Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.
Senecio vulgaris, often known by the common names groundsel and old-man-in-the-spring, is a flowering plant in the daisy family Asteraceae. It is an annual herb, native to Europe and widely naturalised as a ruderal species in suitable disturbed habitats worldwide.
Borage, also known as a starflower, is an annual herb in the flowering plant family Boraginaceae. It is native to the Mediterranean region, and has naturalized in many other locales. It grows satisfactorily in gardens in most of Europe, such as Denmark, France, Germany, and the United Kingdom, remaining in the garden from year to year by self-seeding. The leaves are edible and the plant is grown in gardens for that purpose in some parts of Europe.The plant is also commercially cultivated for borage seed oil extracted from its seeds. The plant contains pyrrolizidine alkaloids, some of which are hepatotoxic, mutagenic, and carcinogenic.
Tussilago farfara, commonly known as coltsfoot, is a plant in the groundsel tribe in the daisy family Asteraceae, native to Europe and parts of western and central Asia. The name "tussilago" is derived from the Latin tussis, meaning cough, and ago, meaning to cast or to act on. It has had uses in traditional medicine, but the discovery of toxic pyrrolizidine alkaloids in the plant has resulted in liver health concerns.
Heliotropium is a genus of flowering plants in the borage family, Boraginaceae. There are around 325 species in this almost cosmopolitan genus, which are commonly known as heliotropes. It is highly toxic for dogs and cats.
Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than 660 PAs and PA N-oxides have been identified in over 6,000 plants, and about half of them exhibit hepatotoxicity. They are found frequently in plants in the Boraginaceae, Asteraceae, Orchidaceae and Fabaceae families; less frequently in the Convolvulaceae and Poaceae, and in at least one species in the Lamiaceae. It has been estimated that 3% of the world’s flowering plants contain pyrrolizidine alkaloids. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines.
Cynoglossum amabile, the Chinese hound's tongue or Chinese forget-me-not, is a species of flowering plant in the family Boraginaceae, native to Asia. A hardy annual growing to 50 cm (20 in), it has hairy leaves and cymes of sky-blue flowers in late summer. This plant, closely related to the common forget-me-not of temperate gardens, is also grown as an ornamental. In cultivation in the UK it has gained the Royal Horticultural Society’s Award of Garden Merit..
A loline alkaloid is a member of the 1-aminopyrrolizidines, which are bioactive natural products with several distinct biological and chemical features. The lolines are insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts of the genus Epichloë. Lolines increase resistance of endophyte-infected grasses to insect herbivores, and may also protect the infected plants from environmental stresses such as drought and spatial competition. They are alkaloids, organic compounds containing basic nitrogen atoms. The basic chemical structure of the lolines comprises a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge—a hallmark feature of the lolines, which is uncommon in organic compounds—joining two distant ring carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield loline species that have variable bioactivity against insects. Besides endophyte–grass symbionts, loline alkaloids have also been identified in some other plant species; namely, Adenocarpus species and Argyreia mollis.
Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris. It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.
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. 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. Pyrrolizidine alkaloidosis is known by many other names such as "Pictou Disease" in Canada and "Winton Disease" in New Zealand. Cereal crops and forage crops can sometimes become polluted with pyrrolizidine-containing seeds, resulting in the alkaloids contaminating flour and other foods, including milk from cows feeding on these plants.
Pyrrolizidine alkaloid sequestration by insects is a strategy to facilitate defense and mating. Various species of insects have been known to utilize molecular compounds from plants for their own defense and even as their pheromones or precursors to their pheromones. A few Lepidoptera have been found to sequester chemicals from plants which they retain throughout their life and some members of Erebidae are examples of this phenomenon. Starting in the mid-twentieth century researchers investigated various members of Arctiidae, and how these insects sequester pyrrolizidine alkaloids (PAs) during their life stages, and utilize these chemicals as adults for pheromones or pheromone precursors. PAs are also used by members of the Arctiidae for defense against predators throughout the life of the insect.
Hair-pencils and coremata are pheromone signaling structures present in lepidopteran males. Males use hair-pencils in courtship behaviors with females. The pheromones they excrete serve as both aphrodisiacs and tranquilizers to females as well as repellents to conspecific males. Hair-pencil glands are stored inside the male until courtship begins, at which point they are forced out of the body by sclerotized levers present on the abdomen. Coremata are very similar structures. Their exact definition is confused by early descriptions but they are more specifically defined as the internal, glandular, eversible structures that bear the hair-pencils and can be voluntarily inflated with hemolymph or air.
Riddelliine is a chemical compound classified as a pyrrolizidine alkaloid. It was first isolated from Senecio riddellii and is also found in a variety of plants including Jacobaea vulgaris, Senecio vulgaris, and others plants in the genus Senecio.
Parasenecio hastatus is a flowering plant species in the genus Parasenecio found in China and East Asia. It contains toxic pyrrolizidine alkaloids.
An iminosugar, also known as an iminosaccharide, is any analog of a sugar where a nitrogen atom has replaced the oxygen atom in the ring of the structure.
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.
Thesinine is a pyrrolizidine alkaloid first isolated from Thesium minkwitzianum from which it derives its name. It is also found in the flowers and seeds of borage.
Hydroxydanaidal is an insect pheromone synthesized by some species of moth from pyrrolizidine alkaloids found in their diet.
Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from Cynoglossum amabile. It is also found in the seeds and flowers of borage and in borage seed oil.
Echites umbellatus is a flowering climber, belonging to subfamily Apocynoideae of the family Apocynaceae and has the English common name devil's potato. It was first described in 1760 by Dutch botanist, Nikolaus Joseph von Jacquin. The species grows in parts of Florida, Tabasco, Yucatán Peninsula, Belize, Honduras, Cayman Islands, Cuba, Hispaniola, Jamaica, Leeward Islands, Bahamas, Turks and Caicos Islands, and the Colombian islands in the Western Caribbean.
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