Inhibition effects of mangosenone F from garcinia mangostana on melanin formation in B16F10 cells

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 34, 2012, Pages 8372-8378

  Ryu, Hyung Won ^a   Jeong, Seong Hun ^a   Curtis Long, Marcus J ^b   Jung, Sunin ^a   Lee, Ji Won ^a   Woo, Hyun Sim ^a   Cho, Jung Keun ^a   Park, Ki Hun ^a  

^a Gyeongsang National University   (South Korea)

^b BRANDEIS UNIVERSITY   (United States)

Author keywords

glucosidase; cytotoxicity; endo H; mangostenone F; melanogenesis

Indexed keywords

DEOXYNOJIRIMYCIN; ENDO H; ENDOGLYCOSIDASE; EXPRESSION LEVELS; GLUCOSIDASE; GLYCOSIDASE INHIBITORS; IN-VITRO; INHIBITION EFFECT; MELANOGENESIS; MELANOMA CELLS; TYROSINASE INHIBITION; WESTERN BLOTS;

CYTOTOXICITY;

CELL CULTURE;

ALPHA GLUCOSIDASE; DOPACHROME ISOMERASE; ENZYME INHIBITOR; ISOMERASE; MANGOSTENONE F; MELANIN; MONOPHENOL MONOOXYGENASE; N ACETYL BETA GLUCOSAMINIDASE; XANTHONE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; EXPERIMENTAL MELANOMA; GARCINIA MANGOSTANA; IC 50; METABOLISM; MOUSE; TUMOR CELL LINE;

ALPHA-GLUCOSIDASES; ANIMALS; CELL LINE, TUMOR; ENZYME INHIBITORS; GARCINIA MANGOSTANA; INHIBITORY CONCENTRATION 50; INTRAMOLECULAR OXIDOREDUCTASES; MANNOSYL-GLYCOPROTEIN ENDO-BETA-N-ACETYLGLUCOSAMINIDASE; MELANINS; MELANOMA, EXPERIMENTAL; MICE; MONOPHENOL MONOOXYGENASE; XANTHONES;

GARCINIA MANGOSTANA;

EID: 84865651914     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf3015987     Document Type: Article

References (23)

