Eugénol
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Nom de la substance
Eugénol (et isoeugénol)
- = 4-allyl-2-méthoxyphénol C10-H12-O2
Famille moléculaire
Phénol monoterpénique (phénylpropène, sous-classe des phénylpropanoïdes)
Source végétale
- Huile essentielle de girofle, muscade, poivre de Guinée, laurier, bois d’Inde, basilic
- Racines de benoite
Propriétés
- Antibactérien [1], l'eugénol et l'isoeugénol sont actifs contre Trichomonas vaginalis, Helicobacter pylori [2], Listeria monocytogenes, Escherichia coli [3], mycoplasmes (Ureaplasma sp. ) [4]
- Synergie antibactérienne entre eugénol, thymol et carvacrol [5]
- Effet synergique en association avec les antibiotiques [6]
- L’eugénol inhibe la formation du biofilm et atténue la virulence de Escherichia coli entéro-hémorragique O157:H7 [7]
- Antifongique [8], vis-à-vis de Cladosporium herbarum et Penicillium glabrum [9], vis-à-vis de Candida, Aspergillus & dermatophytes (y compris résistants au fluconazole) par lésion de la membrane cellulaire et entraine une réduction considérable de la quantité d’ergostérol, un composant spécifique de la membrane cellulaire fungique [10], actif contre des souches de Candida résistantes au fluconazole [11]
- Anthelminthique [12]
- Inhibiteur de la cyclo-oxygénase, inhibe la synthèse de prostaglandines, notamment par la muqueuse du colon, inhibiteur du transit
- Anti-inflammatoire par inhibition de la Cox-2, anti-arthritique [13], agent préventif du cancer [14]
- Effets immunomodulateurs et anti-inflammatoires, l'eugénol inhibe la voie du NF-κB [15]
- Gastroprotecteur par stimulation de la synthèse du mucus gastrique [16], effet de prévention de l'ulcère gastrique [17]
- Antioxydant [18] et protecteur de l'ADN [19]
- Hépatoprotecteur, inhibe la toxicité du tétrachlorure de carbone, inducteur d'enzymes de phase II (NADPH-cytochrome c réductase, NADH-cytochrome réductase, coumarine hydroxylase, 7-éthoxy coumarine-O-deéthylase, UDP-glucuronyltransférase, glutathion-S-transférase) [20]
- Hépatoprotecteur vis-à-vis des lésions hépatiques induites par le trioxyde d'arsenic (As2O3) [21], le tétrachlorure de carbone [22], l’acétaminophène [23], [24], l’alcool éthylique [25]
- Spasmolytique, anticonvulsivant
- Antalgique surtout par voie locale [26], effet analgésique médié par les récepteurs alpha2-adrénergiques et opioïdes, mais non par les récepteurs sérotoninergiques [27], L’effet antalgique de l’eugénol peut d’expliquer par l’activation de TRPA1 [28] et anesthésiant [29]
- Parasympatholytique et sympatholytique, hypotenseur par effet vasodilatateur périphérique
- Antiagrégant plaquettaire [30], [31], [32], [33]
- Effet anti-œstrogénique [34]
- Prévient la réduction de dopamine dans le striatum, prévention de la lipoperoxydation, effet potentiel dans la maladie de Parkinson [35]
- Autres propriétés : potentialités herbicides, non encore exploitées [36], [37]
Effet thérapeutique
- Intéressant dans les infections dentaires, pharyngées, gastro-intestinales, urinaires, génitales
- Douleurs dentaires, pharyngées, œsophagiennes
- Douleurs rhumatismales (par voie locale)
- L'élimination est urinaire à 95% [38]
Effets indésirables
- Effets anticoagulants en association avec des médicaments anti-inflammatoires, aspirine ou anti-agrégants
- Ne pas associer avec les anticoagulants
- Rares allergies
- Cytotoxique [39]
- Néanmoins substance classée GRAS par le FEMA (Flavor and Extract Manufacturers Association) [40]
- GRAS = “generally recognized as safe” (généralement reconnu comme sans danger)
