Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

Zhang, Jiaheng; Du, Fengpei; Peng, Bing; Lu, Renhua; Gao, Haixiang; Zhou, Zhiqiang

doi:10.1016/j.theochem.2010.04.036

Cited by 47 publications

(34 citation statements)

References 22 publications

(25 reference statements)

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“…From the optimized molecular structure of the three flavonoids, it can be seen that the 2, 3-double bond exists in the three flavonoids, and it ensures π-electron delocalization between the B-and C-rings, which contribute to the [19]. For quercetin, 2, 3-double bond and the C3-OH group make it planar and C-ring expands the planar structure as the connect ring.…”

Section: Geometry Optimizationmentioning

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: Geometry Optimizationmentioning

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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“…The 6-31G(d,p) basis set is used for all atoms. The reliability of the selected level for calculations has been previously demonstrated [10,27,28]. For the analysis, the effects of free rotation around the C─O bonds of the OH substituents at C-5 and C-7 (ring A), C-3′ and C-4′ (ring B), and C-3 (ring C) are taken into account (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…In recent years the role of flavonoids as antioxidants is the subject of both theoretical and experimental intense research [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

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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“…The main conclusions which can be drawn from the results of recent studies can be summarized as follows: A) basic studies on genistein structure and physicochemical properties, founded on theoretical calculations and experimental measurements continue, generating new data on the molecule geometry and electron distribution in the ground state as well as in ionized species or complexes [29, 30]. These data help to eliminate widespread but superficial opinions concerning the classification of genistein as an antioxidant or an estrogen, based on quoting insufficient evidence, such as its alleged structural similarity to estrogen as demonstrated by superimposing 2D structural formulae.…”

Section: Structure and Biosynthesis Of Isoflavonesmentioning

confidence: 99%

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

Szeja

Grynkiewicz

Rusin

2016

COC

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Glycosylation of small biologically active molecules, either of natural or synthetic origin, has a profound impact on their solubility, stability, and bioactivity, making glycoconjugates attractive compounds as therapeutic agents or nutraceuticals. A large proportion of secondary metabolites, including flavonoids, occur in plants as glycosides, which adds to the molecular diversity that is much valued in medicinal chemistry studies. The subsequent growing market demand for glycosidic natural products has fueled the development of various chemical and biotechnological methods of glycosides preparation. The review gives an extensive overview of the processes of the synthesis of isoflavones and discusses recently developed major routes towards isoflavone-sugar formation processes. Special attention is given to the derivatives of genistein, the main isoflavone recognized as a useful lead in several therapeutic categories, with particular focus on anticancer drug design. The utility of chemical glycosylations as well as glycoconjugates preparation is discussed in some theoretical as well as practical aspects. Since novel approaches to chemical glycosylations and glycoconjugations are abundant and many of them proved suitable for derivatization of polyphenols a new body of evidence has emerged, indicating that sugar moiety can play a much more significant role, when attached to a pharmacophore, then being a mere “solubilizer”. In many cases, it has been demonstrated that semisynthetic glycoconjugates are much more potent cytostatic and cytotoxic agents than reference isoflavones. Moreover, the newly designed glycosides or glycoside mimics can act through different mechanisms than the parent active molecule.

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Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study

Cited by 47 publications

References 22 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

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

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

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