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

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 3, 2010, Pages 1162-1164

  Park, Jun Seong ^a,c   Kim, Dong Hyun ^a   Lee, Jae Kyoung ^a   Lee, Jin Young ^a   Kim, Duck Hee ^a   Kim, Han Kon ^a   Lee, Hak Ju ^b   Kim, Ho Cheol ^c  

^a AmorePacific Corporation   (South Korea)

^b Korea Forest Research Institute   (South Korea)

^c Kyung Hee University   (South Korea)

Author keywords

Doenjang; Melanin; o Dihydroxyisoflavone; Tyrosinase

Indexed keywords

6,7,4' TRIHYDROXYISOFLAVONE; 7,3',4' TRIHYDROXYISOFLAVONE; 7,8,4' TRIHYDROXYISOFLAVONE; ANTIOXIDANT; ARBUTIN; DAIDZEIN; GENISTEIN; GLYCITEIN; ISOFLAVONE DERIVATIVE; MELAN A; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG; MELANIN; MONOPHENOL MONOOXYGENASE; PLANT EXTRACT;

AGED; ANTIOXIDANT ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; FERMENTED PRODUCT; HUMAN; HUMAN CELL; KOREA; MELANOGENESIS; SOYBEAN; ANTAGONISTS AND INHIBITORS; CELL CULTURE; CELL LINE; CHEMISTRY; FERMENTATION; ISOLATION AND PURIFICATION; METABOLISM; PHYSIOLOGY;

GLYCINE MAX;

CELL LINE; CELLS, CULTURED; FERMENTATION; HUMANS; ISOFLAVONES; KOREA; MELANINS; MONOPHENOL MONOOXYGENASE; PLANT EXTRACTS; SOY FOODS;

EID: 74049104179     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.12.021     Document Type: Article

References (24)

1. Lee N.-K., Son K.-H., Chang H.-W., Kang S.-S., Park H., Heo M.-Y., and Kim H.-P. Arch. Pharm. Res. 27 (2004) 1132
2. Ernest V.C., Cecil K., Heino H., Hansruedi G., Chie S., Victoria V., Vincent J.H., and Tomas P.D. Biochem. Pharmacol. 57 (1999) 663
3. Choi H.-J., Anh S.-M., Lee B.-G., Chang I.-S., and Hwang J.-S. Pigment Cell Res. 18 (2005) 439
4. Dooley T.P., Gadwood R.C., Kilgore K., and Thomasco L.M. Skin Pharmacol. 7 (1994) 188
5. Kim S.-H., and Lee K.-A. Food Chem. 339 (2003) 342
6. Park K.-Y., Jung K.-O., Rhee S.-H., and Choi Y.H. Mutat. Res. 523 (2003) 43
7. Jung K.-O., Park S.-Y., and Park K.-Y. Nutrition 22 (2006) 539
8. Esaki H., Onozaki H., Morimitsu Y., Kawakishi S., and Osawa T. Biosci., Biotechnol., Biochem. 62 (1998) 740
9. Esaki H., Kawakishi S., Morimitsu Y., and Osawa T. Biosci., Biotechnol., Biochem. 63 (1999) 1637
10. 6) δ 103.4 (C-8), 108.7 (C-5), 115.5(C-3′, 5′), 117.0 (C-10), 123.3 (C-3), 123.2 (C-1′), 130.5 (C-2′, 6′), 145.4 (C-6), 151.4 (C-9), 153.0 (C-2), 153.0 (C-7), 157.3 (C-4′), 174.9 (C-4); LC/MS m/z 271.2 [M+H].
11. Maeda K., and Fukuda M. J. Pharmacol. Exp. Ther. 276 (1995) 765
12. Hearing V.J., and Tsukamoto K. FASEB J. 5 (1991) 2902
13. Jiménez-Cervantes C., Solano F., Kobayashi T., Urabe K., Hearing V.J., Lozano J.A., and Garci{dotless}́a-Borrón J.C. J. Biol. Chem. 269 (1994) 17993
14. Liu F., Ooi V.C.E., and Chang S.T. Life Sci. 60 (1997) 763
15. Wright S. J. Dermatolog. Treat. 1 (1990) 47
16. Kalb V.F., and Bernlohr R.W. Anal. Biochem. 82 (1977) 362
17. Jeong P.H., Shin D.H., and Kim Y.S. J. Food Sci. 73 (2008) 187
18. Yasushi T., Akiko H., Chikako M., and Makoto S. J. Invest. Dermatol. 75 (1980) 379
19. Nihei K., and Kubo I. Bioorg. Med. Chem. Lett. 13 (2003) 2409
20. Yan C.H., Chen X.G., Li Y., and Han R. Asian Nat. Prod. Res. 1 (1999) 285
21. Yang E.S., Hwang J.S., Choi H.C., Hong R.H., and Kang S.M. Kor. J. Microbiol. Biotechnol. 36 (2008) 72
22. 4 buffer + 1% Triton X-100 + 100 μg/ml PMSF). The cell lysate was centrifuged at 12,500 rpm for 15 min to remove insoluble material. The protein concentration was determined by the Bradford method using BSA as a standard. The cell homogenate was mixed and incubated with 0.8 mM l-Dopa for 1 h at 37 °C and then the activity was assayed at 475 nm using ELISA micro plate reader.
23. 14 Superoxide radicals were generated in 1 ml 20 mM Tris-HCl buffer pH 8.0 containing 0.05 mM nitroblue tetrazolium (NBT), 0.01 mM phenazine methosulfate (PMS) and test compounds were preincubated for 2 min. The reaction was initiated by the addition of 0.078 mM NADH. Blue chromogen, formed due to NBT reduction, was read at 560 nm.
24. 16