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

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

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 4 , 2012

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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.

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

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Article Details

VOLUME: 9
ISSUE: 4
Year: 2012
Page: [233 - 238]
Pages: 6
DOI: 10.2174/157017812800233697
Price: $65

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