Alkaloidal Glycosides from Solanum dulcamara. IV. The Constitution of beta- and gamma-Solamarine.

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Abstract
Acid hydrolysis of the alkaloidal glycoside [beta]-solamarine gives rise to one mole of [DELTA] 5-tomatidenol-[beta][beta]), one mole of D-glucose, and two moles of L-rhamnose. Permethylation of the glycoside followed by acid hydrolysis results in the isolation of 3,6-di-O-methyl-D-ghicose and 2,3,4-tri-O-methyl-L-rhamnose. Analyses of the molecular rotations of products of partial hydrolysis of [beta]-solamarine indicates the configuration of the glycosidic linkages. The other glycoside, gamma-solamarine, also has [DELTA] 5-tomatidenol-(30) as the aglycone, and the carbohydrate component is formed from one mole of D-glucose and one mole of [beta]-rhamnose. gamma-Solamarine is, together with a new glucoside, [DELTA] 5-tomatidenol-(3[beta])-D-glucoside, isolated as one of the products of partial hydrolysis of [beta] -solamarine. Paper chromatography and electrophoresis of permethylated, hydrolyzed gamma-solamarine identifies 2,3,4-tri-O-methyl-L-rhamnose and 2,3,6-tri-O-methyl-D-glucose. Hence the constitution of gamma-solamarine is considered to be R =C27H42NO[long dash].

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