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]  Ying Wang,et al.  Antibacterial prenylflavone derivatives from Psoralea corylifolia, and their structure-activity relationship study. , 2004, Bioorganic & medicinal chemistry.

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

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

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

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

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

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

[15]  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.

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

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