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ISHS Acta Horticulturae 679: III WOCMAP Congress on Medicinal and Aromatic Plants - Volume 5: Quality, Efficacy, Safety, Processing and Trade in Medicinal and Aromatic Plants

EXTRACTION OF SOLASODINE FROM DRY FRUITS AND LEAVES OF SOLANUM LACINIATUM AIT. AND THE SYNTHESIS OF 16-DEHYDROPREGNENOLONE ACETATE FROM SOLASODINE BY PHASE-TRANSFER CATALYSIS

Authors:   J. Manosroi, A. Manosroi, P. Sripalakit
Keywords:   isolation, oxidizing agent, potassium dichromate, steroid precursor, tetrabutyl-ammonium hydrogen sulfate
Abstract:
A simple extraction and isolation process of solasodine, a natural precursor to synthesize steroidal drugs, from fruits and leaves of Solanum laciniatum Ait. was developed. The optimum concentration of 2-propanol for the extraction of crude glycosides was 70%. The suitable hydrolysis condition of solasodine from crude glycosides was by 1 N hydrochloric acid in 2-propanol. Pure solasodine from both fruits and leaves of Solanum laciniatum Ait. was obtained without any requirement of column chromatography. The yield of pure solasodine were 0.340.04% and 0.440.16% of the dry weight of fruits and leaves, respectively. The maximum yield of 37.0% of pure 16-DPA was obtained by using tetrabutylammonium hydrogen sulfate as a phase-transfer catalyst and potassium dichromate as an oxidizing agent. The results indicated the novel economic with environmental friendly method of solasodine extraction and synthesis of 16-dehydropregnenolone acetate from solasodine by phase-transfer catalysis.

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