Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin

Veiga, Andrex A. S.; Neto, A. M. J. C.; Silva, Albérico Borges Ferreira da; Herculano, Anderson Manoel; Oliveira, Karen Renata Matos; Borges, Rosivaldo dos Santos

doi:10.1007/s00044-018-2147-3

Cited by 14 publications

(8 citation statements)

References 21 publications

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“…Additionally, in the mangiferin–iron complex, the iron improves its superoxide radical scavenging action. Recently, Silva da Veiga et al [53] described the structure–antioxidant relationship of mangiferin using quantum chemistry calculations; they conclude that mangiferin has greater antioxidant capacity by hydrogen transfer than by electron transfer. Furthermore, a synergistic effect can be observed between xanthone and the sugar rings.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Phenolic Compounds from the Agroindustrial Waste of Colombian Mango Cultivars ‘Sugar Mango’ and ‘Tommy Atkins’—An Alternative for Their Use and Valorization

et al. 2019

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The aim of this study was to explore the potential of the agroindustrial waste from two Colombian mango cultivars as sources of bioactive phenolic compounds. Phenolic extracts from mango waste (peels, seed coats, and seed kernels) of ‘sugar mango’ and ‘Tommy Atkins’ cultivars were obtained. The bioactive properties of the phenolic extracts were accessed by measuring their free radical scavenging activity and antioxidant effects against lipid oxidation in food products; moreover, their antiproliferative effects against some cell lines of human cancer were explored. It is observed that the agroindustrial waste studied provides promising sources of bioactive phenolics. ‘Sugar mango’ waste provided extracts with the highest antioxidant effect in food products and antiproliferative activity; these extracts reduced lipid oxidation and cell growth by more than 57% and 75%, respectively. The seed kernel from ‘sugar mango’ supplied the extract with the best bioactive qualities; in addition, some recognized bioactive phenolics (such as mangiferin and several galloyl glucosides) were observed in this extract and related with its properties. The results obtained suggest that ‘sugar mango’ waste may be considered a source of bioactive phenolics, with promising uses in food and pharmaceutical products. Thus, a suitable alternative for the use and valorization of agroindustrial waste from Colombian mango cultivars is presented.

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Section: Resultsmentioning

confidence: 99%

Bioactive Phenolic Compounds from the Agroindustrial Waste of Colombian Mango Cultivars ‘Sugar Mango’ and ‘Tommy Atkins’—An Alternative for Their Use and Valorization

et al. 2019

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“…In light of the potent antioxidant property of coumarin–chalcone hybrids, it is interesting to perform a theoretical study on the antioxidant activity to highlight their structure–activity relationship. During the past decades, density functional theory (DFT) has been successfully used to elucidate the structure–antioxidant activity of phenolic compounds. ,− To the best of our knowledge, only two reports are available about the theoretical studies on the antioxidant properties of coumarin–chalcone hybrids. Mazzone and co-workers theoretically studied the structural characteristics, antioxidant ability, and the spectral properties of a series of coumarin–chalcone hybrids synthesized in Vazquez-Rodriguez’s experiment .…”

Section: Introductionmentioning

confidence: 99%

Antiradical Activity and Mechanism of Coumarin–Chalcone Hybrids: Theoretical Insights

et al. 2018

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In view of the multifunctional features of coumarins and chalcones, coumarin–chalcone hybrids have attracted much attention in recent years. Herein, the free radical scavenging activities of a series of coumarin–chalcone hybrids were investigated using the density functional theory (DFT) method. Three main reaction mechanisms were explored: hydrogen atom transfer (HAT), electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET). Thermodynamic descriptors associated with these mechanisms were calculated in the gas phase and solvents. The results demonstrate that the predicted antioxidant efficiencies are generally in accordance with the experimental results. HAT is proposed as the thermodynamically favored mechanism in the gas phase and nonpolar solution, while SPLET is preferred in polar media. Our results indicate that compound MPHCC possesses potential for inactivating free radicals via double HAT and double SPLET mechanisms depending upon the polarity of environment. In addition, the SPLHAT mechanism provides an alternative pathway to HAT and SPLET for radical scavenging by MPHCC and OPHCC. The results confirmed the crucial role of hydroxyl groups on the chalcone moiety in trapping radicals. 4′-OH in the catechol group is proposed as the primary target for radical attack.

