Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 5, 2003, Pages 1201-1207

  Nerya, Ohad ^a   Vaya, Jacob ^a,b   Musa, Ramadan ^a   Izrael, Sarit ^a   Ben Arie, Ruth ^a   Tamir, Snait ^a,b  

^a MIGAL GALILEE TECHNOLOGY CENTER   (Israel)

^b TEL HAI COLLEGE   (Israel)

Author keywords

Chalcones; Glabrene; Isoflavans; Tyrosinase; Whitening agents

Indexed keywords

CHALCONE; DEPIGMENTING AGENT; DRUG DERIVATIVE; ENZYME INHIBITOR; GLABRENE; GLABRIDIN; ISOFLAVONE DERIVATIVE; ISOLIQUIRITIGENIN; MELANIN; MONOPHENOL MONOOXYGENASE; PEPTIDE; PHENOL DERIVATIVE; PLANT EXTRACT; TYROSINASE INHIBITOR; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CELL CULTURE; CHEMICAL COMPOSITION; CHEMISTRY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DEPIGMENTATION; DOSE RESPONSE; DRUG EFFECT; DRUG MECHANISM; ENZYME INHIBITION; EXTRACTION; GLYCYRRHIZA; HUMAN; HUMAN CELL; KINETICS; MELANOCYTE; MELANOGENESIS; METABOLISM; MOLECULAR STABILITY; MUTAGENICITY; NONHUMAN; PLANT ROOT; SKIN PENETRATION; STRUCTURE ACTIVITY RELATION;

CELLS, CULTURED; CHALCONE; CHALCONES; DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCYRRHIZA; HUMANS; ISOFLAVONES; KINETICS; MELANINS; MELANOCYTES; MONOPHENOL MONOOXYGENASE; PEPTIDES; PHENOLS; PLANT EXTRACTS; PLANT ROOTS; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

GLYCYRRHIZA; LIGUSTICUM; MAMMALIA;

EID: 0037467028     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020935u     Document Type: Article

References (41)