- Hépatotoxicité pour des doses très élevées, par exemple le cas d’un enfant de 15 mois ayant absorbé 10 ml d’HE de girofle [41], et d’une enfant de 3 mois ayant absorbé 8 ml d’HE de girofle [42], traités favorablement tous les deux par N-acétylcystéine
- Hépatotoxique chez le rat [43] et chez la souris ayant reçu préalablement un traitement inhibiteur de synthèse du glutathion [44], [45]
Bibliographie
- ↑ Suresh P, Ingle V. K, Vijayalakshmi V. Antibacterial activity of eugenol in comparison with other antibiotics. Journal of food science and technology, 1992, vol. 29, no4, pp. 254-256
- ↑ G. E. Bergonzelli, D. Donnicola, N. Porta, and I. E. Corthésy-Theulaz. Essential Oils as Components of a Diet-Based Approach to Management of Helicobacter Infection. Antimicrob Agents Chemother. 2003 October; 47(10): 3240–3246. PMID 14506036 intégral en pdf
- ↑ Pérez-Conesa D, McLandsborough L, Weiss J. Inhibition and inactivation of Listeria monocytogenes and Escherichia coli O157:H7 colony biofilms by micellar-encapsulated eugenol and carvacrol. J Food Prot. 2006 Dec;69(12):2947-54. PMID 17186663
- ↑ Sleha R, Mosio P, Vydrzalova M, Jantovska A, Bostikova V, Mazurova J. In vitro antimicrobial activities of cinnamon bark oil, anethole, carvacrol, eugenol and guaiazulene against Mycoplasma hominis clinical isolates. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2014 Jun;158(2):208-11. doi: 10.5507/bp.2012.083. PMID 23128812
- ↑ Nicole Didry, Luc Dubreuil, Madeleine Pinkas. Activity of thymol, carvacrol, cinnamaldehyde and eugenol on oral bacteria. Pharmaceutica Acta Helvetiae, Volume 69, Issue 1, July 1994, Pages 25-28
- ↑ Langeveld WT, Veldhuizen EJ, Burt SA. Synergy between essential oil components and antibiotics: a review. Crit Rev Microbiol. 2014 Feb;40(1):76-94. doi: 10.3109/1040841X.2013.763219. PMID 23445470
- ↑ Kim YG, Lee JH, Gwon G, Kim SI, Park JG, Lee J. Essential Oils and Eugenols Inhibit Biofilm Formation and the Virulence of Escherichia coli O157:H7. Sci Rep. 2016 Nov 3;6:36377. doi: 10.1038/srep36377. PMID 27808174; PMCID: PMC5093407.
- ↑ Boonchird C, Flegel T W. In vitro antifungal activity of eugenol and vanillin against Candida albicans and Cryptococcus neoformans. Canadian journal of microbiology 1982;28(11):1235-41
- ↑ Martini H, Weidenbörner M, Adams S, Kunz B. Eugenol and carvacrol : The main fungicidal compounds in clove and savory. Italian journal of food science, 1996, vol. 8, no1, pp. 63-67
- ↑ Pinto E, Vale-Silva L, Cavaleiro C, Salgueiro L. Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida, Aspergillus and dermatophyte species. J Med Microbiol. 2009 Nov;58(Pt 11):1454-62. doi: 10.1099/jmm.0.010538-0. PMID 19589904
- ↑ Marcos-Arias C, Eraso E, Madariaga L, Quindos G. In vitro activities of natural products against oral Candida isolates from denture wearers. BMC Complementary and Alternative Medicine 2011, 11:119 (26 November 2011. Texte intégral : [1]
- ↑ M. K. Asha, D. Prashanth, , B. Murali, R. Padmaja, A. Amit. Anthelmintic activity of essential oil of Ocimum sanctum and eugenol. Fitoterapia, Volume 72, Issue 6, August 2001, Pages 669-670
- ↑ Jagdish N. Sharma, Krishna C. Srivastava, Ee K. Gan. Suppressive Effects of Eugenol and Ginger Oil on Arthritic Rats. Pharmacology 1994;49:314-318
- ↑ Kim SS, Oh OJ, Min HY, Park EJ, Kim Y, Park HJ, Nam Han Y, Lee SK. Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci. 2003 Jun 6;73(3):337-48. PMID 12757841
- ↑ Bachiega TF, de Sousa JP, Bastos JK, Sforcin JM. Clove and eugenol in noncytotoxic concentrations exert immunomodulatory/anti-inflammatory action on cytokine production by murine macrophages. J Pharm Pharmacol. 2012 Apr;64(4):610-6. doi: 10.1111/j.2042-7158.2011.01440.x. PMID 22420667
