Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors

作者：Park Jun Seong^*; Kim Dong Hyun; Lee Jae Kyoung; Lee Jin Young; Kim Duck Hee; Kim Han Kon; Lee Hak Ju; Kim Ho Cheol

来源：Bioorganic & Medicinal Chemistry Letters, 2010, 20(3): 1162-1164.

DOI：10.1016/j.bmcl.2009.12.021

• o-Dihydroxyisoflavone
• Doenjang
• Melanin
• Tyrosinase

Natural o-dihydroxyisoflavone (ODI) derivatives with variable hydroxyl substituent at the aromatic ring of isoflavone and three known isoflavones were isolated from five-year-old Korean fermented soybean paste (Doenjang) and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells comparing with other known isoflavones, 7,8,4'-trihydroxyisoflavone (1) and 7,3',4'-trihydroxyisoflavone (2) inhibited tyrosinase by 50% at a concentration of 11.21 +/- 0.8 mu M and 5.23 +/- 0.6 mu M (IC(50)), respectively, whereas, 6,7,4'-trihydroxyisoflavone (3), daidzein (4), glycitein (5) and genistein (6) showed very low inhibition activity. Furthermore, those compounds significantly suppressed the cellular melanin formation by 50% at a concentration of 12.23 +/- 0.7 mu M (1), 7.83 +/- 0.7 mu M (2), and 57.83 +/- 0.5(6) and show more activity than arbutin. But, compounds 3, 4, and 5 showed lower inhibition activity. This study shows that the position of hydroxyl substituent at the aromatic ring of isoflavone plays an important role in the intracellular regulation of melanin formation in cell-based assay system.

• 出版日期2010-2-1