title: Characterization of an anti-tuberculosis resin glycoside from the prairie medicinal plant Ipomoea leptophylla.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Northern Iowa, Cedar Falls, Iowa 50614, USA.
authors.forename: Curtis C
authors.initials: CC
authors.lastname: Barnes
authors.forename: Mary K
authors.initials: MK
authors.lastname: Smalley
authors.forename: Kirk P
authors.initials: KP
authors.lastname: Manfredi
authors.forename: Kelly
authors.initials: K
authors.lastname: Kindscher
authors.forename: Hillary
authors.initials: H
authors.lastname: Loring
authors.forename: Douglas M
authors.initials: DM
authors.lastname: Sheeley
mesh_terms: 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
chemical_list: D000995:Antitubercular Agents; D006027:Glycosides; D012116:Resins, Plant; C482480:operculinic acid