Chemical Class: Alkaloids: Pyrrolizidine

According to a study using fruit flies, the mutagenic potential of several pyrrolizidine alkaloids has the following order, highest mutagenic toxicity first, lowest last:

senkirkine, monocrotaline, seneciphylline, senecionine, 7-acetyl intermedine, heliotrine, retrorsine, 7-acetyllycopsamine, symphytine, jacoline, symlandine, intermedine, indicine, lycopsamine, indicine N-oxide, supinine

with supinine having no detectable mutagenic activity. This order may also apply to humans.

The Toxicity of Pyrrolizidines

Most, but not all, Pyrrolizidine alkaloids are hepatotoxic, damaging the liver if ingested in sufficient quantities. PAs themselves show little or no toxicity, it is only in the mammalian liver where they are metabolised to highly toxic alkylating pyrrols but only if their structure includes a double-bond in the 1,2-position of the necine and also has a substituted group on the Nitrogen atom and esterification of the OH-groups of the necine (with mono-esters being less toxic than di-esters). Accordingly, the structure of Tussilagine shows that it is not hepatotoxic.

Chemical Class: Alkaloids: Pyrrolizidine

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