Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/22/2009
Publication Date: 6/1/2009
Citation: Xu, W., Jacob, M.R., Agarwal, A.K., Clark, A.M., Liang, Z., Li, X. 2009. Verbesinosides A-F, Novel 15,27-Cyclooleanane Saponins from the American Native Plant Verbesina virginica . Journal of Natural Products. 72:1022-1027. Interpretive Summary: This manuscript describes the isolation and structure elucidation of six novel triperpenoid saponins from a native American plant, Verbesina virginica.
Technical Abstract: Verbesinosides A-F (1-6), six novel 15,27-cyclooleanane-type triterpenoid saponins carrying different aromatic acyl moieties on the aglycone, were isolated from the leaf and flower of Verbesina virginica. Their structures were established by interpretation of spectroscopic data and chemical methods. The representative major saponin, verbesinoside A, has a structure of 21-trimethoxybenzoyl 15a,27-cycloolean-12-en-3B,21B-diol-28-oic acid 3-O-B-D-xylopyranosyl(1-4)-B-D-xylopyranosyl-(1-2)-B-D-glucopyranoside. This is the first time triterpenoid saponins possessing a unique 15,27-cyclooleanane skeleton have been isolated in nature. The anisotropic effects of the aromatic acyl moieties on the triterpenoid skeleton are also noted.