Advertisement

Natural Products pp 4001-4015 | Cite as

Eugenol as Local Anesthetic

  • Gehoon Chung
  • Seog Bae Oh
Reference work entry

Abstract

Eugenol is an active ingredient of essential oil extracted from cloves and other herbs. Eugenol is used extensively in dentistry for its analgesic and anti-inflammatory activities. However, the molecular mechanism underlying the pharmacological action of eugenol is only recently investigated. This chapter discusses eugenol’s abilities to modulate various ion channels that are responsible for nociception, generation of neuronal spikes, and synaptic transmission. Therapeutic use of eugenol as antibiotic, anti-inflammatory, antitumor, and antioxidant agent is described and then followed by other aspects of eugenol such as cytotoxicity, insecticidal activity, allergic reaction, and olfactory response. In conclusion, eugenol is a versatile natural compound that has many potential uses in wide areas.

Keywords

Eugenol analgesic anesthetic anti-inflammatory antibiotic 

Notes

Acknowledgments

This research was supported by grant (2011-0018614) from National Research Laboratory Program grant (2011-0027592) from Midcareer Researcher program and grant (2011 K000275) from Brain Research Center of the twenty-first Century Frontier Research Program funded by the Ministry of Education, Science and Technology, Republic of Korea. There is no conflict of interest.

