Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity

Bioorg Med Chem Lett. 2012 Jan 15;22(2):793-6. doi: 10.1016/j.bmcl.2011.12.072. Epub 2011 Dec 21.

Abstract

Convenient enzymatic transformation of the phenylpropanoid caffeic acid (1) with polyphenol oxidase originating from pear afforded three new oxidized metabolites, caffeoxynic acid (2), caffeicinic acid (3), and isocaffeicinic acid (4), along with, 7,8-erythro-caffeicin (5) and phellinsin A (6). The structures of the three new caffeic acid oxidation products were elucidated on the basis of spectroscopic methods. The new products 2 and 3 exhibited significantly enhanced inhibitory activity against cyclooxygenase-2 (COX-2) when compared to parent caffeic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caffeic Acids / chemistry
  • Caffeic Acids / metabolism*
  • Caffeic Acids / pharmacology*
  • Cyclooxygenase 2 / metabolism*
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / pharmacology*
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Caffeic Acids
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase 2
  • caffeic acid