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

被引：11

作者：

Katoh, M. ^{[1
]}

Oizumi, Y. ^{[1
]}

Mohri, Y. ^{[1
]}

Hirota, M. ^{[2
]}

Makabe, H. ^{[1
]}

机构：

[1] Shinshu Univ, Grad Sch Agr, Nagano 3994598, Japan

[2] Shinshu Univ, Fac Agr, Dept Biosci & Biotechnol, Nagano 3994598, Japan

来源：

LETTERS IN ORGANIC CHEMISTRY | 2012年 / 9卷 / 04期

关键词：

Anti-inflammatory; equimolar condensation; polyphenol; procyanidin; OCCURRING O-HETEROCYCLES; OLIGOMERIC PROANTHOCYANIDINS; EQUIMOLAR CONDENSATION; EFFICIENT SYNTHESIS; INHIBITORS;

D O I：

10.2174/157017812800233697

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 mu g. Their activities are stronger than those of indomethacin and glycyrrhetinic acid, the normally used anti-inflammatory agent.

引用

收藏

页码：233 / 238

页数：6

相关论文

共 11 条

[1] Oligomeric proanthocyanidins: naturally occurring O-heterocycles [J].

Ferreira, D ;

Li, XC .

NATURAL PRODUCT REPORTS, 2000, 17 (02) :193-212

[2] Oligomeric proanthocyanidins: naturally occurring O-heterocycles [J].

Ferreira, D ;

Slade, D .

NATURAL PRODUCT REPORTS, 2002, 19 (05) :517-541

[3] THE MOUSE EAR EDEMA - A QUANTITATIVELY EVALUABLE ASSAY FOR TUMOR PROMOTING COMPOUNDS AND FOR INHIBITORS OF TUMOR PROMOTION [J].

GSCHWENDT, M ;

KITTSTEIN, W ;

FURSTENBERGER, G ;

MARKS, F .

CANCER LETTERS, 1984, 25 (02) :177-185

[4] Synthesis of (-)-Epicatechin 3-(3-O-Methylgailate) and (+)-Catechin 3-(3-O- Methylgallate), and Their Anti-Inflammatory Activity [J].

Iijima, Takashi ;

Mohri, Yoshihiro ;

Hattori, Yasunao ;

Kashima, Atsushi ;

Kamo, Tsunashi ;

Hirota, Mitsuru ;

Kiyota, Hiromasa ;

Makabe, Hidefumi .

CHEMISTRY & BIODIVERSITY, 2009, 6 (04) :520-526

[5]

KAWAMOTO H, 1991, MOKUZAI GAKKAISHI, V37, P488

[6] Structural analysis of catechin derivatives as mammalian DNA polymerase inhibitors [J].

Mizushina, Y ;

Saito, A ;

Tanaka, A ;

Nakajima, N ;

Kuriyama, I ;

Takemura, M ;

Takeuchi, T ;

Sugawara, F ;

Yoshida, H .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2005, 333 (01) :101-109

[7] An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin [J].

Mohri, Yoshihiro ;

Sagehashi, Masayoshi ;

Yamada, Taiji ;

Hattori, Yasunao ;

Morimura, Keiji ;

Kamo, Tsunashi ;

Hirota, Mitsuru ;

Makabe, Hidefumi .

TETRAHEDRON LETTERS, 2007, 48 (33) :5891-5894

[8] AN EFFICIENT SYNTHESIS OF PROCYANIDINS USING EQUIMOLAR CONDENSATION OF CATECHIN AND/OR EPICATECHIN CATALYZED BY YTTERBIUM TRIFLATE [J].

Mohri, Yoshihiro ;

Sagehashi, Masayoshi ;

Yamada, Taiji ;

Hattori, Yasunao ;

Morimura, Keiji ;

Hamauzu, Yasunori ;

Kamo, Tsunashi ;

Hirota, Mitsuru ;

Makabe, Hidefumi .

HETEROCYCLES, 2009, 79 :549-563

[9] 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 [J].

Oizumi, Yukiko ;

Mohri, Yoshihiro ;

Hirota, Mitsuru ;

Makabe, Hidefumi .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4884-4886

[10]

Saito A, 2003, HETEROCYCLES, V61, P287