CHIH-DFT determination of the molecular structure, infrared and ultraviolet spectra of the flavonoid quercetin

Mendoza–Wilson, Ana María; Glossman‐Mitnik, Daniel

doi:10.1016/j.theochem.2004.04.054

Cited by 57 publications

(30 citation statements)

References 17 publications

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“…B-ring may have changed because no corresponding signals could be observed at 1557.60 cm −1 . The disappearance of the peak at 1318.04 cm −1 in the US spectra also indicated the reaction of adjacent dihydroxyl groups in B-ring after sonication [33]. From the vanishing of C-O vibration at 1244.46 cm −1 , the fused heterocyclic C- ring of quercetin was suspected to be destroyed by US treatment.…”

Section: Resultsmentioning

confidence: 94%

Sonochemical Effects on 14 Flavonoids Common in Citrus: Relation to Stability

et al. 2014

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The sonochemical effects of ultrasound (US) treatment on 14 flavonoids representing the main flavonoids in citrus fruit were investigated in a standard mixture by stability evaluation of a model system. Degradation products were further tentatively identified by Fourier transform infrared spectroscopy and high-performance liquid chromatography–ultraviolet detection–electrospray ionization tandem mass spectrometry. Thirteen flavonoids (i.e., eriocitrin, narirutin, neohesperidin, quercitrin, eridictyol, didymin, naringenin, luteolin, sinensetin, nobiletin, tangeretin, naringin, and hesperidin) were fairly stable whereas quercetin was degraded significantly by US treatment. The types of solvent and temperature used were important factors that determined the resulting degradation reactions. The degradation rate of quercetin was highest in 80% ethanol aqueous solution and decreased with increasing temperature. Longer US durations caused increases in the extent of quercetin degradation. Liquid height, ultrasonic intensity, pulse length, and duty cycle of US affected degradation rates but did not change the nature of degradation of the flavonoids. Four types of reactions occurred simultaneously for quercetin under US treatment: oxidation, addition, polymerization, and decomposition. Eight degradation products were tentatively identified as dimer, alcohol addition, oxidation, and decomposition products.

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Section: Resultsmentioning

confidence: 94%

Sonochemical Effects on 14 Flavonoids Common in Citrus: Relation to Stability

et al. 2014

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“…The three rings are planar and the molecule is relatively polarized. Three intermolecular hydrogen bonds are observed: two with the carbonyl group and the other between the hydroxyl groups in ring B (Mendoza-Wilson and Glossman-Mitnik 2004). Dietary quercetin is mostly present as its glycoside form in which one or more sugar groups is bound to phenolic groups by glycosidic linkage.…”

Section: Chemistry Of Quercetinmentioning

confidence: 99%

Quercetin: A potential drug to reverse multidrug resistance

Chen

Zhou²,

2010

Life Sciences

199

123

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“…The intramolecular hydrogen bond between 5-OH and O-11, which forms a stable six-membered ring, is stronger than that between 3-OH and O-11. 10,35,[38][39][40] For this reason, the QCT, 5-hydroxyflavone, has a dramatically different excited state behavior from that of 3-hydroxy flavone, which have only the -OH group at the C-3. 10,11 Excited state intramolecular proton transfer (ESIPT) between 5-OH and O-11 by "keto-enol tautomerization" has been observed in 5-hydroxyflavone and other many molecules having this kind of intramolecular hydrogen bond.…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic Properties of Quercetin in AOT Reverse Micelles

Park¹,

Im²,

Seo³

et al. 2014

Bulletin of the Korean Chemical Society

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The spectroscopic properties of quercetin (QCT) were studied in the AOT reverse micelle by fluorescence spectroscopy. Because the molecular structure of QCT is completely planar, excited state intramolecular proton transfer (ESIPT) occurs between the -OH at C(5) and carbonyl oxygen via intramolecular hydrogen bonding. This ESIPT happens at the S1 state but not at the S2 state. Because QCT is a good donor-acceptor-conjugated molecule at the excited state, this molecule can emit strong fluorescence but shows no S1 → So emission due to this ESIPT. Since the S2 → S1 internal conversion was very slow due to the small Franck-Condon factors, S2 → So fluorescence emission was observed. All of the experimental results indicated that the QCT resided at the bound water interface and that the position of solute did not change significantly in the micelle at various water concentrations.

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CHIH-DFT determination of the molecular structure, infrared and ultraviolet spectra of the flavonoid quercetin

Cited by 57 publications

References 17 publications

Sonochemical Effects on 14 Flavonoids Common in Citrus: Relation to Stability

Sonochemical Effects on 14 Flavonoids Common in Citrus: Relation to Stability

Quercetin: A potential drug to reverse multidrug resistance

Spectroscopic Properties of Quercetin in AOT Reverse Micelles

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