Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla

被引：40
作者：
Barnes, CC
Smalley, MK
Manfredi, KP [1 ]
Kindscher, K
Loring, H
Sheeley, DM
机构：
[1] Univ No Iowa, Dept Chem, Cedar Falls, IA 50614 USA
[2] NIH, NCRR, Bethesda, MD 20892 USA
[3] Univ Kansas, Kansas Biol Survey, Lawrence, KS 66047 USA
来源：
JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 11期
关键词：
D O I：
10.1021/np030197j
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
The organic soluble extract from the leaves of the native North American prairie plant Ipomoea leptophylla (big root morning glory) showed in vitro activity against M. tuberculosis. Bioassay-guided fractionation of this extract resulted in the identification of two new resin glycosides (6, 7). Base-catalyzed hydrolysis of these glycosides gave operculinic acid (1) as the glycosidic acid component as well as trans-cinnamic acid, propanoic acid, and lauric acid. The complete structure elucidation was accomplished through derivatization, 1D and 2D NMR spectroscopy (TOCSY, ROESY, HSQC, HMBC), and MS/MS experiments on 6 and 7 as well as the permethylated derivative 8.
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页码：1457 / 1462
页数：6
相关论文
共 22 条
[1]  
BUECHEL E, 1983, DICT TETON SIOUX LAK, P440
[2]   A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES [J].
CIUCANU, I ;
KEREK, F .
CARBOHYDRATE RESEARCH, 1984, 131 (02) :209-217
[3]  
Diaz J.L., 1976, USO PLANTAS MED MEXI, P329
[4]   CHARACTERIZATION, BY 2-DIMENSIONAL NMR-SPECTROSCOPY, OF A COMPLEX TETRASACCHARIDE GLYCOSIDE ISOLATED FROM IPOMOEA-STANS [J].
ENRIQUEZ, RG ;
LEON, I ;
PEREZ, F ;
WALLS, F ;
CARPENTER, KA ;
PUZZUOLI, FV ;
REYNOLDS, WF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (03) :1000-1008
[5]  
GERWIG GJ, 1997, CARBOHYD RES, V62, P1978
[6]  
GILMORE M, 1977, USES PLANTS INDIANS, P58
[7]  
Kindscher K., 1992, Medicinal wild plants of the prairie: An ethnobotanical guide
[8]  
KINDSCHER K, 1998, ETHNOBIOL, V18, P229
[9]  
MABBERLEY DJ, 1997, PLANT BOOK, P362
[10]  
MIRANDAPEREDA R, 1993, J NAT PRODUCTS, V56, P571
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