- ↑ Santin JR, Lemos M, Klein-Júnior LC, Machado ID, Costa P, de Oliveira AP, Tilia C, de Souza JP, de Sousa JP, Bastos JK, de Andrade SF. Gastroprotective activity of essential oil of the Syzygium aromaticum and its major component eugenol in different animal models. Naunyn Schmiedebergs Arch Pharmacol. 2011 Feb;383(2):149-58. doi: 10.1007/s00210-010-0582-x. PMID 21140134
- ↑ Capasso R, Pinto L, Vuotto ML, Di Carlo G. Preventive effect of eugenol on PAF and ethanol-induced gastric mucosal damage. Fitoterapia. 2000 Aug;71 Suppl 1:S131-7. PMID 10930724
- ↑ Fujisawa S, Atsumi T, Satoh K, Kadoma Y, Ishihara M, Okada N, Nagasaki M, Yokoe I, Sakagami H. Radical generation, radical-scavenging activity, and cytotoxicity of eugenol-related compounds. In Vitr Mol Toxicol. 2000 Winter;13(4):269-80. PMID 11319278
- ↑ Horvathova E, Navarova J, Galova E, Sevcovicova A, Chodakova L, Snahnicanova Z, Melusova M, Kozics K, Slamenova D. Assessment of antioxidative, chelating, and DNA-protective effects of selected essential oil components (eugenol, carvacrol, thymol, borneol, eucalyptol) of plants and intact Rosmarinus officinalis oil. J Agric Food Chem. 2014 Jul 16;62(28):6632-9. doi: 10.1021/jf501006y. PMID 24955655
- ↑ Parasakthy Kumaravelu, Deepalakshmi P. Dakshinamoorthy, Shanthi Subramaniam, Halagowder Devaraj, Niranjali S. Devaraj. Effect of eugenol on drug-metabolizing enzymes of carbon tetrachloride-intoxicated rat liver. Biochemical Pharmacology, Volume 49, Issue 11, 1995, Pages 1703-1707, https://doi.org/10.1016/0006-2952(95)00083-C.
- ↑ Binu P PhD, Priya N MPHIL, Abhilash S PhD, Vineetha RC PhD, Nair H PhD. Protective Effects of Eugenol against Hepatotoxicity Induced by Arsenic Trioxide: An Antileukemic Drug. Iran J Med Sci. 2018 May;43(3):305-312. PMID 29892148; PMCID: PMC5993899.
- ↑ Nagababu E, Sesikeran B, Lakshmaiah N. The protective effects of eugenol on carbon tetrachloride induced hepatotoxicity in rats. Free Radic Res. 1995 Dec;23(6):617-27. doi: 10.3109/10715769509065281. PMID 8574354.
- ↑ Lister, I. N. E., Ginting, C. N., Girsang, E., Amansyah, A., Chiuman, L., Yanti, N. L. W. E., ... & Widowati, W. (2019, November). Hepatoprotective effect of eugenol on acetaminophen-induced hepatotoxicity in HepG2 cells. In Journal of Physics: Conference Series (Vol. 1374, No. 1, p. 012009). IOP Publishing.
- ↑ Florenly, F., Sugianto, L., Lister, I. N. E., Girsang, E., Ginting, C. N., Afifah, E., ... & Widowati, W. (2021). Protective Effect of Eugenol against Acetaminophen-Induced Hepatotoxicity in Human Hepatocellular Carcinoma Cells via Antioxidant, Anti-Inflammatory, and Anti-Necrotic Potency. Open Access Macedonian Journal of Medical Sciences, 9(A).
- ↑ Anbu, S., & Anuradha, C. V. (2012). Protective effect of eugenol against alcohol-induced biochemical changes in rats. International Journal of Research in Biotechnology and Biochemistry, 2(2), 13-18.
- ↑ Ohkubo T, Shibata M. The selective capsaicin antagonist capsazepine abolishes the antinociceptive action of eugenol and guaiacol. J Dent Res. 1997 Apr;76(4):848-51. doi: 10.1177/00220345970760040501. PMID 9126180.
- ↑ Park SH, Sim YB, Lee JK, Kim SM, Kang YJ, Jung JS, Suh HW. The analgesic effects and mechanisms of orally administered eugenol. Arch Pharm Res. 2011 Mar;34(3):501-7. PMID 21547684
- ↑ Chung G, Im ST, Kim YH, Jung SJ, Rhyu MR, Oh SB. Activation of transient receptor potential ankyrin 1 by eugenol. Neuroscience. 2014 Mar 7;261:153-60. doi: 10.1016/j.neuroscience.2013.12.047. PMID 24384226.
