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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]
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Pyrrolizidine alkaloidosis is a disease caused by chronic poisoning found in humans and other animals caused by ingesting poisonous plants which contain the natural chemical compounds known as pyrrolizidine alkaloids. [1] Pyrrolizidine alkaloidosis can result in damage to the liver, kidneys, heart, brain, smooth muscles, lungs, DNA, lesions all ...
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]
Retronecine is a pyrrolizidine alkaloid found in a variety of plants in the genera Senecio and Crotalaria, and the family Boraginaceae. It is the most common central core for other pyrrolizidine alkaloids. [1]
Alkaloids with partial pyrrolidine structure are usually sub-categorized based on their occurrence and biogenetic origin. Hygrin and cuscohygrin were isolated from the leaves of the coca shrub, [2] while (-)-codonopsinine was isolated from the woodland vine tiger bell.
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]