Antioxidant activity of flavonoids: a QSAR modeling using Fukui indices descriptors

Djeradi, Houria; Rahmouni, Abdelkader; Cheriti, Abdelkrim

doi:10.1007/s00894-014-2476-1

Cited by 63 publications

(25 citation statements)

References 44 publications

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“…e high number of positive (negative) charges of atoms oxygens, carbon, and hydrogen arising from 5-OH and 4-CO is caused by internal hydrogen bonds, thereby stabilizing the structure. e fact is that antioxidant activities of flavonoids further depend on negative centers, whereby hydroxyl groups in ring B are found to act as active sites of radical reactions [20]. As a consequence, considering flavonoid aglycones of studied 3-4 and compound 1, the high values of negative charges occur in 4′-OH in both gas and methanol, agreeing with the smallest BDE outcome.…”

Section: Electronic Propertiesmentioning

confidence: 69%

“…As a general conceptual comprehension, the condensed Fukui parameters evidently provide information on a selective property in a chemical reaction. e atom coupled with the high electronic population displays as the most reactive site when compared to the surrounding atoms in a molecule [20]. Briefly, Fukui descriptors have been shown to associate with nucleophilic (f + k ), electrophilic (f − k ), and/or radical attacks (f 0 k ) and were possibly described by the following equilibriums [20]:…”

Section: Flav-ohmentioning

confidence: 99%

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Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study

Son

Van

2019

Journal of Chemistry

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Isoflavonoids and isoflavonoid glycosides have drawn much attention because of their antioxidant radical-scavenging capacity. Based on computational methods, we now present the antioxidant potential results of genistein (1), biochanin A (2), ambocin (3), and tectorigenin 7-O-[β-D-apiofuranosyl-(1-6)-β-D-glucopyranoside] (4). e optimized structures of the neutral and radical forms have been determined by the DFT-B3LYP method with the 6-311G(d) basis set. From the findings and thermodynamic point of view, the ring B system of isoflavones is considered as an active center in facilitating antioxidant reactions. Antioxidant activities are mostly driven by O-H bond dissociation enthalpy (BDE) following hydrogen atom transfer (HAT) mechanism. Antioxidant ability can be arranged in the following order: compounds (4) > (3) > (2) > (1). Of comprehensive structural analysis, flavonoids with 4′-methylation and 6-methoxylation, especially 7-glycosylation would claim responsibility for antioxidant enhancement.

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Section: Electronic Propertiesmentioning

confidence: 69%

Section: Flav-ohmentioning

confidence: 99%

Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study

Son

Van

2019

Journal of Chemistry

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“…The aim of this study was to measure amount of flavonoids, which are present in aqueous extract of R. crispus fruits, and known to possess a potential antioxidant activity 15 . Furthermore, this study was based on estimation of antioxidant capacity and potentiality of investigated extract.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and cytotoxic activities of curly dock (Rumex crispus L., Polygonaceae) fruit extract

Ćebović¹,

Jakovljević²,

Maksimović³

et al. 2020

VSP

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Background/Aim. Rumex crispus (curly dock) is a wild perennial herbaceous plant, which products are considered as a rich source of biologically active molecules with antioxidant and cytotoxic activities. The aim of this study was to estimate of antioxidant and cytotoxic activities of aqueous extract of curly dock fruits. Methods. The aqueous extract of curly dock fruits was evaluated for its antioxidant activity by in vitro assays for ferric-reducing antioxidant power (FRAP), NO•, OH• and 2,2-diphenyl-1-picrylhydrazyl (DPPH)-free radical scavenging activities and the influence on lipid peroxidation in liposomes. The cytotoxicity of tested extract was examined in vitro in human cervix carcinoma (HeLa), colon adenocarcinoma (HT-29) and breast adenocarcinoma (MCF7) cells. Results. The tested extract showed a potential antioxidant activity manifested in scavenging of free radicals as well as an ability to decrease lipid peroxidation in liposomes. The results indicated tissue-selective cytotoxicity of R. crispus fruit extract in vitro. The most prominent antitumor activity was observed towards HeLa and MCF7 cell lines. Conclusion. The investigated aqueous fruit extract of R. crispus had potential antioxidant and cytotoxic activities, with necrosis as a main mechanism of induced cell-death. Different methods of extraction of R. crispus fruits, apart from aqueous, are recommended for further investigations.

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“…After the successful completion of the optimization process, the obtained results are taken for computing single point energy (SPE) and harmonic vibrational frequency analysis. The frequency analysis result reveals the absence of negative frequencies and then calculations are performed for HOMO and LUMO energy, Mulliken population analysis, molecular descriptors such as ionization potential (IP), electron affinity (EA), hardness (ω), softness (S), electrophilic index (η) and electronegativity (χ) 6 .…”

Section: Methodsmentioning

confidence: 99%

Untitled

2019

IJPSR

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The extensive study on O -methylated flavonoids reveals that substitution with methyl group enhances the radical scavenging behavior in certain compounds. Due to potential applications of C-glycosides in metabolic engineering, methylation in these flavonoids needs to be analyzed in both theoretical and experimental levels for their radical scavenging behavior. In this work naturally occurring C-glycosyl flavonoid apigenin 8-C-glucoside (vitexin) is theoretically simulated by substituting the C4′, C5 and C7 hydroxyl positions with methoxy unit and studied with the aid of density functional theory (DFT) for radical scavenging behavior. Structural stability is attained through B3LYP/6-311G(d,p) theory using Gaussian 03 package which provided the stable conformer for the studied compound without imaginary frequency. Structural activity is analyzed with the support of parameters like kinetic energy (temperature independent), HOMO-LUMO, molecular descriptors, Mulliken charge density analysis and compared with vitexin. Combined investigation of the parameters above revealed the superiority of phenyl hydroxyl vitexin over phenyl methoxy vitexin for radical scavenging activity unlike its O methylated flavonoids.

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Antioxidant activity of flavonoids: a QSAR modeling using Fukui indices descriptors

Cited by 63 publications

References 44 publications

Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study

Isoflavones and Isoflavone Glycosides: Structural-Electronic Properties and Antioxidant Relations—A Case of DFT Study

Antioxidant and cytotoxic activities of curly dock (Rumex crispus L., Polygonaceae) fruit extract

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