)]. 13 C NMR and DEPT spectral data (Table 3) indicated 15 carbon resonances, including three methyls, six methylenes, three methines, and three quaternary carbons.…”

Volatile sesquiterpenes from fungi: what are they good for?

“…Clitocybe conglobata is the producer of a number of oxygenated drimenols. One of them, 3-keto-drimenol (57), has been shown to exhibit inhibitory activities against two isozymes of 11-hydroxysteroid dehydrogenases which catalyze the interconversion of active cortisol and inactive cortisone (Xu et al 2009). The assays were performed on mammalian enzymes and it is not clear if and how these inhibitory functions have an ecological effect.…”