Hypoglycine

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Structural formula
Structural formula of hypoglycine
General
Surname Hypoglycine
other names
  • Hypoglycine A
  • 2-methylenecyclopropanylalanine
  • L - ( S ) -2-amino-3- (2-methylidenecyclopropyl) propionic acid
  • L - ( S ) -2-amino-3 - [( S ) -2-methylidenecyclopropyl] propionic acid
  • (α S , 1 R ) -α-Amino-2-methylidenecyclopropyl propionic acid
Molecular formula C 7 H 11 NO 2
Brief description

yellow plates

External identifiers / databases
CAS number 156-56-9
EC number 663-646-8
ECHA InfoCard 100.189.936
PubChem 11768666
ChemSpider 9943349
Wikidata Q418173
properties
Molar mass 141.17 g mol −1
Physical state

firmly

Melting point

280-284 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hypoglycine is a non-proteinogenic amino acid with hypoglycemic and teratogenic effects.

Occurrence

Akee plant with fruit
Unripe lychee fruits also contain hypoglycine

Hypoglycine is found in the seeds and unripe fruits of the akee plant . Up to 1000 ppm hypoglycine occurs in the immature seed coat ; this corresponds to up to 1 mg per gram of wet weight. In the seeds it is 2-3 times as much. Originating in Africa, the akee plant was introduced to Jamaica 200 years ago, where the ripe fruit is consumed.

Hypoglycine is also found in immature lychees and their seeds.

Poisoning

When consuming Akee, severe symptoms of intoxication can occur, ranging from vomiting ( Jamaican vomiting sickness ) to hypoglycaemia , symptoms of exhaustion , coma and death . Symptoms appear 6-48 hours after ingestion. The cause of the symptoms of intoxication is the inhibition of acyl-CoA dehydrogenases . The inhibition of the oxidation of fatty acids and leucine is also discussed . The effects are likely not caused by hypoglycine itself, but by its primary metabolite, methylenecyclopropylacetyl-CoA (MCPA-CoA). The lethal dose is around 40 mg kg −1 (humans).

Annually occurring illnesses, some resulting in death, in children in the district of Muzaffarpur , India, could be attributed to excessive consumption of lychee. The course of the disease was particularly severe in children from poor backgrounds who did not receive dinner.

In veterinary medicine it was not until 2015 that hypoglycine from seeds of the sycamore maple was recognized as the cause of the often fatal atypical pasture myopathy in horses.

Individual evidence

  1. ↑ a b Entry on Hypoglycins. In: Römpp Online . Georg Thieme Verlag, accessed on January 19, 2015.
  2. ^ Entry on hypoglycine in the Hazardous Substances Data Bank , accessed July 27, 2012.
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ a b S.H. Henry, SW Page, PM Bolger: Hazard Assessment of Ackee Fruit (Blighia sapida) . In: Human and Ecological Risk Assessment . tape 4 , no. 5 , 1998, pp. 1175-1187 , doi : 10.1080 / 10807039891285045 .
  5. ↑ HSA Sherratt: Hypoglycine, the famous toxin of the unripe Jamaican ackee fruit . In: Trends in Pharmacological Sciences . tape 7 , 1986, pp. 186-191 , doi : 10.1016 / 0165-6147 (86) 90310-X .
  6. ↑ Aakash Shrivastava, Anil Kumar, Jerry D Thomas, et al: Association of acute toxic encephalopathy with litchi consumption in an outbreak in Muzaffarpur, India, 2014: a case-control study. (PDF) Lancet Glob Health 2017, January 30, 2017, accessed February 3, 2017 .
  7. ↑ Votion DM: The cause of the atypical pasture myopathy has been found - what now? In: vetline.de. Schlütersche Verlagsgesellschaft mbH & Co. KG, August 26, 2018, accessed on August 26, 2018 (quoted from Pferdeheilkd 31 (6): 571-577).

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