Significant enhancement in radical-scavenging activity of curcuminoids conferred by acetoxy substituent at the central methylene carbon

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 12, 2011, Pages 3793-3800

  Kim, Mi Kyoung ^a   Jeong, Wooseong ^a   Kang, Jihoon ^a   Chong, Youhoon ^a  

^a Konkuk University   (South Korea)

Author keywords

Acetoxy; Carbon centered radical; Curcuminoids; Radical scavenging activity

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 1,7 BIS(3,4 DIHYDROXY 5 METHOXYPHENYL) 3 HYDROXY 5 OXOHEPTA 1,3,6 TRIEN 4 YL ACETATE; 1,7 BIS(3,4 DIHYDROXY 5 METHOXYPHENYL) 5 HYDROXYHEPTA 1,4,6 TRIEN 3 ONE; 1,7 BIS(3,4 DIMETHOXYPHENYL) 3 HYDROXY 5 OXOHEPTA 1,3,6 TRIEN 4 YL ACETATE; 1,7 BIS(3,4 DIMETHOXYPHENYL) 3 HYDROXY 5 OXOHEPTA 1,3,6 TRIEN 4 YL O ETHYL CARBONODITHIOATE; 1,7 BIS(3,4 DIMETHOXYPHENYL) 5 HYDROXY 4 METHOXYHEPTA 1,4,6 TRIEN 3 ONE; 1,7 BIS(3,4 DIMETHOXYPHENYL) 5 HYDROXY 4 METHYLHEPTA 1,4,6 TRIEN 3 ONE; 1,7 BIS(3,4 DIMETHOXYPHENYL) 5 HYDROXYHEPTA 1,4,6 TRIEN 3 ONE; 3 (1 HYDROXYETHYLIDENE)HEX 5 EN 2 ONE; 3 ACETOXY ACETYLACETONE; 3 HYDROXY 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 5 OXOHEPTA 1,3,6 TRIEN 4 YL ACETATE; 3 HYDROXY 1,7 BIS(4 HYDROXYPHENYL)5 OXOHEPTA 1,3,6 TRIEN 4 YL ACETATE; 3 HYDROXY 5 OXO 1,7 BIS(3,4,5 TRIMETHOXYPHENYL)HEPTA 1,3,6 TRIEN 4 YL ACETATE; 4 ALLYL 1,7 BIS(3,4 DIMETHOXYPHENYL) 5 HYDROXYHEPTA 1,4,6 TRIEN 3 ONE; 4 ALLYL 5 HYDROXY 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL)HEPTA 1,4,6 TRIEN 3 ONE; 4 HYDROXY 3 METHOXYPENT 3 EN 2 ONE; 4 HYDROXY 3 METHYLPENT 3 EN 2 ONE; 5 HYDROXY 1,7 BIS(3,4,5 TRIMETHOXYPHENYL)HEPTA 1,4,6 TRIEN 3 ONE; 5 HYDROXY 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 METHOXYHEPTA 1,4,6 TRIEN 3 ONE; 5 HYDROXY 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 4 METHYLHEPTA 1,4,6 TRIEN 3 ONE; 5 HYDROXY 1,7 BIS(4 HYDROXYPHENYL)HEPTA 1,4,6 TRIEN 3 ONE; 5 HYDROXY 1,7 BIS(4 METHOXYPHENYL)HEPTA 1,4,6 TRIEN 3 ONE; 5 HYDROXY 1,7 DIPHENYLHEPTA 1,4,6 TRIEN 3 ONE; ACETYLACETONE; CURCUMIN; O ETHYL 2 HYDROXY 4 OXOPENT 2 EN 3 YL CARBONODITHIOATE; O ETHYL 3 HYDROXY 1,7 BIS(4 HYDROXY 3 METHOXYPHENYL) 5 OXOHEPTA 1,3,6 TRIEN 4 YL CARBONODITHIOATE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; RADICAL RESECTION;

ACETOACETATES; CARBON; CURCUMIN; FREE RADICAL SCAVENGERS; MOLECULAR STRUCTURE;

EID: 79958285142     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.04.055     Document Type: Article

References (24)

1. Y. Sugiyama, S. Kawakishi, and T. Osawa Biochem. Pharmacol. 52 1996 519
2. G. Litwinienko, and K.U. Ingold J. Org. Chem. 69 2004 5888
3. L.R.C. Barclay, and M.R. Vinqvist Org. Lett. 2 2000 2841
4. K.I. Priyadarsini, D.K. Maity, G.H. Naik, M.S. Kumar, M.K. Unnikrishnan, J.G. Satav, and H. Mohan Free Radical Biol. Med. 35 2003 475
5. N. Sreejavan, and M.N.A. Rao Drug Res. 46 1996 169
6. E. Portes, C. Gardrat, and A. Castellan Tetrahedron 63 2007 9092
7. S. Venkateswarlu, M.S. Ramachandra, and G.V. Subbaraju Bioorg. Med. Chem. 13 2005 6374
8. W.M. Weber, L.A. Hunsaker, S.F. Abcouwer, L.M. Deck, and D.L. Vander Jagt Bioorg. Med. Chem. 13 2005 3811
9. E. Font-Sanchis, C. Aliaga, E.V. Bejan, R. Cornejo, and J.C. Scaiano J. Org. Chem. 68 2003 3199
10. E. Font-Sanchis, C. Aliaga, K.-S. Focsaneanu, and J.C. Scaiano Chem. Commun. 15 2002 1576
11. J.C. Scaiano, A. Martin, G.P.A. Yap, and K.U. Ingold Org. Lett. 2 2000 899
12. R.K. Singh, D. Rai, D. Yadav, A. Bhargava, J. Balzarini, and E. De Clercq Eur. J. Med. Chem. 45 2010 1078
13. M.W. Amolins, L.B. Peterson, and B.S.J. Blagg Bioorg. Med. Chem. 17 2009 360
14. L. Lin, Q. Shi, C.-Y. Su, C.C.-Y. Shih, and K.-H. Lee Bioorg. Med. Chem. 14 2006 2527
15. L. Lin, Q. Shi, A.K. Nyarko, K.F. Bastow, C.-C. Wu, C.-Y. Su, C.C.-Y. Shih, and K.-H. Lee J. Med. Chem. 49 2006 3936
16. J.H. Moon, and J. Terao J. Agric. Food Chem. 46 1998 5062
17. H.J.J. Pabon Recl. Trav. Chim. 83 1964 379
18. D. Kalaitzakis, J.D. Rozzell, I. Smonou, and S. Kambourakis Adv. Synth. Catal. 348 2006 1958
19. R.M. Moriarty, R.K. Vaid, V.T. Ravikumar, B.K. Vaid, and T.E. Hopkins Tetrahedron 44 1988 1603
20. L. Valgimigli, G. Brigati, G.F. Pedulli, G.A. DiLabio, M. Mastragostino, C. Arbizzani, and D.A. Pratt Chem. Eur. J. 9 2003 4997
21. W. Brand-Williams, M.E. Cuvelier, and C. Berset Food Sci. Technol. (London) 28 1995 25
22. P. Goupy, C. Dufour, M. Loonis, and O. Dangles J. Agric. Food Chem. 515 2003 615
23. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165
24. L.R.C. Barclay, C.E. Edwards, and M.R. Vinqvist J. Am. Chem. Soc. 121 1999 6226