Tyrosinase inhibitory effects and inhibition mechanisms of nobiletin and hesperidin from citrus peel crude extracts

References

• Linet MS. Evolution of cancer epidemiology. Epidemiol Rev 2000; 22: 35–56
   PubMed Web of Science ®Google Scholar
• Serraino D, Fratino L, Gianni W, Campisi C, Pietropaolo M, Trimarco G, Marigliano V. Epidemiological aspects of cutaneous malignant melanoma (review). Oncol Rep 1998; 5: 905–909
   PubMed Web of Science ®Google Scholar
• Ito S. The IFPCS presidential lecture: A chemist's view of melanogenesis. Pigment Cell Res 2003; 16: 230–236
   PubMedGoogle Scholar
• Seo SY, Sharma VK, Sharma N. Mushroom tyrosinase: Recent prospects. J Agric Food Chem 2003; 51: 2837–2853
   PubMed Web of Science ®Google Scholar
• Uiterkamp AJ, Mason HS. Magnetic dipole-dipole coupled Cu(II) pairs in nitric oxide-treated tyrosinase: A structural relationship between the active sites of tyrosinase and hemocyanin. Proc Natl Acad Sci U S A 1973; 70: 993–996
   PubMed Web of Science ®Google Scholar
• Nishioka K. Particulate tyrosinase of human malignant melanoma. Solubilization, purification following trypsin treatment, and characterization. Eur J Biochem 1978; 85: 137–146
   PubMedGoogle Scholar
• Briganti S, Camera E, Picardo M. Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Res 2003; 16: 101–110
   PubMedGoogle Scholar
• Kubo I, Kinst-Hori I. Tyrosinase inhibitors from cumin. J Agric Food Chem 1988; 46: 5338–5341
   Web of Science ®Google Scholar
• Kubo I, Kinst-Hori I. Flavonols from saffron flower: Tyrosinase inhibitory activity and inhibition mechanism. J Agric Food Chem 1999; 47: 4121–4125
   PubMed Web of Science ®Google Scholar
• Chen QX, Kubo I. Kinetics of mushroom tyrosinase inhibition by quercetin. J Agric Food Chem 2002; 50: 4108–4112
   PubMed Web of Science ®Google Scholar
• No JK, Soung DY, Kim YJ, Shim KH, Jun YS, Rhee SH, Yokozawa T, Chung HY. Inhibition of tyrosinase by green tea components. Life Sci 1999; 65: L241–L246
   Web of Science ®Google Scholar
• Miyazawa M, Oshima T, Koshio K, Itsuzaki Y, Anzai J. Tyrosinase inhibitor from black rice bran. J Agric Food Chem 2003; 51: 6953–6956
   PubMed Web of Science ®Google Scholar
• Yamakoshi J, Otsuka F, Sano A, Tokutake S, Saito M, Kikuchi M, Kubota Y. Lightening effect on ultraviolet-induced pigmentation of guinea pig skin by oral administration of a proanthocyanidin-rich extract from grape seeds. Pigment Cell Res 2003; 16: 629–638
   PubMedGoogle Scholar
• Garg A, Garg S, Zaneveld LJ, Singla AK. Chemistry and pharmacology of the citrus bioflavonoid hesperidin. Phytother Res 2001; 15: 655–669
   PubMed Web of Science ®Google Scholar
• Tanaka T, Makita H, Ohnishi M, Mori H, Satoh K, Hara A, Sumida T, Fukutani K, Tanaka T, Ogawa H. Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis in rats by flavonoids diosmin and hesperidin, each alone and in combination. Cancer Res 1997; 57: 246–252
   PubMed Web of Science ®Google Scholar
• Chinese Pharmacopoeia Committee. Chemical Industry Press, Beijing, China 2005; 132, Chinese Pharmacopoeia. 2005 ed
   Google Scholar
• Chinese Pharmacopoeia Committee. Chemical Industry Press, Beijing, China 2005; 137, Chinese Pharmacopoeia. 2005 ed
   Google Scholar
• Chinese Pharmacopoeia Committee. Chemical Industry Press, Beijing, China 2005; 124, Chinese Pharmacopoeia. 2005 ed
   Google Scholar
• Martinez CC, Vicente O, Yanez Gascon MJ, Alcaraz BM, Canteras JM, avente-Garcia O, Castillo J. Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin. J Agric Food Chem 2005; 53: 6791–6797
   PubMed Web of Science ®Google Scholar
• Yanez J, Vicente V, Alcaraz M, Castillo J, avente-Garcia O, Canteras M, Teruel JA. Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: Relationship between structure and activity. Nutr Cancer 2004; 49: 191–199
   PubMed Web of Science ®Google Scholar
• Wu YQ, Zhou CH, Tao J, Li SN. Antagonistic effects of nobiletin, a polymethoxyflavonoid, on eosinophilic airway inflammation of asthmatic rats and relevant mechanisms. Life Sci 2005
   Web of Science ®Google Scholar
• Nagase H, Omae N, Omori A, Nakagawasai O, Tadano T, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y. Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. Biochem Biophys Res Commun 2005; 337: 1330–1336
   PubMed Web of Science ®Google Scholar
• Suzuki M, Sasaki K, Yoshizaki F, Oguchi K, Fujisawa M, Cyong JC. Anti-hepatitis C virus effect of citrus unshiu peel and its active ingredient nobiletin. Am J Chin Med 2005; 33: 87–94
