Melanogenesis of murine melanoma cells induced by hesperetin, a Citrus hydrolysate-derived flavonoid

Food and Chemical Toxicology

Volumn 50, Issue 3-4, 2012, Pages 653-659

  Huang, Yu Chun ^a   Liu, Kao Chih ^a   Chiou, Yi Ling ^a  

^a PROVIDENCE UNIVERSITY   (Taiwan)

Author keywords

Catenin; CAMP responsive element binding protein; Hesperetin; Melanogenesis; Mitogen activated protein kinase

Indexed keywords

AURANTIIN; BETA CATENIN; CITRUS RETICULATA EXTRACT; CITRUS SINENSIS EXTRACT; CYCLIC AMP RESPONSIVE ELEMENT BINDING PROTEIN; GLYCOGEN SYNTHASE KINASE 3BETA; HESPERETIN; HESPERIDIN; MICROPHTHALMIA ASSOCIATED TRANSCRIPTION FACTOR; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE P38; NARINGENIN; NARIRUTIN; NEOHESPERIDIN; PLANT EXTRACT; PROTEIN KINASE B; SKIN PROTECTIVE AGENT; SOUR ORANGE EXTRACT; UNCLASSIFIED DRUG; WNT PROTEIN;

ANIMAL CELL; ARTICLE; BIOCHEMICAL COMPOSITION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME PHOSPHORYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MANDARIN; MELANOGENESIS; MELANOMA B16; MOUSE; NONHUMAN; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; SKIN DEFECT; SKIN PROTECTION; SOUR ORANGE; SWEET ORANGE; TOXICITY TESTING;

ANIMALS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; FLAVONOIDS; HESPERIDIN; HYDROLYSIS; MELANINS; MELANOMA, EXPERIMENTAL; MICE; PLANT EXTRACTS;

CITRUS; CITRUS AURANTIUM; CITRUS RETICULATA; CITRUS SINENSIS; MURINAE;

EID: 84863254774     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.01.012     Document Type: Article

References (38)

