Antifungal activity of Heterothalamus alienus metabolites.

The chemical study of Heterothalamus alienus gave rutin, spathulenol (1), (1R,7S)-germacra-4(15),5,10(14)-trien-1beta-ol (2), sakuranetin (3), padmatin 3-acetate (4), (2R,3R)-dihydroquercetin-7,3',4'-trimethyl ether (5), (2R,3R)-dihydroquercetin-7,4'-dimethyl ether (6), (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone (7), as the main components of an antifungal extract of the aerial parts of the plant. Compound 2 showed moderate activity, with Epidermophyton floccosum being the most susceptible species (MIC = 100 microg/mL); compound 3 showed the best antifungal behavior having a broad spectrum of action and the lowest MICs. This flavanone along with flavanolol 5 showed very good activity against standardized (MIC = 31.2 microg/mL) as well as clinical isolates of Trichophyton rubrum and T. mentagrophytes (MIC ranges 31.2-62.5 microg/mL and 31.2-125 microg/mL, respectively) and demonstrated not only fungistatic but also fungicide properties. Flavanolol 6 was active against all the dermatophytes tested with MICs of 62.5-250 microg/mL. Rutin, spathulenol (1) and the 3-acetylated flavanones 4 and 7 were inactive or marginally active against the fungal panel. (c) 2008 John Wiley & Sons, Ltd.