Hypoglycin B

Last updated
Hypoglycin B
Hypoglycin B.svg
Names
IUPAC name
γ-Glutamyl-3-[(1R-2-methylidenecyclopropyl]alanine
Systematic IUPAC name
(2S)-5-({(1S)-1-Carboxy-2-[(1S)-2-methylidenecyclopropyl]ethyl}amino)-5-oxopentanoic acid
Other names
L-γ-Glutamyl-L-hypoglycin; L-γ-Glutamyl-3-[(1S)-2-methylenecyclopropyl]-L-alanine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-,9-/m0/s1 Yes check.svgY
    Key: UYDZYCPIQSRXKU-CIUDSAMLSA-N Yes check.svgY
  • InChI=1/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-,9-/m0/s1
    Key: UYDZYCPIQSRXKU-CIUDSAMLBD
  • O=C(N[C@H](C(=O)O)C[C@H]1C(=C)C1)CC[C@@H](C(=O)O)N
Properties
C12H18N2O5
Molar mass 270.285 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hypoglycin B is a naturally occurring organic compound in the species Blighia sapida . It is particularly concentrated in the fruit of the plant especially in the seeds. Hypoglycin B is toxic if ingested and is one of the causative agents of Jamaican vomiting sickness. [1] It is a dipeptide of glutamic acid and hypoglycin A.

Related Research Articles

<span class="mw-page-title-main">Lychee</span> Species of plant

Lychee is a monotypic taxon and the sole member in the genus Litchi in the soapberry family, Sapindaceae.

<span class="mw-page-title-main">Avocado</span> Species of flowering plant in the laurel family Lauraceae

The avocado is a medium-sized, evergreen tree in the laurel family (Lauraceae). It is native to the Americas and was first domesticated in Mesoamerica more than 5,000 years ago. Then as now it was prized for its large and unusually oily fruit. The tree likely originated in the highlands bridging south-central Mexico and Guatemala. Its fruit, sometimes also referred to as an alligator pear or avocado pear, is botanically a large berry containing a single large seed. Avocado trees are partly self-pollinating, and are often propagated through grafting to maintain consistent fruit output. Avocados are presently cultivated in the tropical and Mediterranean climates of many countries. Mexico is the world's leading producer of avocados as of 2020, supplying nearly 30% of the global harvest in that year.

<i>Blighia sapida</i> Species of plant

The ackee, 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 is derived from the West African Akan akye fufo.

<span class="mw-page-title-main">Aril</span> Membranous or fleshy appendage that partly or wholly covers a seed

An aril, also called an arillus, is a specialized outgrowth from a seed that partly or completely covers the seed. An arillode or false aril is sometimes distinguished: whereas an aril grows from the attachment point of the seed to the ovary, an arillode forms from a different point on the seed coat. The term "aril" is sometimes applied to any fleshy appendage of the seed in flowering plants, such as the mace of the nutmeg seed. Arils and arillodes are often edible enticements that encourage animals to transport the seed, thereby assisting in seed dispersal. Pseudarils are aril-like structures commonly found on the pyrenes of Burseraceae species that develop from the mesocarp of the ovary. The fleshy, edible pericarp splits neatly in two halves, then falling away or being eaten to reveal a brightly coloured pseudaril around the black seed.

<span class="mw-page-title-main">Malathion</span> Chemical compound

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

<i>Strychnos nux-vomica</i> Species of plant

Strychnos nux-vomica, the strychnine tree, also known as nux vomica, poison fruit, semen strychnos, and quaker buttons, is a deciduous tree native to India and to southeast Asia. It is a medium-sized tree in the family Loganiaceae that grows in open habitats. Its leaves are ovate and 5–9 centimetres (2–3.5 in) in size. It is known for being the natural source of the extremely poisonous compound strychnine.

Toxication, toxification or toxicity exaltation is the conversion of a chemical compound into a more toxic form in living organisms or in substrates such as soil or water. The conversion can be caused by enzymatic metabolism in the organisms, as well as by abiotic chemical reactions. While the parent drug are usually less active, both the parent drug and its metabolite can be chemically active and cause toxicity, leading to mutagenesis, teratogenesis, and carcinogenesis. Different classes of enzymes, such as P450-monooxygenases, epoxide hydrolase, or acetyltransferases can catalyze the process in the cell, mostly in the liver.

<i>Garcinia gummi-gutta</i> Species of flowering plant

Garcinia gummi-gutta is a tropical species of Garcinia native to South Asia and Southeast Asia. Common names include Garcinia cambogia, as well as brindle berry, and Malabar tamarind. The fruit looks like a small pumpkin and is green to pale yellow in color.

