Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.
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.
Barnes
Curtis C
CC
Department of Chemistry, University of Northern Iowa, Cedar Falls, Iowa 50614, USA.
Smalley
Mary K
MK
Manfredi
Kirk P
KP
Kindscher
Kelly
K
Loring
Hillary
H
Sheeley
Douglas M
DM
D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006868:Hydrolysis; D027741:Ipomoea / Q000737:chemistry*; D007615:Kansas; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012116:Resins, Plant / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000995:Antitubercular Agents; D006027:Glycosides; D012116:Resins, Plant; C482480:operculinic acid