Estragole

De WikiPhyto
(Redirigé depuis Méthyl-chavicol)

Nom de la substance

Estragole, méthyl-chavicol

Famille moléculaire

Source végétale

Propriétés

  • Spasmolytique intestinal
  • Antifongique [1]
  • Activité antibactérienne sur Pseudomonas sp [2]

Effet thérapeutique

Effets indésirables

  • Risque cancérogène et mutagène par l'intermédiaire d'un métabolite, le 1'-hydroxyestragole [3]
    • Néanmoins les effets cancérogènes et pro-oxydants des huiles essentielles contenant le méthylchavicol (estragon, cerfeuil, basilic) ne possèdent pas une toxicité équivalente [4], certains composés du basilic réduisent la toxicité du 1'-hydroxyestragole connu comme procarcinogène (réduisent la formation d'adduits à ADN) [5]
    • Le méthylchavicol serait époxydé chez le rat en époxyestragole, substance cancérogène, mais l'époxyestragole serait métabolisé en dihydroxyestragole non mutagène chez l’homme
  • Génotoxicité pour des doses allant jusqu’à 2 g/kg [6], par formation d'adduits à ADN (sur la guanine [7])
  • Hépatotoxicité chez la souris [8], [9]

Bibliographie

  1. S. K. Oxenham, K. P. Svoboda, D. R. Walters. Antifungal Activity of the Essential Oil of Basil (Ocimum basilicum). Journal of Phytopathology, Volume 153, Issue 3, pages 174–180, March 2005
  2. Wan J, Wilcock A, Coventry MJ. The effect of essential oils of basil on the growth of Aeromonas hydrophila and Pseudomonas fluorescens. J Appl Microbiol. 1998 Feb;84(2):152-8. PMID 9633630
  3. Anthony A, Caldwell J, Hutt AJ, Smith RL. Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1'-hydroxyestragole. Food Chem Toxicol. 1987 Nov;25(11):799-806. PMID 3121480
  4. Bidri M, Conti M, Franetich JF, Tefit M, Mazier D, Arock M, Vouldoukis I. Fresh aromatic herbs containing methylchavicol did not exhibit the pro-oxidative effects of pure methylchavicol on a human hepatoma cell line, HepG2. Ann Pharm Fr. 2012 Sep;70(5):256-63. doi: 10.1016/j.pharma.2012.06.005. PMID 23020916
  5. Jeurissen SM, Punt A, Delatour T, Rietjens IM. Basil extract inhibits the sulfotransferase mediated formation of DNA adducts of the procarcinogen 1'-hydroxyestragole by rat and human liver S9 homogenates and in HepG2 human hepatoma cells. Food Chem Toxicol. 2008 Jun;46(6):2296-302. doi: 10.1016/j.fct.2008.03.010. PMID 18433972
  6. Lutz Müller, P. Kasper, K. Müller-Tegethoff , T. Petr. The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans-anethole. Mutation Research Letters. Vol 325, Issue 4, 1994, Pages 129-136 [1]
  7. Wisemay, R.W. Hepatocarcinogenesis in the preweanling male B6C3F/sub 1/ mouse with alkenylbenzene derivatives: hepatic DNA adducts, structure-carcinogenicity relationships, and activating mutations in the C-HA-ras proto-oncogene. Thèse (Ph. D) Université du Wisconsin, Madison (USA) [2]
  8. Drinkwater NR, Miller EC, Miller JA, Pitot HC. Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria. J Natl Cancer Inst. 1976 Dec;57(6):1323-31. PMID 187802
  9. Wiseman RW, Miller EC, Miller JA, Liem A. Structure-Activity Studies of the Hepatocarcinogenicities of Alkenylbenzene Derivatives Related to Estragole and Safrole on Administration to Preweanling Male C57BL/6J × C3H/HeJ F1 Mice. Cancer Res May 1, 1987 47; 2275 [3]
  • Miller JA, Miller EC. The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole. Br J Cancer. 1983 Jul;48(1):1-15. PMID 6191767
  • Roger W. Wiseman, Timothy R. Fennell, James A. Miller, Elizabeth C. Miller. Further Characterization of the DNA Adducts Formed by Electrophilic Esters of the Hepatocarcinogens 1′-Hydroxysafrole and 1′-Hydroxyestragole in Vitro and in Mouse Liver in Vivo, Including New Adducts at C-8 and N-7 of Guanine Residues. Cancer Res July 1985 45; 3096 (texte intégral [4])
  • De Vincenzi M, Silano M, Maialetti F, Scazzocchio B. Constituents of aromatic plants: II. Estragole. Fitoterapia. 2000 Dec;71(6):725-9. PMID 11077188