   PubMed Web of Science ®Google Scholar
• Suzuki R, Kohno H, Murakami A, Koshimizu K, Ohigashi H, Yano M, Tokuda H, Nishino H, Tanaka T. Citrus nobiletin inhibits azoxymethane-induced large bowel carcinogenesis in rats. Biofactors 2004; 22: 111–114
   PubMed Web of Science ®Google Scholar
• Ju-Ichi M. Chemical study of citrus plants in the search for cancer chemopreventive agents. Yakugaku Zasshi 2005; 125: 231–254
   PubMed Web of Science ®Google Scholar
• Choi CH, Sun KH, An CS, Yoo JC, Hahm KS, Lee IH, Sohng JK, Kim YC. Reversal of p-glycoprotein-mediated multidrug resistance by 5,6,7,3′,4′-pentamethoxyflavone (Sinensetin). Biochem Biophys Res Commun 2002; 295: 832–840
   PubMed Web of Science ®Google Scholar
• Manthey JA, Guthrie N. Antiproliferative activities of citrus flavonoids against six human cancer cell lines. J Agric Food Chem 2002; 50: 5837–5843
   PubMed Web of Science ®Google Scholar
• Sasaki K, Yoshizaki F. Nobiletin as a tyrosinase inhibitor from the peel of citrus fruit. Biol Pharm Bull 2002; 25: 806–808
   PubMed Web of Science ®Google Scholar
• Mason HS, Peterson EW, Melanoproteins I. Reactions between enzyme-generated quinones and amino acids. Biochim Biophys Acta 1965; 111: 134–146
   PubMed Web of Science ®Google Scholar
• Hamilton MA, Russo RC, Thurston RV. Trimmed spearman-karber method for estimating median lethal concentrations in toxicity bioassays. Environ Sci Technol 1977; 11: 714–719
   Web of Science ®Google Scholar
• Kubo I, Nihei K, Tsujimoto K. Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells. Bioorg Med Chem 2004; 12: 5349–5354
   PubMed Web of Science ®Google Scholar
• Cabanes J, Chazarra S, Garcia-Carmona F. Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J Pharm Pharmacol 1994; 46: 982–985
   PubMed Web of Science ®Google Scholar
• Um SJ, Park MS, Park SH, Han HS, Kwon YJ, Sin HS. Synthesis of new glycyrrhetinic acid (GA) derivatives and their effects on tyrosinase activity. Bioorg Med Chem 2003; 11: 5345–5352
   PubMed Web of Science ®Google Scholar
• Li CY, Lee EJ, Wu TS. Antityrosinase principles and constituents of the petals of crocus sativus. J Nat Prod 2004; 67: 437–440
   PubMed Web of Science ®Google Scholar
• Lee KK, Choi J-D. The effects of Areca catechu L extract on antiinflammation and anti-melanogenesis. Intern J Cosmet Sci 1999; 21: 275–284
   PubMedGoogle Scholar
• Kubo I, Kinst-Hori I, Chaudhuri SK, Kubo Y, Sanchez Y, Ogura T. Flavonols from Heterotheca inuloides: Tyrosinase inhibitory activity and structural criteria. Bioorg Med Chem 2000; 8: 1749–1755
   PubMed Web of Science ®Google Scholar
• Hisamoto M, Kikuzaki H, Nakatani N. Constituents of the leaves of peucedanum japonicum thunb. and their biological activity. J Agric Food Chem 2004; 52: 445–450
   PubMed Web of Science ®Google Scholar
• Curto EV, Kwong C, Hermersdorfer H, Glatt H, Santis C, Virador V, Hearing VJ, Jr, Dooley TP. Inhibitors of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem Pharmacol 1999; 57: 663–672
   PubMed Web of Science ®Google Scholar
• Nakamura K, Yoshida M, Uchiwa H, Kawa Y, Mizoguchi M. Down-regulation of melanin synthesis by a biphenyl derivative and its mechanism. Pigment Cell Res 2003; 16: 494–500
   PubMedGoogle Scholar
• Hori I, Nihei K, Kubo I. Structural criteria for depigmenting mechanism of arbutin. Phytother Res 2004; 18: 475–479
   PubMed Web of Science ®Google Scholar
• Maeda K, Fukuda M. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 1996; 276: 765–769
   PubMed Web of Science ®Google Scholar
• Yu L. Inhibitory effects of (S)- and (R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acids on tyrosinase activity. J Agric Food Chem 2003; 51: 2344–2347
   PubMed Web of Science ®Google Scholar
• Dixon M, Webb EC. Enzyme inhibition and activation. Enzymes. Academic Press, New York 1979; 332–467
   Google Scholar
• Badria FA, elGayyar MA. A new type of tyrosinase inhibitors from natural products as potential treatments for hyperpigmentation. Boll Chim Farm 2001; 140: 267–271
   PubMedGoogle Scholar
• Rodriguez J, Yanez J, Vicente V, Alcaraz M, avente-Garcia O, Castillo J, Lorente J, Lozano JA. Effects of several flavonoids on the growth of B16F10 and SK-MEL-1 melanoma cell lines: Relationship between structure and activity. Melanoma Res 2002; 12: 99–107
   PubMed Web of Science ®Google Scholar
• Kawaii S, Tomono Y, Katase E, Ogawa K, Yano M. Effect of citrus flavonoids on HL-60 cell differentiation. Anticancer Res 1999; 19: 1261–1269
   PubMed Web of Science ®Google Scholar