Antioxidant activity and inhibition of α-glucosidase by trans-resveratrol, piceid, and a novel trans-stilbene from the roots of Israeli Rumex bucephalophorus L.

Zohar Kerem*, Itzhak Bilkis, Moshe A. Flaishman, Lior Sivan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

84 Scopus citations

Abstract

The roots of Rumex bucephalophorus, collected in Israel, were analyzed for trans-stilbenes. Two stilbene-O-glycosyl derivatives were identified, in addition to 3,5,4′-trihydroxystilbene (1) (resveratrol). The stilbene-O-glycosyl derivatives were 5,4′-dihydroxystilbene-3-O-β-D- glucopyranoside (2) (piceid) and the new 5,4′-dihydroxystilbene-3-O- α-arabinopyranoside (3), which is being named rumexoid. The structure of rumexoid was elucidated by using spectroscopic data. The antioxidant capacities of stilbenoids 1-3 were determined and expressed as trolox equivalent antioxidant capacity (TEAC). TEAC value for trans-resveratrol was highest (2.7) and for rumexoid lowest (1.5). In vitro, trans-resveratrol and rumexoid demonstrated a potent inhibitory effect on α-glucosidase activity (IC50 < 0.1 and < 0.5 mM, respectively). The commercial antidiabetic agent acarbose was shown to inhibit only 35% of the enzyme activity at 0.5 mM. The addition of piceid to the reaction mixture did not inhibit α-glucosidase in vitro in the range of concentrations used. These findings extend the range of reported beneficial effects of stilbene derivatives, and demonstrate the multifaceted activities that dietary polyphenols may exert in the intestine, where their concentrations are highest in the body.

Original languageAmerican English
Pages (from-to)1243-1247
Number of pages5
JournalJournal of Agricultural and Food Chemistry
Volume54
Issue number4
DOIs
StatePublished - 22 Feb 2006

Keywords

  • Antioxidants
  • Piceid
  • Rumex bucephalophorus L.
  • trans-resveratrol
  • trans-stilbene
  • α-glucosidase

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