1. An S.M., Lee S.I., Choi S.W., Moon S.W., Boo Y.C. p-Coumaric acid, a constituent of Sasa quelpaertensis Nakai, inhibits cellular melanogenesis stimulated by alpha-melanocyte stimulating hormone. Br. J. Dermatol. 2008, 159:292-299.
2. Bellei B., Flori E., Izzo E., Maresca V., Picardo M. GSK3beta inhibition promotes melanogenesis in mouse B16 melanoma cells and normal human melanocytes. Cell Signal. 2008, 20:1750-1761.
3. Benavente-García O., Castillo J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. J. Agric. Food Chem. 2008, 56:6185-6205.
4. Bienz M. Beta-Catenin: a pivot between cell adhesion and Wnt signalling. Curr. Biol. 2005, 15:R64-R67.
5. Bikkavilli R.K., Feigin M.E., Malbon C.C. P38 mitogen-activated protein kinase regulates canonical Wnt-beta-catenin signaling by inactivation of GSK3beta. J. Cell Sci. 2008, 121:3598-3607.
6. Bikkavilli R.K., Malbon C.C. Mitogen-activated protein kinases and Wnt/beta-catenin signaling: molecular conversations among signaling pathways. Commun. Integr. Biol. 2009, 2:46-49.
7. Caverzasio J., Manen D. Essential role of Wnt3a-mediated activation of mitogen-activated protein kinase p38 for the stimulation of alkaline phosphatase activity and matrix mineralization in C3H10T1/2 mesenchymal cells. Endocrinology 2007, 148:5323-5330.
8. Chen Y.C., Shen S.C., Lin H.Y. Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids. Biochem. Pharmacol. 2003, 66:1139-1150.
9. Chiang H.M., Lin J.W., Hsiao P.L., Tsai S.Y., Wen K.C. Hydrolysates of citrus plants stimulate melanogenesis protecting against UV-induced dermal damage. Phytother. Res. 2011, 25:569-576.
10. Drees M., Zimmermann R., Eisenbrand G. 3',5'-Cyclic nucleotide phosphodiesterase in tumor cells as potential target for tumor growth inhibition. Cancer Res. 1993, 53:3058-3061.
11. Englaro W., Rezzonico R., Durand-Clément M., Lallemand D., Ortonne J.P., Ballotti R. Mitogen-activated protein kinase pathway and AP-1 are activated during cAMP-induced melanogenesis in B-16 melanoma cells. J. Biol. Chem. 1995, 270:24315-24320.
12. Filippa N., Sable C.L., Filloux C., Hemmings B., Van Obberghen E. Mechanism of protein kinase B activation by cyclic AMP-dependent protein kinase. Mol. Cell. Biol. 1999, 19:4989-5000.
13. Fishman P., Madi L., Bar-Yehuda S., Barer F., Del Valle L., Khalili K. Evidence for involvement of Wnt signaling pathway in IB-MECA mediated suppression of melanoma cells. Oncogene 2002, 21:4060-4064.
14. Garg A., Garg S., Zaneveld L.J., Singla A.K. Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Phytother. Res. 2001, 15:655-669.
15. Gottardi C.J., Gumbiner B.M. Adhesion signaling: how beta-catenin interacts with its partners. Curr. Biol. 2001, 11:R792-R794.
16. Hakim I.A., Harris R.B., Ritenbaugh C. Citrus peel use is associated with reduced risk of squamous cell carcinoma of the skin. Nutr. Cancer 2000, 37:161-168.
17. Itoh K., Hirata N., Masuda M., Naruto S., Murata K., Wakabayashi K., Matsuda H. Inhibitory effects of Citrus hassaku extract and its flavanone glycosides on melanogenesis. Biol. Pharm. Bull. 2009, 32:410-415.
18. Jansen R.J., Robinson D.P., Stolzenberg-Solomon R.Z., Bamlet W.R., de Andrade M., Oberg A.L., Hammer T.J., Rabe K.G., Anderson K.E., Olson J.E., Sinha R., Petersen G.M. Fruit and vegetable consumption is inversely associated with having pancreatic cancer. Cancer Causes Control 2011, 22:1613-1625.
19. Kanaze F.I., Bounartzi M.I., Georgarakis M., Niopas I. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Eur. J. Clin. Nutr. 2007, 61:472-477.
20. Kim J.H., Sohn K.C., Choi T.Y., Kim M.Y., Ando H., Choi S.J., Kim S., Lee Y.H., Lee J.H., Kim C.D., Yoon T.J. Beta-catenin regulates melanocyte dendricity through the modulation of PKCzeta and PKCdelta. Pigment Cell Melanoma Res. 2010, 23:385-393.
21. Kim Y.J., No J.K., Lee J.H., Chung H.Y. 4,4'-Dihydroxybiphenyl as a new potent tyrosinase inhibitor. Biol. Pharm. Bull. 2005, 28:323-327.
22. Lin J.Y., Fisher D.E. Melanocyte biology and skin pigmentation. Nature 2007, 445:843-850.
23. Maserejian N.N., Giovannucci E., Rosner B., Zavras A., Joshipura K. Prospective study of fruits and vegetables and risk of oral premalignant lesions in men. Am. J. Epidemiol. 2006, 164:556-566.
24. Miller A.J., Mihm M.C. Melanoma. N. Engl. J. Med. 2006, 355:51-65.
25. Nitoda T., Isobe T., Kubo I. Effects of phenolic compounds isolated from Rabdosia japonica on B16-F10 melanoma cells. Phytother. Res. 2008, 22:867-872.
26. O'Connell M.P., Weeraratna A.T. Hear the Wnt Ror: how melanoma cells adjust to changes in Wnt. Pigment Cell Melanoma Res. 2009, 22:724-739.
27. Ohguchi K., Akao Y., Nozawa Y. Stimulation of melanogenesis by the citrus flavonoid naringenin in mouse B16 melanoma cells. Biosci. Biotechnol. Biochem. 2006, 70:1499-1501.
28. Ooghe W.C., Detavernier C.M. Detection of the addition of Citrus reticulata and hybrids to Citrus sinensis by flavonoids. J. Agric. Food Chem. 1997, 45:1633-1637.
29. Orallo F., Alvarez E., Basaran H., Lugnier C. Comparative study of the vasorelaxant activity, superoxide-scavenging ability and cyclic nucleotide phosphodiesterase-inhibitory effects of hesperetin and hesperidin. Naunyn Schmiedebergs Arch. Pharmacol. 2004, 370:452-463.
30. Rouseff R.L., Martin S.F., Youtsey C.O. Quantitative survey of narirutin, naringin, hesperidin, and neohesperodin in Citrus. J. Agric. Food Chem. 1987, 35:1027-1030.
31. Sivamani R.K., Crane L.A., Dellavalle R.P. The benefits and risks of ultraviolet tanning and its alternatives: the role of prudent sun exposure. Dermatol. Clin. 2009, 27:149-154. vi.
32. Stuetz W., Prapamontol T., Hongsibsong S., Biesalski H.K. Polymethoxylated flavones, flavanone glycosides, carotenoids, and antioxidants in different cultivation types of tangerines (Citrus reticulata Blanco cv. Sainampueng) from Northern Thailand. J. Agric. Food Chem. 2010, 58:6069-6074.
33. Tomás-Barberán F.A., Clifford M.N. Flavanones, chalcones and dihydrochalcones- nature, occurrence and dietary burden. J. Sci. Food Agric. 2000, 80:1073-1080.
34. Tomita Y., Seiji M. Inactivation mechanism of tyrosinase in mouse melanoma. J. Dermatol. 1977, 4:245-249.
35. Tripoli E., Guardia M.L., Giammanco S., Majo D.D., Giammanco M. Citrus flavonoids: molecular structure, biological activity and nutritional properties: a review. Food Chem. 2007, 104:466-479.
36. Xu G., Liu D., Chen J., Ye X., Ma Y., Shi J. Juice components and antioxidant capacity of citrus varieties cultivated in China. Food Chem. 2008, 106:545-551.
37. Yamaguchi Y., Hearing V.J. Physiological factors that regulate skin pigmentation. Biofactors 2009, 35:193-199.
38. Ye Y., Wang H., Chu J.H., Chou G.X., Yu Z.L. Activation of p38 MAPK pathway contributes to the melanogenic property of apigenin in B16 cells. Exp. Dermatol. 2011, 20:755-757.