Alpha-pinène

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(Redirigé depuis Alpha pinène)

Nom de la substance

Alpha-pinène

Famille moléculaire

Hydrocarbure monoterpénique

Source végétale

Propriétés

  • Mucolytique et expectorant, oxygénant respiratoire, actif dans les bronchites (mélange standardisé avec limonène et 1,8-cinéole) [1], avec bonne tolérance [2], réduction de la fréquence de de l'intensité des exacerbations aiguës de bronchite chronique [3], efficace dans les bronchites aiguës [4]
  • Antibactérien [5]
    • activité vis-à-vis de Actinomadura madurae, pouvant induire des actinomycétomes [6]
  • Antiviral [7]
  • Anti-inflammatoire, avec une action de stimulation adrénergique [8], chondroprotecteur [9]
  • Cortisone-like (?), action sur le burn-out
  • Thermogène par voie locale
  • Bien absorbé par la peau, les intestins, les voies respiratoires [10]: on peut détecter les monoterpènes alpha-pinène, béta-pinène, limonène dans l'air exhalé, de 20 minutes à 24 heures après bain les contenant, avec un pic à 75 minutes [11]
  • Biotransformation :

Effet thérapeutique

  • Bronchites aiguës et chroniques, BPCO
  • Arthrose, troubles articulaires

Effets indésirables

  • Allergène par contact (identique au (béta-pinène) [14]
  • Pas de mutagénicité au test d'Ames [15]
  • Induction du cytochrome P-450 (sous-famille 2B : CYP4502B1) [16]
  • D’après PubChem [4], la dose létale se situe à environ 150 ml pour un adulte

Bibliographie

  1. Matthys H, de Mey C, Carls C, Ryś A, Geib A, Wittig T. Efficacy and tolerability of myrtol standardized in acute bronchitis. A multi-centre, randomised, double-blind, placebo-controlled parallel group clinical trial vs. cefuroxime and ambroxol. Arzneimittelforschung. 2000 Aug;50(8):700-11. PMID 10994153
  2. Matthys H, de Mey C, Carls C, Ryś A, Geib A, Wittig T. Efficacy and tolerability of myrtol standardized in acute bronchitis. A multi-centre, randomised, double-blind, placebo-controlled parallel group clinical trial vs. cefuroxime and ambroxol. Arzneimittelforschung. 2000 Aug;50(8):700-11. PMID 10994153
  3. Meister R, Wittig T, Beuscher N, de Mey C. Efficacy and tolerability of myrtol standardized in long-term treatment of chronic bronchitis. A double-blind, placebo-controlled study. Study Group Investigators. Arzneimittelforschung. 1999 Apr;49(4):351-8. PMID 10337455
  4. Gillissen A, Wittig T, Ehmen M, Krezdorn HG, de Mey C. A multi-centre, randomised, double-blind, placebo-controlled clinical trial on the efficacy and tolerability of GeloMyrtol® forte in acute bronchitis. Drug Res (Stuttg). 2013 Jan;63(1):19-27. doi: 10.1055/s-0032-1331182. PMID 23447044
  5. Hmamouchi M, Hamamouchi J, Zouhdi M, Bessiere JM. Chemical and Antimicrobial Properties of Essential Oils of Five Moroccan Pinaceae. Journal of Essential Oil Research [J. Essent. Oil Res.]. Vol. 13, no. 4, pp. 298-302. Jul-Aug 2001. [1]
  6. Stojković D, Soković Marina, Glamočlija Jasmina, Džamić Ana, Ristić M., Fahal A., Khalid Sami, Đuić Ivana, Petrović Silvana. Susceptibility of three clinical isolates of Actinomodura madurae to α-pinene, the bioactive agent of Pinus pinaster turpentine oil. Archives of Biological Sciences 2008 Volume 60, Issue 4, Pages: 697-701 https://doi.org/10.2298/ABS0804697S
  7. Astani A, Reichling J, Schnitzler P. Comparative study on the antiviral activity of selected monoterpenes derived from essential oils. Phytother Res. 2010 May;24(5):673-9. PMID 19653195
  8. Martin S, Padilla E, Ocete MA, Galvez J, Jimenez J, Zarzuelo A. Anti-inflammatory activity of the essential oil of Bupleurum fruticescens. Planta Med. 1993 Dec;59(6):533-6. [2]
  9. Rufino AT, Ribeiro M, Judas F, Salgueiro L, Lopes MC, Cavaleiro C, Mendes AF. Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity. J Nat Prod. 2014 Feb 28;77(2):264-9. doi: 10.1021/np400828x. PMID 24455984
  10. Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 3243
  11. Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 650
  12. Eriksson K, Levin JO. Identification of cis- and trans-verbenol in human urine after occupational exposure to terpenes. Int Arch Occup Environ Health. 1990;62(5):379-83. PMID 2228258
  13. Ishida T, Asakawa Y, Takemoto T, Aratani T. Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J Pharm Sci. 1981 Apr;70(4):406-15. PMID 7229954
  14. Dharmagunawardena B, Takwale A, Sanders KJ, Cannan S, Rodger A, Ilchyshyn A. Gas chromatography: an investigative tool in multiple allergies to essential oils. Contact Dermatitis. 2002 Nov;47(5):288-92. PMID 12534533
  15. M.R. Gomes-Carneiro, Márcia E.S. Viana, Israel Felzenszwalb, Francisco J.R. Paumgartten. Evaluation of β-myrcene, α-terpinene and (+)- and (−)-α-pinene in the Salmonella/microsome assay. Food and Chemical Toxicology, Volume 43, Issue 2, February 2005, Pages 247-252 [3]
  16. De-Oliveira AC, Ribeiro-Pinto LF, Paumgartten JR. In vitro inhibition of CYP2B1 monooxygenase by beta-myrcene and other monoterpenoid compounds. Toxicol Lett. 1997 Jun 16;92(1):39-46. PMID 9242356
  • Jian-ya ZHOU, Fa-di TANG, Guo-gen MAO, Ru-lian BIAN. Effect of α-pinene on nuclear translocation of NF-κB in THP-1 cells. Acta Pharmacol Sin 2004 Apr; 25 (4): 480-484. PMID 15066217
  • Wilderman PR, Shah MB, Jang HH, Stout CD, Halpert JR. Structural and thermodynamic basis of (+)-α-pinene binding to human cytochrome P450 2B6. J Am Chem Soc. 2013 Jul 17;135(28):10433-40. doi: 10.1021/ja403042k. PMID 23786449
  • Bell SG, Chen X, Sowden RJ, Xu F, Williams JN, Wong LL, Rao Z. Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam. J Am Chem Soc. 2003 Jan 22;125(3):705-14. PMID 12526670
  • Yang J, Nie Q, Ren M, Feng H, Jiang X, Zheng Y, Liu M, Zhang H, Xian M. Metabolic engineering of Escherichia coli for the biosynthesis of alpha-pinene. Biotechnol Biofuels. 2013 Apr 30;6(1):60. doi: 10.1186/1754-6834-6-60. PMID 23631625