1. Spritz, R. A.; Hearing, V. J., Jr. Genetic disorders of pigmentation. Adv. Hum. Genet. 1994, 22, 1-45.
2. Frenk, E. Treatment of melasma with depigmenting agents. In Melasma: New Approaches to Treatment; Martin Dunitz Ltd.: London, 1995; pp 9-15.
3. Whitaker, J. R. Polyphenol oxidase. In Food Enzymes, Structure and Mechanism; Wong, D. W. S., Ed.; Chapman & Hall: New York, 1995; pp 271-307.
4. Vamos-Vigyazo, L. Polyphenol oxidase and peroxidase in fruits and vegetables. Crit. Rev. Food Sci. Nutr. 1981, 15, 49-127.
5. Seiberg, M.; Paine, C.; Sharlow, 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.
6. Seiberg, M.; Paine, C.; Sharlow, E.; Andrade-Gordon, P.; Costanzo, M.; Eisinger, M.; Shapiro, S. S. The protease-activated receptor 2 regulates pigmentation via keratinocyte-melanocyte interactions. Exp. Cell. Res. 2000, 254, 25-32.
7. Dooley, T. P. Topical skin depigmentation agents: current products and discovery of novel inhibitors of melanogenesis. J. Dematol. Treat. 1997, 7, 188-200.
8. Hermanns, J. F.; Petit, L.; Martalo, O.; Pierard-Franchimont, C.; Cauwenbergh, G.; Pierard, G. E. Unraveling the patterns of subclinical pheomelanin-enriched facial hyperpigmentation: Effect of depigmenting agents. Dermatology 2000, 201, 118-122.
9. Demizu, S.; Kajiyama, K.; Takahashi, K.; Hiraga, Y.; Yamamoto, S.; Tamura, Y.; Okada, K.; Kinoshita, T. Antioxidant and antimicrobial constituents of licorice: Isolation and structure elucidation of a new benzofuran derivative. Chem. Pharm. Bull. (Tokyo) 1988, 36, 3474-3479.
10. Mitscher, L. A.; Park, Y. H.; Clark, D.; Clark, G. W. D.; Hammesfahr, P. D.; Wu, W. N.; Beal, J. L. Antimicrobial agents from higher plants. An investigation of Hunnemannia fumariaefolia pseudoalcoholates of sanguinarine and chelerythrine. Lloydia 1978, 41, 145-150.
11. Belinky, P. A.; Aviram, M.; Fuhrman, B.; Rosenblat, M.; Vaya, J. The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation. Atherosclerosis 1998, 137, 49-61.
12. Vaya, J.; Belinky, P. A.; Aviram, M. Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. Free Radical Biol. Med. 1997, 23, 302-313.
13. Tamir, S.; Eizenberg, M.; Somjen, D.; Stern, N.; Shelach, R.; Kaye, A.; Vaya, J. Estrogenic and antiproliferative properties of glabridin from licorice in human breast cancer cells. Cancer Res. 2000, 60, 5704-5709.
14. Yokota, T.; Nishio, H.; Kubota, Y.; Mizoguchi, M. The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. Pigment Cell Res. 1998, 11, 355-361.
15. Belinky, P. A.; Aviram, M.; Mahmood, S.; Vaya, J. Structural aspects of the inhibitory effect of glabridin on LDL oxidation. Free Radical Biol. Med. 1998, 24, 1419-1429.
16. Tamir, S.; Eizenberg, M.; Somjen, D.; Izrael, S.; Vaya, J. Estrogen-like activity of glabrene and other constituents isolated from licorice root. J. Steroid Biochem. Mol. Biol. 2001, 78, 291-298.
17. Chen, J. S.; Wei, C.; Rolle, R. S.; Otwell, W. S.; Balaban, M. O.; Marshall, M. R. Inhibitory effect of kojic acid on some plant and crustacean polyphenol oxidases. J. Agric. Food Chem. 1991, 39, 1396-1410.
18. Curto, E. V.; Kwong, C.; Hermersdorfer, H.; Glatt, H.; Santis, C.; Virador, V.; Hearing, V. J., Jr.; Dooley, T. P. Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Biochem. Pharmacol. 1999, 57, 663-672.
19. Shin, N. H.; Ryu, S. Y.; Choi, E. J.; Kang, S. H.; Chang, I. M.; Min, K. R.; Kim, Y. Oxyresveratrol as the potent inhibitor on dopa oxidase activity of mushroom tyrosinase. Biochem. Biophys. Res. Commun. 1998, 243, 801-803.
20. Cabanes, J.; Garcia-Canovas, F.; Lozano, J. A.; Garcia-Carmona, F. A kinetic study of the melanization pathway between L-tyrosine and dopachrome. Biochim. Biophys. Acta. 1987, 923, 187-195.
21. Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Tyrosinase: A comprehensive review of its mechanism. Biochim. Biophys. Acta. 1995, 1247, 1-11.
22. Khan, V.; Andrawis, A. Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 1985, 24, 905-908.
23. Kubo, I.; Kinst-Hori, I. Tyrosinase inhibitors from cumin. J. Agric. Food Chem. 1998, 46, 5338-5341.
24. Nakagawa, M.; Kawai, K. Contact allergy to kojic acid in skin care products. Contact Dermatitis 1995, 32, 9-13.
25. Niwa, Y.; Akamatsu, H. Kojic acid scavenges free radicals while potentiating leukocyte functions including free radical generation. Inflammation 1991, 15, 303-315.
26. Schallreuter, K. U.: Wood, J. W. A possible mechanism of action for azelaic acid in the human epidermis. Arch. Dermatol. Res. 1990, 282, 168-171.
27. Matsuda, H.; Higashino, M.; Nakai, Y.; Iinuma, M.; Kubo, M.; Lang, F. A. Studies of cuticle drugs from natural sources. IV. Inhibitory effects of some Arctostaphylos plants on melanin biosynthesis. Biol. Pharm. Bull. 1996, 19, 153-156.
28. Chakraborty, A. K.; Funasaka, Y.; Komoto, M.; Ichihashi, M. Effect of arbutin on melanogenic proteins in human melanocytes. Pigment Cell Res. 1998, 11, 206-212.
29. Shimizu, K.; Kondo, R.; Sakai, K. Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: Structure-activity investigations. Planta Med. 2000, 66, 11-15.
30. Kubo, I.; Kinst-Hori, I. Tyrosinase inhibitory activity of the olive oil flavor compounds. J. Agric. Food Chem. 1999, 47, 4574-4578.
31. Kubo, I.; Kinst-Hori, I. 2-Hydroxy-4-methoxybenzaldehyde: a potent tyrosinase inhibitor from African medicinal plants. Planta Med. 1999, 65, 19-22.
32. Sakuma, K.; Ogawa, M.; Sugibayashi, K.; Yamada, K.; Yamamoto, K. Relationship between tyrosinase inhibitory action and oxidation - reduction potential of cosmetic whitening ingredients and phenol derivatives. Arch. Pharm. Res. 1999, 22, 335-339.
33. Seo, B.; Yun, J.; Lee, S.; Kim, M.; Hwang, K.; Kim, J.; Min, K. R.; Kim, Y.; Moon, D. Barbarin as a new tyrosinase inhibitor from Barbarea orthocerus. Planta Med. 1999, 65, 683-686.
34. Ha, T, J.; Yang, M. S.; Jang, M. S.; Jang, D. S.; Choi, S. U.; Park, K. H. Inhibitory activities of flavanone derivatives isolated from Sophora flavescens for melanogenesis. Bull. Korean Chem. Soc. 2001, 22, 660-701.
35. Lee, H. S. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J. Agric. Food Chem. 2002, 50, 1400-1403.
36. Kim, Y. M.; Yun, J.; Lee, C. K.; Lee, H.; Min, K. R.; Kim, Y. Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. J. Biol. Chem. 2002, 277, 16340-16344.
37. Sasaki, K.; Yoshizaki, F. Nobiletin as a tyrosinase inhibitor from the peel of Citrus fruit. Biol. Pharm. Bull. 2002, 25, 806-808.
38. Jimenez, M.; Chazarra, S.; Escribano, J.; Cabanes, J.; Garcia-Carmona, F. Competitve inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. J. Agric. Food Chem. 2001, 49, 4060-4063.
39. Battaini, G.; Monzani, E.; Casella, L.; Santagostini, L.; Pagliarin, R. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. J. Biol. Inorg. Chem. 2000, 5, 262-268.
40. No, J. K.; Soung, D. Y.; Kim, Y. J.; Shim, K. H.; Jun Y. S.; Rhee, S. H.; Yokozawa, T.; Chung, H. Y. Inhibition of tyrosinase by green tea components. Life Sci. 1999, 65, 241-246.
41. De Vincenzo, R.; Scambia, G.; Benedetti Panici, P.; Ranelletti, F. O.; Bonanno, G.; Ercoli, A.; Delle Monache, F.; Ferrari, F.; Piantelli, M.; Mancuso, S. Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth: structure-activity relationships. Anticancer Drug Des. 1995, 10, 481-490.