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Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian digestion after eating hypoglycin , present in the unripe ackee fruit, grown in Jamaica and in Africa. By blocking coenzyme A and carnitine , MPCA causes a decrease in β-oxidation of fatty acids , and hence gluconeogenesis .

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27-651: Cupania sapida Voigt The ackee ( Blighia sapida ), also known as acki , akee , or ackee apple , is a fruit of the Sapindaceae ( soapberry ) family, as are the lychee and the longan . It is native to tropical West Africa . The scientific name honours Captain William Bligh who took the fruit from Jamaica to the Royal Botanic Gardens in Kew , England, in 1793. The English common name

54-555: A nectar disc between the petals and stamens, their filaments are often hairy. The most frequent number is eight, in two rings of four. The gynoecium contains two or three carpels , sometimes up to six. The usually single style has a lobed stigma. Most often they are pollinated by birds or insects , with a few species pollinated by wind . Ripe fruits may be fleshy or dry. They may be nuts , berries , drupes , schizocarps , capsules ( Bridgesia ), or samaras ( Acer ). The embryos are bent or coiled, without endosperm in

81-465: A concentrated dose causes what is known as Jamaican vomiting sickness . Depending on the severity of the case, the symptoms range from headache, rapid heart beat and sweating to dehydration and low blood pressure stemming from intense vomiting, to delirium and coma, and finally seizures and death. The symptoms stemming from lychee poisoning are nearly identical, both being caused by MCPA, with lychee seeds also containing methylenecyclopropyl glycine (MCPG),

108-401: A dish. In Caribbean cooking, they may be cooked with codfish and vegetables, or may be added to stew, curry, soup or rice with seasonings. Ackee contains a moderate amount of carbohydrates, protein, and fat, providing 51–58% of the dry weight of the arils as composed of fatty acids – linoleic , palmitic , and stearic acids . The raw fruit is a rich source of vitamin C . The ackee

135-399: A rare and potentially toxic amino acid , chemically related to the common amino acid lysine . Hypoglycin is found in the unripe ackee fruit. MCPA forms non-metabolizable esters with coenzyme A (CoA) and carnitine , causing a decrease in their bioavailability and concentration in bodily tissue. Both of these cofactors are necessary for the β-oxidation of fatty acids , which in turn

162-467: A short trunk and a dense crown . The leaves are paripinnately , compound 15–30 centimetres (6–12 inches) long, with 6–10 elliptical to oblong leathery leaflets. Each leaflet is 8–12 cm (3– 4 + 1 ⁄ 2  in) long and 5–8 cm (2–3 in) wide. The inflorescences are fragrant, up to 20 cm long, with unisexual flowers that bloom during warm months. Each flower has five greenish-white petals , which are fragrant. The fruit

189-424: Is a cyclopropane fatty acid named Dihydrosterculic acid ; these have been found in many plants of the order Malvales ( Malvaceae ), in up to 60% of seed oil content, depending on the species but also in leaves, roots and shoots. They are accompanied by small amounts of their cyclopropanoid analogues, i.e. cyclopropyl acetic acid. MPCA is also a metabolite in mammalian digestion after ingestion of hypoglycin ,

216-590: Is a water-soluble liver toxin, that upon ingestion, leads to hypoglycemia through the inhibition of gluconeogenesis, a metabolic pathway that leads to the generation of glucose from non-carbohydrate carbon sources (i.e. glucogenic amino acids , lactate , and glycerol ). In addition, it also limits Acyl and carnitine cofactors, which are instrumental in the oxidation of large fatty acids. Hypoglycin A undergoes deamination , forming α-ketomethylene-cyclopropylpropionic acid (KMCPP), which then forms MCPA through oxidative decarboxylation . Hypoglycin A (and hypoglycin B )

243-517: Is derived from the West African Akan-language name akye fufo . Although having a long-held reputation as being poisonous with potential fatalities, the fruit arils are renowned as delicious when ripe, prepared properly, and cooked and are a feature of various Caribbean cuisines . Ackee is the national fruit of Jamaica and is considered a delicacy. Ackee is an evergreen tree that grows about 10 metres tall, with

