Elucidation of antioxidant properties of wood bark derived saturated diarylheptanoids: A comprehensive (DFT-supported) understanding

Jevgenija Ponomarenko, Patrick Trouillas, Nicolas Martin, Tatyana Dizhbite, Jelena Krasilnikova, Galina Telysheva

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

A series of diarylheptanoids, namely 1,7-bis-(3,4-dihydroxyphenyl)-heptan- 3-one-5-O-d-xylopyranoside (oregonin), 1,7-bis-(3,4-dihydroxyphenyl)-3- hydroxyheptane-5-O-β-d-xylopyranoside and 1,7-bis-(4-hydroxyphenyl)- heptane-3-one-5-O-β-d-glucopyranoside (platyphylloside), were isolated from the bark of alder family trees, a species widely spread over in Europe. As antioxidants, these natural polyphenols have a promising potential in various fields of application, but their redox reactivity is insufficiently characterized. In this work, their antioxidant activity is described using assays based on DPPH and ABTS+ radical scavenging, oxygen anion radicals (O2-) quenching. The standardized ORAC assay was also achieved, which measures the capacity to protect fluorescent molecules against oxidative degradation. The measured antioxidant activity was higher than that of the well-known antioxidant and biologically active diarylheptanoid curcumin. Molecular modeling was used to rationalize the differences in activity and the mechanisms of action. Thermodynamic descriptors mainly O-H bond dissociation enthalpies (BDEs) establish a clear structure-activity relationship.

Original languageEnglish
Pages (from-to)178-187
Number of pages10
JournalPhytochemistry
Volume103
DOIs
Publication statusPublished - Jul 2014

Keywords*

  • Antioxidants
  • Diarylheptanoids
  • DPPH
  • Electron transfer
  • Grey alder (Alnus incana) bark
  • Ionization potentials
  • Molecular modeling
  • O-H bond dissociation enthalpies
  • ORAC
  • Structure-activity relationship
  • Superoxide

Field of Science*

  • 1.6 Biological sciences

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database

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