Development of a classification model for the antigenotoxic activity of flavonoids

Tuenter, Emmy; Creylman, Jan; Verheyen, Geert R.; Pieters, Luc; Miert, Sabine Van

doi:10.1016/j.bioorg.2020.103705

Cited by 8 publications

(3 citation statements)

References 26 publications

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“…Depending on the degree of saturation and oxidation of C-ring, and the position of the B-ring, flavonoids can be organized into different classes (Table 1). Flavones, flavonols, flavanones, flavanols, and anthocyanins, include the largest number of compounds in nature, representing the narrow-sense flavonoids with a 2-phenylchromone nucleus [16]. Isoflavonoids are a class of flavonoids with several subgroups, including isoflavones, isoflavanones, isoflavans, pterocarpans and rotenoids, which share a common 3-phenylchromone scaffold where the B-ring is linked to the C-ring in position 3 [17].…”

Section: Flavonoidsmentioning

confidence: 99%

Chiral Flavonoids as Antitumor Agents

et al. 2021

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Flavonoids are a group of natural products with a great structural diversity, widely distributed in plant kingdom. They play an important role in plant growth, development and defense against aggressors. Flavonoids show a huge variety of biological activities such as antioxidant, anti-inflammatory, anti-mutagenic, antimicrobial and antitumor, being able to modulate a large diversity of cellular enzymatic activities. Among natural flavonoids, some classes comprise chiral molecules including flavanones, flavan-3-ols, isoflavanones, and rotenoids, which have one or more stereogenic centers. Interestingly, in some cases, individual compounds of enantiomeric pairs have shown different antitumor activity. In nature, these compounds are mainly biosynthesized as pure enantiomers. Nevertheless, they are often isolated as racemates, being necessary to carry out their chiral separation to perform enantioselectivity studies. Synthetic chiral flavonoids with promising antitumor activity have also been obtained using diverse synthetic approaches. In fact, several new chiral bioactive flavonoids have been synthesized by enantioselective synthesis. Particularly, flavopiridol was the first cyclin-dependent kinase (CDK) inhibitor which entered clinical trials. The chiral pool approaches using amino acid as chiral building blocks have also been reported to achieve small libraries of chrysin derivatives with more potent in vitro growth inhibitory effect than chrysin, reinforcing the importance of the introduction of chiral moieties to improve antitumor activity. In this work, a literature review of natural and synthetic chiral flavonoids with antitumor activity is reported for the first time.

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Section: Flavonoidsmentioning

confidence: 99%

Chiral Flavonoids as Antitumor Agents

et al. 2021

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“…They are benzo-γpyrone derivatives consisting of aromatic (A and B) and pyrene (C) rings (Figure 1A) and are classified according to structural changes in hydroxylation pattern, conjugation between the aromatic rings, glycosidic moieties, and methoxy group [2,3]. These secondary metabolites have shown many and different applications, such as antiviral activity against zika virus infection [4], anti-hyperglycemic, liver protective [5], and anti-rheumatoid arthritis effects [6], antigenotoxic activity [7], and modulation of cardiovascular K + channels [8], just to mention some cutting-edge studies from the last few years. It is also well known these compounds have anti-oxidative, anti-inflammatory, anti-mutagenic, and anti-carcinogenic properties coupled with their capacity to modulate the cellular key and enzyme function [1].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and Anticancer Activities and Protein Interaction of the Oxidovanadium(IV) Naringin Complex

et al. 2022

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The complex of oxidovanadium(IV) with naringin (Narg) [VO(Narg)2] 8H2O (VONarg) was prepared according to the literature improving the synthetic procedure and physicochemical characterization. In addition, biological activities (cytotoxic, antioxidant, and BSA interaction) were determined. The metal coordinated through the 5-hydroxy and 4-carbonyl groups of rings A and C of naringin, respectively. The antioxidant activity of VONarg, determined in vitro, was higher than those of the flavonoid against superoxide and peroxyl reactive oxygen species (ROS) and DPPH radical. The cytotoxic properties were determined by a MTT assay on adenocarcinoma human alveolar basal epithelial cells (A549). VONarg exerted a 20% decrease in cancer cells viability at 24 h incubation, while naringin and oxidovanadium(IV) cation did not show cytotoxicity. Measurements with the normal HEK293 cell line showed that the inhibitory action of the complex is selective. VONarg generated intracellular reactive oxygen species (ROS), depletion of reduced glutathione and depolarization of mitochondrial membrane potential, typical for apoptotic pathway, producing cell death by oxidative stress mechanism. Moreover, naringin interacted with bovine serum albumin (BSA) through hydrophobic interactions in a spontaneous process, and VONarg showed greater affinity for the protein but can still be transported and delivered by it (Ka 104 L·mol−1 order).

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“…Recent studies on flavonoids consider them as indispensable components in pharmaceutical and medicinal applications for disease prevention. The past few years has seen a surge on major research on flavonoids that primarily focuses on its antigenotoxic activity, 3 anti‐aging, 4 antioxidant, 5 and anti‐inflammatory 6,7 properties. Polyphenols display inhibitory effects against a series of enzymes 8‐10 mainly on cancer causing enzymes like CYP1A, 11 Cytochrome (CYP) P 450 enzymes, 12 and so forth.…”

Section: Introductionmentioning

confidence: 99%

Positional preferences in flavonoids for inhibition of ribonuclease A: Where “OH” where?

et al. 2021

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Flavonoids are a class of polyphenols that possess diverse properties. The structure‐activity relationship of certain flavonoids and resveratrol with ribonuclease A (RNase A) has been investigated. The selected flavonoids have a similar skeleton and the positional preferences of the phenolic moieties toward inhibition of the catalytic activity of RNase A have been studied. The results obtained for RNase A inhibition by flavonoids suggest that the planarity of the molecules is necessary for effective inhibitory potency. Agarose gel electrophoresis and precipitation assay experiments along with kinetic studies reveal Ki values for the various flavonoids in the micromolar range. Minor secondary structural changes of RNase A were observed after interaction with the flavonoids. An insight into the specific amino acid involvement in the binding of the substrate using docking studies is also presented. The dipole moment of the flavonoids that depends on the orientation of the hydroxyl groups in the molecule bears direct correlation with the inhibitory potency against RNase A. The direct association of this molecular property with enzyme inhibition can be exploited for the design and development of inhibitors of proteins.

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Development of a classification model for the antigenotoxic activity of flavonoids

Cited by 8 publications

References 26 publications

Chiral Flavonoids as Antitumor Agents

Chiral Flavonoids as Antitumor Agents

Antioxidant and Anticancer Activities and Protein Interaction of the Oxidovanadium(IV) Naringin Complex

Positional preferences in flavonoids for inhibition of ribonuclease A: Where “OH” where?

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