title: DPPH radical scavenging activity of tricin and its conjugates isolated from "Njavara" rice bran: a density functional theory study.
abstract: Structural, electronic, and energetic characteristics of tricin, tricin-4'-O-(erythro-β-guaiacylglyceryl)ether (TEGE), and tricin-4'-O-(threo-β-guaiacylglyceryl)ether (TTGE), isolated from "Njavara" rice bran have been studied using DFT to explain their experimentally determined radical scavenging activity (EC(50) values) in comparison with known standards such as quercetin, myricetin, and catechin. Among the three mechanisms proposed for explaining the antioxidant activity, proton coupled-electron transfer (PC-ET), sequential proton loss electron transfer (SPLET), and electron transfer-proton transfer (ET-PT), our results support the second one. The O-H bond dissociation enthalpy (BDE) and the spin density on the oxygen with the radical character are excellent descriptors of radical scavenging activity. BDE (in kcal/mol) increased in the order myricetin (74.6) < quercetin (78.1) < catechin (78.3) < tricin (81.5) < TTGE (90.6) < TEGE (91.1), while the EC(50) increased exponentially with increase in BDE, 20.51, 42.98, 45.07, 90.39, 208.01, and 352.04 μg/mL for myricetin, quercetin, catechin, tricin, TTGE, and TEGE, respectively.
authors.affiliation: Computational Modeling and Simulation Section, National Institute for Interdisciplinary Science and Technology (NIIST), CSIR, Trivandrum, India.
authors.forename: Manjaly J
authors.initials: MJ
authors.lastname: Ajitha
authors.forename: Smitha
authors.initials: S
authors.lastname: Mohanlal
authors.forename: Cherumuttathu H
authors.initials: CH
authors.lastname: Suresh
authors.forename: Ananthasankaran
authors.initials: A
authors.lastname: Jayalekshmy
mesh_terms: D001713:Biphenyl Compounds; D005419:Flavonoids / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012275:Oryza / Q000737:chemistry*; D010084:Oxidation-Reduction; D010851:Picrates; D012639:Seeds / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D001713:Biphenyl Compounds; D005419:Flavonoids; D016166:Free Radical Scavengers; D010851:Picrates; C017769:tricin; C004931:1,1-diphenyl-2-picrylhydrazyl