Melanin Biosynthesis Inhibitory and Antioxidant Activities of Quercetin-3′-0-jff-D-glucoside Isolated from Allium cepa

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 66, Issue 5-6, 2011, Pages 209-214

  Arung, Enos Tangke ^a   Shimizu, Kuniyoshi ^a   Kondo, Ryuichiro ^a   Furuta, Shoko ^b   Ishikawa, Hiroya ^c   Tanaka, Hiroyuki ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b MULAWARMAN UNIVERSITY   (Indonesia)

^c FUKUOKA WOMEN'S UNIVERSITY   (Japan)

Author keywords

Antimelanogenesis, Antioxidant; Quercetin 3 O A D glucoside

Indexed keywords

ANTIOXIDANT; FLAVONOID; MELANIN; QUERCETIN 3' O GLUCOSIDE; QUERCETIN 3'-O-GLUCOSIDE;

ANIMAL; ARTICLE; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; EXPERIMENTAL MELANOMA; GARLIC; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MOUSE; PATHOLOGY; TUMOR CELL LINE;

ALLIUM; ANIMALS; ANTIOXIDANTS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; MELANINS; MELANOMA, EXPERIMENTAL; MICE;

ALLIUM CEPA; BASIDIOMYCOTA;

EID: 79959616670     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2011-5-603     Document Type: Article

References (27)

