Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

被引：23

作者：

Fujii, Wataru ^{[2
]}

Toda, Kazuya ^{[1
]}

Kawaguchi, Koichiro ^{[1
]}

Kawahara, Sei-ichi ^{[3
]}

Katoh, Miyuki ^{[2
]}

Hattori, Yasunao ^{[4
]}

Fujii, Hiroshi ^{[1
]}

Makabe, Hidefumi ^{[2
]}

机构：

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

[2] Shinshu Univ, Grad Sch Agr, Sci Funct Foods, Nagano 3994598, Japan

[3] St Cousair Co Ltd, Nagano 3891201, Japan

[4] Kyoto Pharmaceut Univ, Dept Med Chem, Yamashina Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON | 2013年 / 69卷 / 17期

关键词：

Polyphenols; Synthesis; Natural product; Anticancer agents; EFFICIENT STEREOSELECTIVE-SYNTHESIS; MEDIATED EQUIMOLAR CONDENSATION; POLYMERASE INHIBITORY-ACTIVITY; RADICAL SCAVENGING ACTIVITY; OCCURRING O-HETEROCYCLES; OLIGOMERIC PROANTHOCYANIDINS; POLYPHENOL CHEMISTRY; SYSTEMATIC SYNTHESIS; MAILLARD REACTION; INTERFLAVAN BOND;

D O I：

10.1016/j.tet.2013.02.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3543 / 3550

页数：8

共 37 条

[1] Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation [J].

Alharthy, Rima D. ;

Hayes, Christopher J. .

TETRAHEDRON LETTERS, 2010, 51 (08) :1193-1195

[2] Major DNA fragmentation is a late event in apoptosis [J].

Collins, JA ;

Schandl, CA ;

Young, KK ;

Vesely, J ;

Willingham, MC .

JOURNAL OF HISTOCHEMISTRY & CYTOCHEMISTRY, 1997, 45 (07) :923-934

[3] DIRECT SYNTHESIS OF THE BARLEY PROANTHOCYANIDINS PRODELPHINIDIN-B3, PRODELPHINIDIN-C2 AND 2 TRIMERIC PROANTHOCYANIDINS WITH A MIXED PRODELPHINIDIN-PROCYANIDIN STEREOCHEMISTRY [J].

DELCOUR, JA ;

VERCRUYSSE, SAR .

JOURNAL OF THE INSTITUTE OF BREWING, 1986, 92 (03) :244-249

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

Ferreira, D ;

Li, XC .

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

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

Ferreira, D ;

Slade, D .

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

[6] Towards the Synthesis of Proanthocyanidins: Half a Century of Innovation [J].

Ferreira, Daneel ;

Coleman, Christina M. .

PLANTA MEDICA, 2011, 77 (11) :1071-1085

[7] Cell death inhibition: Keeping caspases in check [J].

Goyal, L .

CELL, 2001, 104 (06) :805-808

[8]

Kandasamy K, 2003, CANCER RES, V63, P1712

[9] 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 [J].

Katoh, M. ;

Oizumi, Y. ;

Mohri, Y. ;

Hirota, M. ;

Makabe, H. .

LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (04) :233-238

[10] Studies in polyphenol chemistry and bioactivity.: 4.: Synthesis of trimeric, tetrameric, pentameric, and higher oligomeric epicatechin-derived procyanidins having all-4β,8-interflavan connectivity and their inhibition of cancer cell growth through cell cycle arrest [J].

Kozikowski, AP ;

Tückmantel, W ;

Böttcher, G ;

Romanczyk, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1641-1658

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