A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity

Trouillas, Patrick; Fagnere, Catherine; Lazzaroni, Roberto; Calliste, Claude-Alain; Marfak, Abdelghafour; Duroux, Jean‐Luc

doi:10.1016/j.foodchem.2004.02.009

Cited by 60 publications

(34 citation statements)

References 29 publications

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“…Figen et al [10] have used AM1 to optimize the geometry of naringenin and genistein, while using ab initio RHF including full MP2 to calculate the electronic properties of the system. More recently, Monica et al [11] have used density function theory (DFT) to study the antioxidant activity of apigenin, luteolin and taxifolin, and bond dissociation enthalpy (BDE) is used to measure flavonoids' antioxidant activity [12,13]. Their results show that B-ring of flavonoids is the most important site for antioxidant activity.…”

Section: Introductionmentioning

confidence: 99%

Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues

Cai

Chen

Xie

et al. 2013

Eur Food Res Technol

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Section: Introductionmentioning

confidence: 99%

Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues

Cai

Chen

Xie

et al. 2013

Eur Food Res Technol

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“…3.3 kJ mol -1 ). Trouillas et al (Trouillas, 2004) reported that the C2-C3 double bond in the C-ring conjugated with B-ring plays an important role in radical stability of flavonoids due to the effect of delocalization. In the PM3 calculation, however, the structure of the B-ring (number of OHs and position) itself seems to be more significant for radical stabilization.…”

Section: Resultsmentioning

confidence: 99%

Molecular Orbital Analysis of Antioxidative Activity of Phenolics from Tessaria integrifolia and Piper elongatum

Eto

Masuoka

Yamasaki

et al. 2008

FSTR

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Bond dissociation enthalpies (BDEs) for phenolic constituents from Tessaria integrifolia RUIZ. et Pavon and Piper elongatum VAHL. have been calculated using the semi-empirical molecular orbital (MO) method (PM3). A signifi cant correlation between the BDE of the phenolics and their radical-scavenging effect was found. The BDEs evaluated by semi-empirical MOs can provide a convenient and useful clue for assessment of the antioxidative activity of phenolics.

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“…Bioactive compounds of sarsaparilla, such as astilbin and taxifolin, were shown to inhibit oxidative stress (37,38), whereas ST fraction increased ROS production (7). Here, we found no ROS was induced by SW.…”

Section: Discussionmentioning

confidence: 99%

Sarsaparilla (Smilax Glabra Rhizome) Extract Inhibits Cancer Cell Growth by S Phase Arrest, Apoptosis, and Autophagy via Redox-Dependent ERK1/2 Pathway

She

Wang

et al. 2015

Cancer Prevention Research

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Cancer is still the major cause of death across the world. Regular approaches cannot effectively solve the emerging problems, including drug/radiation resistance, side effects, and therapeutic ineffectiveness. Natural dietary supplements have shown effectiveness in the prevention and treatment of cancer. Sarsaparilla (Smilax Glabra Rhizome) has growth-inhibitory effects on several cancer cell lines in vitro and in vivo, with little toxicity on normal cells. However, the mechanism underlying its function remains elusive. In the present study, we examined the anticancer activity of the supernatant of the water-soluble extract (SW) from sarsaparilla. Liquid chromatography/mass spectrometry-ion trap-time-of-flight (LC/MS-IT-TOF) analysis identified flavonoids, alkaloids, and phenylpropanoids as the major bioactive components of SW. SW was shown to markedly inhibit the growth of a broad spectrum of cancer cell lines in the in vitro and in vivo assays. S phase arrest, autophagy, or/and apoptosis were partly responsible for SW-induced growth inhibition. Results of microarray analysis and validation by quantitative RT-PCR indicated the involvement of oxidative stress and the MAPK1 pathway in SW-treated cells. We further found that SW destroyed intracellular-reduced glutathione/oxidized glutathione (GSH/GSSG) balance, and supplement with N-acetylcysteine (NAC) or glutathione (GSH) significantly antagonized SW-induced S phase arrest, apoptosis, and autophagy. In addition, SW-induced GSH/GSSG imbalance activated the ERK1/2 pathway, which contributed to SW-induced S phase arrest, apoptosis, autophagy, and resultant growth-inhibitory effect. Together, our results provide a molecular basis for sarsaparilla as an anticancer agent. Cancer Prev Res; 8(5); 464-74.Ó2015 AACR.

show abstract

A theoretical study of the conformational behavior and electronic structure of taxifolin correlated with the free radical-scavenging activity

Cited by 60 publications

References 29 publications

Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues

Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues

Molecular Orbital Analysis of Antioxidative Activity of Phenolics from Tessaria integrifolia and Piper elongatum

Sarsaparilla (Smilax Glabra Rhizome) Extract Inhibits Cancer Cell Growth by S Phase Arrest, Apoptosis, and Autophagy via Redox-Dependent ERK1/2 Pathway

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