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.
Pacciaroni
Adriana del V
Adel V
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, (5000) Córdoba, Argentina, IMBIV-CONICET.
Gette
María de los Angeles
Mde L
Derita
Marcos
M
Ariza-Espinar
Luis
L
Gil
Roberto R
RR
Zacchino
Susana A
SA
Silva
Gloria L
GL
D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D004821:Epidermophyton / Q000187:drug effects; D044950:Flavanones / Q000737:chemistry / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology; D014249:Trichophyton / Q000187:drug effects; D000094162:Phytoalexins
D000935:Antifungal Agents; D044950:Flavanones; D005419:Flavonoids; D010936:Plant Extracts; D012717:Sesquiterpenes; C468910:3-hydroxyflavanone; C099724:sakuranetin; D000094162:Phytoalexins