References

  1. 1.
    Gayoso CW, Lima EO, Oliveira VT, Pereira FO, Souza EL, Lima IO, Navarro DF (2005) Sensitivity of fungi isolated from onychomycosis to Eugenia cariophyllata essential oil and eugenol. Fitoterapia 76:247–249CrossRefGoogle Scholar
  2. 2.
    Chaieb K, Hajlaoui H, Zmantar T, Kahla-Nakbi AB, Rouabhia M, Mahdouani K, Bakhrouf A (2007) The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): a short review. Phytother Res 21:501–506CrossRefGoogle Scholar
  3. 3.
    Sarrami N, Pemberton MN, Thornhill MH, Theaker ED (2002) Adverse reactions associated with the use of eugenol in dentistry. Br Dent J 193:257–259CrossRefGoogle Scholar
  4. 4.
    Hume WR (1986) The pharmacologic and toxicological properties of zinc oxide-eugenol. J Am Dent Assoc 113:789–791Google Scholar
  5. 5.
    Newman MG, Hulem C, Colgate J, Anselmo C (1979) Antibacterial susceptibility of plaque bacteria. J Dent Res 58:1722–1732CrossRefGoogle Scholar
  6. 6.
    Chami F, Chami N, Bennis S, Bouchikhi T, Remmal A (2005) Oregano and clove essential oils induce surface alteration of Saccharomyces cerevisiae. Phytother Res 19:405–408CrossRefGoogle Scholar
  7. 7.
    Zheng GQ, Kenney PM, Lam LK (1992) Sesquiterpenes from clove (Eugenia caryophyllata) as potential anticarcinogenic agents. J Nat Prod 55:999–1003CrossRefGoogle Scholar
  8. 8.
    Miyazawa M, Hisama M (2001) Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002 umu test. J Agric Food Chem 49:4019–4025CrossRefGoogle Scholar
  9. 9.
    Kim HM, Lee EH, Hong SH, Song HJ, Shin MK, Kim SH, Shin TY (1998) Effect of Syzygium aromaticum extract on immediate hypersensitivity in rats. J Ethnopharmacol 60:125–131CrossRefGoogle Scholar
  10. 10.
    Ogata M, Hoshi M, Urano S, Endo T (2000) Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem Pharm Bull 48:1467–1469CrossRefGoogle Scholar
  11. 11.
    Park IK, Lee HS, Lee SG, Park JD, Ahn YJ (2000) Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae). J Agric Food Chem 48:2528–2531CrossRefGoogle Scholar
  12. 12.
    Heldt H-W, Piechulla B, Heldt FC (2010) Plant biochemistry, 4th ed. Academic Press, WalthamGoogle Scholar
  13. 13.
    Duke JA, EA (2006) Handbook of medicinal herbs. CRC Press LLC, Boca Raton, pp 1–893Google Scholar
  14. 14.
    Dexter R, Qualley A, Kish CM, Ma CJ, Koeduka T, Nagegowda DA, Dudareva N, Pichersky E, Clark D (2007) Characterization of a petunia acetyltransferase involved in the biosynthesis of the floral volatile isoeugenol. Plant J 49:265–275CrossRefGoogle Scholar
  15. 15.
    Koeduka T, Fridman E, Gang DR, Vassão DG, Jackson BL, Kish CM, Orlova I, Spassova SM, Lewis NG, Noel JP, Baiga TJ, Dudareva N, Pichersky E (2006) Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. ProcNatlAcadSci USA 103:10128–10133CrossRefGoogle Scholar
  16. 16.
    Yeon K-Y, Chung G, Kim YH, Hwang JH, Davies AJ, Park M-K, Ahn DK, Kim JS, Jung SJ, Oh SB (2011) Eugenol reverses mechanical allodynia after peripheral nerve injury by inhibiting hyperpolarization-activated cyclic nucleotide-gated (HCN) channels. Pain 152:2108–2116CrossRefGoogle Scholar
  17. 17.
    Park C-K, Kim K, Jung SJ, Kim MJ, Ahn DK, Hong S-D, Kim JS, Oh SB (2009) Molecular mechanism for local anesthetic action of eugenol in the rat trigeminal system. Pain 144:84–94CrossRefGoogle Scholar
  18. 18.
    Park C-K, Li HY, Yeon K-Y, Jung SJ, Choi S-Y, Lee SJ, Lee S, Park K, Kim JS, Oh SB (2006) Eugenol inhibits sodium currents in dental afferent neurons. J Dent Res 85:900–904CrossRefGoogle Scholar
  19. 19.
    Chung G, Rhee JN, Jung SJ, Kim JS, Oh SB (2008) Modulation of CaV23 calcium channel currents by eugenol. J Dent Res 87:137–141CrossRefGoogle Scholar
  20. 20.
    Lee MH, Yeon K-Y, Park C-K, Li HY, Fang Z, Kim MS, Choi S-Y, Lee SJ, Lee S, Park K, Lee J-H, Kim JS, Oh SB (2005) Eugenol inhibits calcium currents in dental afferent neurons. J Dent Res 84:848–851CrossRefGoogle Scholar
