Estragole

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Nom de la substance

Estragole, méthyl-chavicol

Famille moléculaire

Source végétale

Propriétés

  • Spasmolytique intestinal
  • Antifongique [1]
  • Activité antibactérienne sur Pseudomonas sp [2]
  • Anti-inflammatoire [3]
  • Potentialités anticancéreuses [4]
  • Insecticide, le méthylchavicol est toxique vis-à-vis d’insectes ravageurs comme Lasioderma serricorne (rillette du tabac), Oryzaephilus surinamensis (silvain ou cucujide dentelé) [5], Ephestia kuehniella, Plodia interpunctella [6], Tribolium castaneum [7], et d’autres [8]

Effet thérapeutique

Effets indésirables

  • Risque cancérogène et mutagène par l'intermédiaire d'un métabolite, le 1'-hydroxyestragole [9]
  • Génotoxicité pour des doses allant jusqu’à 2 g/kg [12], par formation d'adduits à ADN (sur la guanine [13])
  • Hépatotoxicité chez la souris [14], [15]
  • En cas d'administration in vivo d'estragole chez l'homme, il est probable que les processus toxicocinétiques et toxicologiques soient similaires à ceux des rongeurs chez lesquels une cancérogénicité a été observée [16]
  • Les études sur les rongeurs montrent que la toxicité du méthyleugénol et de l'estragole sont probablement minimes dans l'intervalle posologique de 1 à 10 mg / kg de poids corporel, soit environ 100 à 1000 fois l'exposition humaine prévue à ces substances. Pour ces raisons, il est conclu que l'exposition actuelle résultant de la consommation d'aliments, principalement des épices, ne présente pas de risque significatif de cancer [17]
  • ADI = 0,01 mg/kg/jour
  • Limite nutritionnelle recommandée 0,05 mg / kg [18]

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. Roy, A., Park, H. J., Jung, H. A., & Choi, J. S. (2018). Estragole Exhibits Anti-inflammatory Activity with the Regulation of NF-κB and Nrf-2 Signaling Pathways in LPS-induced RAW 264.7 cells. Natural Product Sciences, 24(1), 13-20.
  4. Lashkari, A., Najafi, F., Kavoosi, G., & Niazi, S. (2020). Evaluating the In vitro anti-cancer potential of estragole from the essential oil of Agastache foeniculum [Pursh.] Kuntze. Biocatalysis and Agricultural Biotechnology, 27, 101727.
  5. Ebadollahi, Asgar ; Mohammad Safaralizadeh ; Ali Pourmirza ; Seyyed Gheibi. Toxicity of Essential Oil of Agastache Foeniculum (Pursh) Kuntze to Oryzaephilus Surinamensis L. and Lasioderma Serricorne F. Journal of Plant Protection Research, Vol. 50, No. 2 (2010) DOI: 10.2478/v10045-010-0037-x
  6. Ebadollahi, A., Safaralizadeh, M. H., Hoseini, S. A., Ashouri, S. & Sharifian, I. (2010). Insecticidal activity of essential oil of Agastache foeniculum against Ephestia kuehniella and Plodia interpunctella (Lepidoptera: Pyralidae). Munis Entomology & Zoology, 5 (2): 785-791
  7. Ebadollahi, A., Khosravi, R., Sendi, J. J., Honarmand, P., & Amini, R. M. (2013). Toxicity and physiological effects of essential oil from Agastache foeniculum (Pursh) Kuntze against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) larvae. Annual Research & Review in Biology, 649-658.
  8. Ebadollahi, A. (2011). Chemical constituents and toxicity of Agastache foeniculum (Pursh) Kuntze essential oil against two stored-product insect pests. Chilean Journal of Agricultural Research, 71(2), 212.
  9. 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
  10. 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
  11. 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
  12. 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]
  13. 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]
  14. 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
  15. 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]
  16. EMA, Public statement on the use of herbal medicinal products containing estragole pdf
  17. Smith RL, Adams TB, Doull J, Feron VJ, Goodman JI, Marnett LJ, Portoghese PS, Waddell WJ, Wagner BM, Rogers AE, Caldwell J, Sipes IG. Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole. Food Chem Toxicol. 2002 Jul;40(7):851-70. PMID 12065208
  18. De Vincenzi M, Silano M, Maialetti F, Scazzocchio B. Constituents of aromatic plants: II. Estragole. Fitoterapia. 2000 Dec;71(6):725-9. PMID 11077188
  • 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])