1. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors
- Author
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Duck Hee Kim, Jin Young Lee, Hocheol Kim, Jun-Seong Park, Donghyun Kim, Jae Kyoung Lee, Hak-Ju Lee, and Han Kon Kim
- Subjects
Stereochemistry ,Tyrosinase ,Clinical Biochemistry ,Pharmaceutical Science ,Genistein ,Biochemistry ,Cell Line ,Melanin ,chemistry.chemical_compound ,Drug Discovery ,Humans ,Molecular Biology ,Cells, Cultured ,Melanins ,Korea ,Monophenol Monooxygenase ,Plant Extracts ,Organic Chemistry ,Daidzein ,Arbutin ,Soy Foods ,Biological activity ,Glycitein ,Isoflavones ,chemistry ,Fermentation ,Molecular Medicine - Abstract
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 microM and 5.23+/-0.6 microM (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 microM (1), 7.83+/-0.7 microM (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.
- Published
- 2009