  21. 21.
    Li HY, Lee BK, Kim JS, Jung SJ, Oh SB (2008) Eugenol inhibits ATP-induced P2X currents in trigeminal ganglion neurons. Korean J Physiol Pharmacol 12:315–321CrossRefGoogle Scholar
  22. 22.
    Li HY, Park C-K, Jung SJ, Choi S-Y, Lee SJ, Park K, Kim JS, Oh SB (2007) Eugenol inhibits K + currents in trigeminal ganglion neurons. J Dent Res 86:898–902CrossRefGoogle Scholar
  23. 23.
    Clapham DE (2003) TRP channels as cellular sensors. Nature 426:517–524CrossRefGoogle Scholar
  24. 24.
    Szallasi A, Blumberg PM (1999) Vanilloid (Capsaicin) receptors and mechanisms. Pharmacol Rev 51:159–212Google Scholar
  25. 25.
    Ohkubo T, Kitamura K (1997) Eugenol activates Ca(2+)-permeable currents in rat dorsal root ganglion cells. J Dent Res 76:1737–1744CrossRefGoogle Scholar
  26. 26.
    Yang BH, Piao ZG, Kim Y-B, Lee C-H, Lee JK, Park K, Kim JS, Oh SB (2003) Activation of vanilloid receptor 1 (VR1) by eugenol. J Dent Res 82:781–785CrossRefGoogle Scholar
  27. 27.
    Xu H, Delling M, Jun JC, Clapham DE (2006) Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. Nat Neurosci 9:628–635CrossRefGoogle Scholar
  28. 28.
    Anand P, Bley K (2011) Topical capsaicin for pain management: therapeutic potential and mechanisms of action of the new high-concentration capsaicin 8 % patch. Br J Anaesth 107:490–502CrossRefGoogle Scholar
  29. 29.
    Guénette SA, Ross A, Marier J-F, Beaudry F, Vachon P (2007) Pharmacokinetics of eugenol and its effects on thermal hypersensitivity in rats. Eur J Pharmacol 562:60–67CrossRefGoogle Scholar
  30. 30.
    Larsson HP (2010) How is the heart rate regulated in the sinoatrial node? Another piece to the puzzle. J Gen Physiol 136:237–241CrossRefGoogle Scholar
  31. 31.
    Lee DH, Chang L, Sorkin LS, Chaplan SR (2005) Hyperpolarization-activated, cation-nonselective, cyclic nucleotide-modulated channel blockade alleviates mechanical allodynia and suppresses ectopic discharge in spinal nerve ligated rats. J Pain Off J Am Pain Soc 6:417–424CrossRefGoogle Scholar
  32. 32.
    Momin A, Cadiou H, Mason A, McNaughton PA (2008) Role of the hyperpolarization-activated current Ih in somatosensory neurons. J Physiol (Lond) 586:5911–5929CrossRefGoogle Scholar
  33. 33.
    Chaplan SR, Guo H-Q, Lee DH, Luo L, Liu C, Kuei C, Velumian AA, Butler MP, Brown SM, Dubin AE (2003) Neuronal hyperpolarization-activated pacemaker channels drive neuropathic pain. J Neurosci 23:1169–1178Google Scholar
  34. 34.
    Chen CC, Akopian AN, Sivilotti L, Colquhoun D, Burnstock G, Wood JN (1995) A P2X purinoceptor expressed by a subset of sensory neurons. Nature 377:428–431CrossRefGoogle Scholar
  35. 35.
    Lewis C, Neidhart S, Holy C, North RA, Buell G, Surprenant A (1995) Coexpression of P2X2 and P2X3 receptor subunits can account for ATP-gated currents in sensory neurons. Nature 377:432–435CrossRefGoogle Scholar
  36. 36.
    Burnstock G (1996) A unifying purinergic hypothesis for the initiation of pain. Lancet 347:1604–1605CrossRefGoogle Scholar
  37. 37.
    Keene J, Noakes D, Moccia R (1998) The efficacy of clove oil as an anaesthetic for rainbow trout, Oncorhynchus mykiss (Walbaum). Aquacult Res 29(2):89–101Google Scholar
  38. 38.
    Anderson W, McKinley R (1997) The use of clove oil as an anesthetic for rainbow trout and its effects on swimming performance. N Am J Fish Manag 17(2):301–307CrossRefGoogle Scholar
  39. 39.
    Waterstrat P (1999) Induction and recovery from anesthesia in channel catfish Ictalurus punctatus fingerlings exposed to clove oil. J World Aquac Soc 30(2):250–255CrossRefGoogle Scholar
  40. 40.
    Guenette SA, Beaudry F, Marier JF, Vachon P (2006) Pharmacokinetics and anesthetic activity of eugenol in male Sprague-Dawley rats. J Vet Pharmacol Ther 29:265–270CrossRefGoogle Scholar
