Intermedine N-oxide

Intermedine N-oxide (CAS 95462-14-9) is the oxidized form the pyrrolizidine alkaloid Intermedine, isolated from comfrey root (Symphytum officinale). Intermedine and Lycopsamine and their N-oxide forms are compounds of interest in comfrey root for their hepatoxic activity. 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. Intermedine and lycopsamine are epimeric monoesters in retronecine-type pyrrolizidine alkaloids. Intermedine and lycopsamine are the predominant pyrrolizidine alkaloids in comfrey (Symphytum officinale). The alkaloids and their N-oxides inhibit the ability of hepatocyte cells to proliferate, colonize, and migrate. These alkaloids also induced hepatocyte apoptosis, indicating they are the cause of hepatotoxicity.

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