Hesperidin and hesperetin membrane interaction: Understanding the role of 7-O-glycoside moiety in flavonoids

Londoño, Jorge Eliécer Ossa; Lima, Vânia Rodrigues de; Jaramillo, Consuelo; Creczynski-Pasa, Tânia B.

doi:10.1016/j.abb.2010.04.023

Cited by 48 publications

(26 citation statements)

References 56 publications

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“…All compounds used in this study ( Figure 2) were purchased (compounds: 2,4,7, 6,11-15,17; Alfa Aesar, Massachusetts, USA and Sigma-Aldrich, Saint Louis, USA) or isolated from their natural source according to the previously reported procedures [24][25][26][27][28]. The constructed small library for the present study consisted of six non-glycosylated flavonoids (i.e., aglycones; 1-6), six glycosylated flavonoids (7)(8)(9)(10)(11)(12), and other miscellaneous phenolic derivatives (13-22).…”

Section: Library Constructionmentioning

confidence: 99%

Flavonoids as Potential anti-MRSA Agents through Modulation of PBP2a: A Computational and Experimental Study

et al. 2020

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Recently, the interest in plant-derived antimicrobial agents has increased. However, there are no sufficient studies dealing with their modes of action. Herein, we investigate an in-house library of common plant-based phenolic compounds for their potential antibacterial effects against the methicillin-resistant Staphylococcus aureus (MRSA), a widespread life-threatening superbug. Flavonoids, which are considered major constituents in the plant kingdom, were found to be a promising class of compounds against MRSA, particularly the non-glycosylated ones. On the other hand, the glycosylated derivatives, along with the flavonolignan silibinin A, were able to restore the inhibitory activity of ampicillin against MRSA. To explore the mode of action of this class, they were subjected to an extensive inverse virtual screening (IVS), which suggested penicillin-binding protein 2a (PBP2a) as a possible target that mediates both the antibacterial and the antibiotic-synergistic effects of this class of compounds. Further molecular docking and molecular dynamic simulation experiments were conducted to support the primary IVS and the in vitro results and to study their binding modes with PBP2a. Our findings shed a light on plant-derived natural products, notably flavonoids, as a promising and readily available source for future adjuvant antimicrobial therapy against resistant strains.

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Section: Library Constructionmentioning

confidence: 99%

Flavonoids as Potential anti-MRSA Agents through Modulation of PBP2a: A Computational and Experimental Study

et al. 2020

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“…36 Similarly, hesperetin (HT) was found to 3 be more interactive with DMPC liposomes than its glucoside hesperidin (HD). 37 Biophysical 4 studies in conjunction with human studies reported that absorption of aglycones was not only 5 faster but also in five times greater than their glucoside forms. 38 …”

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confidence: 99%

Experimental Modeling of Flavonoid–Biomembrane Interactions

Sanver

Murray²,

Sadeghpour³

et al. 2016

Langmuir

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and visualization of the surface with BAM revealed a pronounced monolayer stabilization effect 10 with both quercetin and tiliroside, whereas rutin disrupted the monolayer structure rendering the 11 surface entirely smooth. SAXS showed a monotonous membrane thinning for all compounds 12 studied associated with an increase in the root mean square fluctuations of the membrane. Rutin, 13 quercetin and tiliroside decreased the bilayer thickness of DOPC by ~0.45 Å, 0.8 Å, and 1.1 Å at 14 6 mol %, respectively. In addition to the novelty of using lipid monolayers to systematically 15 characterize the structure activity relationship (SAR) of a variety of flavonoids; this is the first 16 report investigating the effect of tiliroside with biomimetic membrane models. All the flavonoids 17 studied are believed to be localized in the lipid/water interface region. Both this localization and 18 the membrane perturbations have implications for their therapeutic activity.

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“…As previously demonstrated in a biophysical study, hesperetin (i.e., the aglycone form) interacts with membranes more strongly than hesperidin (the glycoside form) does. Hesperidin, due to its rutinoside moiety, is located at the level of the polar headgroup, whereas hesperetin interacts better with acyl chains and adopts a more planar conformation [ 46 ]. Indeed, this difference could impair hesperidin transport across cellular and organelle membranes, thus decreasing its prooxidant action within hepatocytes.…”

Section: Discussionmentioning

confidence: 99%

Citrus Flavanones Affect Hepatic Fatty Acid Oxidation in Rats by Acting as Prooxidant Agents

Constantin

Nascimento

Constantin

et al. 2013

BioMed Research International

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Citrus flavonoids have a wide range of biological activities and positive health effects on mammalian cells because of their antioxidant properties. However, they also act as prooxidants and thus may interfere with metabolic pathways. The purpose of this work was to evaluate the effects of three citrus flavanones, hesperidin, hesperetin, and naringenin, on several parameters linked to fatty acid oxidation in mitochondria, peroxisomes, and perfused livers of rats. When exogenous octanoate was used as substrate, hesperetin and naringenin reduced the mitochondrial NADH/NAD+ ratio and stimulated the citric acid cycle without significant changes on oxygen uptake or ketogenesis. When fatty acid oxidation from endogenous sources was evaluated, hesperetin and naringenin strongly reduced the mitochondrial NADH/NAD+ ratio. They also inhibited both oxygen uptake and ketogenesis and stimulated the citric acid cycle. Hesperidin, on the other hand, had little to no effect on these parameters. These results confirm the hypothesis that citrus flavanones are able to induce a more oxidised state in liver cells, altering parameters related to hepatic fatty acid oxidation. The prooxidant effect is most likely a consequence of the ability of these substances to oxidise NADH upon production of phenoxyl radicals in the presence of peroxidases and hydrogen peroxide.

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Hesperidin and hesperetin membrane interaction: Understanding the role of 7-O-glycoside moiety in flavonoids

Cited by 48 publications

References 56 publications

Flavonoids as Potential anti-MRSA Agents through Modulation of PBP2a: A Computational and Experimental Study

Flavonoids as Potential anti-MRSA Agents through Modulation of PBP2a: A Computational and Experimental Study

Experimental Modeling of Flavonoid–Biomembrane Interactions

Citrus Flavanones Affect Hepatic Fatty Acid Oxidation in Rats by Acting as Prooxidant Agents

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