Glycoalkaloids and saponins of Solanum kieseritzkii

Chemistry of Natural Compounds
1970.0

Abstract

Solanum kieseritzkii C. Ao M. (family Solanaceae) is an endemic plant growing in the shady damp woods of the lower mountain zone of the Lenkoran-Astara region of the Azerbaidzhan SSR. Its chemical composition has not been studied before. This paper presents the results of isolating glycoalkaloids and saponins from the epigeal parts of this plant. The plant material, collected in the budding phase, was extracted with methanol. The extract was concentrated and defatted with benzene-ether (4:1). Glycoalkaloids were precipitated with ammonia, filtered, dried in vacuum at 40-50°C, extracted with methanol, and purified on a silica gel column (eluted with methanol-ammonia 3:1), with a yield of 0.41% (based on the weight of raw material). Five individual substances were isolated by silica gel column chromatography: I (mp 275-278°C, yield 0.084%, Rf 0.16), II (mp 300-302°C, yield 0.169%, Rf 0.44), III (mp 269-271°C, yield 0.062%, Rf 0.19), IV (mp 287-291°C, yield 0.042%, Rf 0.58), and V (mp 285-286°C, yield 0.0074%, Rf 0.22). Compounds I, II, and III were identified as solasonine, solamarginine, and tomatine, respectively, by comparing their melting points and IR spectra with authentic samples. Compounds IV and V yielded solasodine (mp 200-201°C) as the aglycone after acid hydrolysis. In addition, the epigeal part contained about 0.36% (of raw material weight) of ethanol-soluble saponins. Acid hydrolysis of the combined saponins gave 0.203% of aglycones, which consisted of four substances with Rf values 0.45, 0.66, 0.68, and 0.69 as shown by thin-layer chromatography (silica gel adsorbent, chloroform-ethyl acetate-benzene 65:35:5 solvent, 20% SbCl3 in chloroform as revealing agent).

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