Metal chelation by a plant lignan, secoisolariciresinol diglucoside

Flavia Fucassi, Adam Heikal, Lyuba I. Mikhalovska, Guy Standen, Iain U. Allan, Sergey V. Mikhalovsky, Peter J. Cragg

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Secoisolariciresinol diglucoside (SDG) is a polyphenolic phytoestrogen which is particularly abundant in flaxseed. As a diphenolic compound, SDG is expected to function as a metal chelating ligand. The affinity of SDG for metal cations was determined using a mass spectrometric approach. Experiments yielded equilibrium constants in aqueous solution for SDGCa2+, SDGCu2+, SDGPb2+, SDGNi2+, SDGFe2+ and SDG Ag+ of 20.34, 5.99, 4.26, 2.77, 2.46 and 1.90, respectively. These values are consistent with those determined for plant phenolics. Semiempirical calculations for the SDG metal complexes yield an insight into their likely structures.

Original languageEnglish
Pages (from-to)345-351
Number of pages7
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume80
Issue number3-4
DOIs
Publication statusPublished - Dec 2014

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Keywords

  • Mass spectrometry
  • Metal chelation
  • Secoisolariciresinol diglucoside
  • Semiempirical model

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Fucassi, F., Heikal, A., Mikhalovska, L. I., Standen, G., Allan, I. U., Mikhalovsky, S. V., & Cragg, P. J. (2014). Metal chelation by a plant lignan, secoisolariciresinol diglucoside. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 80(3-4), 345-351. https://doi.org/10.1007/s10847-014-0411-9