270-452: Is divided into four subfamilies, Dodonaeoideae (about 38 genera), Sapindoideae (about 114 genera), Hippocastanoideae (5 genera) and Xanthoceroideae (1 genus). The largest genera are Serjania (about 220 species), Paullinia (about 180 species), and Allophylus (about 200 species) in the tropical Sapindoideae and Acer (about 110 species) in the temperate Hippocastanoideae. The largely temperate genera formerly separated in

297-471: Is found in both the seeds and the arils, while hypoglycin B is found only in the seeds. Minimal quantities of the toxin are found in the ripe arils. In the unripe fruit, depending on the season and exposure to the sun, the concentrations may be up to 10 to 100 times greater. These two molecules are converted in the body to methylenecyclopropylacetic acid (MCPA), and are toxic with potential lethality . MCPA and hypoglycin A inhibit several enzymes involved in

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324-401: Is found in the ackee fruit, the national fruit of Jamaica, and, like Litchi chinensis , is a member of the family Sapindaceae . The fruit is rich in fatty acids, zinc, protein, and vitamin A. In the fully ripened arils of the fruit, Hypoglycin A is present at only 0.1ppm, but in the unripened fruit it can exceed a concentration of 1000ppm. Ingestion of the unripened fruit containing such

351-447: Is pear-shaped and has three lobes (two to four lobes are common). When it ripens it turns from green to a bright red to yellow-orange and splits open to reveal three large, shiny black seeds, each partly surrounded by soft, creamy or spongy, white to yellow flesh — the aril having a nut-like flavor and texture of scrambled eggs. The fruit typically weighs 100–200 grams ( 3 + 1 ⁄ 2 –7 ounces). The tree can produce fruit throughout

378-497: Is prominently featured in the Jamaican mento style folksong " Linstead Market ". In the song, a market seller laments, "Carry mi ackee go a Linstead market. Not a quattie worth sell". The Beat 's 1982 album Special Beat Service includes the song "Ackee 1-2-3". The unripened aril and the inedible portions of the fruit contain hypoglycin toxins including hypoglycin A and hypoglycin B , known as "soapberry toxins". Hypoglycin A

405-409: Is the source of Indian macassar oil . Saponins extracted from the drupe of Sapindus species are effective surfactants and are used commercially in cosmetics and detergents . Methylene cyclopropyl acetic acid Methylene cyclopropyl acetic acid (MCPA) is a compound found in lychee ( Litchi chinensis ) seeds. The major carbocyclic fatty acid in the seed oils of Litchi chinensis

432-456: Is vital for gluconeogenesis . MCPA also inhibits the dehydrogenation of a number of Acyl-CoA dehydrogenases. The inhibition of one in particular, butyryl CoA dehydrogenase (a short-chain acyl-CoA dehydrogenase ), causes β-oxidation to cease before fully realized, which leads to a decrease in the production of NADH and Acetyl-CoA . The cascading effect continues, as this decrease in concentration further inhibits gluconeogenesis. Hypoglycin A

459-506: The Caribbean Islands, including use of its "soap" properties as a laundering agent or fish poison. The fragrant flowers may be used as decoration or cologne , and the durable heartwood used for construction, pilings , oars, paddles and casks. In African traditional medicine , the ripe arils, leaves or bark were used to treat minor ailments. The seeds were formerly used as standardized weights for weighing gold dust, leading to

486-526: The arils convert to hypoglycin B in the seeds. In other words, the seeds help in detoxifying the arils, bringing the concentration of hypoglycin A to a level which is generally safe for consumption. Ackee canned in brine is a commodity item and is used for export by Jamaica, Haiti and Belize. If propagated by seed, trees will begin to fruit in 3–4 years. Cuttings may yield fruit in 1–2 years. The fruit has various uses in West Africa and in rural areas of

