Effects of selected organo-sulfur compounds on melanin formation

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 15, 2009, Pages 7072-7077

  Chu, Heuy Ling ^a   Wang, Bor Sen ^a   Duh, Pin Der ^a  

^a CHIA NAN UNIVERSITY OF PHARMACY AND SCIENCE   (Taiwan)

Author keywords

Melanin; Organo sulfur compounds; Reactive oxygen species; Tyrosinase

Indexed keywords

FUNGAL PROTEIN; MELANIN; MONOPHENOL MONOOXYGENASE; PEPTIDE; REACTIVE OXYGEN METABOLITE; SULFUR DERIVATIVE;

AGARICALES; ANIMAL; ARTICLE; BIOLOGICAL MODEL; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; KINETICS; METABOLISM; SKIN; SKIN PIGMENTATION; TUMOR CELL LINE;

AGARICALES; ANIMALS; CELL LINE, TUMOR; FUNGAL PROTEINS; KINETICS; MELANINS; MODELS, BIOLOGICAL; MONOPHENOL MONOOXYGENASE; PEPTIDES; REACTIVE OXYGEN SPECIES; SKIN; SKIN PIGMENTATION; SULFUR COMPOUNDS;

EID: 68249112372     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9005824     Document Type: Article

References (41)

1. Park, Y. D.; Lee, S. J.; Park, K. H.; Kim, S. Y.; Hahn, M. J.; Yang, J. M. Effect of thiohydroxyl compounds on tyrosinase: Inactivation and reactivation study. J. Protein Chem. 2003, 22, 613-623.
2. Riley, P. A. Melanin. Int. J. Biochem. Cell Biol. 1997, 29, 1235-1239.
3. Lee, M. H.; Lin, Y. P.; Hsu, F. L.; Zhan, G. R.; Yen, K. Y. Bioactive constituents of Spatholohus suberectus in regulating tyrosinaserelated proteins and mRNA in HEMn cells, Phytochemistry 2006, 67, 1262-1270.
4. Sato, K.; Toriyama, M. Effect of pyrroloquinoline quinone (PQQ) on melanogenic protein expression in murine B16 melanoma. J. Dermatol. Sci. 2009, 53, 140-145.
5. Karioti, A.; Protopappa, A.; Megoulas, N.; Skaltsa, H. Identifica-tion of tyrosinase inhibitors from Marrubium velutinum and Marru-bium cylleneum. Bioorg. Med. Chem. 2007, 15, 2708-2714.
6. Hsu. C.-K.; Chang, C.-T.; Lu. H.-Y.; Chung, Y.-C. Inhibitory effects of the water extracts of Lavendula sp. on mushroom tyrosinase activity. Food Chem. 2007, 105, 1099-1105.
7. Nerya, O.; Vaya, J.; Musa, R.; Izrael, S.; Ben-Arie, R.; Tamir, S. Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. J. Agric. Food Chem. 2003, 51, 1201-1207.
8. Sciberg, M.; Paine, C.; Shadow, E.; Andrade-Gordon, P.; Costanzo, M.; Eisinger, M.; Shapiro, S. S. Inhibition of melanosome transfer results in skin lightening. J. Invest. Dermatol. 2000, 115, 162-167.
9. Khatib, S.; Nerya. O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety. Bioorg. Med. Chem. 2005, 13, 433-441.
10. Kim, Y. J.; Uyama, H. Tyrosinase inhibitors from natural and synthetic sources: Structure, inhibition mechanism and perspective for the future. Cell. Mol Life Sci. 2005, 62, 1707-1723.
11. 2 extract of Cinnamomum zeylanicum: Chemical characterization and antityro-sinase activity. J. Agric. Food Chem. 2007, 55, 10022-10027.
12. Schurink, M.; van Berkel, W. J.; Wichers, H. J.; Boeriu. C. G. Novel peptides with tyrosinase inhibitory activity, Peptides 2007, 28, 485-495.
13. Casanola-Martin, G. M.; Marrero-Ponce, Y.; Khan, M. T.; Torrens, F.; Perez-Gimenez, F.; Rescigno, A. Atom- and bond-based 2D TOMOCOMD-CARDD approach and ligand-based virtual screening for the drug discovery of new tyrosinase inhibitors. J. Biomol. Screening 2008, 13, 1014-1024.
14. Park, K.-W.; Kim, S.-Y.; Jeong, I.-Y.; Byun, M.-W.; Park, K.-H.; Yamada, K.; Seo, K.-I. Cytotoxic and antitumor activities of thiosulfinates from Allium tuberosum L. J. Agric. Food Chem. 2007, 55, 7957-7961.
15. Corzo-Martinez, M.; Corzo, N.; Villamiel, M. Biological properties of onions and garlic. Trends Food Sci. Technol. 2007, 18, 609-625.
16. Shon. M. Y.; Choi. S. D.; Kahng, G. G.; Nam, S. H.; Sung, N. J. Antimutagenic, antioxidant and free radical scavenging activity of ethyl acetate extracts from white, yellow and red onions, Food Chem. Toxicol. 2004, 42, 659-666.
17. Sundaram, S. G.; Milner, J. A. Diallyl disulfide inhibits the pro-liferation of human tumor cells in culture. Biochim. Biophys. Acta 1996, 1315, 15-20.
18. Teyssier, C.; Siess, M. H. Metabolism of dipropyl disulfide by rat liver phase I and phase II enzymes and by isolated perfused rat liver. Drug Metab. Dispos. 2000, 28, 648-654.
