Steroidal saponins from the fruits of Solanum torvum

被引:11
作者
Colmenares, Alida Perez [1 ,2 ]
Rojas, Luis B. [2 ]
Mitaine-Offer, Anne-Claire [1 ]
Pouysegu, Laurent [3 ,4 ]
Quideau, Stephane [3 ,4 ]
Miyamoto, Tomofumi [5 ]
Tanaka, Chiaki [5 ]
Paululat, Thomas [6 ]
Usubillaga, Alfredo [2 ]
Lacaille-Dubois, Marie-Aleth [1 ]
机构
[1] Univ Bourgogne, Fac Pharm, Lab Pharmacognosie, EA FDE UFC 4267, F-21079 Dijon, France
[2] Univ Los Andes, Res Inst, Fac Pharm & Bioanal, Merida 5101, Venezuela
[3] Univ Bordeaux, Inst Mol Sci, CNRS UMR 5255, F-33607 Pessac, France
[4] Univ Bordeaux, Inst Europeen Chim & Biol, F-33607 Pessac, France
[5] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan
[6] Univ Siegen, Nat Wissensch Tech Fak, D-57076 Siegen, Germany
关键词
Solanum torvum; Solanaceae; Steroidal saponins; Furostane-type; Spirostane-type; GLYCOSIDES; SAPOGENINS; LEAVES;
D O I
10.1016/j.phytochem.2012.10.010
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Seven steroidal glycosides have been isolated from the fruits of Solanum torvum Swartz. Their structures were established by 2D NMR spectroscopic techniques (H-1,H-1-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as (25S)-26-(beta-D-glucopyranosyloxy)-3-oxo-5 alpha-furost-20 (22)-en-6 alpha-yl-O-beta-D-xylopyranoside (1), (25S)-26-(beta-D-glucopyranosyloxy)-3-oxo-22 alpha-methoxy-5 alpha-furostan-6 alpha-yl-O-beta-D-xylopyranoside (2), (25S)-26-(beta-D-glucopyranosyloxy)-3 beta-hydroxy-22 alpha-methoxy-5 alpha-furostan-6 alpha-yl-O-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-glucopyranoside (3), (25S)-3 beta-hydroxy-5 alpha-spirostan-6 alpha-yl-O-beta-D-xylopyranoside (4), (25S)-3-oxo-5 alpha-spirostan-6 alpha-yl-O-beta-D-xylopyranoside (5), (25S)-3 beta-hydroxy-5 alpha-spirostan-6 alpha-yl-O-beta-D-glucopyranoside (6), (25S)-3 beta,27-dihydroxy-5 alpha-spirostan-6 alpha-yl-O-beta-D-glucopyranoside (7). (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:137 / 143
页数:7
相关论文
共 24 条
[1]   Furostane-Type Steroidal Saponins from the Roots of Chlorophytum borivilianum [J].
Acharya, Debabrata ;
Mitaine-Offer, Anne-Claire ;
Kaushik, Nutan ;
Miyamoto, Tomofumi ;
Paululat, Thomas ;
Lacaille-Dubois, Marie-Aleth .
HELVETICA CHIMICA ACTA, 2008, 91 (12) :2262-2269
[2]   Assigning stereodiversity of the 27-Me group of furostane-type steroidal saponins via NMR chemical shifts [J].
Agrawal, PK .
STEROIDS, 2005, 70 (10) :715-724
[3]   25R/25S stereochemistry of spirostane-type steroidal sapogenins and steroidal saponins via chemical shift of geminal protons of ring-F [J].
Agrawal, PK .
MAGNETIC RESONANCE IN CHEMISTRY, 2003, 41 (11) :965-968
[4]  
AGRAWAL PK, 1989, HETEROCYCLES, V29, P1895
[5]   Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum [J].
Arthan, D ;
Svasti, J ;
Kittakoop, P ;
Pittayakhachonwut, D ;
Tanticharoen, M ;
Thebtaranonth, Y .
PHYTOCHEMISTRY, 2002, 59 (04) :459-463
[6]   Structure-activity relationships for Saponins from Allium hirtifolium and Allium elburzense and their antispasmodic activity [J].
Barile, E ;
Capasso, R ;
Izzo, AA ;
Lanzotti, V ;
Sajjadi, SE ;
Zolfaghari, B .
PLANTA MEDICA, 2005, 71 (11) :1010-1018
[7]  
CHAKRAVARTY AK, 1979, PHYTOCHEMISTRY, V18, P902, DOI 10.1016/0031-9422(79)80049-7
[8]  
Colmenares AP, 2010, NAT PROD COMMUN, V5, P1743
[9]   Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships [J].
González, M ;
Zamilpa, A ;
Marquina, S ;
Navarro, V ;
Alvarez, L .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (06) :938-941
[10]  
HARA S, 1987, CHEM PHARM BULL, V35, P501