Coriamyrtin

Coriamyrtin[1]
Names
IUPAC name
(1S,2R,3S,5R,6R,7R,9S,12R)-2-Hydroxy-7-methyl-12-prop-1-en-2-ylspiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxirane]-11-one
Other names
Coriamyrtine
Identifiers
3D model (JSmol)
  • InChI=1S/C15H18O5/c1-6(2)8-7-4-13(3)14(5-18-14)10-11(20-10)15(13,17)9(8)12(16)19-7/h7-11,17H,1,4-5H2,2-3H3/t7-,8+,9+,10+,11-,13-,14+,15-/m0/s1
    Key: BWWDLKVKPVKBGJ-TWMZOSGRSA-N
  • CC(=C)C1C2CC3(C4(CO4)C5C(C3(C1C(=O)O2)O)O5)C
Properties
C15H18O5
Molar mass 278.304 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coriamyrtin is a toxic γ-lactone naturally present in a multitude of plants.

Natural occurrence

Coriamyrtin can be found in Scurrula parasitica,[2] Coriaria microphylla,[3] and certain other plants.

Toxicity

Coriamyrtin is a convulsant.[4] It appears to act via antagonism of GABAA receptors.[5] Poisoning is usually from ingestion of parts of the plants containing it. A case of poisoning was able to be treated with repeated administration of diazepam, an anticonvulsant.[6]

References

  1. ^ "Coriamyrtin".
  2. ^ PubChem. "Scurrula parasitica". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-11.
  3. ^ PubChem. "Coriaria microphylla". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-02-11.
  4. ^ "T3DB: Coriamyrtin". www.t3db.ca. Retrieved 2024-02-11.
  5. ^ Pérez, Claudia; Becerra, José; Manríquez-Navarro, Paula; Aguayo, Luis Gerardo; Fuentealba, Jorge; Guzmán, José Leonardo; Joseph-Nathan, Pedro; Jiménez, Verónica; Muñoz, Marcelo Andrés; Silva, Mario (2011). "Inhibitory activities on mammalian central nervous system receptors and computational studies of three sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia". Chemical & Pharmaceutical Bulletin. 59 (2): 161–165. doi:10.1248/cpb.59.161. ISSN 1347-5223. PMID 21297293.
  6. ^ de Haro, Luc; Pommier, Philip; Tichadou, Lucia; Hayek-Lanthois, Maryvonne; Arditti, Jocelyne (November 2005). "Poisoning by Coriaria myrtifolia Linnaeus: a new case report and review of the literature". Toxicon. 46 (6): 600–603. Bibcode:2005Txcn...46..600D. doi:10.1016/j.toxicon.2005.06.026. ISSN 0041-0101. PMID 16165183.


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