QUININE

Description

This alkaloid from Solanum dulcamara forms colourless plates when crystallized from MeOH. It is laevorotatory with [α]_D - 50° (c 0.4, CHCI₃). The alkaloid forms the O,N-diformyl derivative which exists as two rotational isomers, the trans with m.p. 222-4°C; [α]²⁰_D - 21.2° (CHCI₃) and the cis isomer with m.p. 202-4°C; [α]²⁰_D - 69.6° (CHCI₃).

Uses

Soladulcidine is a steroidal glycoalkaloid extracted from tomato leaves and berries and can induce craniofacial malformations in hamsters.

Definition

ChEBI: Soladulcidine is an azaspiro compound, a steroid and an oxaspiro compound.

References

Schreiber., Planta Med., 6,93 (1958)
Alkemeyer, Sandor., Naturwiss., 46, 207 (1959)
Schreiber, Adam., Experientia, 17,13 (1961)
Schreiber, Adam., Annalen, 666, 155 (1963)
Synthesis:
Adam, Schreiber., Experientia, 21,471 (1965)
Adam, Schreiber., Tetrahedron, 22, 3591 (1966)
Absolute configuration:
Boll, von Philipsborn., Acta Chem. Scand., 19,1365 (1965)