SOLASONINE Chemical Properties

Melting point:

301-303℃

alpha 

D23 -88° (c = 1.01 in pyridine); D22 -74.5° (c = 0.51 in methanol)

Density 

1.42

solubility 

DMSO : 100 mg/mL (113.11 mM; Need ultrasonic)

form 

powder

pka

12.78±0.70(Predicted)

color 

White-beige

LogP

4.350 (est)

SOLASONINE Usage And Synthesis

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]²⁵_D - 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)

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