Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis.
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.
Hyun
Sook Kyung
SK
Division of Food Science and Biotechnology, Pukyong National University, Busan 608-737, Korea.
Lee
Won-Hee
WH
Jeong
Da Mi
DM
Kim
Youngsoo
Y
Choi
Jae Sue
JS
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
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