Properties and applications of flavonoid metal complexes

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Abstract

Flavonoid metal complexes have a wide spectrum of activities as well as potential and actual applications.

Flavonoids are widely occurring polyphenol compounds of plant origin with multiple biological and chemical activities. Due to the presence of carbonyl and hydroxyl groups they can coordinate metal ions and form complexes. Metal complexes of flavonoids have many interesting properties: they are colored, often fluorescent, anti- or pro-oxidant, antimicrobial, antiproliferative and biologically active in many other ways. There are many papers covering specific aspects of activity of flavonoid metal complexes, e.g. their antioxidant properties, enzyme-mimicking behavior, therapeutic potential or use in chemical analysis. However, for a researcher interested in this theme, it would be useful to find an extensive review on more than one selected area. Our aim was to cover a wide spectrum of possible activities and potential applications of flavonoids coordinated to metal ions in order to give our readers a broad view on the topic of this class of compounds, their activity and potential applications. While a significant amount of information on the chemical properties and biological activity of flavonoid metal complexes can be found in the literature, an in-depth understanding of structure–property relationships is still lacking. In an attempt to address this issue, a comprehensive discussion of the available data is presented.

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Flavonoids: antioxidants or signalling molecules?

Robert J P Williams, Jeremy Spencer, Catherine Rice-Evans (2004)

Many studies are accumulating that report the neuroprotective, cardioprotective, and chemopreventive actions of dietary flavonoids. While there has been a major focus on the antioxidant properties, there is an emerging view that flavonoids, and their in vivo metabolites, do not act as conventional hydrogen-donating antioxidants but may exert modulatory actions in cells through actions at protein kinase and lipid kinase signalling pathways. Flavonoids, and more recently their metabolites, have been reported to act at phosphoinositide 3-kinase (PI 3-kinase), Akt/protein kinase B (Akt/PKB), tyrosine kinases, protein kinase C (PKC), and mitogen activated protein kinase (MAP kinase) signalling cascades. Inhibitory or stimulatory actions at these pathways are likely to affect cellular function profoundly by altering the phosphorylation state of target molecules and by modulating gene expression. A clear understanding of the mechanisms of action of flavonoids, either as antioxidants or modulators of cell signalling, and the influence of their metabolism on these properties are key to the evaluation of these potent biomolecules as anticancer agents, cardioprotectants, and inhibitors of neurodegeneration

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Recent advances in understanding the antibacterial properties of flavonoids.

T P Tim Cushnie, Andrew Lamb (2011)

Antibiotic resistance is a major global problem and there is a pressing need to develop new therapeutic agents. Flavonoids are a family of plant-derived compounds with potentially exploitable activities, including direct antibacterial activity, synergism with antibiotics, and suppression of bacterial virulence. In this review, recent advances towards understanding these properties are described. Information is presented on the ten most potently antibacterial flavonoids as well as the five most synergistic flavonoid-antibiotic combinations tested in the last 6 years (identified from PubMed and ScienceDirect). Top of these respective lists are panduratin A, with minimum inhibitory concentrations (MICs) of 0.06-2.0 μg/mL against Staphylococcus aureus, and epicatechin gallate, which reduces oxacillin MICs as much as 512-fold. Research seeking to improve such activity and understand structure-activity relationships is discussed. Proposed mechanisms of action are also discussed. In addition to direct and synergistic activities, flavonoids inhibit a number of bacterial virulence factors, including quorum-sensing signal receptors, enzymes and toxins. Evidence of these molecular effects at the cellular level include in vitro inhibition of biofilm formation, inhibition of bacterial attachment to host ligands, and neutralisation of toxicity towards cultured human cells. In vivo evidence of disruption of bacterial pathogenesis includes demonstrated efficacy against Helicobacter pylori infection and S. aureus α-toxin intoxication. Copyright © 2011 Elsevier B.V. and the International Society of Chemotherapy. All rights reserved.