Absolute structures of C-glucosides of resveratrol oligomers from Shorea uliginosa

被引：34

作者：

Ito, Tetsuro ^{[1
]}

Abe, Naohito ^{[1
]}

Oyama, Masayoshi ^{[1
]}

Iinuma, Munekazu ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Lab Pharmacognosy, Gifu 5028585, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 21期

关键词：

Absolute structure; C-Glucoside; epsilon-Viniferin; Enantiomeric aglycone; Diastereomeric aglycone; Shorea uliginosa; Dipterocarpaceae; SMALL-MOLECULE ACTIVATORS; STEM BARK; VATERIA-INDICA; PLANTS; OLIGOSTILBENES; CONFIGURATION; TETRAMER;

D O I：

10.1016/j.tetlet.2009.03.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two C-glucosides of resveratrol dimers (uliginoside A (1) and hemsleyanoloside B (2)) consisting of enantiomeric aglycones and two C-glucosides of resveratrol trimers (uliginosides B (3) and C (4)) consisting of diastereomeric aglycones were isolated from Shorea uliginosa (Dipterocarpaceae). These structures were elucidated by spectroscopic analysis including NMR experiments, and their absolute configurations were determined based on circular dichroism data. Resveratrol oligomers of C-glucosides with a 1,2-diaryldihydrobenzofuran ring are produced with specific biogenetic routes. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2516 / 2520

页数：5

共 17 条

[1] Diptoindonesin A, a new C-glucoside of ε-viniferin from Shorea seminis (Dipterocarpaceae) [J].

Aminah, NS ;

Achmad, SA ;

Aimi, N ;

Ghisalberti, EL ;

Hakim, EH ;

Kitajima, M ;

Syah, YM ;

Takayama, H .

FITOTERAPIA, 2002, 73 (06) :501-507

[2] Stilbene oligomers from Parthenocissus laetevirens:: Isolation, biomimetic synthesis, absolute configuration, and implication of antioxidative defense system in the plant [J].

He, Shan ;

Wu, Bin ;

Pan, Yuanjiang ;

Jiang, Liyan .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5233-5241

[3] Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan [J].

Howitz, KT ;

Bitterman, KJ ;

Cohen, HY ;

Lamming, DW ;

Lavu, S ;

Wood, JG ;

Zipkin, RE ;

Chung, P ;

Kisielewski, A ;

Zhang, LL ;

Scherer, B ;

Sinclair, DA .

NATURE, 2003, 425 (6954) :191-196

[4]

Hui M.G., 2006, Eur. J. Org. Chem, P5551

[5] Rotational isomerism of a resveratrol tetramer, shoreaketone, in Shorea uliginosa [J].

Ito, T ;

Furusawa, M ;

Iliya, I ;

Tanaka, T ;

Nakaya, K ;

Sawa, R ;

Kubota, Y ;

Takahashi, Y ;

Riswan, S ;

Iinuma, M .

TETRAHEDRON LETTERS, 2005, 46 (17) :3111-3114

[6] New resveratrol oligomers in the stem bark of Vatica pauciflora [J].

Ito, T ;

Tanaka, T ;

Iinuma, M ;

Iliya, I ;

Nakaya, K ;

Ali, Z ;

Takahashi, Y ;

Sawa, R ;

Shirataki, Y ;

Murata, J ;

Darnaedi, D .

TETRAHEDRON, 2003, 59 (28) :5347-5363

[7] Two new oligostilbenes with dihydrobenzofuran from the stem bark of Vateria indica [J].

Ito, T ;

Tanaka, T ;

Iinuma, M ;

Nakaya, K ;

Takahashi, Y ;

Sawa, R ;

Naganawa, H ;

Chelladurai, V .

TETRAHEDRON, 2003, 59 (08) :1255-1264

[8] Four new stilbenoid C-glucosides isolated from the stem bark of Shorea hemsleyana [J].

Ito, T ;

Tanaka, T ;

Ido, Y ;

Nakaya, K ;

Iinuma, M ;

Riswan, S .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (12) :1959-1963

[9] Oligostilbenoids from Dipterocarpaceaeous Plants: A New Resveratrol Tetramer from Vateria indica and the Revised Structure of Isohopeaphenol [J].

Ito, Tetsuro ;

Abe, Naohito ;

Oyama, Masayoshi ;

Iinuma, Munekazu .

HELVETICA CHIMICA ACTA, 2008, 91 (10) :1989-1998

[10] Cancer chemopreventive activity of resveratrol, a natural product derived from grapes [J].

Jang, MS ;

Cai, EN ;

Udeani, GO ;

Slowing, KV ;

Thomas, CF ;

Beecher, CWW ;

Fong, HHS ;

Farnsworth, NR ;

Kinghorn, AD ;

Mehta, RG ;

Moon, RC ;

Pezzuto, JM .

SCIENCE, 1997, 275 (5297) :218-220

← 1 2 →