[Synthesis and characterization of some cardenolide glucuronides and sulphates (author's transl)].
Cardenolide glucuronides are synthesized in the following way: firstly cardenolide glucosides are prepared by the reaction with acetobromglucose; secondly the hydroxymethyl group of the glucose moiety is oxydized in presence of a platinum catalyst to the carboxyl group of the final glucuronic acid. Glucuronides of the following cardenolides are prepared and described: digoxin, digoxigenin, digitoxin, digitoxigenin-monodigitoxoside, digitoxigenin, and 3-epi-digitoxigenin. Sulphates of digoxigenin, digitoxigenin, and 3-epi-digitoxigenin are prepared by direct reaction of these cardenolides with chlorosulphonic acid in pyridine. The assumed structure of some conjugates has been confirmed by n.m.r. spectroscopy. A high water solubility (6.7-65.1 g/l), a minute chloroform solubility (0.0002-0.0005 g/l), and a low octanol/polar nature of these compounds. Inotropic or toxic cardiac activities of the conjugates are examined on isolated guinea pig papillary muscles and by the Hatcher method on cats. Conjugates with at least one digitoxose show cardioactivities comparable to digoxin or digitoxin. In contrast to that the conjugated genins indicate decreased activities which are at least one-tenth of the potency of the unconjugated glycosides.
D000818:Animals; D002298:Cardenolides / Q000138:chemical synthesis* / Q000494:pharmacology; D002415:Cats; D004073:Digitoxigenin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D004074:Digitoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D004076:Digoxigenin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D004077:Digoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D005965:Glucuronates / Q000138:chemical synthesis; D006168:Guinea Pigs; D006321:Heart / Q000187:drug effects; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D012995:Solubility; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000138:chemical synthesis
D002298:Cardenolides; D005965:Glucuronates; D013431:Sulfates; D004073:Digitoxigenin; D004077:Digoxin; D004074:Digitoxin; D004076:Digoxigenin
Darstellung und Eigenschaften einiger Glukuronide und Sulfate von Cardenoliden und Cardenolid-glykosiden