Bond dissociation free energy as a general parameter for flavonoid radical scavenging activity

Stepanić, Višnja; Trošelj, Koraljka Gall; Lučić, Bono; Marković, Zoran; Amić, Dragan

doi:10.1016/j.foodchem.2013.03.072

Cited by 85 publications

(56 citation statements)

References 49 publications

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“…The fact that LAMF and LAMR, along with relevant phytophenols, have inhibitory effects on PTIO• and reductive effects on Fe 3+ , implies that their ROS-scavenging action may include H + -transfer and ET pathways (Table 1) [15, 18, 21–23]. Our assumption is further supported by previous evidence concerning chlorogenic acid [30], maclurin [18], flavonoids [31], morin [31, 32], astragalin [29], morin [32], rutin and isoquercitrin [15, 33]. In short, direct antioxidation (ROS-scavenging) may take place in the protection of •OH-induced MSCs by LAMF and LAMR, and the direct mechanism at least includes a H + -transfer and an ET, and possibly includes a HAT.…”

Section: Resultssupporting

confidence: 83%

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Jiang

Yuan

et al. 2017

BMC Complement Altern Med

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Background Mori Fructus and Mori Ramulus are two traditional Chinese herbal medicines from mulberries. The present work explores their beneficial effects on •OH–treated mesenchymal stem cells (MSCs) and discusses possible mechanisms.MethodsLyophilized aqueous extracts of Mori Fructus (LAMF) and Mori Ramulus (LAMR) were prepared and analyzed using HPLC. LAMF and LAMR (along with morin) were further investigated for their effects on •OH-treated MSCs using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl (MTT) assay. The direct antioxidation mechanisms were studied using 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (PTIO•)-scavenging, 2,2′-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid (ABTS+•)-scavenging and 1,1-diphenyl-2-picryl-hydrazl (DPPH•)-scavenging, as well as Cu2+-reducing and Fe3+-reducing antioxidant power. Finally, the indirect antioxidant mechanism was investigated based on the UV-vis spectra of Fe2+-chelation.ResultsIn each LAMF and LAMR, seven phytophenols were successfully measured by HPLC, including five flavonoids (morin, rutin, astragalin, isoquercitrin and luteolin) and two non-flavonoids (chlorogenic acid and maclurin). MTT assays revealed that LAMF, LAMR and morin could effectively increase the survival of •OH-treated MSCs at 10–100 μg/mL, and could effectively scavenge PTIO• (IC 50 6609.7 ± 756.6, 4286.9 ± 84.9 and 103.4 ± 0.9 μg/mL, respectively), DPPH• (IC 50 208.7 ± 3.0, 97.3 ± 3.1 and 8.2 ± 0.7 μg/mL, respectively) and ABTS+• (IC 50 73.5 ± 5.8, 34.4 ± 0.1 and 4.2 ± 0.2 μg/mL, respectively), and reduce Cu2+ (IC 50 212.5 ± 7.0, 123.2 ± 0.9 and 14.1 ± 0.04 μg/mL, respectively) & Fe3+ (IC 50 277.0 ± 3.1, 191.9 ± 5.2 and 5.0 ± 0.2 μg/mL, respectively). In the Fe2+-chelating assay, the five flavonoids produced much stronger shoulder-peaks than the two non-flavonoids within 420–850 nm.Conclusion Mori Fructus and Mori Ramulus, can protect MSCs from •OH-induced damage. Such beneficial effects can mainly be attributed to the antioxidant action of phytophenols, which occurs via direct (ROS-scavenging) and indirect mechanism (Fe2+-chelating). The ROS-scavenging mechanism, however, include at least a H+-transfer and an electron-transfer (ET), and possibly includes a hydrogen-atom-transfer (HAT). In the Fe2+-chelating, flavonoids are more effective than non-flavonoids. This can be attributed to several adjacent planar chelating-sites between the 3-OH and 4-C = O, between the 4-C = O and 5-OH, or between the 3′-OH and 4′-OH in flavonoids. Such multiple-Fe2+-chelating reactions cause overlap in the UV-vis absorptions to deepen the complex color, enhance the peak strength, and form shoulder-peaks. By comparison, two non-flavonoids with catechol moiety produce only a weak single peak.Electronic supplementary materialThe online version of this article (doi:10.1186/s12906-017-1730-3) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 83%

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Jiang

Yuan

et al. 2017

BMC Complement Altern Med

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“…Values of the calculated parameters gas-phase bond dissociation enthalpy (BDEg) and aqueous bond dissociation free energy (BDFEaq) were used for comparing radical scavenging capacities of our polyphenolic derivatives mutually as well as with corresponding natural polyphenols ( Table 2). As expected, compounds 24, 25, and 26 with catechol fragment have stronger radical scavenging ability than compounds 13, 17, and 21 with para-phenyl substituent and compounds 12, 16, and 20 with guaiacyl-like moiety 52 . Compounds within each of these three subgroups have mutually similar radical scavenging capacities.…”

Section: Biological Activitysupporting

confidence: 76%

“…The reaction enthalpies BDE, IP, PA, and ETE and corresponding free energies (Table 2 in Supplementary Material) were calculated by a known method 52 . These reaction parameters were calculated by applying the DFT model (U)B3LYP/6-31 + G(d, p) as implemented in software Gaussian 03 (Gaussian, Inc., Wallingford, CT) 53 .…”

Section: Density Functional Theory (Dft) Calculationsmentioning

confidence: 99%

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Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Verbanac

Malik

Chand

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.

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“…In recent years, a lot of research showed that APG have different pharmacological activities, such as anti‐oxidant, anti‐inflammatory, anti‐depressant, anti‐mutagenic, anti‐cancer, anti‐viral, anti‐bacterial, anti‐thrombotic, cardioprotective, hepatoprotective, and immunostimulant effects . The antioxidant activity of APG was previously reported using DFT method . But these studies were carried out only on the pristine APG structure.…”

Section: Introductionmentioning

confidence: 99%

Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

2020

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Adsorption and antiradical activity of apigenin on the surface of B12N12 nanocluster has been investigated by using density functional theory (DFT) within B3PW91‐D and M06‐2X−D methods. Adsorption values and analysis of topologies showed that the molecule has chemisorbed to the nanocluster surface and induces significant changes in electronic properties of the fullerene. Antioxidative activities of the APG and APG/B12N12 complex have been investigated using the M06‐2X−D level of theory based on the hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET‐PT) and sequential proton loss electron transfer (SPLET). For this purpose, the bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA) and electron transfer enthalpy (ETE) values were calculated in gas, benzene, ethanol, and water phases to better understand the antioxidative properties of the investigated compounds. The results showed that in the gas and the solvent phases, the BDE and IP values of APG are slightly smaller than those of APG/B12N12 complex. Also, in gas and the phases, the PA values of APG/B12N12 complex are much smaller than those of APG especially in the gas and benzene phases. This work confirms the adsorption of APG on B12N12 nanocluster would enhance the antiradical activity of the APG.

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Bond dissociation free energy as a general parameter for flavonoid radical scavenging activity

Cited by 85 publications

References 49 publications

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis

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Bond dissociation free energy as a general parameter for flavonoid radical scavenging activity

Cited by 85 publications

References 49 publications

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Improvement of Antioxidative Activity of Apigenin by B12N12 Nanocluster: Antioxidative Mechanism Analysis

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Improvement of Antioxidative Activity of Apigenin by B₁₂N₁₂ Nanocluster: Antioxidative Mechanism Analysis