Glycosidic alkaloids of Solanum persicum

Chemistry of Natural Compounds
1974.0

Abstract

Solanum persicum Willd was collected in July 1972 in the village of Makhmudkende, Nakhichevan ASSR. The air-dry mass of the leaves was extracted with 5% CH3COOH and the alkaloids were precipitated with 25% ammonia. The dry residue was extracted with methanol to obtain total crystalline glycoalkaloids (0.8%). TLC analysis showed the total glycoalkaloids contained two substances, which were separated to yield two compounds: (I) C45H73O15N (mp 276-278°C, [α]D²⁰ -58°) and (II) C45H73O15N (mp 301-303°C, [α]D²⁰ -97.2°). Acid hydrolysis revealed both had the same aglycone (solasodine). Carbohydrate fraction analysis showed substance (I) contained one mole each of D-glucose, D-galactose, and L-rhamnose, while substance (II) contained one mole of D-glucose and two moles of L-rhamnose. By comparing melting points and IR spectra with authentic materials, the two compounds were identified as solasenine and solamargine, respectively.

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