Stability of ferric complexes with 3-hydroxyflavone (flavonol), 5,7-dihydroxyflavone (chrysin), and 3',4'-dihydroxyflavone - PubMed (original) (raw)
. 2005 Apr 20;53(8):2953-60.
doi: 10.1021/jf048298q.
Affiliations
- PMID: 15826045
- DOI: 10.1021/jf048298q
Stability of ferric complexes with 3-hydroxyflavone (flavonol), 5,7-dihydroxyflavone (chrysin), and 3',4'-dihydroxyflavone
Mark D Engelmann et al. J Agric Food Chem. 2005.
Abstract
The acid dissociation and ferric stability constants for complexation by the flavonoids 3-hydroxyflavone (flavonol), 5,7-dihydroxyflavone (chrysin), and 3',4'-dihydroxyflavone in 50:50 (v/v) ethanol/water are determined by pH potentiometric and spectrophotometric titrations and the linear least-squares curve-fitting program Hyperquad. Over the entire range of pH and reagent concentrations spanning the titration experiments, the stoichiometry for iron-flavonoid complex formation was 1:1 for all three flavonoids examined. The three flavonoids were chosen for their hydroxy substitution pattern, with each possessing one of the three most commonly suggested sites for metal binding by the flavonoids. On the basis of the calculated stability constants, the intraflavonoid-binding site competition is illustrated as a function of pH via speciation curves. The curves indicate that the binding site comprised of the 3',4'-hydroxy substitutions, the catecholic site, is most influential for ferric complexation at the physiological pH of 7.4. The possibility for antioxidant activity by flavonoid chelation of ferric iron in the presence of other competitive physiological complexing agents is demonstrated through additional speciation calculations.
Similar articles
- Characterization of the aqueous iron(III) chelation chemistry of a potential Trojan Horse antimicrobial agent: chelate structure, stability and pH dependent speciation.
Harrington JM, Gootz T, Flanagan M, Lall M, O'Donnell J, Winton J, Mueller J, Crumbliss AL. Harrington JM, et al. Biometals. 2012 Oct;25(5):1023-36. doi: 10.1007/s10534-012-9568-0. Epub 2012 Aug 2. Biometals. 2012. PMID: 22855208 - The dissociation constants of the cytostatic bosutinib by nonlinear least-squares regression of multiwavelength spectrophotometric and potentiometric pH-titration data.
Meloun M, Nečasová V, Javůrek M, Pekárek T. Meloun M, et al. J Pharm Biomed Anal. 2016 Feb 20;120:158-67. doi: 10.1016/j.jpba.2015.12.012. Epub 2015 Dec 12. J Pharm Biomed Anal. 2016. PMID: 26730513 - Glycosiderophores: synthesis of tris-hydroxamate siderophores based on a galactose or glycero central scaffold, Fe(III) complexation studies.
Neff C, Bellot F, Waern JB, Lambert F, Brandel J, Serratrice G, Gaboriau F, Policar C. Neff C, et al. J Inorg Biochem. 2012 Jul;112:59-67. doi: 10.1016/j.jinorgbio.2012.02.030. Epub 2012 Mar 7. J Inorg Biochem. 2012. PMID: 22551986 - Iron chelation properties of an extracellular siderophore exochelin MN.
Dhungana S, Miller MJ, Dong L, Ratledge C, Crumbliss AL. Dhungana S, et al. J Am Chem Soc. 2003 Jun 25;125(25):7654-63. doi: 10.1021/ja029578u. J Am Chem Soc. 2003. PMID: 12812507 - In vitro analysis of iron chelating activity of flavonoids.
Mladěnka P, Macáková K, Filipský T, Zatloukalová L, Jahodář L, Bovicelli P, Silvestri IP, Hrdina R, Saso L. Mladěnka P, et al. J Inorg Biochem. 2011 May;105(5):693-701. doi: 10.1016/j.jinorgbio.2011.02.003. Epub 2011 Feb 16. J Inorg Biochem. 2011. PMID: 21450273
Cited by
- Plant-derived chelators and ionophores as potential therapeutics for metabolic diseases.
Lee VJ, Janisse SE, Heffern MC. Lee VJ, et al. Chem Soc Rev. 2023 Jun 6;52(11):3927-3945. doi: 10.1039/d3cs00167a. Chem Soc Rev. 2023. PMID: 37203389 Free PMC article. Review. - Bioactivity and Therapeutic Potential of Kaempferol and Quercetin: New Insights for Plant and Human Health.
Jan R, Khan M, Asaf S, Lubna, Asif S, Kim KM. Jan R, et al. Plants (Basel). 2022 Oct 5;11(19):2623. doi: 10.3390/plants11192623. Plants (Basel). 2022. PMID: 36235488 Free PMC article. Review. - Experimental and theoretical investigation of cyclometalated phenylpyridine iridium(iii) complex based on flavonol and ibuprofen ligands as potent antioxidant.
Tabrizi L, Nguyen TLA, Dao DQ. Tabrizi L, et al. RSC Adv. 2019 Jun 3;9(30):17220-17237. doi: 10.1039/c9ra02726b. eCollection 2019 May 29. RSC Adv. 2019. PMID: 35519868 Free PMC article. - Selected Natural Products in Neuroprotective Strategies for Alzheimer's Disease-A Non-Systematic Review.
Wojtunik-Kulesza K, Oniszczuk T, Mołdoch J, Kowalska I, Szponar J, Oniszczuk A. Wojtunik-Kulesza K, et al. Int J Mol Sci. 2022 Jan 21;23(3):1212. doi: 10.3390/ijms23031212. Int J Mol Sci. 2022. PMID: 35163136 Free PMC article. Review. - Multiple reactivities of flavonoids towards pathological elements in Alzheimer's disease: structure-activity relationship.
Nam G, Hong M, Lee J, Lee HJ, Ji Y, Kang J, Baik MH, Lim MH. Nam G, et al. Chem Sci. 2020 Sep 8;11(37):10243-10254. doi: 10.1039/d0sc02046j. Chem Sci. 2020. PMID: 34094290 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources