Characterization of an Anti-tuberculosis Resin Glycoside from the Prairie Medicinal PlantIpomoealeptophylla

Curtis C. Barnes, Mary K. Smalley, Kirk P. Manfredi, Kelly Kindscher, Hillary Loring, Douglas M. Sheeley
2003 Journal of natural products  
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
more » ... tructure 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.
doi:10.1021/np030197j pmid:14640518 fatcat:qmuwsw3wvzf75aebizrzfmraci