513-429: The breakdown of acyl CoA compounds, often binding irreversibly to coenzyme A , carnitine and carnitine acyltransferase I and II , reducing their bioavailability and consequently inhibiting beta oxidation of fatty acids . Glucose stores are consequently depleted leading to hypoglycemia , and to a condition called Jamaican vomiting sickness . These effects occur only when the unripe aril (or an inedible part of

540-474: The currency issued by Great Britain in the former colony of Gold Coast to be named the " Gold Coast ackey ". Sapindaceae The Sapindaceae are a family of flowering plants in the order Sapindales known as the soapberry family . It contains 138 genera and 1,858 accepted species. Examples include horse chestnut , maples , ackee and lychee . The Sapindaceae occur in temperate to tropical regions, many in laurel forest habitat, throughout

567-911: The families Aceraceae ( Acer , Dipteronia ) and Hippocastanaceae ( Aesculus , Billia , Handeliodendron ) were included within a more broadly circumscribed Sapindaceae by the Angiosperm Phylogeny Group . Recent research has confirmed the inclusion of these genera in the Sapindaceae. The Sapindaceae include many species of economically valuable tropical fruit , including the lychee , longan , pitomba , guinip/mamoncillo , korlan , rambutan , pulasan , and ackee . Other products include guaraná , soapberries , and maple syrup . Some species of maple and buckeye are valued for their wood, while several other genera, such as Koelreuteria , Cardiospermum , and Ungnadia , are popular ornamentals . Schleichera trijuga

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594-399: The fruit) is consumed. Though ackee is used widely in traditional dishes, research on its potential hypoglycin toxicity has been sparse and preliminary, requiring evaluation in well-designed clinical research to better understand its pharmacology , food uses, and methods for detoxification. In 2011, it was found that as the fruit ripens, the seeds act as a sink whereby the hypoglycin A in

621-634: The seed, and frequently with an aril . The Sapindaceae are related to the Rutaceae , and both are usually placed in an order Sapindales or Rutales , depending on whether they are kept separate and which name is used for the order. The most basal member appears to be Xanthoceras . Some authors formerly maintained some or all of Hippocastanaceae and Aceraceae , however this resulted in paraphyly . The former Ptaeroxylaceae , now placed in Rutaceae, were sometimes placed in Sapindaceae. The family

648-819: The temperate maples ( Acer ), Aesculus , and a few other genera are opposite. They are most often pinnately compound , but are palmately compound in Aesculus , and simply palmate in Acer . The petiole has a swollen base and lacks stipules . Some genera and species have laurel forest foliage due to convergent evolution . The flowers are small and unisexual , or functionally unisexual, though plants may be either dioecious or monoecious. They are usually found in cymes grouped in panicles . They most often have four or five petals and sepals (petals are absent in Dodonaea ). The stamens range from four to 10, usually on

675-463: The use of ackee in Jamaican cuisine is prominent. Ackee is the national fruit of Jamaica, whilst ackee and saltfish is the official national dish of Jamaica. The ackee is allowed to open fully before picking in order to eliminate toxicity. When it has "yawned" or "smiled", the seeds are discarded and the fresh, firm arils are parboiled in salted water or milk, and may be fried in butter to create

702-459: The world. Many are laticiferous , i.e. they contain latex , a milky sap , and many contain mildly toxic saponins with soap -like qualities in either the foliage and/or the seeds, or roots. The largest genera are Serjania , Paullinia , Allophylus and Acer . Plants of this family have a variety of habits, from trees to herbaceous plants to lianas . The leaves of the tropical genera are usually spirally alternate, while those of

729-468: The year, although January–March and October–November are typically periods of fruit production. There are up to as many as forty-eight cultivars of ackee, which are grouped into either "butter" or "cheese" types. The cheese type is pale yellow in color and is more robust and finds use in the canning industry. The butter type is deeper yellow in color, and is more delicate and better suited for certain cuisine. Imported to Jamaica from West Africa before 1773,

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