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Chemistry of Natural Compounds

, Volume 8, Issue 2, pp 184–190 | Cite as

Cardenolides of Strophanthus kombe. II

  • I. F. Makarevich
Article

Summary

The seeds ofStrophanthus kombe Oliv. have yielded 12 cardiac glycosides. Of them, six were identified with known cardenolides: S 1 - periplocymarin; S 2 - cymarin; S 4 -periplocin; S 5 - k-strophanthin-β; S 7 - erysimoside; S 8 - k-strophanthoside. The structure of k-strophanthoside as strophanthidin 3β-[O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranoside] has been confirmed.

This is apparently the first time that the other six glycosides have been isolated fromStrophanthus kombe in the pure state. Cardenolides S 9, S 11, and S 12 have strophanthotriose as the carbohydrate component, and their aglycones are, respectively, strophanthidol, strophanthidin-19-carboxylic acid, and 17βH-strophanthidin. These glycosides have been named in accordance with the structures established for them: k-strophanthol-γ (S 9), strophanthoside-19-carboxylic acid (S 12) and 17βH-strophanthoside (S 11). Cardenolide S 10, which has been called neoglucoerysimoside, is strophanthidin 3β-[O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-β-D-digitoxopyranoside]. From neoglucoerysimoside a new trisaccharide has been obtained which we have called gentiobiosyldigitoxose. The structure of the latter can be characterized as O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-D-digitoxose.

Keywords

Glycoside Paper Chromatography Cardenolide Gentiobiose Barium Carbonate 

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Copyright information

© Consultants Bureau 1974

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  • I. F. Makarevich

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