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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]
Riddelliine is a naturally occurring pyrrolizidine alkaloid, a class of compounds occurring in rangeland plants of the genera Crotalaria, Amsinckia, and Senecio. [5] It consists of a macrocyclic diester of retronecine (an unsaturated alcohol) and riddelliic acid (an oxygenated, branched, dicarboxylic acid). [5]
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]
Pages in category "Pyrrolizidine alkaloids" The following 12 pages are in this category, out of 12 total. This list may not reflect recent changes. ...
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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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]