Unravelling the Competence of Leucocyanidin in Free Radical Scavenging: A Theoretical Approach Based on Electronic Structure Calculations

Augustine, Cyril

doi:10.1134/s0022476619020045

Cited by 6 publications

(3 citation statements)

References 56 publications

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“…These values indicate that these molecules have distortion from planarity. Calculations show that leucoanthocyanidins are significantly twisted, in agreement with the reported results for leucocyanidin [43]. Different from the other cationic anthocyanidins, ( +)-catechin has a neutral charge.…”

Section: Conformational Analysessupporting

confidence: 89%

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

2023

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Anthocyanidins, leucoanthocyanidins, and flavonols are natural compounds mainly known due to their reported biological activities, such as antiviral, antifungal, anti-inflammatory activities, and antioxidant activity. In the present study, we performed a comparative structural, conformational, electronic, and nuclear magnetic resonance analysis of the reactivity of the chemical structure of primary anthocyanidins, leucoanthocyanidins, and flavonoids. We focused our analysis on the following molecular questions: (i) differences in cyanidin catechols ( +)-catechin, leucocyanidin, and quercetin; (ii) the loss of hydroxyl presents in the R1 radical of leucoanthocyanidin in the functional groups linked to C4 (ring C); and (iii) the electron affinity of the 3-hydroxyl group (R7) in the flavonoids delphinidin, pelargonidin, cyanidin, quercetin, and kaempferol. We show unprecedented results for bond critical point (BCP) of leucopelargonidin and leucodelphirinidin. The BCP formed between hydroxyl hydrogen (R2) and ketone oxygen (R1) of kaempferol has the same degrees of covalence of quercetin. Kaempferol and quercetin exhibited localized electron densities between hydroxyl hydrogen (R2) and ketone oxygen (R1). Global molecular descriptors showed quercetin and leucocyanidin are the most reactive flavonoids in electrophilic reactions. Complementary, anthocyanidins are the most reactive in nucleophilic reactions, while the smallest gap occurs in delphinidin.Local descriptors indicate that anthocyanidins and flavonols are more prone to electrophilic attacks, while in leucoanthocyanidins, the most susceptible to attack are localized in the ring A. The ring C of anthocyanidins is more aromatic than the same found in flavonols and leucoanthocyanidins. Methods For the analysis of the molecular properties, we used the DFT to evaluate the formation of the covalent bonds and intermolecular forces. CAM-B3LYP functional with the def2TZV basis set was used for the geometry optimization. A broad analysis of quantum properties was performed using the assessment of the molecular electrostatic potential surface, electron localization function, Fukui functions, descriptors constructed from frontier orbitals, and nucleus independent chemical shift.

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Section: Conformational Analysessupporting

confidence: 89%

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

2023

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“…These values indicate that these molecules have distortion from planarity. Calculations show that leucoanthocyanidins are signi cantly twisted, in agreement with the reported results for leucocyanidin [41]. Different from the other cationic anthocyanidins, (+)-catechin has a neutral charge.…”

Section: Conformational Analysessupporting

confidence: 89%

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Farias

Costa

Martins

2023

Preprint

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In the present study, we performed a comparative structural, conformational, electronic, and nuclear magnetic resonance analysis of the reactivity of the chemical structure of primary flavonoids, anthocyanidins, and leucoanthocyanidins. We focused our analysis on the following molecular questions: i) differences in cyanidin catechols (+)-catechin, leucocyanidin and quercetin; ii) the loss of a hydroxyl presents in the R1 radical of leucoanthocyanidin due to possible differences in the functional groups linked to C4 (ring C), and, iii) the electron affinity of the 3-hydroxyl group (R7) in the flavonoids delphinidin, pelargonidin, cyanidin, quercetin and kaempferol. For the analysis of the molecular properties, we used the density functional theory (DFT) to evaluate the formation of the covalent bonds and intermolecular forces. A broad analysis of quantum properties was performed using the assessment of the molecular electrostatic potential (MEP) surface, electron localization function (ELF), Fukui functions, descriptors constructed from frontier orbitals, and nucleus independent chemical shift (NICS).

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“…Moreover, leucocyanidin has anti-inflammatory properties that may help minimize the risk of chronic inflammatory illnesses. It also benefits cardiovascular health by promoting healthy blood vessels and heart function [146]. While further study is needed, leucocyanidin's antioxidant, anti-inflammatory, and cardiovascular effects make it a promising molecule for overall well-being and disease prevention.…”

Section: Flavonoidsmentioning

confidence: 99%

Unlocking Potentially Therapeutic Phytochemicals in Capadulla (Doliocarpus dentatus) from Guyana Using Untargeted Mass Spectrometry-Based Metabolomics

Smith,

Lewis,

Narine

et al. 2023

Metabolites

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Doliocarpus dentatus is thought to have a wide variety of therapeutic phytochemicals that allegedly improve libido and cure impotence. Although a few biomarkers have been identified with potential antinociceptive and cytotoxic properties, an untargeted mass spectrometry-based metabolomics approach has never been undertaken to identify therapeutic biofingerprints for conditions, such as erectile dysfunction, in men. This study executes a preliminary phytochemical screening of the woody vine of two ecotypes of D. dentatus with renowned differences in therapeutic potential for erectile dysfunction. Liquid chromatography–mass spectrometry-based metabolomics was used to screen for flavonoids, terpenoids, and other chemical classes found to contrast between red and white ecotypes. Among the metabolite chemodiversity found in the ecotype screens, using a combination of GNPS, MS-DIAL, and SIRIUS, approximately 847 compounds were annotated at levels 2 to 4, with the majority of compounds falling under lipid and lipid-like molecules, benzenoids and phenylpropanoids, and polyketides, indicative of the contributions of the flavonoid, shikimic acid, and terpenoid biosynthesis pathways. Despite the extensive annotation, we report on 138 tentative compound identifications of potentially therapeutic compounds, with 55 selected compounds at a level-2 annotation, and 22 statistically significant therapeutic biomarkers, the majority of which were polyphenols. Epicatechin methyl gallate, catechin gallate, and proanthocyanidin A2 had the greatest significant differences and were also relatively abundant among the red and white ecotypes. These putatively identified compounds reportedly act as antioxidants, neutralizing damaging free radicals, and lowering cell oxidative stress, thus aiding in potentially preventing cellular damage and promoting overall well-being, especially for treating erectile dysfunction (ED).

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Unravelling the Competence of Leucocyanidin in Free Radical Scavenging: A Theoretical Approach Based on Electronic Structure Calculations

Cited by 6 publications

References 56 publications

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Unlocking Potentially Therapeutic Phytochemicals in Capadulla (Doliocarpus dentatus) from Guyana Using Untargeted Mass Spectrometry-Based Metabolomics

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