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Hypoglycin B
Hypoglycin B
Names
IUPAC name
(2S)-2-Amino-4-(1S)-1-carboxy-2-[(1S)-2-methylidenecyclopropyl]ethyl]carbamoyl]butanoic acid
Other names
L-γ-Glutamyl-L-hypoglycin; L-γ-Glutamyl-3-[(1S)-2-methylenecyclopropyl]-L-alanine
Identifiers
3D model (JSmol)
ChemSpider
  • 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 checkY
    Key: UYDZYCPIQSRXKU-CIUDSAMLSA-N checkY
  • 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).
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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.

Sources

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Hypoglycin B is commonly found in the Ackee tree's fruit when unripe. Hypoglycin A is typically found in the arilli and the raphe of the fruit while Hypoglycin B is found more commonly in the seeds. It is also found in relatives of the ackee fruit such as lychee and rambutan as well as another uncommon amino acid: α-(methylenecyclopropyl)glycine.

Toxicity

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Hypoglycin B is a protoxin and thus is non toxic in this form. The initial amino acid undergoes a deamination and is metabolized in the body to form Methylene cyclopropyl acetic acid-Coenzyme A. In this form, the complex can block certain enzymes responsible for gluconeogenesis[2].

Studies on adult rats, kittens, and guinea pigs have determined that Hypoglycin B is about half as toxic as its more common analogue Hypoglycin A. The LD50 was determined to be approximately 180 mg/kg although in animals who were fasting, the toxicity doubled[3]. In all animals that were tested, blood glucose levels dropped significantly

See Also

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References

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  1. ^ "Ackee Fruit Toxicity". Medscape.
  2. ^ "THE ACKEE FRUIT (BLIGHIA SAPIDA) AND ITS ASSOCIATED TOXIC EFFECTS". University of British Columbia. 2005-11-17. {{cite web}}: Missing or empty |title= (help); Missing or empty |url= (help)CS1 maint: numeric names: authors list (link)
  3. ^ Hassall, C. H. (20, February 1954). "Hypoglycin A,B: Biologically Active Polypeptides from Blighia sapida". Nature. 173: 356–357. doi:https://doi.org/10.1038/173356b0. {{cite journal}}: Check |doi= value (help); Check date values in: |date= (help); External link in |doi= (help)

Category:Dipeptides Category:Dicarboxylic acids Category:Toxic amino acids

 

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