The Characterization and Structure−Activity Evaluation of Toxic Norditerpenoid Alkaloids from Two Delphinium Species

A new N-(methylsuccinimido)anthranoyllycoctonine norditerpenoid alkaloid, geyerline, has been isolated and characterized from extracts of the poisonous larkspur Delphinium glaucum. A previously described norditerpenoid alkaloid, grandiflorine, has also been isolated from Delphinium geyeri. Both alka...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-09, Vol.61 (9), p.1086-1089
Main Authors: Manners, Gary D, Panter, Kip E, Pfister, James A, Ralphs, Michael H, James, Lynn F
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - toxicity
Animals
Biological and medical sciences
Chromatography, High Pressure Liquid
Diterpenes - chemistry
Diterpenes - toxicity
Lethal Dose 50
Magnetic Resonance Spectroscopy
Male
Medical sciences
Mice
Plant poisons toxicology
Plants, Toxic - chemistry
Spectrophotometry, Ultraviolet
Structure-Activity Relationship
Toxicology
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Summary:A new N-(methylsuccinimido)anthranoyllycoctonine norditerpenoid alkaloid, geyerline, has been isolated and characterized from extracts of the poisonous larkspur Delphinium glaucum. A previously described norditerpenoid alkaloid, grandiflorine, has also been isolated from Delphinium geyeri. Both alkaloids are closely related structurally to the potent neurotoxin methyllycaconitine, established as the primary toxin in many larkspurs poisonous to cattle. Mouse bioassay tests showed grandiflorine to possess toxicity comparable to methyllycaconitine, while its synthetically derived monoacetate, grandiflorine acetate, and geyerline are significantly less toxic.
ISSN:0163-3864
1520-6025
DOI:10.1021/np980013e