1. Abou-Donia A. H., Toaima S. M., Hammoda H. M., Shawky E., Kinoshita E., and Takayama H. (2008), Phytochemical and biological investigation of Hyme-nocallis littoralis SALISB. Chem. Biodiv. 5, 32-40.
2. Alluis B. and Dangles O. (2001), Quercetin (= 2-(3, 4-di-hydroxyphenyl)-3, 5, 7-trihydroxy-4H-1-benzopyran-4-one) glycosides and sulfates: chemical synthesis, complexation, and antioxidant properties. Helv. Chim. Acta 84, 1133-1156.
3. Ando H., Matsui M. S., and Ichihashi M. (2010), Quasi-drugs developed in Japan for the prevention or treatment of hyperpigmentary disorders. Int. J. Mol. Sci. 11, 2566-2575.
4. Arung E. T., Shimizu K., and Kondo R. (2007), Structure-activity relationship of prenyl-substituted polyphenols from Artocarpus heterophyllus as inhibitors of melanin biosynthesis in cultured melanoma cells. Chem. Biodiv. 4, 2166-2171.
5. Choi M. Y., Song H. S., Hur H. S., and Sim S. S. (2008), Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Arch. Pharmacal Res. 31, 1166-1171.
6. de Padua L. S., Bunyapraphatsara N., and Lemmens R. H. M. J. (1999), Plant Resources of South-East Asia: Medicinal and Poisonous Plants, Vol. 12 (1). Prosea Press, Bogor, pp. 93-97.
7. Fujii T. and Saito M. (2009), Inhibitory effect of quercetin isolated from rose rip (Rosa canina L.) against melanogenesis by mouse melanoma cells. Biosci. Biotech. Biochem. 73, 1989-1993.
8. Gulsen A., Makris D. P., and Kefalas P. (2007), Biomi-metic oxidation of quercetin: isolation of a naturally occurring quercetin heterodimer and evaluation of its in vitro antioxidant properties. Food Res. Int. 40, 7-14.
9. Kaneko T. and Baba N. (1999), Protective effect of flavonoids on endothelial cells against linoleic acid hydroperoxide-induced toxicity. Biosci. Biotechnol. Biochem. 63, 323-328.
10. Kawaii S., Tomono Y., Katase E., Ogawa K., and Yano M. (1999), Antiproliferative activity of flavonoids on several cancer cell lines. Biosci. Biotechnol. Biochem. 63, 896-899.
11. Kohri S., Fujii H., Oowada S., Endoh N., Sueishi Y., Kusakabe M., Shimmei M., and Kotake Y. (2009), An oxygen radical absorbance capacity-like assay that directly quantifies the antioxidantʼns scavenging capacity against AAPH-derived free radicals. Anal. Biochem. 386, 167-171.
12. Kubo I. and Kinst-Hori I. (1999), Flavonols from saf-fron flower: Tyrosinase inhibitory activity and inhibition mechanism. J. Agric. Food Chem. 47, 4121-4125.
13. Kubo I., Nitoda T., and Nihei K. (2007), Effects of quercetin on mushroom tyrosinase and B16-F10 melanoma cells. Molecules 12, 1045-1056.
14. Lai X., Liang H., Zhao Y., and Wang B. (2009), Simultaneous determination of seven active flavonols in the flowers of Abelmoschus manihot by HPLC. J. Chromatogr. Sci. 47, 206-210.
15. Liu M. and Chen Z. (2008), Protective effect of quercetin-3′-0-y8-glucoside on myocardial ischemic injury in mice. Anhui Yike Daxue Xuebao 43, 683-685.
16. Nagata H., Susumu T., Takeyama R., Homma T., and Osamura R. Y. (2004), Quercetin enhances melanogenesis by increasing the activity and synthesis of tyrosinase in human melanoma cells and in normal human melanocytes. Pigment Cell Res. 17, 66-73.
17. Ou B., Hampsch-Woodill M., and Prior R. L. (2001), Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J. Agric. Food Chem. 49, 4619-4626.
18. Perluigi M., De Marco F., Foppoli C., Coccia R., Blarzi-no C., Marcante M. L., and Cini C. (2003), Tyrosinase protects human melanocytes from ROS-generating compounds. Biochem. Biophys. Res. Commun. 305, 250-256.
19. Pietta P. G. (2000), Flavonoids as antioxidants. J. Nat. Prod. 63, 1035-1042.
20. Prakash D., Upadhyay G., Singh B. N., and Singh H. B. (2007), Antioxidant and free radical-scavenging activities of seeds and agri-wastes of some varieties of soybean (Glycine max). Food Chem. 104, 783-790.
21. Prior R. L., Hoang H., Gu L., Wu X., Bacchioca M., Howard L., Hampsch-Woodill M., Huang D., Ou B., and Jacob R. (2003), Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity, ORACFL) of plasma and other biological and food samples. J. Agric. Food Chem. 51, 3273-3279.
22. Sanchez-Ferrer A., Rodngez-Lopez J. N., and Garcia-Car-mona F. (1995), Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta 1247, 1-11.
23. Sanderson J., Mclauchlin W., and Williamson G. (1999), Quercetin inhibits hydrogen peroxide-induced oxidation of the rat lens. Free Radical Biol. Med. 26, 639-645.
24. Shutenko Z., Henry Y., Pinard E., Seylaz J., Potier P., Berthet F., Girard P., and Sercombe R. (1999), Influence of the antioxidant quercetin in vivo on the level of nitric oxide determined by electron paramagnetic resonance in rat brain during global ischemia and reperfusion. Biochem. Pharmacol. 57, 199-208.
25. Singh B. N., Singh B. R., Singh R. L., Prakash D., Singh D. P., Sarma B. K., Upadhyay G., and Singh H. B. (2009), Polyphenolics from various extracts/fractions of red onion (Allium cepa) peel with potent antioxidant and antimutagenic activities. Food Chem. Toxicol. 47, 450-452.
26. Wu T., Abdulla R., Yang Y., and Aisa A. (2008), Flavonoid from Gossypium hirsutum flowers. Chem. Nat. Compd. 44, 370-371.
27. Yoon J. H., Shim J. S., Cho Y., Baek N. I., Lee C. W., Kim H. S., and Hwang J. K. (2007), Depigmentation of melanocytes by isopanduratin A and 4-hydroxy-panduratin A isolated from Kaempferia pandurata RoxB. Biol. Pharm. Bull. 30, 2141-2145.