Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis

Abstract

The phytochemcal profiles of Cudrania cochinchinensis leaf, twig, stem and root were compared by HPLC analysis. It was found that C. cochinchinensis stem extract contained some unknown natural products with potential tyrosinase inhibitory activities. Therefore, the chemical constitutes in extract (95% ethanol) of C. cochinchinensis stem were further investigated in this study. A new racemic mixture, (±)2,3-cis-dihydromorin, and fifteen known phenolic compounds, dihydrokaempferol 7-O-β-d-qlucopyranoside, skimmin, quercetin-7-O-β-d-glucoside, 2,3-dihydroquercetin 7-O-β-d-glucoside, kaempferol-7-O-β-glucopyranoside, quercetin-3,7-di-O-β-d-glucoside, morin-7-O-β-d-glucoside, 1,3,5,8-tetrahydroxyxanthen-9-one, 2,3-trans-dihydromorin, aromadendrin, oxyresveratrol, genistin, protocatechuic acid, kaempferol 3,7-di-O-β-glucopyranoside, and naringenin were isolated. Spectral techniques (MS, 1H NMR and 13C NMR) were utilized for their structural identification and their inhibitory activities on mushroom tyrosinase were also evaluated. The results showed that tyrosinase inhibitory activities of (±)2,3-cis-dihydromorin (IC 50 = 31.1 μM), 2,3-trans-dihydromorin (IC 50 = 21.1 μM), and oxyresveratrol (IC 50 = 2.33 μM), were more potent than that of kojic acid (IC 50 = 50.8 μM), a well-known tyrosinase inhibitor, indicating that Cudrania cochinchinensis stem will be a great potential agent for the development of effective natural tyrosinase inhibitors. © 2011 The Royal Society of Chemistry.