Senecionine
Title: Senecionine
CAS Registry Number: 130-01-8
CAS Name: 12-Hydroxysenecionan-11,16-dione
Additional Names: aureine
Molecular Formula: C18H25NO5
Molecular Weight: 335.39
Percent Composition: C 64.46%, H 7.51%, N 4.18%, O 23.85%
Literature References: Hepatotoxic pyrrolizidine alkaloid from whole plant of Senecio vulgaris L., Compositae and several other Senecio spp. Isoln: Barger, Blackie, J. Chem. Soc. 1936, 743. Structure: Adams, Govindachari, J. Am. Chem. Soc. 71, 1953 (1949); Koekmoer, Warren, J. Chem. Soc. 1955, 63. Conformation: Culvenor, Tetrahedron Lett. 1966, 1091. Toxicity study: P. N. Harris et al., J. Pharmacol. Exp. Ther. 75, 69 (1942). Review of toxicology of senecionine and other pyrrolizidine alkaloids: E. K. McLean, Pharmacol. Rev. 22, 429-483 (1970). Comprehensive reviews of 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; D. J. Robins, Fortschr. Chem. Org. Naturst. 41, 115-203 (1982).
Properties: Bitter plates, mp 236°. [a]D25 -55.1° (c = 0.034 in chloroform). Practically insol in water. Freely sol in chloroform; slightly sol in alcohol, ether. LD50 i.v. in mice: 64.12 ±2.24 mg/kg (Harris).
Melting point: mp 236°
Optical Rotation: [a]D25 -55.1° (c = 0.034 in chloroform)
Toxicity data: LD50 i.v. in mice: 64.12 ±2.24 mg/kg (Harris)
 
Derivative Type: C15-trans Isomer
Additional Names: Integerrimine; squalidine; [15(20)E]-12-hydroxysenecionan-11,16,dione
Literature References: Isolated from several Senecio and Crotalaria spp.: L. Bull et al., loc. cit.; F. L. Warren, loc. cit. Identity of squalidine and integerrimine: A. G. Gonzalez, A. Calero, Chem. Ind. (London) 1958, 126.
Properties: mp 172-172.5°; [a]D28 +4.3° (c = 0.8 in methanol).
Melting point: mp 172-172.5°
Optical Rotation: [a]D28 +4.3° (c = 0.8 in methanol)

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