Caffeic acid oligomers with hyaluronidase inhibitory activity from Clinopodium gracile

Chem Pharm Bull (Tokyo). 2012;60(4):499-507. doi: 10.1248/cpb.60.499.

Abstract

Eight new caffeic acid oligomers, clinopodic acids J-Q (1-8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC(50) (19 µM) among the 22 compounds isolated from this plant.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caffeic Acids / chemistry*
  • Caffeic Acids / isolation & purification
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Hyaluronoglucosaminidase / antagonists & inhibitors*
  • Hyaluronoglucosaminidase / metabolism
  • Lamiaceae / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation

Substances

  • Caffeic Acids
  • Enzyme Inhibitors
  • Hyaluronoglucosaminidase
  • caffeic acid