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“…Our results demonstrated that chloroquine (1) exhibits the best antioxidant capacity through the single electron transfer mechanism (SET) when compared to quinine (2) [31,33]. When comparing these compounds, we observed comparable HOMO values for chloroquine (-5.91 eV) and quinine (-5.77 eV), but different LUMO values (-1.53 and − 1.73 eV, respectively).…”

Section: Electron Donation Capacity Of Chloroquine Related To Quininementioning

confidence: 65%

“…The spin density contributions involved on resonance effect were used for a comparative study of chemical stability between the main contributions on chloroquine (1) and quinine (2) cation free-radical [30][31][32].…”

Section: Molecular Calculationsmentioning

confidence: 99%

Structural requirements for nucleophilicity and antioxidant capacity on quinoline derivatives: a theoretical study

Borges

Santos

et al. 2023

Preprint

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Context Quinoline derivatives play a crucial role in antimalarial therapy, and their biological properties are highly dependent on the basicity, particularly on the amine groups. The Amine moieties significantly contribute to the antioxidant capacity of quinoline derivatives through electron transfer mechanisms. Notably, each amine group has a distinct contribution to the antioxidant capacity, with the aliphatic amine displaying a potent electron donating capacity, the exo-aromatic amine showing an intermediate capacity, and the endo-aromatic amine demonstrating the least potent capacity. Our findings reveal a synergistic effect between the 4-amino-quinoline and tertiary amine in quinoline derivatives, enhancing their overall antioxidant capacity. However, the presence of the chlorine atom decreases its contribution as an electron withdrawing group. In comparison, chloroquine exhibits a higher antioxidant capacity than quinine, and their respective electron donation abilities are correlated with their pKa values. The synergistic effect between the 4-amino-quinoline and tertiary amine is particularly evident in chloroquine, surpassing the antioxidant capacity of 6-methoxy-4-methyl-quinoline moiety in quinine. Additionally, we have successfully proposed two new strategies for the development of chloroquine derivatives. Methods A theoretical study was conducted to investigate the structure-nucleophilicity and antioxidant capacity of quinoline derivatives, specifically chloroquine and quinine, through electron transfer using DFT/B3LYP/6–31 + G(d,p) methods. The HOMO values were utilized to assess nucleophilicity, while the ionization potential was indicative of electron donating capacity. To explore different aspects of the molecules, four approaches of molecular modifications were proposed: molecular fragmentation, molecular modification on amine moieties, and molecular association. These approaches aimed to provide insights into the relationships between molecular structure and nucleophilicity or antioxidant capacity. The study also involved the development of new strategies in drug design, leveraging theoretical methods to explore potential modifications and optimizations for quinoline derivatives.

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Sugar moiety has a synergistic effect on hydroxylated xanthone for better antioxidant activity of mangiferin

Cited by 14 publications

References 21 publications

Bioactive Phenolic Compounds from the Agroindustrial Waste of Colombian Mango Cultivars ‘Sugar Mango’ and ‘Tommy Atkins’—An Alternative for Their Use and Valorization

Bioactive Phenolic Compounds from the Agroindustrial Waste of Colombian Mango Cultivars ‘Sugar Mango’ and ‘Tommy Atkins’—An Alternative for Their Use and Valorization

Antiradical Activity and Mechanism of Coumarin–Chalcone Hybrids: Theoretical Insights

Structural requirements for nucleophilicity and antioxidant capacity on quinoline derivatives: a theoretical study

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