SOLANIDINE-T

Description

This alkaloid occurs in Solanum tuberosum (potato) and is also the hydrolytic product of solanine (q.v.). It crystallizes from EtOH in colourless needles and has [α]²⁷_D - 28.5° (EtOH) or - 27° (CHCI3). The hydrochloride forms rhombic prisms, m.p. 345°C (dec.); the platinichloride is amorphous; the methiodide has m.p. 280°C (dec.); the O-acetate, m.p. 204-8°C and the p-toluenesulphonyl derivative, m.p. l6l-2°C. When the hydrochloride is heated, a molecule of H20 is eliminated with the formation of solanidene, C27H41N, m.p. 167°C. According to Bergel and Wagner, this compound is identical with solanthrine, m.p. 170°C; [α] ^b_{7 - 92.3° (CHCI3) isolated from potato shoots. On selenium dehydrogenation, the alkaloid gives a mixture of chrysene, pyridine and phenanthrene together with other products. The products formed on reduction of the base have been extensively investigated with the result that all four stereoisomeric dihydro derivatives and the two corresponding solanidanes have been prepared, emphasizing the similarity between solanidine-T and cholesterol.}

References

Firbas., Monatsh., 10,541 (1889)
Schopf, Herrmann., Ber., 66, 298 (1933)
Oddo, Caronna., ibid, 67,451 (1934)
Heiduschka, Philippi., ibid, 68, 669 (1935)
Dieterle, Rochelmeyer., Arch. Pharm., 273, 532 (1935)
Soltys, Wallenfels., Ber., 69,811 (1936)
Clemo, Morgan, Raper.,l. Chem. Soc., 1299 (1936)
Prelog, Szpilfogel., Helv. Chim. Acta, 27, 390 (1944)
Uhle, Jacobs., J. Bioi. Chem., 160,243 (1945
)Hohne et al., Tetrahedron, 22,673 (1966)
Kessar et al., Tetrahedron Lett., 1547 (1968)