19. Lanzotti, V. The analysis of onion and garlic. J. Chromatogr., A 2006, 1112, 3-22.
20. Takahashi. M.; Shibamoto, T. Chemical compositions and antiox-idant /anti-inflammatory activities of steam distillate from freeze-dried onion (Allium cepa L.) sprout. J. Agric. Food Chem. 2008, 56, 10462-10467.
21. Lee, S.-N.; Kim, N.-S.; Lee. D.-S. Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography-mass spectrometry, Anal. Bioanal. Chem. 2003, 377, 749-756.
22. 1-induced oxidative stress in HepG2 cells by volatile extract from Allli fistulosi bulbus. Life Sci. 2005, 77, 2896-2910.
23. Mallick, S.; Singh, S. K.; Sarkar, C.; Saha, B.; Bhadra, R. Human placental lipid induces melanogenesis by increasing the expression of tyrosinase and its related proteins in vitro. Pigm. Cell Res. 2005, 18, 25-33.
24. Waite, J. H. Calculating extinction coefficients for enzymatically produced o-quinones, Anal. Biochem. 1976, 75, 211-218.
25. Wang, B.-S.; Chen, J.-H.; Liang, Y.-C.; Duh. P.-D. Effects of Welsh onion on oxidation of low-density lipoprotein and nitric oxide production in macrophage cell line RAW 264.7. Food Chem. 2005, 91, 147-155.
26. Tsuboi, T.; Kondoh, H.; Hiratsuka, J.; Mishima, Y. Enhanced melanogenesis induced by tyrosinase gene-transfer increases bor-on-uptake and killing effect of boron neutron capture therapy for amelanotic melanoma. Pigm. Cell Res. 1998, 11, 275-282.
27. Wang, H.; Joseph, J. A. Quantifying cellular oxidative stress by dichlorofluorescein assay using microplate reader. Free Radical Biol Med- 1999, 27, 612-616.
28. Pandey, A. K. S. Inactivation of yeast glutathione reductase by o-phthalaldehyde. J. Enzyme Inhih. 1996, 11 (2), 141-149.
29. Senft, A. P.; Dalton. T. P.; Shertzer, H. G. Determining glutathione and glutathione disulfide using the fluorescence probe o-phthalalde-hyde. Anal. Biochem. 2000, 280, 80-86.
30. Dogan, S.; Turan, Y.; Erturk, H.; Arslan. O. Characterization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.). J. Agric. Food Chem. 2005, 53, 776-785.
31. Perez-Gilabert, M.; Garcia-Carmona, F. Dimethyl sulfide, a volatile flavor constituent, is a slow-binding inhibitor of tyrosinase. Biochem. Biophys. Res. Commun. 2001, 285, 257-261.
32. Friedman. M.; Bautista, F. F. Inhibition of polyphenol oxidase by thiols in the absence and presence of potato tissue suspensions. J. Agric. Food Chem. 1995, 43, 69-76.
33. Wang, K. H.; Lin, R. D.; Hsu, F. L.; Huang, Y. H.; Chang, H. C.; Huang, C. Y.; Lee. M. H. Cosmetic applications of selected traditional Chinese herbal medicines. J. Ethnopharmacol 2006, 106, 353-359.
34. Kovacic, P. Unifying mechanism for addiction and toxicity of abused drugs with application to dopamine and glutamate media-tors: Electron transfer and reactive oxygen species. Med. Hypotheses 2005, 65, 90-96.
35. Herrling, T.; Jung, K.; Fuchs, J. The role of melanin as protector against free radicals in skin and its role as free radical indicator in hair. Spectrochim. Acta. Part A 2008, 69, 1429-1435.
36. Yasui, H.; Sakurai, H. Age-dependent generation of reactive oxygen species in the skin of live hairless rats exposed to UVA light. Exp-Dermatol. 2003, 12, 655-661.
37. Kim, Y.-J. Antimelanogenic and antioxidant properties of gallic acid. Biol. Pharm. Bull. 2007, 30, 1052-1055.
38. 2-catalyzed oxidation of dihdrox-yindoles: Synthesis of melanin pigments and study of their antioxidant properties, Free Radical Biol. Med. 1999, 26, 446-453.
39. Yen, G. C.; Yeh, C. T.; Chen, Y. J. Protective effect of Mesona procumbens against Tert-butyl hydroperoxide-induced acute hepatic damage in rats. J. Agric. Food Chem. 2004, 52, 4121-4127.
40. Ye, Y. N.; Liu, E. S.; Li, Y.; So, H. L.; Cho, C. C.; Sheng, H. P.; Lee, S. S.; Cho, C. H. Protective effect of polysaccharides-enriched fraction from Angelica sinensis on hepatic injury. Life Sci. 2001, 69, 637-646.
41. Yamamura, T.; Onishi, J.; Nishiyama, T. Antimelanogenic activity of hydrocoumarins in cultured normal human melanocytes by stimulating intracellular glutathione synthesis, Arch. Dermatol. Res. 2002, 294, 349-354.