1. 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
2. Spritz, R. A.; Hearing, V. J., Jr. Genetic disorders of pigmentation Adv. Hum. Genet. 1994, 22, 1-45
3. Hu, X.; Wu, J. W.; Wang, M.; Yu, M. H.; Zhao, Q. S.; Wang, H. Y.; Hou, A. J. 2-Arylbenzofuran, flavonoid, and tyrosinase inhibitory constituents of Morus yunnanensis J. Nat. Prod. 2012, 75, 82-87
4. Durairaj, R. B. Resorcinol: Chemistry, Technology, And Applications; Springer Verlag: Heidelberg, Germany, 2005; pp 688-690.
5. Ando, H.; Kondoh, H.; Ichihashi, M.; Hearing, V. J. Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase J. Invest. Dematol. 2007, 127, 751-761
6. Petrescu, S. M.; Petrescu, A. J.; Titu, H. N.; Dwek, R. A.; Platt., F. M. Inhibition of N-glycan processing in B16 melanoma cells results in inactivation of tyrosinase but does not prevent its transport to the melanosome J. Biol. Chem. 1997, 272, 15796-15803
7. Kornfeld, R.; Kornfeld, S. Assembly of asparagines-liked oligosaccharides Annu. Rev. Biochem. 1985, 54, 631-664
8. Wang, N.; Hebert, D. N. Tyrosinase maturation through the mammalian secretory pathway: bring color to life Pigment Cell Res. 2006, 19, 3-18
9. Elbein, A. D. Inhibitors of the biosynthesis and processing of N-linked oligosaccharide chains Annu. Rev. Biochem. 1987, 56, 497-534
10. Lubas, W. A.; Spiro, R. G. Goligi endo-α- d -mannosidase from rat liver, a novel linked carbohydrate unit processing enzyme J. Biol. Chem. 1987, 262, 3775-3781
11. Ryu, H. W.; Cho, J. K.; Curtis-Long, M. J.; Yuk, H. J.; Kim, Y. S.; Jung, S. I.; Kim, Y. S.; Lee, B. W.; Park, K. H. α-Glucosidase inhibition and antihyperglycemic activity of prenylated xanthones from Garcinia mangostana Phytochemistry 2011, 72, 2148-2154
12. Ryu, H. W.; Curtis-Long, M. J.; Jung, S. I.; Jin, Y. M.; Cho, J. K.; Ryu, Y. B.; Lee, W. S.; Park, K. H. Xanthones with neuraminidase inhibitory activity from the seedcases of Garcinia mangostana Bioorg. Med. Chem. 2010, 18, 6258-6264
13. Kubo, I.; Kinst-Hori, I. Tyrosinase inhibitors from cumin J. Agric. Food Chem. 1998, 46, 5338-5341
14. Kim, J. Y.; Lee, J. W.; Lee, Y. N.; Ryu, Y. B.; Kim, S. M.; Kim, Y. S.; Ryu, H. W.; Curtis-Long, M. J.; Lee, K. W.; Lee, W. S.; Park, K. H. A novel competitive class of α-glucosidase inhibitors: (E)-1-phenyl-3-(4- styrylphenyl)urea derivatives ChemBioChem. 2010, 11, 2125-2131
15. Lee, Y. J.; Chung, D. Y.; Lee, S. J.; Ja, J. G.; Lee, Y. S. Enhanced radiosensitization of p53 mutant cells by oleamide Int. J. Radiat. Oncol. Biol. Phys. 2006, 64, 1466-1474
16. Yang, J. Y.; Koo, J. H.; Song, Y. G.; Kwon, K. B.; Lee, J. H.; Sohn, H. S.; Park, B. H.; Jhee, E. C.; Park, J. W. Stimulation of melanogenesis by scoparone in B16 melanoma cells Acta. Pharmacol. Sin. 2006, 27, 1467-1473
17. Ohguchi, K.; Ito, M.; Yokoyama, K.; Iinuma, M.; Itoh, T.; Nozawa, Y.; Akao, Y. Effects of sesquiterpene lactones on melanogenesis in mous B16 melanoma cells Biol. Pharm. Bull. 2009, 32, 308-310
18. Halaban, R.; Sevedine, S.; Cheng, E.; Smicun, Y.; Aron, R.; Hebert, D. N. Endoplsmic reticulum retention is a common defect associated with tyrosinase-negative albinism Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 5889-5894
19. Atsumi, S.; Nosaka, C.; Ochi, Y.; Iinuma, H.; Umezawa, K. Inhibition of experimental metastasis by an α-glucosidase inhibitor, 1,6-epi-cyclophellitol Cancer Res. 1993, 53, 4896-4899
20. Imperiali, B.; Shannon, K. L. Differences between Asn-Xaa-Thr-containing peptides: acomparision of solution conformation and substrate behavior with oligosaccharyl transferase Biochemistry 1991, 30, 4374-4380
21. Ujvari, A.; Aron, R.; Eisenhaure, T.; Cheng, E.; Parag, H. A.; Smicun, Y.; Halaban, R.; Hebert, D. N. Translation rate of human tyrosinase determines its N-linked glycosylation level J. Biol. Chem. 2001, 276, 5924-5931
22. Petrescu, S. M.; Nichita, B. N.; Negroiu, G.; Petrescu, A. J.; Dwek, R. A. Tyrosinase and glycoprotein folding: roles of chaperones that recognize glycans Biochemistry 2000, 39, 5229-5237
23. Halaban, R.; Chang, E.; Zhang, Y.; Moellmann, G.; Hanlon, D.; Michalak, M.; Setaluri, V.; Hebert, D. N. Aberrant retention of tyrosinase in the endoplasmic reticulum mediates accelerated degradation of the enzyme and contributes to the dedifferentiated phenotype of amellanotic melanoma cells Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 6210-6215