  41. 41.
    Kozam G (1977) The effect of eugenol on nerve transmission. Oral Surg Oral Med Oral Pathol 44:799–805CrossRefGoogle Scholar
  42. 42.
    Ozeki M (1975) The effects of eugenol on the nerve and muscle in crayfish. Comp Biochem Physiol C Comp Pharmacol 50:183–191Google Scholar
  43. 43.
    Trowbridge H, Edwall L, Panopoulos P (1982) Effect of zinc oxide-eugenol and calcium hydroxide on intradental nerve activity. J Endod 8:403–406CrossRefGoogle Scholar
  44. 44.
    Brodin P, Røed A (1984) Effects of eugenol on rat phrenic nerve and phrenic nerve-diaphragm preparations. Arch Oral Biol 29:611–615CrossRefGoogle Scholar
  45. 45.
    Moreira-Lobo DCA, Linhares-Siqueira ED, Cruz GMP, Cruz JS, Carvalho-de-Souza JL, Lahlou S, Coelho-de-Souza AN, Barbosa R, Magalhães PJC, Leal-Cardoso JH (2010) Eugenol modifies the excitability of rat sciatic nerve and superior cervical ganglion neurons. Neurosci Lett 472:220–224CrossRefGoogle Scholar
  46. 46.
    Brodin P (1985) Differential inhibition of A, B and C fibres in the rat vagus nerve by lidocaine, eugenol and formaldehyde. Arch Oral Biol 30:477–480CrossRefGoogle Scholar
  47. 47.
    Hodgkin AL, Huxley AF (1952) The dual effect of membrane potential on sodium conductance in the giant axon of Loligo. J Physiol (Lond) 116:497–506Google Scholar
  48. 48.
    Cho JS, Kim TH, Lim J-M, Song J-H (2008) Effects of eugenol on Na + currents in rat dorsal root ganglion neurons. Brain Res 1243:53–62CrossRefGoogle Scholar
  49. 49.
    Müller M, Pape H-C, Speckmann E-J, Gorji A (2006) Effect of eugenol on spreading depression and epileptiform discharges in rat neocortical and hippocampal tissues. Neuroscience 140:743–751CrossRefGoogle Scholar
  50. 50.
    Ardjmand A, Fathollahi Y, Sayyah M, Kamalinejad M, Omrani A (2006) Eugenol depresses synaptic transmission but does not prevent the induction of long-term potentiation in the CA1 region of rat hippocampal slices. Phytomedicine 13:146–151CrossRefGoogle Scholar
  51. 51.
    Petersen M, Wagner G, Pierau FK (1989) Modulation of calcium-currents by capsaicin in a subpopulation of sensory neurones of guinea pig. Naunyn Schmiedebergs Arch Pharmacol 339:184–191Google Scholar
  52. 52.
    Bleakman D, Brorson JR, Miller RJ (1990) The effect of capsaicin on voltage-gated calcium currents and calcium signals in cultured dorsal root ganglion cells. Br J Pharmacol 101:423–431CrossRefGoogle Scholar
  53. 53.
    Wie MB, Won MH, Lee KH, Shin JH, Lee JC, Suh HW, Song DK, Kim YH (1997) Eugenol protects neuronal cells from excitotoxic and oxidative injury in primary cortical cultures. Neurosci Lett 225:93–96CrossRefGoogle Scholar
  54. 54.
    Aoshima H, Hamamoto K (1999) Potentiation of GABAA receptors expressed in Xenopus oocytes by perfume and phytoncid. Biosci Biotechnol Biochem 63:743–748CrossRefGoogle Scholar
  55. 55.
    Hashimoto S, Uchiyama K, Maeda M, Ishitsuka K, Furumoto K, Nakamura Y (1988) In vivo and in vitro effects of zinc oxide-eugenol (ZOE) on biosynthesis of cyclo-oxygenase products in rat dental pulp. J Dent Res 67:1092–1096CrossRefGoogle Scholar
  56. 56.
    Lee Y-Y, Hung S-L, Pai S-F, Lee Y-H, Yang S-F (2007) Eugenol suppressed the expression of lipopolysaccharide-induced proinflammatory mediators in human macrophages. J Endod 33:698–702CrossRefGoogle Scholar
  57. 57.
    Yogalakshmi B, Viswanathan P, Anuradha CV (2010) Investigation of antioxidant, anti-inflammatory and DNA-protective properties of eugenol in thioacetamide-induced liver injury in rats. Toxicology 268:204–212CrossRefGoogle Scholar
  58. 58.
    Yoo C-B, Han K-T, Cho K-S, Ha J, Park H-J, Nam J-H, Kil U-H, Lee K-T (2005) Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett 225:41–52CrossRefGoogle Scholar
