Polyphenols Displaying Tyrosinase Inhibition from the Seed of Psoralea corylifolia

Three chalcones and two flavanones displaying tyrosinase inhibitory activity were isolated from the seed of Psoralea corylifolia, a cultivated edible plant. The isolated compounds were elucidated as known isovabachalcone, 4'-O-methylbavachalcone, isobavachromene, corylifolin, and bavachinin. The inhibitory potencies of the polyphenols toward monophenolase activity of mushroom tyrosinase were investigated. The inhibitory concentration (IC50) values of compounds 1-5 for monophenolase activity were determined to be 12.3, 48.8, 15.8, 23.6, and 143.9 μM, respectively. The potent inhibitors 1-4 exhibited the competitive inhibition characteristics in analysis of Lineweaver-Burks and Dixon-plot.

[1]  J. Y. Kim,et al.  Glycosidase inhibitory phenolic compounds from the seed of Psoralea corylifolia , 2010 .

[2]  K. Park,et al.  Tyrosinase inhibitory polyphenols from roots of Morus lhou. , 2009, Journal of agricultural and food chemistry.

[3]  K. Park,et al.  Tyrosinase inhibitory effects of 1,3-diphenylpropanes from Broussonetia kazinoki. , 2009, Bioorganic & medicinal chemistry.

[4]  Y H Moon,et al.  Kurarinol, tyrosinase inhibitor isolated from the root of Sophora flavescens. , 2008, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[5]  K. Park,et al.  Tyrosinase Inhibitory Xanthones from Cudrania tricuspidata , 2007 .

[6]  Jun Wang,et al.  Inhibition of the activity of mushroom tyrosinase by alkylbenzoic acids , 2006 .

[7]  Kaishun Bi,et al.  Antioxidants from a Chinese medicinal herb--Psoralea corylifolia L , 2005 .

[8]  S. Balasubramanian,et al.  Antidermatophytic activity of extracts from Psoralea corylifolia (Fabaceae) correlated with the presence of a flavonoid compound. , 2004, Journal of ethnopharmacology.

[9]  M. Gross,et al.  Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases. , 2002, Carcinogenesis.

[10]  N F Box,et al.  Human pigmentation genes: identification, structure and consequences of polymorphic variation. , 2001, Gene.

[11]  F. García-Carmona,et al.  Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. , 2001, Journal of agricultural and food chemistry.

[12]  F. Cadet,et al.  Inhibition of palmito (Acanthophoenix rubra) polyphenol oxidase by carboxylic acids , 1997 .

[13]  V. del Marmol,et al.  Tyrosinase and related proteins in mammalian pigmentation , 1996, FEBS letters.

[14]  F. García-Carmona,et al.  Kojic Acid, a Cosmetic Skin Whitening Agent, is a Slow‐binding Inhibitor of Catecholase Activity of Tyrosinase , 1994, The Journal of pharmacy and pharmacology.

[15]  E. Valero,et al.  Time-dependent inhibition of grape polyphenol oxidase by tropolone , 1991 .

[16]  G. Prota.  Progress in the chemistry of melanins and related metabolites , 1988, Medicinal research reviews.