<i>Solanum nigrum</i> Species of flowering plant in the nightshade family Solanaceae

Solanum nigrum, the European black nightshade or simply black nightshade or blackberry nightshade, is a species of flowering plant in the genus Solanum, native to Eurasia and introduced in the Americas, Australasia, and South Africa. Ripe berries and cooked leaves of edible strains are used as food in some locales, and plant parts are used as a traditional medicine. A tendency exists in literature to incorrectly refer to many of the other "black nightshade" species as "Solanum nigrum".

<span class="mw-page-title-main">Tephritidae</span> Family of fruit flies

The Tephritidae are one of two fly families referred to as fruit flies, the other family being the Drosophilidae. The family Tephritidae does not include the biological model organisms of the genus Drosophila, which is often called the "common fruit fly". Nearly 5,000 described species of tephritid fruit fly are categorized in almost 500 genera of the Tephritidae. Description, recategorization, and genetic analyses are constantly changing the taxonomy of this family. To distinguish them from the Drosophilidae, the Tephritidae are sometimes called peacock flies, in reference to their elaborate and colorful markings. The name comes from the Greek τεφρος, tephros, meaning "ash grey". They are found in all the biogeographic realms.

<i>Podophyllum peltatum</i> Species of flowering plants belonging to the barberry family

Podophyllum peltatum is an herbaceous perennial plant in the family Berberidaceae. Its common names are mayapple, American mandrake, wild mandrake, and ground lemon. It is widespread across most of the eastern United States and southeastern Canada.

<span class="mw-page-title-main">Fenthion</span> Chemical compound

Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.

<span class="mw-page-title-main">Ochratoxin</span> Group of chemical compounds

Ochratoxins are a group of mycotoxins produced by some Aspergillus species and some Penicillium species, especially P. verrucosum. Ochratoxin A is the most prevalent and relevant fungal toxin of this group, while ochratoxins B and C are of lesser importance.

Jamaican vomiting sickness, also known as toxic hypoglycemic syndrome (THS), acute ackee fruit intoxication, or ackee poisoning, is an acute illness caused by the toxins hypoglycin A and hypoglycin B, which are present in fruit of the ackee tree. While in the fully ripened arils, hypoglycin A is at levels of less than 0.1 ppm, in unripe arils it can be over 1000 ppm and can cause vomiting and even death. Some countries in the Caribbean and Western Africa experience frequent cases.

<span class="mw-page-title-main">Hypoglycin A</span> Chemical compound

Hypoglycin A is a naturally occurring amino acid derivative found in the unripened fruit of the Ackee tree and in the seeds of the box elder tree. It is toxic if ingested, and is the causative agent of Jamaican vomiting sickness. A 2017 Lancet report established a link between the consumption of unripened lychees resulting in hypoglycaemia and death from acute toxic encephalopathy.

<i>Tasmannia stipitata</i> Species of shrub

Tasmannia stipitata, commonly known as the Dorrigo pepper or northern pepperbush is a rainforest shrub of temperate forests of the Northern Tablelands of New South Wales, Australia. Leaves are fragrant, narrow-lanceolate to narrow-elliptic, 8–13 cm long. Dark bluish to mauve berries follow the flowers on female shrubs. The species is dioecious, with male and female flowers on separate plants.

<i>Swietenia macrophylla</i> Species of plant

Swietenia macrophylla, commonly known as mahogany, Honduran mahogany, Honduras mahogany, or big-leaf mahogany is a species of plant in the Meliaceae family. It is one of three species that yields genuine mahogany timber (Swietenia), the others being Swietenia mahagoni and Swietenia humilis. It is native to South America, Mexico and Central America, but naturalized in the Philippines, Singapore, Malaysia and Hawaii, and cultivated in plantations and wind-breaks elsewhere.

<span class="mw-page-title-main">Cucurbitacin</span> Class of biochemical compounds

Cucurbitacins are a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defense against herbivores. Cucurbitacins and their derivatives have also been found in many other plant families, in some mushrooms and even in some marine mollusks.

<i>Amanita exitialis</i> Species of fungus

Amanita exitialis, also known as the Guangzhou destroying angel, is a mushroom of the large genus Amanita. It is distributed in eastern Asia, and probably also in India where it has been misidentified as A. verna. Deadly poisonous, it is a member of section Phalloideae and related to the death cap A. phalloides. The fruit bodies (mushrooms) are white, small to medium-sized with caps up to 7 cm (2.8 in) in diameter, a somewhat friable ring and a firm volva. Unlike most agaric mushrooms which typically have four-spored basidia, the basidia of A. exitialis are almost entirely two-spored. Eight people were fatally poisoned in China after consuming the mushroom in 2000, and another 20 have been fatally poisoned since that incident. Molecular analysis shows that the species has a close phylogenetic relationship with three other toxic white Amanitas: A. subjunquillea var. alba, A. virosa and A. bisporigera.

Hypoglycin may refer to:

References

  1. "Ackee Fruit Toxicity". Medscape. 28 March 2022.