Antioxidant properties of 4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid (8-8-diferulic acid, non-cyclic form)

M. T. Garcia-Conesa, David P Wilson, G. W. Plumb, J. Ralph, G. Williamson

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Abstract

8-8-Diferulic acid (non-cyclic form) (4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid) was chemically synthesised and the antioxidant properties were assessed using (a) inhibition of ascorbate/iron-induced peroxidation of phosphatidylcholine liposomes, and (b) scavenging of the radical cation of ABTS (2,2'-azinobis (3-ethyl-benzothiazoline-6-sulphonate)) relative to the water-soluble vitamin E analogue, Trolox C. The structure of the chemically synthesised 8-8 dimer was confirmed by 1H-NMR and mass spectrometry. Its absorption properties in ethanol were: λ(max1): 320nm; λ(max2): 287nm; λ(min): 256nm; ε(λmax1) (M-1cm-1): 14200±1700 and ε(λmax2) (M-1cm-1): 14300 ± 1300. The 8-8 dimer showed the best antioxidant properties in the aqueous phase assay among the esterified dimers present in plant cell walls. Like the other ferulic dimers, 8-8-diferulic acid is a better inhibitor of lipid peroxidation than ferulic acid on a molar basis. Some of the factors possibly involved in the antioxidant effect of these compounds are: number of free hydroxyl groups in the molecule, stability of transient radical and partition coefficient.

Original languageEnglish
Pages (from-to)379-384
Number of pages6
JournalJournal of the Science of Food and Agriculture
Volume79
Issue number3
DOIs
Publication statusPublished - 1 Jan 1999
Externally publishedYes

Keywords

  • 8-8-diferulic acid
  • Antioxidant capacity
  • Diferulic acids
  • Ferulic acid

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