[Synthesis and properties of digitoxigenin-3 beta-O-alpha-L-arabinofuranoside].
The synthesis of a cardenolide glycoside with a furanoide sugar component, digitoxigenin-3 beta-O-alpha-L-arabinofuranoside (4), is described for the first time. 4 was prepared by the reaction of digitoxigenin with 2,3,5-tri-O-benzoyl-alpha-L-arabinofuranosylchloride and Fétizon-reagent in benzene/dioxan followed by debenzoylation with ammonia in dry methanol. Compound 4 is cleaved by alpha-L-arabinofuranosidase (Aspergillus niger K1) into digitoxigenin and L-arabinose. Hydrolytic stability against methanolic HCl (0.1 mol/l) is relatively high. 4 X 10(-8) mol/l 4 gives a 50% inhibition of the Na,K-ATPase (pig heart muscle) and is 2.5 times more active at this receptor than the aglycon digitoxigenin.
D000818:Animals; D002301:Cardiac Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004073:Digitoxigenin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004355:Drug Stability; D006868:Hydrolysis; D009206:Myocardium / Q000201:enzymology; D000254:Sodium-Potassium-Exchanging ATPase / Q000037:antagonists & inhibitors*; D013552:Swine
D002301:Cardiac Glycosides; D004073:Digitoxigenin; C037190:digitoxigenin arabinoside; D000254:Sodium-Potassium-Exchanging ATPase
Synthese und Eigenschaften des Digitoxigenin-3 beta-O-alpha-L-arabinofuranosids.