Description
This hepatotoxic alkaloid occurs in certain Senecio species and was first isolated
from S. isatideus D.C. It occurs abundantly in S. retrorsus D.C. and S. scleratus
Schw. The alkaloid crystallizes in rhombic prisms as the dihydrate and has [α]
27D . 8.25° (H 20). It is soluble in MeOH, hot EtOH and hot H20 but virtually insoluble in Et 20, Me2CO or CHCl 3. On reduction it absorbs 4 molecules of H2 to
give hexahydrodeoxyisatidine which melts at l15-l20°C and then remelts at
l83-4°C following an intermediate solidification. This compound gives a hydrochloride, m.p. 218°C (dec.); [α]
20D - 52.5° (H20) and may be hydrolyzed with
Ba(OHh to give a basic product, tetrahydroisatinecine, CSH1703N, m.p.
l74.5°C; [α]
20D - 88° (H 20). The alkaloid itself, on hydrolysis with Ba(OHh
yields isatinecine and two acid products, isatinecic acid and the monolactone,
the latter almost certainly being formed by the action of the base upon the acid.
Uses
Retrorsine N-oxide-D4 is a labelled analogue of Retrorsine N-oxide (R279005). Retrorsine N-oxide is a pyrrolizidine alkaloid that is naturally found in Senecio isatideus, a flowering plant that is native to the Netherlands. Retrorsine N-oxide is also known to raise blood pressure and can induce abnormal changes in the liver if ingested by animals or humans.
Definition
ChEBI: Isatidine is a citraconoyl group.
Safety Profile
Poison by ingestion and intraperitoneal routes. Moderately toxic by intravenous route. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NO,. See also ESTERS.
References
Blackie., Pharrn. J., 138, 102 (1937)
de Waal., Onderstepoort J., 12, 155 (1939)
de Waal., Nature, 146, 777 (1940)
de Waal., Pretorius., OnderstepoortJ., 17,181 (1941)
Leisegang, Warren., J. Chern. Soc., 702 (1950)