  59. 59.
    Ogunwande I, Olawore N, Ekundayo O, Walker T, Schmidt J, Setzer W (2005) Studies on the essential oils composition, antibacterial and cytotoxicity of L. Int J Aromather 15:147–152CrossRefGoogle Scholar
  60. 60.
    Tiku AB, Abraham SK, Kale RK (2004) Eugenol as an in vivo radioprotective agent. J Radiat Res 45:435–440CrossRefGoogle Scholar
  61. 61.
    Abraham SK (2001) Anti-genotoxicity of trans-anethole and eugenol in mice. Food Chem Toxicol 39:493–498CrossRefGoogle Scholar
  62. 62.
    Yokota H, Hashimoto H, Motoya M, Yuasa A (1988) Enhancement of UDP-glucuronyltransferase, UDP-glucose dehydrogenase, and glutathione S-transferase activities in rat liver by dietary administration of eugenol. Biochem Pharmacol 37:799–802CrossRefGoogle Scholar
  63. 63.
    Pal D, Banerjee S, Mukherjee S, Roy A, Panda CK, Das S (2010) Eugenol restricts DMBA croton oil induced skin carcinogenesis in mice: downregulation of c-Myc and H-ras, and activation of p53 dependent apoptotic pathway. J Dermatol Sci 59:31–39CrossRefGoogle Scholar
  64. 64.
    Kim BJ, Kim JH, Kim HP, Heo MY (1997) Biological screening of 100 plant extracts for cosmetic use (II): anti-oxidative activity and free radical scavenging activity. Int J Cosmet Sci 19:299–307CrossRefGoogle Scholar
  65. 65.
    Laughton MJ, Halliwell B, Evans PJ, Hoult JR (1989) Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochem Pharmacol 38:2859–2865CrossRefGoogle Scholar
  66. 66.
    Fujisawa S, Atsumi T, Kadoma Y, Sakagami H (2002) Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177:39–54CrossRefGoogle Scholar
  67. 67.
    Jirovetz L, Buchbauer G, Stoilova I, Stoyanova A, Krastanov A, Schmidt E (2006) Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem 54:6303–6307CrossRefGoogle Scholar
  68. 68.
    Kumaravelu P, Dakshinamoorthy DP, Subramaniam S, Devaraj H, Devaraj NS (1995) Effect of eugenol on drug-metabolizing enzymes of carbon tetrachloride-intoxicated rat liver. Biochem Pharmacol 49:1703–1707CrossRefGoogle Scholar
  69. 69.
    Atsumi T, Iwakura I, Fujisawa S (2001) Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH. Biomaterials 22(12):1459–1466, ScienceDirect.com – BiomaterialsCrossRefGoogle Scholar
  70. 70.
    Wright SE, Baron DA, Heffner JE (1995) Intravenous eugenol causes hemorrhagic lung edema in rats: proposed oxidant mechanisms. J Lab Clin Med 125:257–264Google Scholar
  71. 71.
    Suzuki Y, Sugiyama K, Furuta H (1985) Eugenol-mediated superoxide generation and cytotoxicity in guinea pig neutrophils. Jpn J Pharmacol 39:381–386CrossRefGoogle Scholar
  72. 72.
    McDonald JW, Heffner JE (1991) Eugenol causes oxidant-mediated edema in isolated perfused rabbit lungs. Am Rev Respir Dis 143:806–809CrossRefGoogle Scholar
  73. 73.
    Mihara S, Shibamoto T (1982) Photochemical reactions of eugenol and related compounds: synthesis of new flavor chemicals. J Agric Food Chem 30:1215–1218CrossRefGoogle Scholar
  74. 74.
    Larhsini M, Oumoulid L, Lazrek H (2001) Antibacterial activity of some Moroccan medicinal plants. Phytother Res 15(3):250–252CrossRefGoogle Scholar
  75. 75.
    Friedman M, Henika PR, Mandrell RE (2002) Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. J Food Prot 65:1545–1560Google Scholar
  76. 76.
    Feres M, Figueiredo LC, Barreto IMQ, Coelho MHM, Araujo MWB, Cortelli SC (2005) In vitro antimicrobial activity of plant extracts and propolis in saliva samples of healthy and periodontally-involved subjects. J Int Acad Periodontol 7:90–96Google Scholar
  77. 77.
    Cressy HK, Jerrett AR, Osborne CM, Bremer PJ (2003) A novel method for the reduction of numbers of Listeria monocytogenes cells by freezing in combination with an essential oil in bacteriological media. J Food Prot 66:390–395Google Scholar
  78. 78.
