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Study of Radical Scavenging Activities of a Series of Flavonoids through 3D-QSAR Analysis
Corresponding Author(s) : Atish Dipankar Jana
Asian Journal of Chemistry,
Vol. 30 No. 11 (2018): Vol 30 Issue 11
Abstract
Flavonoids are efficient antioxidants having free radical scavenging property. A set of 29 flavonoids whose radical scavenging activities are known, have been chosen to understand the origin of their radical scavenging activities. 3D-QSAR models have been established through comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) procedure which reveal that the electron withdrawing groups from pyrone ring is likely to increase the radical scavenging activities. Also hydrogen bond donor groups on pyrone moiety and its adjacent ring are preferred for better radical scavenging activitiies.
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- M.G. Simic, D.S. Bergtold and L.R. Karam, Mutat. Res., 214, 3 (1989); https://doi.org/10.1016/0027-5107(89)90192-9.
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References
M.G. Simic, D.S. Bergtold and L.R. Karam, Mutat. Res., 214, 3 (1989); https://doi.org/10.1016/0027-5107(89)90192-9.
E.J. Middleton, C. Kandaswami and T.C. Theoharides, Pharmacol. Rev., 52, 673 (2000).
G. Block, Nutr. Rev., 50, 207 (1992); https://doi.org/10.1111/j.1753-4887.1992.tb01329.x.
J.E. Middleton, Adv. Exp. Med. Biol., 439, 175 (1998); https://doi.org/10.1007/978-1-4615-5335-9_13.
M. Gabor, Prog. Clin. Biol. Res., 213, 471 (1986).
M. Valko, M. Izakovic, M. Mazur, C.J. Rhodes and J. Telser, Mol. Cell. Biochem., 266, 37 (2004); https://doi.org/10.1023/B:MCBI.0000049134.69131.89.
P.A. Ward, J.S. Warren and K.J. Johnson, Free Radic. Biol. Med., 5, 403 (1988); https://doi.org/10.1016/0891-5849(88)90114-1.
K. Sugamura and J.F. Keaney Jr., Free Radic. Biol. Med., 51, 978 (2011); https://doi.org/10.1016/j.freeradbiomed.2011.05.004.
B. Halliwell, R. Aeschbach, J. Loliger and O.I. Aruoma, Food Chem. Toxicol., 33, 601 (1995); https://doi.org/10.1016/0278-6915(95)00024-V.
N. Cotelle, J.L. Bernier, J.P. Catteau, J. Pommery, J.C. Wallet and E.M. Gaydou, Free Radic. Biol. Med., 20, 35 (1996); https://doi.org/10.1016/0891-5849(95)02014-4.
H.Y. Zhang, Curr. Computeraided Drug Des., 1, 257 (2005); https://doi.org/10.2174/1573409054367691.
G. Di Carlo, N. Mascolo, A.A. Izzo and F. Capasso, Life Sci., 65, 337 (1999); https://doi.org/10.1016/S0024-3205(99)00120-4.
P.C.H. Hollman and I.C.W. Arts, J. Sci. Food Agric., 80, 1081 (2000); https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1081::AIDJSFA566>3.0.CO;2-G.
S.A. Aherne and N.M. O’Brien, Nutrition, 18, 75 (2002); https://doi.org/10.1016/S0899-9007(01)00695-5.
P.G. Pietta, J. Nat. Prod., 63, 1035 (2000); https://doi.org/10.1021/np9904509.
X. Du, C. Guo, E. Hansell, P.S. Doyle, C.R. Caffrey, T.P. Holler, J.H. McKerrow and F.E. Cohen, J. Med. Chem., 45, 2695 (2002); https://doi.org/10.1021/jm010459j.
J. Verma, V.M. Khedkar and E.C. Coutinho, Curr. Top. Med. Chem. 10, 95 (2010); https://doi.org/10.2174/156802610790232260.
R.D. Cramer, D.E. Patterson and J.D. Bunce, J. Am. Chem. Soc., 110, 5959 (1988); https://doi.org/10.1021/ja00226a005.
H. Kubinyi, G. Folkers and Y.C. Martin, 3D QSAR in Drug Design, Kluwer, Dordrecht (1988).
G. Klebe, U. Abraham and T. Mietzner, J. Med. Chem., 37, 4130 (1994); https://doi.org/10.1021/jm00050a010.
S. Burda and W. Oleszek, J. Agric. Food Chem., 49, 2774 (2001); https://doi.org/10.1021/jf001413m.
SYBYL-X 2.0, Tripos Inc, St. Louis.
M.D.M. AbdulHameed, A. Hamza, J. Liu and C.-G. Zhan, J. Chem. Inf. Model., 48, 1760 (2008); https://doi.org/10.1021/ci800147v.
D.M. Hawkins, S.C. Basak and D. Mills, J. Chem. Inf. Comput. Sci., 43, 579 (2003); https://doi.org/10.1021/ci025626i.
P.P. Roy and K. Roy, QSAR Comb. Sci., 27, 302 (2008); https://doi.org/10.1002/qsar.200710043.