Anisatine

Anisatine
Image illustrative de l’article Anisatine
Structure de l'anisatine
Identification
Nom UICPA 1,5,6a,7-tétrahydroxy-5,9-diméthylhexahydrospiro[4,9a-méthanocyclopenta[d]oxocine-6,3’-oxétane]-2,2’(1H)-dione
No CAS 51372-90-8
No ECHA 100.208.646
No CE 207-540-8
PubChem 171029
SMILES
InChI
Propriétés chimiques
Formule C15H20O8  [Isomères]
Masse molaire[1] 328,314 5 ± 0,015 8 g/mol
C 54,87 %, H 6,14 %, O 38,99 %,
Écotoxicologie
DL50 0,7–1,0 mg·kg-1 (souris,?) [2]
Unités du SI et CNTP, sauf indication contraire.
modifier 

L'anisatine est une lactone sesquiterpénique toxique retrouvé dans le fruit et la graine de la badiane japonaise.

Effets

L'anisatine est un antagoniste non-compétitif de l'acide γ-aminobutyrique (GABA)[3],[4] et se lie aux récepteurs GABAA[2]. Son ingestion peut provoquer des épisodes convulsifs[5],[6] et divers problèmes digestifs tels des vomissements, des maux d'estomac et des diarrhées.

Voir aussi

Références

  1. ↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. ↑ a et b Wink, M., Van Wyk, B.-E., Mind-Altering and Poisonous Plants of the World, Timber Press, Portland, 2008, 464 p. (ISBN 978-0-88192-952-2)
  3. ↑ Bruneton, J., Pharmacognosie - Phytochimie, plantes médicinales, 4e éd., revue et augmentée, Paris, Tec & Doc - Éditions médicales internationales, , 1288 p. (ISBN 978-2-7430-1188-8)
  4. ↑ (en) Kudo Y., Oka, J. I., Yamada, K., (1981), Anisatin, a potent GABA antagonist, isolated from Illicium anisatum, Neurosci. Lett., 25, 83-8.
  5. ↑ Biessels, G. J., Vermeji, F. H. et Leijten, F. S. S. (2002), Epiletische aanval na drinken van Sterrenmixthee: intoxicatie mit Japanse steranijs, Ned. Tijdschr. Geneeskd., 146, 808,811.
  6. ↑ Johanns, E. S. D., van der Kolk, L. E., van Gemert, H. M. A., et al.(2002), Een epidemie van epileptische aanval na drinken van kruidenthee, Ned. Tijdschr. Geneeskd., 146, 813-816.

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