    Reinders R (2003) Antibacterial activity of selected plant essential oils against Escherichia coli O157: H7. Lett Appl Microbiol 36(3):162–167CrossRefGoogle Scholar
  79. 79.
    Mytle N, Anderson G, Doyle M (2006) Antimicrobial activity of clove (Syzygium aromaticum) oil in inhibiting Listeria monocytogenes on chicken frankfurters. Food Control 17:102–107CrossRefGoogle Scholar
  80. 80.
    Neely A (2000) Survival of enterococci and staphylococci on hospital fabrics and plastic. J Clin Microbiol 38(2):724–726Google Scholar
  81. 81.
    Zaika L (1988) Spices and herbs: their antimicrobial activity and its determination1. J Food Safety 9(2):97–118Google Scholar
  82. 82.
    Smith-Palmer A, Stewart J (1998) Antimicrobial properties of plant essential oils and essences against five important food-borne pathogens. Lett Appl Microbiol 26(2):118–122CrossRefGoogle Scholar
  83. 83.
    Cai L, Wu CD (1996) Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens. J Nat Prod 59:987–990CrossRefGoogle Scholar
  84. 84.
    Manohar V, Ingram C, Gray J, Talpur NA, Echard BW, Bagchi D, Preuss HG (2001) Antifungal activities of origanum oil against Candida albicans. Mol Cell Biochem 228:111–117CrossRefGoogle Scholar
  85. 85.
    Tampieri MP, Galuppi R, Macchioni F, Carelle MS, Falcioni L, Cioni PL, Morelli I (2005) The inhibition of Candida albicans by selected essential oils and their major components. Mycopathologia 159:339–345CrossRefGoogle Scholar
  86. 86.
    Velluti A, Sanchis V, Ramos AJ, Turon C, Marín S (2004) Impact of essential oils on growth rate, zearalenone and deoxynivalenol production by Fusarium graminearum under different temperature and water activity conditions in maize grain. J Appl Microbiol 96:716–724CrossRefGoogle Scholar
  87. 87.
    López P, Sánchez C, Batlle R, Nerín C (2005) Solid- and vapor-phase antimicrobial activities of six essential oils: susceptibility of selected foodborne bacterial and fungal strains. J Agric Food Chem 53:6939–6946CrossRefGoogle Scholar
  88. 88.
    Pawar VC, Thaker VS (2006) In vitro efficacy of 75 essential oils against Aspergillus niger. Mycoses 49:316–323CrossRefGoogle Scholar
  89. 89.
    Cox SD, Mann CM, Markham JL (2001) Interactions between components of the essential oil of Melaleuca alternifolia. J Appl Microbiol 91:492–497CrossRefGoogle Scholar
  90. 90.
    Hussein G, Miyashiro H, Nakamura N, Hattori M, Kakiuchi N, Shimotohno K (2000) Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. Phytother Res 14:510–516CrossRefGoogle Scholar
  91. 91.
    Su C-Y, Menuz K, Carlson JR (2009) Olfactory perception: receptors, cells, and circuits. Cell 139:45–59CrossRefGoogle Scholar
  92. 92.
    Kajiya K, Inaki K, Tanaka M, Haga T, Kataoka H, Touhara K (2001) Molecular bases of odor discrimination: reconstitution of olfactory receptors that recognize overlapping sets of odorants. J Neurosci 21:6018–6025Google Scholar
  93. 93.
    Koch G, Magnusson B, Nyquist G (1971) Contact allergy to medicaments and materials used in dentistry. II. Sensitivity to eugenol and colophony. Odontol Revy 22:275–289Google Scholar
  94. 94.
    Koch G, Magnusson B, Nobréus N, Nyquist G, Söderholm G (1973) Contact allergy to medicaments and materials used in dentistry. IV. Sensitizing effect of eugenol-colophony in surgical dressing. Odontol Revy 24:109–114Google Scholar
  95. 95.
    Hensten-Pettersen A, Orstavik D, Wennberg A (1985) Allergenic potential of root canal sealers. Endod Dent Traumatol 1:61–65CrossRefGoogle Scholar
  96. 96.
    Vilaplana J, Grimalt F, Romaguera C, Conellana F (1991) Contact dermatitis from eugenol in mouthwash. Contact Dermat 24:223–224CrossRefGoogle Scholar
  97. 97.
    Barkin ME, Boyd JP, Cohen S (1984) Acute allergic reaction to eugenol. Oral Surg Oral Med Oral Pathol 57:441–442CrossRefGoogle Scholar
  98. 98.
