Synthesis of procyanidin B3 and its anti-inflammatory activity. the effect of 4-alkoxy group of catechin electrophile in the Yb(OTf)(3)-catalyzed condensation with catechin nucleophile.

Abstract

Yb(OTf)(3)-catalyzed equimolar condensation of the benzylated catechin with various 4-alkoxy catechin derivatives was studied. In particular, the reaction using 4-(2''-ethoxyethoxy)flavan derivative gave good yield with excellent stereoselectivity. The condensed product was successfully converted to procyanidin B3 (1). The anti-inflammatory effect of procyanidin B3 (1) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears was examined. The anti-inflammatory activity of 1 was stronger than that of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agents.

• Authors: Yukiko Oizumi, Yoshihiro Mohri, Mitsuru Hirota, Hidefumi Makabe
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 75 Issue 14 Pg. 4884-6 (Jul 16 2010) ISSN: 1520-6904 [Electronic] United States
• PMID: 20568787 (Publication Type: Journal Article)

Chemical References

• Alcohols
• Anti-Inflammatory Agents
• Biflavonoids
• Flavonoids
• Mesylates
• Organometallic Compounds
• Phenols
• Polyphenols
• Proanthocyanidins
• alkoxyl radical
• procyanidin B3
• ytterbium(III) triflate
• Catechin

Topics

• Alcohols (chemistry)
• Animals
• Anti-Inflammatory Agents (chemical synthesis, chemistry, pharmacology)
• Biflavonoids (chemical synthesis, chemistry, pharmacology)
• Catalysis
• Catechin (chemical synthesis, chemistry, pharmacology)
• Flavonoids (chemistry, pharmacology)
• Mesylates (chemistry)
• Mice
• Molecular Structure
• Organometallic Compounds (chemistry)
• Phenols (chemistry, pharmacology)
• Polyphenols
• Proanthocyanidins (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism