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.
^Römpp, Hermann; Falbe, Jürgen; Regitz, Manfred (1992). Römpp Lexikon Chemie (in German) (9 ed.). Stuttgart: Georg Thieme Verlag.
^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. ISBN9781482208689. OCLC 908078665.
^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.
^List, PH; Hörhammer, L, eds. (1979). Hagers Handbuch der pharmazeutischen Praxis (in German) (4 ed.). Springer Verlag. ISBN3-540-07738-3.
^ abBerger, Artur; Wachter, Helmut, eds. (1998). Hunnius Pharmazeutisches Wörterbuch (in German) (8 ed.). Walter de Gruyter Verlag. ISBN3-11-015793-4.
^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. PMC4342611. PMID 25729484.
^Verbraucherschutz, Bundesamt für (2014-09-12). List of Substances of the Competent Federal Government and Federal State Authorities: Category "Plants and plant parts". Springer. ISBN9783319107325.
^Lewis, Robert Alan (1998-03-23). Lewis' Dictionary of Toxicology. CRC Press. ISBN9781566702232.
^Handbuch der organischen Chemie, Leopold Gmelin (in German)
January 01, 1970
protoanemonin, sometimes, called, anemonol, ranunculol, toxin, found, plants, buttercup, family, ranunculaceae, when, plant, wounded, macerated, unstable, glucoside, found, plant, ranunculin, enzymatically, broken, down, into, glucose, toxic, protoanemonin, la. 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 Protoanemonin 1 Names Preferred IUPAC name 5 Methylidenefuran 2 5H one Other names 4 Methylenebut 2 en 4 olide Identifiers CAS Number 108 28 1 3D model JSmol Interactive image ChemSpider 60307 Y ECHA InfoCard 100 003 244 PubChem CID 66948 UNII 66FQZ1A5SO Y CompTox Dashboard EPA DTXSID10148346 InChI InChI 1S C5H4O2 c1 4 2 3 5 6 7 4 h2 3H 1H2 YKey RNYZJZKPGHQTJR UHFFFAOYSA N YInChI 1 C5H4O2 c1 4 2 3 5 6 7 4 h2 3H 1H2Key RNYZJZKPGHQTJR UHFFFAOYAD SMILES C C1C CC O O1 Properties Chemical formula C 5H 4O 2 Molar mass 96 08 g mol Appearance Pale yellow oil Boiling point 73 2 C 163 F 346 K Hazards Lethal dose or concentration LD LC LD50 median dose 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 Y verify what is Y N Infobox references 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 edit nbsp ranunculin glucose maceration enzymatically nbsp protoanemonin dimerization air or water contact nbsp anemonin hydrolyzation nbsp 4 7 dioxo 2 decenedioic acidReferences edit Rompp Hermann Falbe Jurgen Regitz Manfred 1992 Rompp Lexikon Chemie in German 9 ed Stuttgart Georg Thieme Verlag 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 Martin ML San Roman L Dominguez 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 List PH Horhammer L eds 1979 Hagers Handbuch der pharmazeutischen Praxis in German 4 ed Springer Verlag ISBN 3 540 07738 3 a b Berger Artur Wachter Helmut eds 1998 Hunnius Pharmazeutisches Worterbuch in German 8 ed Walter de Gruyter Verlag ISBN 3 11 015793 4 Yilmaz Bulent Yilmaz Baris Aktas 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 Verbraucherschutz Bundesamt fur 2014 09 12 List of Substances of the Competent Federal Government and Federal State Authorities Category Plants and plant parts Springer ISBN 9783319107325 Lewis Robert Alan 1998 03 23 Lewis Dictionary of Toxicology CRC Press ISBN 9781566702232 Handbuch der organischen Chemie Leopold Gmelin in German Retrieved from https en wikipedia org w index php title Protoanemonin amp oldid 1192897205, wikipedia, wiki, book, books, library,
