Concise Synthesis of Catechin Metabolites 5-(3',4'-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

Molecules. 2020 Apr 23;25(8):1970. doi: 10.3390/molecules25081970.

Abstract

A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(3',4'-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexenol. Noticeably, the different skin wrinkle-reducing activities of each metabolite were revealed via our unique syntheses of DHPVs in an enantiomerically pure form.

Keywords: catechin metabolite; concise synthesis; skin wrinkle-reducing activity; γ-valerolactone.

MeSH terms

  • Catechin / chemical synthesis*
  • Catechin / pharmacology*
  • Humans
  • Lactones / chemical synthesis*
  • Lactones / pharmacology*
  • Molecular Structure
  • Oxidation-Reduction
  • Skin / drug effects*
  • Skin Aging / drug effects

Substances

  • Lactones
  • Catechin
  • gamma-valerolactone