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Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Their use dates back centuries and is intertwined with the discovery, understanding, and eventual recognition of their toxicity on humans and animals.
Pyrrolizidine alkaloidosis can result in damage to the liver, kidneys, heart, brain, smooth muscles, lungs, DNA, lesions all over the body, and could be a potential cause of cancer. [ 1 ] [ 2 ] Pyrrolizidine alkaloidosis is known by many other names such as "Pictou Disease" in Canada [ 3 ] and "Winton Disease" in New Zealand. [ 4 ]
Pyrrolizidine is a heterocyclic organic compound. Formally, it is a saturated derivative of pyrrolizine. Pyrrolizidine forms the central chemical structure of a variety of alkaloids known collectively as pyrrolizidine alkaloids. [1] It is one of five classes of iminosugars. These are often synthesized from a carbohydrate. [2]
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Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from Cynoglossum amabile. [1] It is also found in the seeds and flowers of borage (Borago officinalis) [2] and in borage seed oil. [3] [4] Chemically, it is the ester derived from viridifloric acid and supinidine. [5]
Like other pyrrolizidine alkaloids, senecionine is toxic when ingested. The ingested molecule is a protoxin that is metabolized to its active form. [3] In large quantities, ingestion can lead to critical illness, including convulsions and death. Studies in rodents have shown an LD 50 of 65 mg/kg. [4]
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Pyrrolizidine alkaloid sequestration by insects is a strategy to facilitate defense and mating. Various species of insects have been known to use molecular compounds from plants for their own defense and even as their pheromones or precursors to their pheromones.
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