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

• Published in: Bioorganic & medicinal chemistry letters Vol. 20; no. 3; pp. 1162 - 1164
• Main Authors: Park, Jun-Seong, Kim, Dong Hyun, Lee, Jae Kyoung, Lee, Jin Young, Kim, Duck Hee, Kim, Han Kon, Lee, Hak-Ju, Kim, Ho Cheol
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.02.2010; Elsevier
• Subjects: Biological and medical sciences; Cell Line; Cells, Cultured; Doenjang; Fermentation - physiology; Food industries; Fruit and vegetable industries; Fundamental and applied biological sciences. Psychology; General pharmacology; Humans; Isoflavones - chemistry; Isoflavones - isolation & purification; Isoflavones - metabolism; Korea; Medical sciences; Melanin; Melanins - antagonists & inhibitors; Melanins - metabolism; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; o-Dihydroxyisoflavone; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - metabolism; Soy Foods; Tyrosinase; Asia; Korea; o-Dihydroxyisoflavone; Doenjang; Melanin; Tyrosinase; Vegetables; Enzyme; Monophenol monooxygenase; Soybean; Antioxidant; Fermented product; Isoflavone derivatives; Flavonoid; Radical scavenger; Biological activity; Traditional food stuff; Phenols; Pigments; Isolation; Inhibitor; Superoxide radicals; Oxidoreductases
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2009.12.021

Natural melanin formation inhibitors from aged Korean fermented soybean paste ( 1– 2) are reported. 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 μM and 5.23 ± 0.6 μM (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 μM ( 1), 7.83 ± 0.7 μM ( 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.