Solasodine-Synonyms Solancarpidine; Solanidine-S; Purapuridine

A.1 Solasodine

Synonyms Solancarpidine; Solanidine-S; Purapuridine.

Biological Sources It is obtained from the fruits of Capsicum annuum L. (Solanaceae) (Chili, Paprika, Sweet Peppers); shoots and berries of S. dulcamara L. (Solanaceae) (Bittersweet, Bitter Nightshade, Felonwood); leaves of S. nigrum L. (Solanaceae) (Wonderberry, Black Nightshade, Prairie Huckleberry).

Chemical Structure

(3b, 22a, 25R)-Spirosol-5-en-3-ol; (C₂₇H₄₃NO₂).

Isolation It is obtained by the hydrolysis of solasonine which yields solasodine, L-rhamnose, Dgalactose and D-glucose respectively. It is the dehydrated product.

Characteristic Features

(i) It is obtained as hexagonal plates from methanol or by sublimation under high vacuum.

(ii) It has mp 200-202°C; [α]_D²⁵ -98^o [c = 0.14 in methanol); [α]_D –113° (CHCl₃); pKb 6.30.

(iii) It is freely soluble in benzene, pyridine, and chloroform; moderately soluble in ethanol, methanol, and acetone; slightly soluble in water and practically insoluble in ether.

Identification Tests (for Solanum Alkaloids)

1. Dissolve 5-10 mg of the alkaloid in a few drops of hot amyl alcohol or ethanol and allow it cool gradually. The appearance of jelly-like product gives the characteristic test of the solanum alkaloids.

2. When a few mg of the alkaloids is treated with antimony trichloride solution in dry chloroform, it gives rise to a distinct red colouration.

3. The solanum alkaloids, in general, produces an instant red-violet colour with formaldehyde (HCHO) and sulphuric acid (H₂SO₄). This particular test is so distinct and sensitive that it is used for the quantitative estimation of these alkaloids colorimetrically.

Uses It is invariably used as a starting material for steroidal drugs.

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* GGPP = Geranylgeranyl diphosphate
Source:Pharmacognosy And Pharmacobiotechnology By Ashutosh Kar