Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

Bioorg Med Chem Lett. 2005 Feb 15;15(4):873-6. doi: 10.1016/j.bmcl.2004.12.070.

Abstract

Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 microM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Arachidonic Acid / metabolism
  • Catechin / analogs & derivatives*
  • Catechin / metabolism
  • Catechin / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Humans
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Nitric Oxide / biosynthesis
  • Structure-Activity Relationship
  • Tea / chemistry

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • Lipopolysaccharides
  • Tea
  • Arachidonic Acid
  • Nitric Oxide
  • Catechin