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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 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]
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]
Another group of alkaloids, the senecio-type alkaloids, are produced by various plants and like the lolines, the senecio alkaloids possess a pyrrolizidine ring structure. Unlike the lolines, however, the senecio alkaloids exhibit strong hepatotoxicity, [13] owing to a double bond between C-1 and C-2 in their ring structure. [13]
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Among the most important representatives of the pyrrolidine alkaloids are hygrin and cuscohygrin. [2] Another representative is the (-)-codonopsinine. [3] Furthermore, ruspolinone, norruspolinone and norruspoline also belong to this alkaloid group. [4]
Legonmycins are a group of chemical compounds that belong to the pyrrolizidine family of naturally occurring alkaloids.Discovered by a joint team of researchers from University of Ghana, University of Aberdeen, and Wuhan University, the compounds were isolated from Streptomyces microorganisms in Legon, a suburb of Accra, Ghana.
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.