- ↑ Dallmeier K, Carlini EA. Anesthetic, hypothermic, myorelaxant and anticonvulsant effects of synthetic eugenol derivatives and natural analogues. Pharmacology. 1981;22(2):113-27. PMID 7208593
- ↑ K.C. Srivastava. Antiplatelet principles from a food spice clove (Syzgium aromaticum L). Prostaglandins, Leukotrienes and Essential Fatty Acids, Volume 48, Issue 5, 1993, Pages 363-372, https://doi.org/10.1016/0952-3278(93)90116-E.
- ↑ Laekeman GM, Haemers A, Herman AG, Vlietinck AJ. Eugenol and analogues as antiplatelet compounds. Planta Med. 1986 Oct;(5):431. doi: 10.1055/s-2007-969242. PMID 17345398.
- ↑ XIA Meng-yuan,WANG Li,WANG Yue-hu. Antiplatelet and Antithrombotic Activities of Piper Plants[J]. Natural product research and development, 2016, 28(10): 1676-1685.
- ↑ Chen SJ, Wang MH, Chen IJ. Antiplatelet and calcium inhibitory properties of eugenol and sodium eugenol acetate. General Pharmacology. 1996 Jun;27(4):629-633. DOI: 10.1016/0306-3623(95)02089-6. PMID 8853295.
- ↑ Howes MJ, Houghton PJ, Barlow DJ, Pocock VJ, Milligan SR. Assessment of estrogenic activity in some common essential oil constituents. J Pharm Pharmacol. 2002 Nov;54(11):1521-8. PMID 12495555
- ↑ Hideaki Kabuto, Mika Tada, Masahiro Kohno. Eugenol [2-Methoxy-4-(2-propenyl)phenol] Prevents 6-Hydroxydopamine-Induced Dopamine Depression and Lipid Peroxidation Inductivity in Mouse Striatum. Biological and Pharmaceutical Bulletin, Vol. 30 (2007) No. 3 P 423-427. PMID 17329831
- ↑ Nitina Ahuja, N. Ahuja, Daizy R. Batish, D. R. Batish, Harminder Pal Singh, H. Pal Singh, & Ravinder K. Kohli, R. K. Kohli. (0000). Herbicidal activity of eugenol towards some grassy and broad-leaved weeds. Journal of pest science, 88, 209-218. doi: 10.1007/s10340-014-0570-x
- ↑ Tworkoski, T. (2002). Herbicide effects of essential oils. Weed Science, 50(4), 425-431. doi:10.1614/0043-1745(2002)050[0425:HEOEO]2.0.CO;2
- ↑ POIROT Tony. Bon usage des huiles essentielles, effets indésirables et toxicologie. Thèse en Pharmacie, 2016, faculté de Pharmacie de Nancy [https://docnum.univ-lorraine.fr/public/BUPHA_T_2016_POIROT_TONY.pdf
- ↑ Satoh K, Ida Y, Sakagami H, Tanaka T, Fujisawa S. Effect of antioxidants on radical intensity and cytotoxic activity of eugenol. Anticancer Res. 1998 May-Jun;18(3A):1549-52. PMID 9673369
- ↑ http://www.femaflavor.org/public/about_fema/index.php
- ↑ Janes SE, Price CS, Thomas D. Essential oil poisoning: N-acetylcysteine for eugenol-induced hepatic failure and analysis of a national database. Eur J Pediatr. 2005 Aug;164(8):520-2. doi: 10.1007/s00431-005-1692-1. PMID 15895251.
- ↑ Eisen JS, Koren G, Juurlink DN, Ng VL. N-acetylcysteine for the treatment of clove oil-induced fulminant hepatic failure. J Toxicol Clin Toxicol. 2004;42(1):89-92. doi: 10.1081/clt-120028751. PMID 15083943.
- ↑ Soundran V, Namagiri T, Manonayaki S, Vanithakumari G. Hepatotoxicity of eugenol. Anc Sci Life. 1994 Jan;13(3-4):213-7. PMID 22556649; PMCID: PMC3336525.
- ↑ Mizutani T, Satoh K, Nomura H, Nakanishi K. Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine. Res Commun Chem Pathol Pharmacol. 1991 Feb;71(2):219-30. PMID 2047567.
- ↑ Mizutani T, Satoh K, Nomura H. Hepatotoxicity of eugenol and related compounds in mice depleted of glutathione: structural requirements for toxic potency. Res Commun Chem Pathol Pharmacol. 1991 Jul;73(1):87-95. PMID 1882130.