SENKIRKIN

Description

A further hepatotoxiC alkaloid present in Senecio kirkii Hook, S. renardi and Nardosrnia laevigata. The base has [α]²⁵_D - 16° (c 1.89, MeOH) or[α]¹⁵_D - 6.2° (c 1.91, CHCI₃). It forms colourless plates when crystallized from either Me₂CO or AcOEt and yields a picrate, m.p. 225.5-226°C and a picrolonate, m.p. 109- 110°C. The ultraviolet spectrum shows a single absorption maximum at 219 mp.. Several crystalline salts and derivatives are known, e.g. the aurichloride, m.p. 182.5-183.5°C; platinichloride, m.p. 196-7°C (dec.); bitartrate, m.p. 201°C; reineckate, m.p. 169-171°C; picrate, m.p. 225- 225.5°C; picrolonate, m.p. 138°C and the methiodide, m.p. 194-6°C (dec.). The O-acetate occurs naturally (q.v.) in Senecio kirkii.

The Uses of SENKIRKIN

Senkirkine is a hepatotoxic pyrrolizidine alkaloid. Studies show that Senkirkine has carincogenic activity as it induced chromosomal aberrations in cultured mammalian cells as well as hepatic tumors in rats.

Definition

ChEBI: Senkirkine is a macrolide.

Safety Profile

Poison by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Nox

References

Briggs, Mangan, Russell., J. Chern. Soc., 1891 (1948)
Massagetov, Kuzovkov.,J. Gen. Chern., USSR, 23, 158 (1953)
Danilova, Konovalova., ibid, 30, 1921 (1961)
Danilova, Koretskaya, Utkin., ibid, 31, 3815 (1961)
Wunderlich., Chern. Ind., 2089 (1962)
Briggs et al., J. Chern. Soc., 2492 (1965)