Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes

Journal of Medicinal Chemistry

Volumn 49, Issue 1, 2006, Pages 329-333

  Okombi, Sabrina ^a   Rival, Delphine ^b   Bonnet, Sébastien ^b   Mariotte, Anne Marie ^a   Perrier, Eric ^b   Boumendjel, Ahcène ^a  

^a Laboratoire de Pharmacochimie   (France)

^b Engelhard   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4,6,4' TRIHYDROAURONE; APIGENIN; BENZOFURAN DERIVATIVE; BENZYLIDENE DERIVATIVE; BENZYLIDENEBENZOFURAN 3(2H) ONE; COPPER; ENZYME INHIBITOR; HYDROXYL GROUP; KOJIC ACID; LEVODOPA; MONOPHENOL MONOOXYGENASE; QUINONE DERIVATIVE; TYROSINASE INHIBITOR; TYROSINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; ENZYME INHIBITION; ENZYME MECHANISM; FEMALE; HUMAN; HUMAN CELL; HYPERPIGMENTATION; MELANOCYTE; MELANOGENESIS; NONHUMAN; NORMAL HUMAN; OXIDATION; RAT; STRUCTURE ACTIVITY RELATION;

EID: 30444441800     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050715i     Document Type: Article

References (31)

1. Schoot-Uiterkamp, A. J. M.; Mason, H. S. Magnetic dipole-dipole coupled Cu(II) pairs in nitric oxide-treated tyrosinase: A structural relationship between the active sites of tyrosinase and hemocyanin. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 993-996.
2. van Gelder, C. W. G.; Flurkey, W. H.; Wichers, H. J. Sequence and structural features of plant and fungal tyrosinases. Phytochemistry 1997, 45, 1309.
3. Mason, H. S. The chemistry of melanin. III. Mechanism of the oxidation of trihydroxyphenylalanine by tyrosinase. J. Biol. Chem. 1948, 172, 83-99.
4. Lerner, A. B.; Fitzpatrich, T. B.; Calkins, E.; Summerson, W. H. Mammalian tyrosinase-preparation and properties. J. Biol. Chem. 1949, 179, 185-195.
5. Xu, Y.; Storkes, A. H.; Freeman, W. M.; Kumer, S. C.; Vogt, B. A.; Vrana, K. E. Tyrosinase mRNA is expressed in human substantia nigra. Brain Res. Mol. Brain Res. 1997, 45, 159-162.
6. Mayer, A. M. Polyphenol oxidases in plants-recent progress. Phytochemistry 1987, 26, 11-20.
7. Friedman, M. Food Browning and Its Prevention: An Overview. J. Agric. Food. Chem. 1996, 44, 631-653.
8. Maeda, K.; Fukuda, M. Arbutin: mechanism of its depigmenting action in human melanocyte culture. J. Pharm. Exp. Ther. 1996, 276, 765-769.
9. Nihei, K.-I.; Kubo, I. Identification of oxidation product of arbutin in mushroom tyrosinase assay system. Bioorg. Med. Chem. Lett. 2003, 13, 2409-2412.
10. Saruno, R.; Kato, F.; Ikeno, T. Kojic acid, a tyrosinase inhibitor from Aspergillus albus. Agric. Biol. Chem. 1979, 43, 1337-1338.
11. Saruno, R.; Kato, F. Kojic acid, a tyrosinase inhibitor from Aspergillus albus. Agric. Biol. Chem. 1979, 43, 1337-1338.
12. Maeda, K.; Fukuda, M. In vitro effectiveness of several whitening cosmetic components in human melanocytes. J. Soc. Cosmet. Chem. 1991, 42, 361-368.
13. Kahn, V.; Andrawis, A. Inhibition of mushroom tyrosinase by tropolone. Phytochemistry 1985, 24, 905-908.
14. Seo, S. Y.; Sharma, V. K.; Sharma, N. Mushroom Tyrosinase: Recent Prospects. J. Agric. Food. Chem. 2003, 51, 2837-2853.
