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Amabiline
Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from '' Cynoglossum amabile''. It is also found in the seeds and flowers of borage (''Borago officinalis'') and in borage seed oil. Chemically, it is the ester derived from viridifloric acid and supinidine. Amabiline is hepatotoxic Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn fro ... and may contribute to the potential liver damage caused by consumption of borage and its seed oil. References {{reflist pyrrolizidine alkaloids Esters Diols ...
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Pyrrolizidine Alkaloid
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. Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disea ...
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Cynoglossum Amabile
''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 , 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 ('' Myosotis sylvatica''), is also grown as an ornamental. In cultivation in the UK it has gained the Royal Horticultural Society’s Award of Garden Merit. (confirmed 2017). The Latin specific epithet ''amabile'' means “lovely”. Toxicity ''Cynoglossum amabile'' contains tumorigenic pyrrolizidine alkaloids such as amabiline Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from '' Cynoglossum amabile''. It is also found in the seeds and flowers of borage (''Borago officinalis'') and in borage seed oil. Chemically, it is the ester derived from viridiflor .... References {{Taxonbar, from=Q2564008 amabile Garden plants of Asia Flor ...
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Borage
Borage ( or ; ''Borago officinalis''), also known as 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 (see below under Phytochemistry). Description ''B. officinalis'' grows to a height of , and is bristly or hairy all over the stems and leaf, leaves; the leaves are Alternate leaf, alternate, Simple leaf, simple, and long. The flowers are Complete flower, complete, Perfect flower, perfect with five narrow, trian ...
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Borage Seed Oil
Borage seed oil is derived from the seeds of the plant, ''Borago officinalis'' (borage).Borage
at website
Borage seed oil has one of the highest amounts of γ-linolenic acid (GLA) of seed oils — higher than blackcurrant seed oil or , to which it is considered similar. GLA typically comprises about 24% of the oil.


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Ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ...
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Hepatotoxic
Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn from the market after approval. The liver plays a central role in transforming and clearing chemicals and is susceptible to the toxicity from these agents. Certain medicinal agents, when taken in overdoses (e.g. paracetamol) and sometimes even when introduced within therapeutic ranges (e.g. halothane), may injure the organ. Other chemical agents, such as those used in laboratories and industries, natural chemicals (e.g., microcystins), and herbal remedies (two prominent examples being kava, mechanism unknown, and comfrey, through its pyrrolizidine alkaloid content) can also induce hepatotoxicity. Chemicals that cause liver injury are called hepatotoxins. More than 900 drugs have been implicated in causing liver injury (see LiverTox, exter ...
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Memorial Sloan Kettering Cancer Center
Memorial Sloan Kettering Cancer Center (MSK or MSKCC) is a cancer treatment and research institution in the borough of Manhattan in New York City, founded in 1884 as the New York Cancer Hospital. MSKCC is one of 52 National Cancer Institute–designated Comprehensive Cancer Centers. Its main campus is located at 1275 York Avenue, between 67th and 68th streets, in Manhattan. According to U.S. News & World Report 2021-2022 Best Hospitals, Memorial Sloan Kettering Cancer Center (MSK) has been ranked as the number two hospital for cancer care in the nation. History New York Cancer Hospital (1884–1934) Memorial Hospital was founded on the Upper West Side of Manhattan in 1884 as the New York Cancer Hospital by a group that included John Jacob Astor III and his wife Charlotte. The hospital appointed as an attending surgeon William B. Coley, who pioneered an early form of immunotherapy to eradicate tumors. Rose Hawthorne, daughter of author Nathaniel Hawthorne, trained there in th ...
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Pyrrolizidine Alkaloids
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. Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disea ...
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Esters
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology The ...
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