Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetamides
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Carboxylic Acids / chemistry
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Chloroacetates*
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Disaccharides / chemical synthesis
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Disaccharides / metabolism
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Esters / chemistry
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Glycosides / chemical synthesis*
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Glycosides / pharmacology
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Glycosylation
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Hemolysis / drug effects*
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Oleanolic Acid / analogs & derivatives*
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Oleanolic Acid / chemical synthesis*
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Oleanolic Acid / pharmacology
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Saponins / chemistry
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Saponins / metabolism
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Structure-Activity Relationship
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Trichloroacetic Acid / chemistry
Substances
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Acetamides
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Carboxylic Acids
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Chloroacetates
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Disaccharides
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Esters
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Glycosides
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Saponins
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Trichloroacetic Acid
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Oleanolic Acid
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trichloroacetamide
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hederagenin