Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors.
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.
Park
Jun-Seong
JS
R&D Center, AmorePacific Corporation, Kyounggi-do, Republic of Korea. superbody@amorepacific.com
Kim
Dong Hyun
DH
Lee
Jae Kyoung
JK
Lee
Jin Young
JY
Kim
Duck Hee
DH
Kim
Han Kon
HK
Lee
Hak-Ju
HJ
Kim
Ho Cheol
HC
D002460:Cell Line; D002478:Cells, Cultured; D005285:Fermentation / Q000502:physiology; D006801:Humans; D007529:Isoflavones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D007723:Korea; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D045730:Soy Foods
D007529:Isoflavones; D008543:Melanins; D010936:Plant Extracts; D014442:Monophenol Monooxygenase