Description
This gly<:oalkaloid occurs in several species of Solanum including S. aviculare, S.
sodomeum, S. verbascifolium and S. xanthocarpum. The alkaloid crystallizes
from 80 per cent EtOH with 4.5 H20, m.p. 245-250°C (dec.), the anhydrous
form being obtained from absolute MeOH. It has [α]
25D - 68° (EtOH) and
yields the following salts: hydrochloride, m.p. 265°C; picrate, m.p. 199-201 °C;
picrolonate, m.p. 230-loC and the acetyl derivative, m.p. l35-8°C. On alkaline
hydrolysis, the alkaloid gives solasodine and one mole each of galactose, glucose
and rhamnose. The solution in concentrated H2S04 eventually gives a crimson
colour with a brown fluorescence.
Uses
α-Solasonine is a natural glycoalkaloid compound which has been shown to inhibit Gli-mediated transcritional activity.
Definition
ChEBI: Solasonine is an azaspiro compound, an oxaspiro compound and a steroid.
Purification Methods
Solasonine crystallises from aqueous 80% dioxane or MeOH in needles. [Bell & Briggs J Chem Soc 1 1942, Briggs et al. J Chem Soc 4645 1961, Briggs et al. J Chem Soc 2848 1963.] The picrate crystallises from 30% aqueous EtOH with m 197-198o(dec) [Briggs & Cambie J Chem Soc 1422 1958]. [Beilstein 27 III/IV 2006.]
References
Oddo et a/., Gazzetta, 35, 27 (1905)
Levi., J. Soc. Chem. Ind., 49, 395T (1930)
Briggs., Nature, 144, 247 (1939)
Briggs.,J. Chem. Soc., 3 (1942)
Briggs, Vining., ibid, 2809 (1953)
Hayes, Scaforth., ibid, 74S (1963)
