Protoanemonin

Last updated
Protoanemonin [1]
Protoanemonina.svg
Protoanemonin 3D spacefill.png
Names
Preferred IUPAC name
5-Methylidenefuran-2(5H)-one
Other names
4-Methylenebut-2-en-4-olide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.244 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2 Yes check.svgY
    Key: RNYZJZKPGHQTJR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
    Key: RNYZJZKPGHQTJR-UHFFFAOYAD
  • C=C1C=CC(=O)O1
Properties
C5H4O2
Molar mass 96.08 g/mol
AppearancePale yellow oil
Boiling point 73 [2]  °C (163 °F; 346 K)
Hazards
Lethal dose or concentration (LD, LC):
190 mg·kg−1 (mouse) [3]
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 ?)

Protoanemonin (sometimes called anemonol or ranunculol [4] ) is a toxin found in all plants of the buttercup family (Ranunculaceae). When the plant is wounded or macerated, the unstable glucoside found in the plant, ranunculin, is enzymatically broken down into glucose and the toxic protoanemonin. [5] It is the lactone of 4-hydroxy-2,4-pentadienoic acid.

Contact with a wounded plant causes itch, rashes or blistering on contact with the skin or mucosa. Ingesting the toxin can cause nausea, vomiting, dizziness, spasms, acute hepatitis, jaundice, or paralysis. [6] [7] [8]

When drying the plant, protoanemonin comes into contact with air and dimerizes to anemonin, which is further hydrolyzed to a non-toxic dicarboxylic acid. [5] [9]

Biological pathway

Ranunculin skeletal.svg ranunculin
↓ – glucose (maceration, enzymatically)
Protoanemonina.svg protoanemonin
dimerization (air or water contact)
Anemonin.svg anemonin
hydrolyzation
Anemoninsaure.svg 4,7-dioxo-2-decenedioic acid

Related Research Articles

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Ranunculin is an unstable glucoside found in plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin.

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References

  1. Römpp, Hermann; Falbe, Jürgen; Regitz, Manfred (1992). Römpp Lexikon Chemie (in German) (9 ed.). Stuttgart: Georg Thieme Verlag.
  2. Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2014). "3". CRC Handbook of Chemistry and Physics (95th ed.). Boca Raton, Florida: CRC Press. p. 370. ISBN   9781482208689. OCLC   908078665.
  3. Martín, ML; San Román, L; Domínguez, A (1990). "In vitro activity of protoanemonin, an antifungal agent". Planta Medica. 56 (1): 66–9. doi:10.1055/s-2006-960886. PMID   2356244. S2CID   260283223. The LD50 of protoanemonin in male Swiss albino mice was 190 mg/kg.
  4. List, PH; Hörhammer, L, eds. (1979). Hagers Handbuch der pharmazeutischen Praxis (in German) (4 ed.). Springer Verlag. ISBN   3-540-07738-3.
  5. 1 2 Berger, Artur; Wachter, Helmut, eds. (1998). Hunnius Pharmazeutisches Wörterbuch (in German) (8 ed.). Walter de Gruyter Verlag. ISBN   3-11-015793-4.
  6. Yilmaz, Bulent; Yilmaz, Barış; Aktaş, Bora; Unlu, Ozan; Roach, Emir Charles (2015-02-27). "Lesser celandine (pilewort) induced acute toxic liver injury: The first case report worldwide". World Journal of Hepatology. 7 (2): 285–288. doi: 10.4254/wjh.v7.i2.285 . ISSN   1948-5182. PMC   4342611 . PMID   25729484.
  7. Verbraucherschutz, Bundesamt für (2014-09-12). List of Substances of the Competent Federal Government and Federal State Authorities: Category "Plants and plant parts". Springer. ISBN   9783319107325.
  8. Lewis, Robert Alan (1998-03-23). Lewis' Dictionary of Toxicology. CRC Press. ISBN   9781566702232.
  9. Handbuch der organischen Chemie, Leopold Gmelin (in German)