A Systematic Computational Study on Flavonoids

Aparício, Santiago

doi:10.3390/ijms11052017

Cited by 68 publications

(44 citation statements)

References 44 publications

(45 reference statements)

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“…The possibility of formation of hydrogen bonds between donors and acceptors residing on different rings of polycyclic molecules or, in case of flavonoid glycosides – residing on flavonoid and sugar moieties, has also been shown [ 114 , 115 ]. Semiempirical studies (AM1, PM3) of the geometry of quercetin [ 116 ], as well as some recent studies on a number of flavonoids using DFT calculations and AIM or NBO analysis [ 106 , 117 ], have supported the hypothesis about the formation of an unusual intramolecular hydrogen bond between C3-OH in flavonoid's C ring and C2'/C6' in B ring which could stabilise the planar conformations in flavonols [ 118 ]. No bond critical points were discovered between C3'-OH, C4'-OH and C5'-OH in the B ring [ 117 , 119 ] in any of the flavonoid molecules under study, which was interpreted as an impossibility of formation of these molecule-stabilising hydrogen bonds [ 117 ] (Fig.…”

Section: Quantum Chemical Modelling Of the Free Radical-scavenging Prmentioning

confidence: 99%

“…Semiempirical studies (AM1, PM3) of the geometry of quercetin [ 116 ], as well as some recent studies on a number of flavonoids using DFT calculations and AIM or NBO analysis [ 106 , 117 ], have supported the hypothesis about the formation of an unusual intramolecular hydrogen bond between C3-OH in flavonoid's C ring and C2'/C6' in B ring which could stabilise the planar conformations in flavonols [ 118 ]. No bond critical points were discovered between C3'-OH, C4'-OH and C5'-OH in the B ring [ 117 , 119 ] in any of the flavonoid molecules under study, which was interpreted as an impossibility of formation of these molecule-stabilising hydrogen bonds [ 117 ] (Fig. 4c ), possibly decreasing the BDE of these hydroxyl groups (no analysis of the hydrogen bonding in phenoxyl radicals has been reported, however).…”

Section: Quantum Chemical Modelling Of the Free Radical-scavenging Prmentioning

confidence: 99%

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Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

Alov¹,

Tsakovska²,

Pajeva

2015

CTMC

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For more than half a century free radical-induced alterations at cellular and organ levels have been investigated as a probable underlying mechanism of a number of adverse health conditions. Consequently, significant research efforts have been spent for discovering more effective and potent antioxidants / free radical scavengers for treatment of these adverse conditions. Being by far the most used antioxidants among natural and synthetic compounds, mono- and polyphenols have been the focus of both experimental and computational research on mechanisms of free radical scavenging. Quantum chemical studies have provided a significant amount of data on mechanisms of reactions between phenolic compounds and free radicals outlining a number of properties with a key role for the radical scavenging activity and capacity of phenolics. The obtained quantum chemical parameters together with other molecular descriptors have been used in quantitative structure-activity relationship (QSAR) analyses for the design of new more effective phenolic antioxidants and for identification of the most useful natural antioxidant phenolics. This review aims at presenting the state of the art in quantum chemical and QSAR studies of phenolic antioxidants and at analysing the trends observed in the field in the last decade.

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Section: Quantum Chemical Modelling Of the Free Radical-scavenging Prmentioning

confidence: 99%

Section: Quantum Chemical Modelling Of the Free Radical-scavenging Prmentioning

confidence: 99%

Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

Alov¹,

Tsakovska²,

Pajeva

2015

CTMC

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“…In general weaker character of hydrogen bond was in agreement with the shorter O-H bond distance for the OH group, while the longer the OH bond distance, the stronger the hydrogen bonding. As reported in the previous work [31] the quercetin 5-OH have longer bond length than other OH groups, which may be due to stronger hydrogen bond interaction between 5-OH and with the carbonyl group in C-ring. Similarly the interaction between 3-OH and 6'-H sites come next to the 5-OH and C ring carbonyl group interaction.…”

Section: Electronic Properties Of Studied Flavonoid Moleculesmentioning

confidence: 51%

Electronic Description of Few Selected Flavonoids by Theoretical Study

Rajendran¹,

Ravichandran²,

Devapiriam³

2013

IJCA

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The electronic properties responsible for free radical scavenging and metal chelation of a set of 7 flavonoids compounds were studied. Electronic parameters were calculated using semi empirical PM3 method. The structure activity relationship of OH substitution, C2-C3 double bond, chelation site of flavonoid and related property of antioxidant efficiency, BDE, mulliken atomic charge, electron current movement among A, B and C-rings were investigated. The relative change in energy (H f ) associated with the formation of phenoxyl radicals and spin density distribution of phenoxyl radicals were determined. The complexation mechanism of seven flavonoids quercetin, morin, apigenin, naringenin, chrysin, taxifolin and fisetin with metal ions, by molecular mechanics (UFF) method was investigated. Flavonoids metal chelation site order on toxic metals Pb, Bi and Cd was investigated. The most likely chelation site for metal ion was 5-OH & 4=O group, followed by 4=O & 3-OH group and the 3'& 4' hydroxyl for all the flavonoid molecules studied. In the absence of C2-C3 double bond (taxifolin) the order of metal chelation site with metal was 3-OH & 4=O, followed by 5-OH & 4=O group and 3' & 4' hydroxyl.

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“…3a and c). Dipole moment changes against small structural modifications have been observed in other flavonoids [13,30]. Moreover, these results show that μ has separable contributions, one associated with changes in the catechol ring and another related to the different conformations of the resorcinol ring, such as has been reported for other compounds [18,22,30].…”

Section: Molecular Polarizability and Dipole Momentmentioning

confidence: 63%

Exploratory conformational study of (+)-catechin. Modeling of the polarizability and electric dipole moment

2014

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The extension of the study of the conformational space of the structure of (+)-catechin at the B3LYP/6-31G(d,p) level of theory is presented in this paper. (+)-Catechin belongs to the family of the flavan-3-ols, which is one of the five largest phenolic groups widely distributed in nature, and whose biological activity and pharmaceutical utility are related to the antioxidant activity due to their ability to scavenge free radicals. The effects of free rotation around all C-O bonds of the OH substituents at different rings are taken into account, obtaining as the most stable conformer, one that had not been previously reported. One hundred seven structures, and a study of the effects of charge delocalization and stereoelectronic effects at the B3LYP/6-311++G(d,p) level are reported by natural bond orbital analysis, streamlining the order of these structures. For further analysis of the structural and molecular properties of this compound in a biological environment, the calculation of polarizabilities, and the study of the electric dipole moment are performed considering the whole conformational space described. The results are analyzed in terms of accumulated knowledge for (4α → 6″, 2α → O → 1″)-phenylflavans and (+)-catechin in previous works, enriching the study of both types of structures, and taking into account the importance of considering the whole conformational space in modeling both the polarizability and the electric dipole moment, also proposing to define a descriptive subspace of only 16 conformers.

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A Systematic Computational Study on Flavonoids

Cited by 68 publications

References 44 publications

Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

Computational Studies of Free Radical-Scavenging Properties of Phenolic Compounds

Electronic Description of Few Selected Flavonoids by Theoretical Study

Exploratory conformational study of (+)-catechin. Modeling of the polarizability and electric dipole moment

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