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For the first time the composition of the bufadienolide complex in URGINEA HESPERIA Webb & Berth. has been investigated. From an extract of lyophilized plants, thirteen bufadienolides were isolated. By means of FAB-MS, (1)H-NMR, and (13)C-NMR studies the compounds were structurally elucidated as scillarenin, scilliphaeosidin, scillarenin-3- O-alpha- L-rhamnoside, scilliphaeosidin-3- O-alpha- L-rhamnoside, gamabufotalin-3- O-alpha- L-rhamnoside, 11alpha-hydroxyscilliglaucosidin-3- O-alpha- L-rhamnoside, scillarenin-3- O-alpha- L-2',3'-diacetylrhamnosido-4'-beta- D-glucoside, scillarenin-3- O-alpha- L-rhamnosido-4'-beta- D-glucosido-3''-beta- D-glucoside, scillarenin-3- O-alpha- L-rhamnosido-4'-beta- D-glucosido-4''-beta- D-glucoside, scillarenin-3- O-alpha- L-2',3'-diacetylrhamnosido-4'-beta- D-glucosido-3''-beta- D-glucoside, scillarenin-3- O-alpha- L-2',3'-diacetylrhamnosido-4'-beta- D-glucosido-4''-beta- D-glucoside, scilliphaeosidin-3- O-alpha- L-rhamnosido-4'-beta- D-glucosido-3''-beta- D-glucoside, and scilliphaeosidin-3- O-alpha- L-rhamnosido-4'-beta- D-glucosido-4''-beta- D-glucoside.

From the leaves of Convallaria majalis L. eight glycosides of strophanthidin, cannogenol, sarmentogenin and 19-hydroxysarmentogenin, resp., were isolated and structurally elucidated as strophanthidin-3-O-6'-deoxy-beta-D-allosido-alpha-L-rhamnoside, strophanthidin-3-O-6'-deoxy-beta-D-allosido-alpha-L-arabinoside, strophanthidin-3-O-alpha-L-rhamnosido-2'-beta-D-glucoside, cannogenol-3-O-6'-deoxy-beta-D-allosido-beta-D-glucoside, cannogenol-3-O-6'-deoxy-beta-D-allosido-alpha-L-rhamnoside, 19-hydroxy-sarmentogenin-3-O-alpha-L-rhamnoside, sarmentogenin-3-O-6'-deoxy-beta-D-allosido-alpha-L-rhamnoside and sarmentogenin-3-O-6'-deoxy-beta-D-guloside, mainly by means of their H-NMR-spectra, by EI-MS and LD-MS. This is the first report of the occurrence of 19-hydroxy-sarmentogenin in nature. The presence of arabinosido-6-deoxyallose within the sugar chain of a cardiac glycoside was detected for the first time, as well. Including the new glycosides, a total of 38 cardenolides, derived from nine aglycones, have now been found in Convallaria majalis.

From leaves and bulbs of ORNITHOGALUM BOUCHEANUM (Kunth) Aschers. et Graebn. (Liliaceae), cardenolides were isolated by a combination of column and droplet counter-current chromatography. Their structure elucidation was performed mainly by means of (1)H-NMR, (13)C-NMR, EI-MS, and LD-MS studies as well as by acid and/or enzymatic hydrolysis of the glycosides followed by identification of genins and sugar moieties (TLC, GC). Eight cardenolides were identified as sarmentogenin-3- O-6'-deoxy-beta- D-allosido-beta- D-xylosido-alpha-L-rhamnoside, sarmentogenin-3- O-6'-deoxy-beta- D-allosido-beta- D-xylosido-beta- D-apioside, 15beta, 16alpha-dihydroxyuzarigenin-3- O-beta- D-digitoxosido-beta- D-xylosido-alpha- L-rhamnoside, sarmentogenin-3- O-beta- D-digitoxosido-beta- D-xylosido-beta- D-apioside, syriogenin-3- O-beta- D-digitoxosido-beta- D-xylosido-alpha- L-rhamnoside, sarmentogenin-3- O-alpha- L-rhamnosido-beta- D-apioside, uzarigenin-3- O-beta- D-digitoxosido-beta- D-xylosido-alpha- L-rhamnoside, and digitoxigenin-3- O-6'-deoxy-beta- D-allosido-beta- D-xyloside. This is the first report of the occurrence of 15beta, 16alpha-dihydroxyuzarigenin. The presence of three genins - syriogenin, uzarigenin, and digitoxigenin - in the genus ORNITHOGALUM is described for the first time. For cardenolides, not only the combination of three different monosaccharides in one glycoside is unusual, but, especially, the occurrence of apiose, which was not known for cardiac glycosides until now.