Verbesinosides A-F, 15,27-cyclooleanane saponins from the American native plant Verbesina virginica.
ABSTRACT 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.
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ABSTRACT: Phytochemical investigation of the chemical constituents of the roots of Actaea pachypoda afforded 12 9,19-cyclolanostane type triterpenoids, including the new 7,8-dihydroactaeaepoxide 3-O-beta-d-xylopyranoside (1), 12-deacetoxyactaeaepoxide 3-O-beta-d-xylopyranoside (2), and 12beta-acetoxycimigenol (3). Their structures were determined by spectroscopic and chemical methods.Journal of Natural Products 02/2007; 70(1):107-10. · 3.13 Impact Factor
Article: Sclerotiamide: a new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum.[show abstract] [hide abstract]
ABSTRACT: Sclerotiamide (1), a new fungal natural product related to the paraherquamides, was isolated by bioassay-guided fractionation of antiinsectan organic extracts from the sclerotia of Aspergillus sclerotiorum (NRRL 5167). The structure was determined primarily through 1H-NMR, 13C-NMR, HMQC, and HMBC experiments. Sclerotiamide causes significant mortality and unusual physiological effects in dietary assays against the corn earworm Helicoverpa zea.Journal of Natural Products 12/1996; 59(11):1093-5. · 3.13 Impact Factor