Theoretical elucidation of structure-activity relationship of flavonoid antioxidants
- 109 Downloads
AM1 method was emyloyed to calculate flavonoid antioxidants, and the results obtained are as follows. Firstly, flavonoid hydroxyls atortho position were more active than the hydroxyls atmeta position in scavenging oxygen-free raidicals, which resulted from the facts that (i) the former were stabilized by forming intramolecular hydrogen bond and (ii)ortho benzocluinone formed in the former structures through resonance, which resulted in large percentage of distribution of spin density or1ortho oxygen and low internal energy. Secondly, electron-attracting effect of ring C of chromone-flavonoids showed some passive efftrts on hydroxyls of ring A, making the OH less active. As ring C had little effect on ring B and hydroxyls of ring B in most flavonoids were atortho position, the rule summarized from experiments showing that hydroxyls of ring B were more active in scavenging oxygen-free radicals was elucidated.
Keywordsflavunoid antioxidants AM1 method structure-activity relationship theoretical elucidation
Unable to display preview. Download preview PDF.
- 1.Liu, W. L. (ed.),Concise Biophysics (in Chinese), Beijing:Higher Education Press, 1995, 138.Google Scholar
- 2.Cao, G. F., Werlg, X. C., Studies on oxidation stability of fish oil (I),China Oils and Fats (in Chinese), 1995, 20(4): 49.Google Scholar
- 3.Cao, G. F., Werng, X. C., Studies on oxidation stability of fish oil (II),China Oils and Fats (in Chinese), 1995, 20(5): 44.Google Scholar
- 5.Harkme, J. B. (ed.),The Flavonoids:Advances in Research Since 1980, London:Chapman & Hall Press, 1988.Google Scholar
- 6.Harborne, J. B. (ed.),The Flavonoids:Advances in Research Since 1986, London:Chapman & Hall Press, 1994.Google Scholar
- 7.Wang, X. K. (ed.),Medicinal Chemistry of Natural Products (in Chinese), Beijing:People’s Medical Publishing House, 1993, 272.Google Scholar
- 8.Hu, C., Antioxidative property of flavonoid,China Oils and Fats (in Chinese), 1996, 21(4): 18.Google Scholar
- 11.Zhang, H. Y., Selection of theoretical parameter characterizing scavenging activity of antioxidants on free radicals,J. Am. OilChem. Soc., 1998. 75(12):in press.Google Scholar
- 12.Gajewski, J. J., Gilbert, K. E., Mckelvey, J.,MMX. an enhanced version of MM2, Adv. Mol. Model, 1990, 2: 65.Google Scholar
- 14.Hu, C., Ding, X. L., Antioxidant effect of flavonoid in different oxidation systems,Food and Fermentation Industries (in Chinese), 1996, 22(3): 46.Google Scholar