25R/25S stereochemistry of spirostane-type steroidal sapogenins and steroidal saponins via chemical shift of geminal protons of ring-F

被引:73
作者
Agrawal, PK [1 ]
机构
[1] Cent Inst Med & Aromat Plants, Lucknow 226016, Uttar Pradesh, India
关键词
NMR; H-1; steroidal sapogenins; steroidal saponins; stereochemistry; ring-F;
D O I
10.1002/mrc.1278
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method based on the differences among the H-1 NMR chemical shifts of geminal protons of ring-F methylene resonances (H-2-23, H-2-24 and H-2-26) is proposed for ascertaining the 25R/25S stereochemistry of ring-F unsubstituted spirostane-type steroidal sapogenins and steroidal saponins. Copyright (C) 2003 John Wiley Sons, Ltd.
引用
收藏
页码:965 / 968
页数:4
相关论文
共 35 条
[1]  
Agrawal PK, 1997, MAGN RESON CHEM, V35, P441, DOI 10.1002/(SICI)1097-458X(199707)35:7<441::AID-OMR104>3.0.CO
[2]  
2-Q
[3]  
Agrawal PK, 1996, ADV EXP MED BIOL, V405, P299
[4]   Dependence of the 1H NMR chemical shifts of ring F resonances on the orientation of the 27-methyl group of spirostane-type steroidal sapogenins [J].
Agrawal, PK ;
Bunsawansong, P ;
Morris, GA .
PHYTOCHEMISTRY, 1998, 47 (02) :255-257
[5]   NMR spectroscopy of steroidal sapogenins and steroidal saponins: An update [J].
Agrawal, PK ;
Jain, DC ;
Pathak, AK .
MAGNETIC RESONANCE IN CHEMISTRY, 1995, 33 (12) :923-953
[6]   C-13 NMR SPECTRAL INVESTIGATIONS .10. C-13 NMR-SPECTROSCOPY OF STEROIDAL SAPOGENINS AND STEROIDAL SAPONINS [J].
AGRAWAL, PK ;
JAIN, DC ;
GUPTA, RK ;
THAKUR, RS .
PHYTOCHEMISTRY, 1985, 24 (11) :2479-2496
[7]   A TIGOGENIN PENTASACCHARIDE FROM CESTRUM-DIURNUM [J].
AHMAD, VU ;
BAQAI, FT ;
AHMAD, R .
PHYTOCHEMISTRY, 1993, 34 (02) :511-515
[8]  
BRANKE JT, 1995, LIEBIGS ANN, P587
[9]   Porrigenins A and B, novel cytotoxic and antiproliferative sapogenins isolated from Allium porrum [J].
Carotenuto, A ;
Fattorusso, E ;
Lanzotti, V ;
Magno, S ;
DeFeo, V ;
Carnuccio, R ;
DAcquisto, F .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (10) :1003-1007
[10]  
CAROTENUTO A, 2002, PHYTOCHEMISTRY, V65, P1815