Alkaloidal Glycosides from Solanum dulcamara. II. Three New Alkaloidal Glycosides and a Reassessment of Soladulcamaridine.

Abstract

Three new alkaloidal glycosides, named [alpha]-, [beta]- and gamma-solamarine, were isolated from S. dulcamara. The aglycone is [DELTA] 5-tomatidenol-(3[beta]) and the carbohydrate component of [alpha]-solamarine is formed from glucose (1 mole), galactose (1 mole) and rhamnose (1 mole), of [beta]-solamarine from glucose (1 mole) and rhamnose (2 moles), and of gamma-solamarine from glucose (1 mole) and rhamnose (1 mole). Furthermore, solasodine and yamogenin are isolated from the same plant. The previously reported soladulcamaridine is found to be inhomogeneous, separable on thin-layer chromatography into [DELTA] 5-tomatidenol-(3[beta]) in addition to traces of [DELTA] 3,5-tomatidiene and solasodine. The name, hence, should be discontinued.