Demethoxycurcumin-Metal Complexes: Fragmentation and Comparison with Curcumin-Metal Complexes, as Studied by ESI-MS/MS

Author:

Ostrowski Wojciech1ORCID,Śniecikowska Lidia1,Hoffmann Marcin1,Frański Rafał1

Affiliation:

1. Adam Mickiewicz University, Faculty of Chemistry, Umultowska 89B, 61-614 Poznań, Poland

Abstract

Two questions are asked: the first is if the lack/presence of methoxyl moiety at aromatic ring essentially affects the stability of curcuminoid-metal complexes, and the second is if it is possible that in the metal complexes one of the possible demethoxycurcumin structures predominates. To answer the first question, the ESI-MS/MS spectra were taken of ions containing demethoxycurcumin, curcumin, and metal cation (e.g., ion [dCurc + Curc-H + Pb]+), and in order to answer the second question the ESI-MS/MS spectra were recorded of ions containing demethoxycurcumin and metal cation (e.g., ion [dCurc-H + Zn]+). An interpretation of the mass spectra has indicated that (i) for some metals, curcumin-metal complexes are more stable than demethoxycurcumin-metal complexes and for some metals vice versa, and (ii) in demethoxycurcumin-metal complexes structure B1 [(1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one] is more stable than structure B2 [(1E,4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one].

Funder

PL-Grid Infrastructure

Publisher

Hindawi Limited

Subject

Spectroscopy,Atomic and Molecular Physics, and Optics,Analytical Chemistry

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