(-)-SINOACUTINE

Description

A morphine type alkaloid isolated from Sinomenium acutum Rehd. and Wils, the base is laevorotatory with[α]¹⁶_D - 112° (EtOH) or - 81.60 (CHCI₃). It yields a series of crystalline salts and derivatives including the perchlorate, m.p. 117°C; tartrate, m.p. 203-4°C; picrate, m.p. 222°C (dec.); oxime, m.p. 223°C and the methiodide, m.p. 216°C. The alkaloid also forms the O-acetate, m.p. 175°C; [α]_D - 125° (EtOH) with AC₂0 in pyridine, indicative of a phenolic hydroxyl group. On hydrogenation it forms tetrahydrosinoacutinol, C₁₉H₂₇0₄N, m.p. 216°C. The O-methyl ether yields a crystalline methiodide which contains Me₂CO when obtained from this solvent, m.p. 163-6°C. According to Johns and his co-workers, the alkaloid is also present in Cassytha pubescens R. Br.

Uses

Sinoacutine is an isoquinoline alkaloid used as a prolyl oligopeptidase inhibitor.

References

Chu, Lo, Chou., Acta Chirn. Sinica., 30,265 (1964)
Barton, Korby, Kirby., Chern. Cornrnun., 52 (1965)
Chambers, Haynes, Stuart., ibid, 449 (1966)
Johns, Lamberton, Sioumis., Austral. J. Chern., 19,2331 (1966)
Circular dichroism:
Snatzke, Wollenberg.,l. Chern. Soc., C, 1681 (1966)