Description
A constituent of the leaves of Securinega suffructicosa Rehd., the base also occurs in Phyllanthus disco ides. It is obtained as yellow crystals and is strongly laevorotatory having [α]
20D - 1106°(CHC1
3), [α]
30D - 1106°(CHC1
3) and[α]
20D - 1042° (c 1.0, EtOH). The alkaloid yields a crystalline methiodide, m.p. 235-6°C.
Uses
Extracted from leaves and roots of Securinega suffruticosa Rehder. The most widely studied of these alkaloids, Securinine, is a specific GABA receptor antagonist and has been found to have significant in vivo CNS activity.
References
Murav'eva, Ban'kovskii., Dokl. Akad. Nauk, SSSR, 110,998 (1956)
Saito et al., Chem. & Ind., 1652 (1962)
Satoda et al., Tetrahedron Lett., 1199 (1962)
Mukherjee et al., Naturwiss., 50, 155 (1963)
Nakano et aI., Chem. & Ind., 1763 (1963)
Horii et al., ibid, 664 (1964)
Bevan et aI., ibid, 838 (1964)
Absolute configuration:
Bevan et al., Chern. Ind., 838 (1964)
Imadoetal., ibid, 1691 (1964)
Synthesis:
Horii et al., Tetrahedron, 23, 2265 (1967)
