Conjugation Length Dependence of Free Radical Scavenging Efficiency of Retinal and Retinylisoflavonoid Homologues

Research output: Contribution to journalJournal articleResearchpeer-review

  • Yang-Lin Jiang
  • Bai-Ling Chen
  • Xiao-Kun Yan
  • Yi Xu
  • Chen-Chen Zhao
  • Zi-Li Chen
  • Peng Wang
  • Jian-Ping Zhang
  • Skibsted, Leif Horsfelt

Retinal (C20) and the C25 and C30 homologues were compared as radical scavengers together with their C22, C27, and C32 homologues linked with daidzein through a B′3 (isoflavonoid) to oxo-carbon (aldehyde) covalent bond. Oxidation potential in acetonitrile determined by cyclic voltammetry and ionization potential calculated by density functional theory for the aldehydes and dyads (conjugates), of which the two longer are new, decreased linearly with the wavenumber for absorption maximum. The logarithm of the second-order rate constant for scavenging of the ABTS•+ increased linearly with decreasing oxidation potential suggesting that longer conjugation in the antioxidant increases the rate of electron transfer. A similar linear free energy relationship was found for the rate of scavenging DPPH•, including daidzein, which may indicate involvement of hydrogen atom transfer from an isoflavonoid phenol. Prediction of radical scavenging efficiency from visible absorption spectra was demonstrated with the perspective of rational design of bifunctional amphiphilic antioxidants.

Original languageEnglish
JournalACS Omega
Volume5
Issue number23
Pages (from-to)13770-13776
Number of pages7
ISSN2470-1343
DOIs
Publication statusPublished - 2020

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