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Properties and Applications of Flavonoid Metal Complexes Cite This: DOI: 10.1039/X0xx00000x

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Properties and Applications of Flavonoid Metal Complexes Cite This: DOI: 10.1039/X0xx00000x RSC Advances This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. This Accepted Manuscript will be replaced by the edited, formatted and paginated article as soon as this is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/advances Page 1 of 24 RSC Advances Flavonoid metal complexes have a wide spectrum of activities as well as potential and actual applications. Manuscript Accepted Advances RSC RSC Advances Page 2 of 24 Journal Name RSCPublishing ARTICLE Properties and applications of flavonoid metal complexes Cite this: DOI: 10.1039/x0xx00000x Maria M. Kasprzak,a Andrea Erxlebenc, Justyn Ochockia Received 00th January 2012, Accepted 00th January 2012 a Departement of Bioinorganic Chemistry, Medical University of Lodz, DOI: 10.1039/x0xx00000x Ul. Muszynskiego 1, Lodz, Poland c School of Chemistry, National University of Ireland, Galway, Ireland www.rsc.org/ Corresponding author: [email protected] 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 Manuscript 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 Accepted 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. Keywords: flavonoids; metal ions; complexes Advances 1. Introduction 7.1. Cytostatic activity 2. Metal ion chelation 7.2. Antimicrobial and antiviral activity 2.1. Metal binding sites and complex stability 7.3. Anti-inflammatory activity 2.2. Structural properties 7.4. Applications in non-cancer diseases RSC 2.3. Optical properties 8. Interaction with biomolecules other than DNA 2.4. Computational studies 8.1. Interaction with lipids 3. Applications in chemical analysis 8.2. Interaction with serum albumin 4. Photochemical and electrochemical applications 8.3. Interaction with enzymes 5. Application as pigments and dyes 9. Applications in biomimetic studies 6. Redox properties of flavonoids and their metal 10. Conclusions complexes 6.1. Antioxidant activity 6.2. Pro-oxidant activity 6.3. In vitro and in vivo chemo-protective activity 7. Applications in medicine This journal is © The Royal Society of Chemistry 2013 J. Name., 2013, 00, 1-3 | 1 Page 3 of 24 RSC Advances ARTICLE Journal Name 1. Introduction Table 1 Examples for natural flavonoids Flavonoids, a group of compounds based on the 2- phenylchromen-4-one (2-phenyl-1-benzopyran-4-one) structure, occur in nature mostly as polyphenol compounds of Basic structure of selected flavonoids, with carbon atoms plant origin (Table 1). Depending on the degree of oxidation of numbered the -pyranone ring, they can be categorised into different 3' subclasses, such as flavones, flavonols, and flavanones (Table 2' 4' 1). In nature flavonoids occur mostly as glycosides, as the sugar 8 B O 5' group enhances the water solubility of the hydrophobic 7 1 2 6' flavonoid molecules. There are also many synthetic flavonoid- A C derived substances.1-5 Most, if not all, flavonoids are colored 6 3 4 substances (flavonoid from Latin flavus ‘yellow’) and thus, 5 along with carotenoids, chlorophyll, etc., are the source of color O in leaves, flowers and fruits of many plants. Natural flavonoids Flavanones Naringenin 5,7-dyhydroxyflavanone are widely believed to prevent many conditions, such as cancer Liquirtigenin 7,4’-dihydroxyflavanone or cardiovascular diseases.6 Their beneficial properties are Hesperetin 5,7,5’-trihydroxyflavanone ascribed to their antioxidant activity which depends mostly on Eriodictyol 5,7,3’,4’-tetrahydroxyflavanone the number and position of hydroxyl moieties.7 However, the Homoeriodictyol 5,7,4’-trihydroxy-3’-methohyflavanone wide variety of biological activities of flavonoids is not limited Pinostrobin 5-hydroxy-7-methoxyflavanone to antioxidant properties. They also act as enzyme inhibitors,8 9,10 11,12 Flavones signaling molecules, DNA intercalators and chelators of Chrysin 5,7-dihydroxyflavone Manuscript 13 metal ions. Furthermore, they are not always beneficial for