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http://dx.doi.org/10.5012/jkcs.2018.62.1.19

Synthesis of Rhamnazin and Ombuin as Methylated Metabolites of Quercetin  

Jang, Jongyun (Department of Pharmaceutical Science and Technology, Catholic University of Daegu)
Kang, Dong Wook (Department of Pharmaceutical Science and Technology, Catholic University of Daegu)
Publication Information
Journal of the Korean Chemical Society / v.62, no.1, 2018 , pp. 19-23 More about this Journal
Abstract
The methylated metabolites of quercetin, rhamnazin and ombuin are highly likely to develop as anticancer and anti-inflammatory agents. In this study, we synthesized rhamnazin through selective methylation of quercetin hydroxyl group, which has not been reported so far. In addition, a new synthetic method was developed to correct the problems of previous synthetic method of ombuin, one of the methylated metabolites of quercetin.
Keywords
Rhamnazin; Ombuin; Quercetin; Methylation;
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1 Packer, L.; Flavonoids and other Polyphenols. Methods in Enzymology, Ed.; Academic: San Diego, 2001; Vol. 335.
2 Pietta, P. G. J. Nat. Prod. 2000, 63, 1035.   DOI
3 Choi, J. A.; Kim, J. Y.; Lee, J. Y.; Kang, C. M.; Kwon, H. J.; Yoo, Y. D.; Kim, T. W.; Lee, Y. S.; Lee, S. J. Int. J. Oncol. 2001, 19, 837.
4 Yoshizumi, M.; Tsuchiya, K.; Kirima, K.; Kyaw, M.; Suzaki, Y.; Tamaki, T. Mol. Pharmacol. 2001, 60, 656.
5 Schroeter, H.; Spencer, J. P. E.; Rice-Evans, C.; Williams, R. J. Biochem. J. 2001, 358, 547.   DOI
6 Wang, H. K. Expert Opin. Investig. Drugs, 2000, 9, 2103.   DOI
7 Lamson, D. W.; Brignall, M. S. Altern. Med. Rev. 2000, 5, 196.
8 Ader, P.; Wessmann, A.; Wolffram, S. Free Rad. Biol. Med. 2000, 28, 1056.   DOI
9 Manach, C.; Texier, O.; Morand, C.; Crespy, V.; Regerat, F.; Demigne, C.; Remesy, C. Free Rad. Biol. Med. 1999, 27, 1259.   DOI
10 Boulton, D. W.; Walle, U. K.; Walle, T. J. Pharm. Pharmacol. 1999, 51, 353.   DOI
11 O'Leary, K. A.; Day, A. J.; Needs, P. W.; Sly, W. S.; O'Brien, N. M.; Williamson, G. FEBS Lett. 2001, 503, 103.   DOI
12 Yu, Y.; Cai, W.; Pei, C.G.; Shao, Y. Biochem. Biophys. Res. Commun., 2015, 458, 913.   DOI
13 Rao, Y. K.; Fang, S. H.; Tzeng, Y. M. Phytother. Res., 2008, 22, 957.   DOI
14 Bouktaib, M.; Lebrun, S.; Atmani, A.; Ronaldo, C. Tetrahydron, 2002, 58, 10001.   DOI
15 Rao, K. V.; Owoyale, J. A. J. Heterocycl. Chem. 1976, 13, 1293.   DOI
16 Li, N. G.; Wang, J. X.; Liu, X. R.; Lin, C. J.; You, Q. D.; Guo, Q. L. Tetrahedron Lett. 2007, 48, 6586.   DOI
17 Shi, Z. H.; Li, N. G.; Tang, Y. P.; Li, W.; Yin, L.; Yang, J. P.; Tang, H.; Duan, J. A. Eur. J. Med. Chem., 2012, 54, 210.   DOI