LYCORINE (Narcissine)

Description

This alkaloid was first obtained from Narcissus pseudonarcissus L. and named Narcissine by Gerrard. Some twenty years later, a supposed new alkaloid was obtained by Morishima from Lycoris radiata Herb and designated Lycorine, the identity of the two bases being confirmed by Gorter. The alkaloid has subsequently been discovered in numerous Amaryllidaceous species including Amaryllis belladonna L., Clivia miniata Benth, Cooperia Drummondii Herb., C. peduncuiata, Crinum asiaticum L., C. gigantum Andr., C. pratense Herb., C. scabrum, Cyrtanthus pallidus Sims., Eucharis grandiflora Blanck, Eurycles sylvestris Salis b., Sprekelia [ormosissima Herb., Ungernia Sewertzovii Rgl., U. tadshicorum Uved., Zephyranthes rosea Lindl. and Z. texana. The alkaloid forms colourless prisms and has [α]²⁹_D~6 - 129° (EtOH). It is best purified as the crystalline hydrochloride monohydrate, m.p. 217°C (dry, dec.). The perchlorate, m.p. 230°C (dec.) and the picrate, m.p. 196°C have also been prepared. Lycorine contains a methylenedioxy group and two non-phenolic hydroxyl groups, yielding the 1-0-acetate, m.p. 2l5-6°C; [α]_D - 69° (hydrochloride, m.p. 266°C dec.) and the diacetate, m.p. 216°C; [α]_D + 31.5°. Oxidation with alkaline KMn04 furnishes hydrastic and oxalic acids. Catalytic hydrogenation yields the dihydro derivative, m.p. 247°C. Lycorine forms two methiodides, -a m.p. 247°C (dec.); [α]²⁹_D~O - 46.1 ° (H20) and -{3, m.p. 281°C (dry, dec.); [α]²⁹_D~O + 128° (H2 0). Either of these yields lycorineanhydromethine, m.p. 98.5°C on Hofmann degradation. The alkaloid is relatively non-toxic to mammals. When given by mouth or subcutaneously to the cat or dog in small doses it produces increased salivation while in large doses it causes vomiting and diarrhoea. The blood pressure does not seem to be affected and in lethal doses, death appears to be due to a generalized collapse. A post-mortem examination usually reveals hyperaemia and ecchymoses in the intestine and stomach, pulmonary pleura and endocardium.

References

Gerrard.,Pharm. J., 8,214 (1877) Morishima.,Arch. expo Path. Pharm., 40,221 (1897) Molle., Jarhesb. Pharm., 27 (1903) Ewins., J. Chem. Soc., 97, 2406 (1910) Gorter., Bull. Jard. Bot. Buit., 1,352 (1920) Kondo, Tomimura., J. Pharm. Soc., Japan, 52, 51 (1932) Oliveros, Santos., Univ. Philipp. Nat. Sci. Bull., 4,41 (1934) Norkina, Orekhov., Ber., 69,550 (1936) Tanaka.,J. Pharm. Soc., Japan, 57, 139 (1937) Reichert., Arch. Pharm., 226,328 (1938) Greathouse, Rigler., Amer. J. Bot., 28,702 (1941) Stereochemistry: Kotera et al., Tetrahedron Lett., 2009 (1966) Mass spectra: Kinstle, Wildman, Brown., Tetrahedron Lett., 4659 (1966) Nakagawa., ibid, 4745 (1966)