lycorenine

Description

An alkaloid isolated from Lycoris radiata Herb. the base crystallizes from Me2CO in rhombic prisms and has [α]²⁰_D + 149.3°. The alkaloid yields crystalline salts and derivatives, e.g. the aurichloride decomposing at 116°C, platinichloride, also decomposing before melting at 210°C; picrate, m.p. 162°C (dec.); monoacetyl derivative, m.p. 185 _7°C. The diacetyl compound has been prepared although with some difficulty and under forcing conditions, m.p. 17 5-6°C. The alkaloid behaves as a pseudo-base giving an oxime hydrochloride which decomposes at 258°C. On catalytic hydrogenation it yields the dihydro-derivative, m.p. 175- 7°C and prolonged hydrogenation eventually forms deoxytetrahydrolycorenine, ClsH2S03N, m.p. 165-8°C although other compounds are also formed at the same time, e.g. C1sH27 0 2N, m.p. l65-7°C and ClsH2S03N, m.p. l20-3°C. The methiodide decomposes when heated at 260°C and on treatment with silver oxide forms two methine bases, of which the (±)-form has been isolated as the methiodide, m.p. 223°C (dec.). The complete structure has been determined primarily from the mass spectrum.

The Uses of lycorenine

Lycorenine is an antibacterial agent extracted from the bulb of Lycoris radiata.

Definition

ChEBI: Lycorenine is an alkaloid.

References

Kondo, Tomimura, Ishiwatari., J. Pharrn. Soc., Japan, 52, 51 (1932) Spectra: Inuka et aI., Tetrahedron Lett., 4745 (1966) Stereochemistry: Mizukami., Tetrahedron, 11,89 (1960)