    McCarter RF (1966) An unusual allergy. Midwest Dent 42:20Google Scholar
  99. 99.
    Buckley DA, Basketter DA, Smith Pease CK, Rycroft RJG, White IR, McFadden JP (2006) Simultaneous sensitivity to fragrances. Br J Dermatol 154:885–888CrossRefGoogle Scholar
  100. 100.
    Marie Api A, Belsito D, Bickers D, Bruze M, Calow P, Greim H, Hanifin JM, McNamee PM, Rogers AE, Saurat J-H, Sipes IG, Tagami H (2010) Quantitative risk assessment of contact sensitization: clinical data to assess utility of the model. Dermatitis 21:207–213Google Scholar
  101. 101.
    Basketter DA, Pons-Guiraud A, van Asten A, Laverdet C, Marty J-P, Martin L, Berthod D, Siest S, Giordano-Labadie F, Tennstedt D, Baeck M, Vigan M, Lainé G, Le Coz CJ, Jacobs M-C, Bayrou O, Germaux M-A (2010) Fragrance allergy: assessing the safety of washed fabrics. Contact Derm 62:349–354CrossRefGoogle Scholar
  102. 102.
    White JML, White IR, Glendinning A, Fleming J, Jefferies D, Basketter DA, McFadden JP, Buckley DA (2007) Frequency of allergic contact dermatitis to isoeugenol is increasing: a review of 3636 patients tested from 2001 to 2005. Br J Dermatol 157:580–582CrossRefGoogle Scholar
  103. 103.
    Alpar B, Günay H, Geurtsen W, Leyhausen G (1999) Cytocompatibility of periodontal dressing materials in fibroblast and primary human osteoblast-like cultures. Clin Oral Investig 3:41–48CrossRefGoogle Scholar
  104. 104.
    Lindqvist L, Otteskog P (1980) Eugenol: liberation from dental materials and effect on human diploid fibroblast cells. Scand J Dent Res 88:552–556Google Scholar
  105. 105.
    Kozam G, Mantell GM (1978) The effect of eugenol on oral mucous membranes. J Dent Res 57:954–957CrossRefGoogle Scholar
  106. 106.
    Hume WR (1984) An analysis of the release and the diffusion through dentin of eugenol from zinc oxide-eugenol mixtures. J Dent Res 63:881–884CrossRefGoogle Scholar
  107. 107.
    El Hag EA, El Nadi AH, Zaitoon AA (1999) Toxic and growth retarding effects of three plant extracts on Culex pipiens larvae (Diptera: Culicidae). Phytother Res 13:388–392CrossRefGoogle Scholar
  108. 108.
    Trongtokit Y, Rongsriyam Y, Komalamisra N, Apiwathnasorn C (2005) Comparative repellency of 38 essential oils against mosquito bites. Phytother Res 19:303–309CrossRefGoogle Scholar
  109. 109.
    Yang Y-C, Lee S-H, Lee W-J, Choi D-H, Ahn Y-J (2003) Ovicidal and adulticidal effects of Eugenia caryophyllata bud and leaf oil compounds on Pediculus capitis. J Agric Food Chem 51:4884–4888CrossRefGoogle Scholar
  110. 110.
    Ho S, Cheng L, Sim K (1994) Potential of cloves Syzygium aromaticum(L.) Merr. and Perry as a grain protectant against Tribolium castaneum(Herbst) and Sitophilus zeamais. Postharvest Biol Technol 4(1–2):179–183CrossRefGoogle Scholar
  111. 111.
    Kim E-H, Kim H-K, Ahn Y-J (2003) Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). J Agric Food Chem 51:885–889CrossRefGoogle Scholar
  112. 112.
    Perrucci S, Macchioni G, Cioni PL, Flamini G, Morelli I (1995) Structure/activity relationship of some natural monoterpenes as acaricides against Psoroptes cuniculi. J Nat Prod 58:1261–1264CrossRefGoogle Scholar
  113. 113.
    Park I-K, Shin S-C (2005) Fumigant activity of plant essential oils and components from garlic (Allium sativum) and clove bud (Eugenia caryophyllata) oils against the Japanese termite (Reticulitermes speratus Kolbe). J Agric Food Chem 53:4388–4392CrossRefGoogle Scholar
  114. 114.
    O’Brien DJ (1999) Treatment of psoroptic mange with reference to epidemiology and history. Vet Parasitol 83:177–185CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.National Research Laboratory for Pain, Dental Research Institute and Department of Neurobiology and Physiology, School of Dentistry, Seoul National UniversitySeoulKorea

Personalised recommendations