13C NMR spectral data and molecular descriptors to predict the antioxidant activity of flavonoids

Scotti, Luciana; Fernandes, Mariane B.; Muramatsu, Eric; Emereciano, Vicente; Tavares, Josean Fechine; Silva, Marcelo Sobral da; Scotti, Marcus Tullius

doi:10.1590/s1984-82502011000200005

Cited by 17 publications

(10 citation statements)

References 20 publications

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“…Thus, these flavonoids have anticancer properties. The antioxidant properties of flavonoids can be accessed through 13 C-NMR and QSAR methods [ 130 , 131 ].…”

Section: Effects Of Flavonoids On Human Healthmentioning

confidence: 99%

Important Flavonoids and Their Role as a Therapeutic Agent

et al. 2020

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Flavonoids are phytochemical compounds present in many plants, fruits, vegetables, and leaves, with potential applications in medicinal chemistry. Flavonoids possess a number of medicinal benefits, including anticancer, antioxidant, anti-inflammatory, and antiviral properties. They also have neuroprotective and cardio-protective effects. These biological activities depend upon the type of flavonoid, its (possible) mode of action, and its bioavailability. These cost-effective medicinal components have significant biological activities, and their effectiveness has been proved for a variety of diseases. The most recent work is focused on their isolation, synthesis of their analogs, and their effects on human health using a variety of techniques and animal models. Thousands of flavonoids have been successfully isolated, and this number increases steadily. We have therefore made an effort to summarize the isolated flavonoids with useful activities in order to gain a better understanding of their effects on human health.

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“…Thus, these flavonoids have anticancer properties. The antioxidant properties of flavonoids can be accessed through 13 C-NMR and QSAR methods [ 130 , 131 ].…”

Section: Effects Of Flavonoids On Human Healthmentioning

confidence: 99%

Important Flavonoids and Their Role as a Therapeutic Agent

et al. 2020

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“…The isolated compounds were identified using a variety of spectroscopic methods, including: UV, HRMS, 1 H-NMR, and DEPT-Q NMR analyses as well as Co-TLC with authentic samples, and data comparison with the published literature. The isolated compounds were identified as; β-sitosterol ( 1 ) [ 22 ], ursolic acid ( 2 ) [ 23 , 24 ], corosolic acid ( 3 ) [ 25 ], 3- O - trans-p -coumaroylcrosolic acid ( 4 ) [ 23 , 26 ], 3,6,19 trihydroxy-ursolic acid ( 5 ) [ 27 ], β-sitosterol 3- O -β-glucoside ( 6 ) [ 28 ], quercetin ( 7 ) [ 29 ], luteolin ( 8 ) [ 30 ], quercetin-3- O -glucoside ( 9 ) [ 31 ], quercetin 3- O - β -xyloside ( 10 ) [ 32 , 33 ],4-hydroxybenzoic acid ( 11 ) [ 34 ], 4-methoxy benzoic acid ( 12 ) [ 34 ], 3,4-dihydroxybenzoic acid ( 13 ) [ 35 ], p -coumaric acid ( 14 ) [ 36 ], rutin ( 15 ) [ 37 ], and luteolin-7- O -β-glucoside ( 16 ) [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

Characterization of Promising Cytotoxic Metabolites from Tabebuia guayacan Hemsl.: Computational Prediction and In Vitro Testing

El‐Hawary

Mohammed

Taher

et al. 2022

Plants

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Genus Tabebuia is famous for its traditional uses and valuable phytoconstituents. Our previous investigation of Tabebuia species noted the promising anticancer activity of T. guayacan Hemsl. leaves extract, however, the mechanism underlying the observed anticancer activity is still unexplored. The current research was designed to explore the phytochemical content as well as to address the phytoconstituent(s) responsible for the recorded anticancer activity. Accordingly, sixteen compounds were isolated, and their structures were elucidated using different spectroscopic techniques. The drug-likeness of the isolated compounds, as well as their binding affinity with four anticancer drug target receptors: CDK-2/6, topoisomerase-1, and VEGFR-2, were evaluated. Additionally, the most promising compounds were in vitro evaluated for inhibitory activities against CDK-2/6 and VEGFR-2 enzymes using kinase assays method. Corosolic acid (3) and luteolin-7-O-β-glucoside (16) were the most active inhibitors against CDK-2 (−13.44 kcal/mol) and topoisomerase 1 (−13.83 kcal/mol), respectively. Meanwhile, quercetin 3-O-β-xyloside (10) scored the highest binding free energies against both CDK-6 (−16.23 kcal/mol) as well as against VEGFR-2 protein targets (−10.39 kcal/mol). Molecular dynamic simulation indicated that quercetin 3-O-β-xyloside (10) exhibited the least fluctuations and deviations from the starting binding pose with RMSD (2.6 Å). Interestingly, in vitro testing results confirmed the potent activity of 10 (IC50 = 0.154 µg/mL) compared to IC50 = 0.159 µg/mL of the reference drug ribociclib. These findings suggest the three noted compounds (3, 10, and 16) for further in vivo anticancer studies.

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“…Similar results were found for the calculated 13 C NMR concerning previous experimental studies. 49 , 53 , 54…”

Section: Resultsmentioning

confidence: 99%

Analysis of Conformational, Structural, Magnetic, and Electronic Properties Related to Antioxidant Activity: Revisiting Flavan, Anthocyanidin, Flavanone, Flavonol, Isoflavone, Flavone, and Flavan-3-ol

2021

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Understanding the antioxidant activity of flavonoids is important to investigate their biological activities as well as to design novel molecules with low toxicity and high activity. Aromaticity is a chemical property found in cyclic structures that plays an important role in their stability and reactivity, and its investigation can help us to understand the antioxidant activity of some heterocyclic compounds. In the present study, we applied the density functional theory (DFT) to investigate the properties of seven flavonoid structures with well-reported antioxidant activity: flavan, anthocyanidin, flavanone, flavonol, isoflavone, flavone, and flavan-3-ol. Conformational, structural, magnetic, and electronic analyses were performed using nuclear magnetic resonance, ionization potentials, electron affinity, bond dissociation energy, proton affinity, frontier molecular orbitals (highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO)), and aromaticity through nucleus-independent chemical shifts to analyze these seven flavonoid structures. We revised the influence of hydroxyl groups on the properties of flavonoids and also investigated the influence of the aromaticity of these seven flavonoids on the antioxidant activity.

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13C NMR spectral data and molecular descriptors to predict the antioxidant activity of flavonoids

Cited by 17 publications

References 20 publications

Important Flavonoids and Their Role as a Therapeutic Agent

Important Flavonoids and Their Role as a Therapeutic Agent

Characterization of Promising Cytotoxic Metabolites from Tabebuia guayacan Hemsl.: Computational Prediction and In Vitro Testing

Analysis of Conformational, Structural, Magnetic, and Electronic Properties Related to Antioxidant Activity: Revisiting Flavan, Anthocyanidin, Flavanone, Flavonol, Isoflavone, Flavone, and Flavan-3-ol

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