title: Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis.
abstract: Previously, it was reported that some prenylated flavonoids contained in the dichloromethane fraction of the ethanolic extract of Sophora flavescens, such as kuraridin, sophoraflavanone G, kurarinone, and kushenol F, are tyrosinase inhibitors; however, based on the level of these inhibitors in the extract, its inhibitory effect on tyrosinase activity was higher than expected. This has led us to further investigate other possible constituents that may contribute to the extract's strong inhibitory activity. The results of this study indicate that kurarinol (1), kuraridinol (2), and trifolirhizin (3), from the ethyl acetate fraction of Sophora extract, can inhibit tyrosinase activity. Compared with kojic acid (16.22+/-1.71 microM), compounds 1-3 possessed potent tyrosinase inhibitory activity with IC(50) values of 8.60+/-0.51, 0.88+/-0.06, and 506.77+/-4.94 microM, respectively. These three compounds were further tested for their inhibitory effects on melanogenesis. In cultured B16 melanoma cells, 1-3 markedly inhibited (>50%) melanin synthesis at 50 microM. This is the first study indicating that 1-3 exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, and therefore, are candidates as skin-whitening agents.
authors.affiliation: Division of Food Science and Biotechnology, Pukyong National University, Busan 608-737, Korea.
authors.forename: Sook Kyung
authors.initials: SK
authors.lastname: Hyun
authors.forename: Won-Hee
authors.initials: WH
authors.lastname: Lee
authors.forename: Da Mi
authors.initials: DM
authors.lastname: Jeong
authors.forename: Youngsoo
authors.initials: Y
authors.lastname: Kim
authors.forename: Jae Sue
authors.initials: JS
authors.lastname: Choi
mesh_terms: D015056:1-Methyl-3-isobutylxanthine / Q000494:pharmacology; D000818:Animals; D001578:Benzopyrans / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D005419:Flavonoids / Q000494:pharmacology*; D005960:Glucosides / Q000494:pharmacology*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000494:pharmacology*; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000378:metabolism / Q000473:pathology; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000494:pharmacology*; D029909:Sophora / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D001578:Benzopyrans; D004791:Enzyme Inhibitors; D005419:Flavonoids; D005960:Glucosides; D006576:Heterocyclic Compounds, 4 or More Rings; D008543:Melanins; D010936:Plant Extracts; C526228:kuraridinol; C526229:kurarinol; C526230:trifolirhizin; D014442:Monophenol Monooxygenase; D015056:1-Methyl-3-isobutylxanthine