8452. Seneciphylline

Nomenclature

CAS number: 480-81-9
13,19-Didehydro-12-hydroxysenecionan-11,16-dione; jacodine; α-longilobine.
C18H23NO5; mol wt 333.38.
C 64.85%, H 6.95%, N 4.20%, O 24.00%.

Description and references

Hepatotoxic pyrrolizidine alkaloid, common constituent of Senecio species. Isoln from Senecio platyphllus DC. Compositae: A. Orechoff, W. Tiedebel, Ber. 68, 650 (1935); from S. jacobaea L.: G. Barger, J. J. Blackie, J. Chem. Soc. 1937, 584; from Crotalaria juncea L. Leguminosae: R. Adams, M. Gianturco, J. Am. Chem. Soc. 78, 1919 (1956). Identity with α-longilobine: R. Adams, J. H. Looker, ibid. 73, 134 (1951). Identity with jacodine: R. B. Bradbury, C. C. J. Culvenor, Chem. Ind. (London) 1954, 1021. Structural study: R. Adams et al., J. Am. Chem. Soc. 74, 700 (1952). Revised structure: S. Masume, Chem. Ind. (London) 1959, 21. Review and evaluation of toxicity and carcinogenicity studies: IARC Monographs 10, 319-325, 333-342 (1976). Comprehensive reviews of seneciphylline and other pyrrolizidine alkaloids: L. Bull et al., The Pyrrolizidine Alkaloids (North-Holland, Amsterdam, 1968) 293 pp; F. L.Warren in The Alkaloids vol. 12, R. H. F. Manske, Ed. (Academic Press, New York, 1970) pp 245-331.

Chemical structure

Properties

Small rhombic platelets from hot alcohol or acetone, mp 217-218°. [α]D -128° (chloroform). Easily sol in chloroform, ethylene chloride; less sol in alc, acetone. Difficultly sol in ether, ligroin.