Dihydrochalcones: Evaluation as novel radical scavenging antioxidants

Yoshimasa Nakamura, Shigeo Watanabe, Nobuyuki Miyake, Hiroyuki Kohno, Toshihiko Osawa

Research output: Contribution to journalArticle

144 Citations (Scopus)

Abstract

Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The 1H NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2′-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2′-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.

Original languageEnglish
Pages (from-to)3309-3312
Number of pages4
JournalJournal of agricultural and food chemistry
Volume51
Issue number11
DOIs
Publication statusPublished - May 21 2003
Externally publishedYes

Keywords

  • 1,1-diphenyl-2-picrylhydrazyl
  • Antioxidant
  • Dihydrochalcone
  • Erythrocyte
  • Flavanone
  • Lipid peroxidation

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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