Baicalein 5,6,7-trihydroxyflavone 8 14 health. For example, quercetin alone is carcinogenic in rats Luteolin 5,7,3’,4’-tetrahydroxyflavone and upon oxidation it may produce toxic metabolites and cause Apigenin 5,7,4’-trihydroxyflavone 15 depletion of the intracellular thiol pool. Scutellarein 5,6,7,4’-tetrahydroxyflavone Wogonin 5,7-dihydroxy-8-methoxyflavone Due to the presence of oxo and hydroxyl groups (and nitrogen Tangeritin 5,6,7,8,4’-pentamethoxyflavone 5 donors in some synthetic compounds ), many flavonoids can Diosmetin 5,7,3’-trihydroxy-4’-methoxyflavone 16-27 coordinate and chelate various metal ions (Fig. 2). Flavonols However, reactions between flavonoids and metal ions are not Flavonol 3-hydroxyflavone Accepted always limited to simple coordination bond formation. Galangin 3,5,7-trihydroxyflavone Depending on the metal ion, redox reactions between the metal Kaempferol 3,5,7,4’-tetrahydroxyflavone ions and the ligands may occur, as most flavonoids have good Morin 3,5,7,2’,4’-pentahydroxyflavone reducing capacity. This is particularly relevant for metal ions Myricetin 3,5,7,3’,4’,5’-hexahydroxyflavone with oxidizing properties, e.g. FeIII,28 RuIV,29 RuIII,30 AuIII,31 or Quercetin 3,5,7,3’,4’-pentahydroxyflavone OsVIII.32 This review focuses on the ability of flavanones, Fisetin 3,7,3’,4’-tetrahydroxyflavone flavones and flavonols, as well as their glycosides to form Azaleatin 3,7,3’,4’-tetrahydroxy-5-methoxyflavone metal complexes, the various consequences of this process, and the properties and applications of such complexes. Isoflavones and flavanols (catechins), because of their distinct structure that Advances affects the geometry of their chelating sites (Fig 1), will not be the subject of this paper. RSC Fig. 1 Structures of different classes of flavonoids. 2 | J. Name., 2012, 00, 1-3 This journal is © The Royal Society of Chemistry 2012 RSC Advances Page 4 of 24 Journal Name ARTICLE and coordination occurs through the ortho-dihydroxyl group with a 1:1 metal/ligand stoichiometry. Cornard and Merlin reported the formation of a 1:1 Al3+ quercetin complex with chelation through the 3-4 or 4-5 site in acidic solution.45 At alkaline pH, these authors observed binding of a second Al3+ ion to the catechol moiety leading to a 2:1 metal/ligand stoichiometry. By contrast, Dimitric Markovic et al. reported the stepwise coordination of Al3+ to the 3-4 and 3’-4’ sites of fisetin also at pH 5 (albeit at a Al3+ : ligand ratio different to that in Cornard and Merlin’s study)46 and the 2:1 Al3+ complex of luteolin involving coordination to the 3-4 and 3’-4’ sites was proposed by Rygula et al. to co-exist with the 1:1 complex in acidic solution.38 On the other hand, the suggestion that the ortho-dihydroxyl group of the B ring is not a binding site for Al3+ in strongly acidic medium is in line with a report that flavonoids that lack the 3- and 5-hydroxy groups, such as 3’4’- Fig. 2 Possible chelating sites of quercetin. Flavonoids can dihydroxyflavone do not react with Al3+ at acidic pH.47 coordinate metal ions in their neutral (as shown) or anionic form. 2. Metal ion chelation Ahmedova et al. carried out a combined 1H, 13C MAS NMR and DFT study on the Al quercetin complex and pointed out 2. Metal ion chelation that the chelating site in the solid-state and in solution are likely to be different.48 Cr3+ ions were found to favor the deprotonated 2.1. Metal binding sites and complex stability 4-5 site of quercetin49 and luteolin,50 while Pb2+ ions Manuscript 51,52 As shown in Fig. 1, flavonoids present more than one possible preferentially bind to the 3’-4’ site. There are a large chelating site for metal ions. Metal coordination to the number of theoretical studies on the preferential coordination pentahydroxyflavone quercetin, the most common flavonoid, mode in metal flavonoid complexes in the literature that will be can occur via the 3-hydroxyl and 4-carbonyl group of the C discussed in section 2.4. ring (denoted as 3-4 site), the 4-carbonyl-5-hydroxyl site of the A and C rings (4-5 site) or via the catechol moiety of the B ring (3’-4’ site).
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