Soluble polyphenols: synthesis and bioavailability of 3,4',5-tri(alpha-D-glucose-3-O-succinyl) resveratrol

Bioorg Med Chem Lett. 2009 Dec 1;19(23):6721-4. doi: 10.1016/j.bmcl.2009.09.114. Epub 2009 Oct 3.

Abstract

We report the development of a chemical modification method of general applicability to polyphenols, which increases solubility to influence absorption. Glucosyl groups were added to the resveratrol kernel via a succinate linker, yielding 3,4',5-tri-(alpha-D-glucose-3-O-succinyl) resveratrol. The construct was only slowly hydrolyzed in acid and at pH 6.8, but it was destroyed by blood esterases in less than 1h. In rats its administration resulted in a blood concentration versus time curve shifted to longer times in comparison to resveratrol, a useful modulation of pharmacokinetics. The area-under-curve parameter and the metabolite mix were similar to those of resveratrol. The method may be advantageously employed to solubilize other polyphenols and to make them more palatable.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Availability
  • Flavonoids / chemical synthesis*
  • Flavonoids / chemistry
  • Flavonoids / pharmacokinetics*
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glucosides / pharmacokinetics*
  • Molecular Structure
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Phenols / pharmacokinetics*
  • Polyphenols
  • Rats
  • Solubility
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry
  • Stilbenes / pharmacokinetics*
  • Time Factors

Substances

  • 3,4',5-tri(glucose-3-O-succinyl)resveratrol
  • Flavonoids
  • Glucosides
  • Phenols
  • Polyphenols
  • Stilbenes