Verbénone

De WikiPhyto

Nom de la substance

Verbénone, 2-pinene-4-one

Famille moléculaire

Cétone monoterpénique bicyclique

Source végétale

Propriétés

  • Expectorante, broncho-dilatatrice, inhibe le bronchospasme induit par l'histamine [1]
  • Anti-inflammatoire [2], [3]
  • Antiagrégante
  • Phéromone [4]
  • Insecticide [5], vis-à-vis de Dendroctonus ponderosae, le dendroctone du pin ou « Mountain pine beetle » [6]
  • Hydroxylé par le cytochrome P450 (CYP2A6) [7]

Effet thérapeutique

  • Traitement des pathologies bronchopulmonaires dues à une inflammation et/ou une infection, accompagnées d'une obstruction des voies respiratoires, dosage envisagé entre 10 et 100 milligrammes par jour [8]

Effets indésirables

  • Peu de toxicité de la verbénone, qui reste une cétone [9]
  • La DL50 de la verbénone serait de 1800 mg/kg, les premiers signes de toxicité sont les tremblements et les convulsions, puis une perte de poids et enfin une léthargie [10], cité par USDA, Forest Service [11]

Bibliographie

  1. Chiariello M, Campana G, Delfanti G, Capuano D. Bradykinin bronchospasm in guinea pigs: effects of indomethacin and verbenone. Boll Chim Farm. 1986 Nov;125(11):390-1. PMID 3593547
  2. Chiariello M, Campana G, Delfanti G, Capuano D. The effect of verbenone on prostaglandin production in vivo. Boll Chim Farm. 1986 Nov;125(11):392-4. PMID 3593548
  3. Folisi V, Chiariello M, Pighi R, Vigano V, Vitali R. Principi attivi terpenici: standardizzazione (PATS) identificazione, sintesi e caratterizzazione farmacologica di un monoterpene antiinflammatorio: Verbenone. III. Convegno Nazionale Divisione Chimica Farmaceutica - Societa Chimica Italiana - Montecatini Terme, 18-21 ottobre 1982.
  4. Rudinsky J. A. Multiple Functions of the Southern Pine Beetle Pheromone Verbenone. Environmental Entomology, Volume 2, Number 4, August 1973 , pp. 511-514(4)
  5. Gene D. Amman, Ralph W. Thier, Mark D. McGregor, Richard F. Schmitz. Efficacy of verbenone in reducing lodgepole pine infestation by mountain pine beetles in Idaho. Revue canadienne de recherche forestière, 1989, 19(1): 60-64, [1]
  6. John H Borden, Leslie J Chong, Tracy J Earle, Dezene P.W. Huber. Protection of lodgepole pine from attack by the mountain pine beetle, Dendroctonus ponderosae (Coleoptera: Scolytidae) using high doses of verbenone in combination with nonhost bark volatiles. The Forestry Chronicle, 2003, 79(3): 685-691
  7. Miyazawa M, Sugie A, Shimada T. Roles of human CYP2A6 and 2B6 and rat CYP2C11 and 2B1 in the 10-hydroxylation of (-)-verbenone by liver microsomes.Drug Metab Dispos. 2003 Aug;31(8):1049-53. PMID 12867494
  8. Davide Vegezzi. Method for the preparation of verbenone, myrtenal and pinocarveol and their therapeutical use patent US4190675A [2]
  9. Verbenone - Human Health and Ecological Risk Assessment Final Report, Prepared for: USDA, Forest Service [3]
  10. Deenihan M. 1987b. Verbenone--Acute Toxicology Testing: NVP Report No. X7J055G.
  11. Verbenone - Human Health and Ecological Risk Assessment Final Report, Prepared for: USDA, Forest Service
  • Uzi Ravid, Eli Putievsky, Irena Katzir, Efraim Lewinsohn, Nativ Dudai. Identification of (1R)(+)-Verbenone in Essential Oils of Rosmarinus officinalis L. Flavour and Fragrance Journal, Volume 12, Issue 2, pages 109–112, March 1997
  • Mitsuo MIYAZAWA, Atsushi SUGIE and Masaki SHINDO, “Biotransformation of (−)-Verbenone by Human Liver Microsomes”, Biosci. Biotechnol. Biochem., Vol. 66, 2458-2460 (2002). [4]