Verbesinosides A-F, 15,27-cyclooleanane saponins from the American native plant Verbesina virginica.
Verbesinosides A-F (1-6), six new 15,27-cyclooleanane-type triterpenoid saponins carrying different aromatic acyl moieties on the aglycon, were isolated from the leaves and flowers of Verbesina virginica. Their structures were established by interpretation of spectroscopic data and chemical methods. The representative major saponin, verbesinoside A (1), has the structure 21-trimethoxybenzoyl 15alpha,27-cycloolean-12-en-3beta,21beta-diol-28-oic acid 3-O-beta-D-xylopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->2)-beta-D-glucopyranoside. This is the first report of triterpenoid saponins possessing the unique 15,27-cyclooleanane skeleton. The anisotropic effects of the aromatic acyl moieties on the triterpenoid skeleton are discussed.
Xu
Wen-Hui
WH
National Center for Natural Products Research, Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
Jacob
Melissa R
MR
Agarwal
Ameeta K
AK
Clark
Alice M
AM
Liang
Zong-Suo
ZS
Li
Xing-Cong
XC
D035264:Flowers / Q000737:chemistry; D008923:Missouri; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification*; D018515:Plant Leaves / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D031208:Verbesina / Q000737:chemistry*
D012503:Saponins; C542047:verbesinoside A; D009828:Oleanolic Acid