Lycopsamine N-oxide

Pyrrolizidine alkaloids are secondary metabolites in plants; about half of these alkaloids exhibit toxicity and carcinogenicity. Pyrrolizidine alkaloids poison grazing animals and domestic livestock through contaminated plants or feed. These alkaloids then poison humans through contaminated food (e.g., grains, honey, and milk), herbal medicine, and supplements. The compounds are epimeric monoesters in retronecine-type pyrrolizidine alkaloids. Intermedine and lycopsamine and the N-oxides, Intermidine N-oxide and Lycopsamine N-oxide (CAS 95462-15-0), are the predominant pyrrolizidine components of interest in comfrey (Symphytum officinale). Intermedine and lycopsamine inhibit the ability of hepatocyte cells to proliferate, colonize, and migrate. These alkaloids also induced hepatocyte apoptosis, indicating they are the cause of hepatotoxicity. Intermedine and lycopsamine are more often found in their oxidized form in plant material: Intermedine N-oxide and Lycopsamine N-oxide.

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