Inhibitory effects of geranic acid derivatives on melanin biosynthesis

Journal of Cosmetic Science

Volumn 63, Issue 6, 2012, Pages 351-358

  Choi, Sang Yoon ^a  

^a Korea Food Research Institute   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CITRONELLIC ACID; CITRONELLOL; DECAPRENOIC ACID; DEPIGMENTING AGENT; GERANIOL; KOJIC ACID; MELANIN; MONOPHENOL MONOOXYGENASE; OCTANOIC ACID DERIVATIVE; PYRONE DERIVATIVE; TERPENE;

ANIMAL; ARTICLE; BIOSYNTHESIS; CELL LINE; CELL SURVIVAL; CYTOLOGY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; MELANOCYTE; METABOLISM; MOUSE; SKIN;

ANIMALS; CAPRYLATES; CELL LINE; CELL SURVIVAL; MELANINS; MELANOCYTES; MICE; MONOPHENOL MONOOXYGENASE; MONOTERPENES; PYRONES; SKIN; SKIN LIGHTENING PREPARATIONS; TERPENES;

EID: 84873962699     PISSN: 15257886     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. S. Suola and B. Kitchell, The biology of melanocytes, Vet. Dermatol., 14, 57–65 (2003).
2. J. Y. Lin and D. E. Fisher, Melanocyte biology and skin pigmentation, Nature, 445, 843–850 (2007).
3. L. Baumann, Cosmetic Dermatology (The McGraw-Hill Companies, New York, 2001).
4. Y. Miyamura, S. Coelho, R. Wolber, S. Miller, K. Wakamatsu, B. Z. Zmudzka, S. Ito, C. Smuda, T. Passeron, W. Choi, J. Batzer, Y. Yamaguchi, J. Z. Beer, and V. J. Hearing, Regulation of human skin pigmentation and responses to ultraviolet radiation, Pigment Cell Res., 20, 2–13 (2006).
5. N. Wang and D. N. Hebert, Tyrosinase maturation through the mammalian secretory pathway: bringing color to life, Pigment Cell Res., 19, 3–18 (2006).
6. H. Ando, H. Kondoh, M. Ichihashi, and V. J. Hearing, Approaches to identify inhibitors of melanin biosynthesis via the quality control of tyrosinase. J. Invest. Dermatol., 127, 751–761 (2007).
7. S. Parvez, M. Kang, H. S. Chung, C. Cho, M. C. Hong, M. K. Shin, and H. Bae, Survey and mechanism of skin depigmenting and lightening agents, Phytother. Res., 20, 921–934 (2006).
8. S. Okombi, D. Rival, S. Bonnet, A. Mariotte, E. Perrier, and A. Boumendjel, Discovery of benzylidenebenzofuran-3(2H)-one(Aurones) as inhibitors of tyrosinase derived from human melanocytes, J. Med. Chem., 49, 329–333 (2006).
9. B. Hoschle and D. Jendrossek, Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol, Microbiology, 151, 2277–2283 (2005).
10. W. A. M. Wolken and M. J. Werf, Geraniol biotransformation-pathway in spores of Penicillium digitatum, Appl. Microbiol. Biotechnol., 57, 731–737 (2001).
11. T. Masuda, Y. Odaka, N. Ogawa, K. Nakamoto, and H. Kuninaga, Identification of geranic acid, a tyrosinase inhibitor in Lemongrass (Cymbopogon citratus), J. Agric. Food Chem., 56, 597–601 (2008).
12. J. J. Mateo, N. Gentilini, T. Huerta, M. Jimenez, and R. Stefano, Fractionation of glycoside precursors of aroma in grapes and wine, J. Chromatogr. A, 778, 219–224 (1997).
13. S. Selli, T. Cabaroglu, A. Canbas, H. Erten, and C. Nurgel, Effect of skin contact on the aroma composition of musts of Vitis vinifera L. cv. Muscat of Bornova and Narince grown in Turkey, Food Chem., 81, 341–347 (2003).
14. T. Chatterjee, Biotransformation of geraniol by Rhodococcus sp. Strain GR3, Biotechnol. Appl. Biochem., 39, 303–306 (2004).
15. S. S. Joglekar and R. S. Dhavlikar, Microbial transformation of terpenoids, Appl. Microbiol., 18, 1084–1087 (1969).
16. W. Wolken, J. Tramper, and M. Werf, Toxicity of terpenes to spores and mycelium of Penicillium digitatum, Biotechnol. Bioeng., 80, 685–690 (2002).
17. Y. H. Kong, Y. O. Jo, C. Cho, D. Son, S. Park, J. Rho, and S. Y. Choi, Inhibitory effects of cinnamic acid on melanin biosynthesis in skin, Biol. Pharm. Bull., 31, 946–948 (2008).
18. T. P. Dooley, R. C. Gadwood, K. Kilgore, and L. M. Thomasco, Development of an in vitro primary screen for skin depigmentation and antimelanoma agents, Skin Pharmacol., 7, 188–200 (1994).
19. J. H. Kim, S. H. Baek, D. H. Kim, T. Y. Choi, T. J. Yoon, J. S. Hwang, M. R. Kim, H. J. Kwon, and C. H. Lee, Downregulation of melanin synthesis by haginin A and its application to in vivo lightening model, J. Invest. Dermatol., 128, 1227–1235 (2008).
20. A. Poma, S. Bianchini, and M. Miranoa, Inhibition of L-tyrosine-induced micronuclei production by phenylthiourea in human melanoma cells, Mutation Res., 446, 143–148 (1999).
21. S. R. Gallagher, Digital image processing and analysis with image J, Current Protocols Essential Laboratory Techniques, 3, A.3C.1–A.3C.24 (2010).
22. S. Shono and K. Toda, “The Effect of Fatty Acids on Tyrosinase Activity,” in Pigment Cell, M. Seiji Ed. (University of Tokyo Press, Tokyo, 1981), pp. 263–268.
23. V. Kahn, Effect of kojic acid on the oxidation of DL-DOPA, norepinephrine, and dopamine by mushroom tyrosinase, Pigment Cell Res., 8, 234–240 (1995).
24. D. Bennett, P. Cooper, and I. Hart, A line of non-tumorigenic mouse melanocytes, syngeneic with the B16 melanoma and requiring a tumor promoter for growth, Int. J. Cancer, 39, 414–418 (1987).
25. S. Y. Seo, V. K. Sharma, and N. Sharma, Mushroom tyrosinase: recent prospects, J. Agric. Food Chem., 51, 2837–2853 (2003).
26. M. Sugumaran, Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects, Pigment Cell Res., 15, 2–9 (2002).
27. J. Martinez, F. Solano, J. Garcia, J. Jara, and J. Lozano, α-MSH and other melanogenic activators mediate opposite effects on tyrosinase and dopachrome tautomerase in B16/F10 mouse melanoma cells, J. Invest. Dermatol., 99, 435–439 (1992).