Synthesis and hemolytic activity of some hederagenin diglycosides.
Glycosylation of hederagenin with the trichloroacetimidate derivatives of six commercial disaccharides (D-cellobiose, D-lactose, D-maltose, D-melibiose, D-gentiobiose, D-isomaltose) was performed giving the protected saponins in high yields. Deprotection then gave the saponins which were transformed into the corresponding methyl esters. The hemolytic activity of these synthetic hederagenin diglycosides was measured in order to establish structure-activity relationships based on the type and sequence of the attached sugar for the free carboxylic acid and methyl ester saponins.
Chwalek
Martin
M
CNRS FRE 2715 Isolement, Structure, Transformation et Synthèse de Substances Naturelles, Université de Reims Champagne-Ardenne, IFR 53 Biomolécules, CPCBAI, Reims, France.
Plé
Karen
K
Voutquenne-Nazabadioko
Laurence
L
D000081:Acetamides; D002264:Carboxylic Acids / Q000737:chemistry; D062845:Chloroacetates; D004187:Disaccharides / Q000138:chemical synthesis / Q000378:metabolism; D004952:Esters / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D006461:Hemolysis / Q000187:drug effects*; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D012503:Saponins / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D002264:Carboxylic Acids; D062845:Chloroacetates; D004187:Disaccharides; D004952:Esters; D006027:Glycosides; D012503:Saponins; D014238:Trichloroacetic Acid; D009828:Oleanolic Acid; C009528:trichloroacetamide; C025763:hederagenin