15. Ley, J. P.; Bertram, H.-J. Hydroxy-or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors. Bioorg. Med. Chem. 2001, 9, 1879-1885.
16. Khatib, S.; Nerya, O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Chalcones as potent tyrosinase inhbitors: the importance of a 2,4-substituted resorcinaol moiety. Bioorg. Med. Chem. 2005, 13, 433-441.
17. Kim, S. J.; Son, K. H.; Chang, H. W.; Kang, S. S.; Kim, H. P. Tyrosinase inhbitory prenylated flavonoids from Sophora flavescens. Biol. Pharm. Bull. 2003, 26, 1348-1350.
18. Harborne, J. R. The Flavonoids: Advances in Research Since 1986; Chapman and Hall: London, 1994; pp 399-341.
19. Atta-ur-Rahman, Choudhary, M. I.; Hayat, S.; Khan, A. M.; Ahmed, A. Two New Aurones from Marine Brown Alga Spatoglossum variabile. Chem. Pharm. Bull. 2001, 49, 105-107.
20. Paré, P. W.; Mischke, C. F.; Edwards, R.; Dixon, R. A.; Norman, H. A.; Mabry, T. J. Induction of phenylpropanoid pathway enzymes in elicitor-treated cultures of Cephalocereus senilis. Phytochemistry 1992, 31, 149-153.
21. Liu, Q.; Markham, K. R.; Paré, P. W.; Dixon, R. A.; Mabry, T. J. Flavonoids from elicitor-treated cell suspension cultures of Cephalocereus senilis. Phytochemistry 1993, 32, 925-928.
22. Paré, P. W.; Dmitrieva, N.; Mabry, T. J. Phytoalexin aurone induced in Cephalocereus senilis liquid suspension culture. Phytochemistry 1991, 30, 1133-1135.
23. Boumendjel, A. Aurones: a subclass of flavonoids with promising biological potential. Curr. Med. Chem. 2003, 10, 2621-2630.
24. Lawrence, N. J.; Rennison, D.; McGown, A. T.; Hadfield, J. A. The total synthesis of an aurone isolated from Uvaria hamiltonii: Aurones and flavones as anticancer agents. Bioorg. Med. Chem. Lett. 2003, 13, 3759-3763.
25. Beney, C.; Mariotte, A.-M.; Boumendjel, A. An efficient synthesis of 4,6-dimethoxy aurones. Heterocycles 2001, 55, 967-972.
26. Li, W. S.; Guo, Z.; Thornton, J.; Katipally, K.; Polniaszek, R.; Thottathil, J.; Vu, T.; Wong, M. Synthesis of substituted 2,3-dihydrobenzofuran in a process involving a facile acyl migration. Tetrahedron Lett. 2002, 43, 1923-1925.
27. Fougerousse, A.; Gonzalez, E.; Brouillard, R. A Convenient Method for Synthesizing 2-Aryl-3-hydroxy-4-oxo-4H-1-benzopyrans or Flavonols. J. Org. Chem. 2000, 65, 583-586.
28. Winder, A. J.; Harris, H. New assays for the tyrosine hydroxylase and dopa oxidase activities of tyrosinase. Eur. J. Biochem. 1991, 198, 317-326.
29. Funayama, M.; Arakawa, H.; Yamamoto, R.; Nishino, T.; Shin, T.; Murao, S. Effects of alpha- and beta-arbutin on activity of tyrosinases from mushroom and mouse melanoma. Biosci. Biotechnol. Biochem. 1995, 59, 143-144.
30. Alvaro, S. F.; Neptuno, R.-L. J.; Francisco, G.-C.; Francisco, G. C. Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta 1995, 1247, 1-11.
31. Yang, T. T.; Sinai, P.; Kain, S. R. An acid phosphatase assay for quantifying the growth of adherent and nonadherent cells. Anal. Biochem. 1996, 241, 103-108.