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.
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.
Oizumi
Yukiko
Y
Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University8304, Minami-minowa, Kami-ina, Nagano 399-4598, Japan.
Mohri
Yoshihiro
Y
Hirota
Mitsuru
M
Makabe
Hidefumi
H
D000438:Alcohols / Q000737:chemistry*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D044946:Biflavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D002392:Catechin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D008698:Mesylates / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology*; D059808:Polyphenols; D044945:Proanthocyanidins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D000438:Alcohols; D000893:Anti-Inflammatory Agents; D044946:Biflavonoids; D005419:Flavonoids; D008698:Mesylates; D009942:Organometallic Compounds; D010636:Phenols; D059808:Polyphenols; D044945:Proanthocyanidins; C059688:alkoxyl radical; C479581:procyanidin B3; C518808:ytterbium(III) triflate; D002392:Catechin