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Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes

Monatshefte fur Chemie (2016) 147(11) 1871-1881
DOI: 10.1007/s00706-016-1822-7
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Abstract

Four new metal complexes [Cu(ISO)2], [Cu(BUT)2] and [Zn(ISO)2], [Zn(BUT)2] of the polyhydroxychalcones (isoliquiritigenin and butein) are synthesized, structurally characterized and their antioxidant activity is investigated. The formation of the complexes [Cu(ISO)2] and [Zn(ISO)2] is followed by Job’s plot using NMR titration. The resulting compounds are characterized by mass spectrometry, IR spectroscopy, and elemental analysis. Studies on the radical scavenging activity are performed using DPPH as substrate. The results showed that the antioxidant activities of isoliquiritigenin and butein are enhanced after binding to copper or zinc. Graphical abstract: [Figure not available: see fulltext.]

Figures

  • Fig. 1 Proposed structure of a general M(II)–chalcone complex
  • Table 1 Comparison of protecting groups for synthesis of butein
  • Fig. 2 Job’s plot determined from the chemical shift changes of H-50 of isoliquiritigenin (9, ISO) with Cu(OAc)2 in methanol-d4. Summed concentration of isoliquiritigenin (9, ISO) and Cu(OAc)2 is 13 mM
  • Fig. 3 1H NMR titration of the Job’s plot of isoliquiritigenin (9, ISO) and Zn2? with increasing amount of Zn2? from the bottom to the top (methanol-d4). Colored indications highlight additional small signals attributed to H60, Hb, and Ha (color figure online)
  • Fig. 4 Electrospray ionization mass spectra of Cu2?/polyhydroxychalcones 1:2 system for [Cu(ISO)2] (a) in negative mode, [Cu(BUT)2] (b) in positive mode. The spectra a and b show the typical isotopic spectral pattern of the experimentally observed copper complexes Cu/L 1:2 in comparison with the corresponding
  • Table 2 The percentage of inhibition of the free DPPH radical in the presence of different Me-polyhydroxychalcone systems at 1.5 molar ratio (mol Me-polyhydroxychalcone/mol DPPH) for the studies with isoliquiritigenin (9, ISO) and the Me-isoliquiritigenin system and 0.75 molar ratio for the butein (10, BUT) and the Cu-butein system

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CITATION STYLE

APA

Sulpizio, C., Müller, S. T. R., Zhang, Q., Brecker, L., & Rompel, A. (2016). Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes. Monatshefte Fur Chemie, 147(11), 1871–1881. https://doi.org/10.1007/s00706-016-1822-7

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