Synthesis of Procyanidin B1, B2, and B4 and Their Anti-Inflammatory Activity: The Effect of 4-Alkoxy Group of Catechin and/or Epicatechin Electrophiles for Condensation

Title:Synthesis of Procyanidin B1, B2, and B4 and Their Anti-Inflammatory Activity: The Effect of 4-Alkoxy Group of Catechin and/or Epicatechin Electrophiles for Condensation

Volume: 9 Issue: 4

Author(s): M. Katoh, Y. Oizumi, Y. Mohri, M. Hirota, H. Makabe

Affiliation:

Keywords: Anti-inflammatory, equimolar condensation, polyphenol, procyanidin, flavan-3-ol, oligomeric mixtures, nucleophile, ethoxyethoxy, dimeric product, epicatechin

Abstract: Procyanidin B1, B2, and B3 were synthesized based on a Yb(OTf)3 catalyzed equimolar condensation using methoxy and/or 4-(2”-ethoxyethoxy)drivatives as electrophiles. The anti-inflammatory effect of synthetic procyanidin B1, B2, and B4 on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. Procyanidin B1, B2, B 4 suppressed TPA-induced inflammation of mouse ears by 48%, 34%, and 29%, respectively, at a dose of 200 μg. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used antiinflammatory agent.

Cite this article as:

M. Katoh, Y. Oizumi, Y. Mohri, M. Hirota, H. Makabe , Synthesis of Procyanidin B1, B2, and B4 and Their Anti-Inflammatory Activity: The Effect of 4-Alkoxy Group of Catechin and/or Epicatechin Electrophiles for Condensation , Letters in Organic Chemistry 2012; 9 (4) . https://dx.doi.org/10.2174/157017812800233697