The characterisation of structural and antioxidant properties of isoflavone metal chelates

Journal of Inorganic Biochemistry
Stephen DowlingHelen Hughes

Abstract

Isoflavone metal chelates are of interest as isoflavones act as oestrogen mimics. Metal interactions may enhance isoflavones biological properties so understanding isoflavone metal chelation is important for the commercial application of isoflavones. This work aimed to determine if isoflavones, daidzein (4',7-dihydroxyisoflavone) and genistein (4',5,7-trihydroxyisoflavone) could chelate with metals as isoflavone chelates. Biochanin A (4'-methoxy-5,7-dihydroxyisoflavone) was also examined for it's ability to chelate with Cu(II) and Fe(III). This study found daidzein does not chelate with Cu(II) and Fe(III) but genistein and biochanin A chelate with a 1:2 M/L stoichiometry. The copper and iron chelates were synthesised and characterised by elemental analysis, FTIR, thermogravimetric analysis (TGA) and electrospray ionisation mass spectrometry (ESI-MS). These studies indicated a 1:2 M/L stoichiometry and suggested the isoflavones bind with the metals at the 4-keto and the 5-OH site. 2,2-diphenyl-1-picrylhydrazyl (DPPH) inhibition assays showed that copper isoflavone chelates have higher antioxidant activity than free isoflavones while the iron isoflavone chelates showed pro-oxidant activity compared to the free isoflavone. Synergi...Continue Reading

Citations

Jan 14, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdulkadhar Mohamed JalaludeenHyuk Song
Nov 11, 2011·Journal of Inorganic Biochemistry·Li-Jun TangXiao-Kun Li
Sep 17, 2013·Medicinal Research Reviews·Stalin SelvarajUma Maheswari Krishnan
Aug 15, 2015·Oxidative Medicine and Cellular Longevity·Jana KarlíčkováPřemysl Mladěnka
May 20, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yuanzhen Liu, Mingquan Guo
Oct 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jing YangLeif H Skibsted
May 4, 2011·Chembiochem : a European Journal of Chemical Biology·Alaina S DeTomaMi Hee Lim

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