Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 39, 2009 - Issue 9
294
Views
11
CrossRef citations to date
0
Altmetric
Research Article

Cytochrome P450-catalysed arene-epoxidation of the bioactive tea tree oil ingredient p-cymene: indication for the formation of a reactive allergenic intermediate?

, &
Pages 663-671 | Received 22 Feb 2009, Accepted 22 Apr 2009, Published online: 29 May 2009

References

  • Aberer W. (2008). Contact allergy and medicinal herbs. J Ger Soc Dermatol 6:15–24.
  • Apted JH. (1991). Contact dermatitis associated with the use of tea-tree oil. Aust J Dermatol 32:177.
  • Baron JM, Merk HF. (2001). Drug metabolism in the skin. Curr Opin Allerg Clin Immunol 1:287–91.
  • Bhushan M, Beck MH. (1997). Allergic contact dermatitis from tea tree oil in a wart paint. Contact Dermat 36:117–18.
  • Bylund J, Kunz T, Valmsen K, Oliw EH. (1998). Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther 284:51–60.
  • Carson CF, Hammer KA, Riley TV. (2006). Melaleuca alternifolia (tea tree) oil: a review of antimicrobial and other medicinal properties. Clin Microbiol Rev 19:50–62.
  • Carson CF, Riley TV. (2001). Safety, efficacy and provenance of tea tree (Melaleuca alternifolia) oil. Contact Dermat 45:65–7.
  • Chorianopoulos N, Kalpoutzakis E, Aligiannis N, Mitaku S, Nychas GJ, Haroutounian SA. (2004). Essential oils of Satureja, Origanum, and Thymus species: chemical composition and antibacterial activities against foodborne pathogens. J Agricult Food Chem 52:8261–7.
  • Duisken M, Benz D, Peiffer TH, Blomeke B, Hollender J. (2005a). Metabolism of Delta(3)-carene by human cytochrome p450 enzymes: identification and characterization of two new metabolites. Curr Drug Metab 6:593–601.
  • Duisken M, Sandner F, Blomeke B, Hollender J. (2005b). Metabolism of 1,8-cineole by human cytochrome P450 enzymes: identification of a new hydroxylated metabolite. Biochim Biophys Acta Gen Subj 1722:304–11.
  • Edris AE. (2007). Pharmaceutical and therapeutic potentials of essential oils and their individual volatile constituents: a review. Phytother Res 21:308–23.
  • Goeptar AR, Scheerens H, Vermeulen NP. 1995. Oxygen and xenobiotic reductase activities of cytochrome P450. Crit Rev Toxicol 25:25–65.
  • Guengerich FP. (2003). Cytochrome P450 oxidations in the generation of reactive electrophiles: epoxidation and related reactions. Arch Biochem Biophys 409:59–71.
  • Hammer KA, Carson CF, Riley TV. (2003). Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil. J Appl Microbiol 95:853–60.
  • Hammer KA, Carson CF, Riley TV, Nielsen JB. (2006). A review of the toxicity of Melaleuca alternifolia (tea tree) oil. Food Chem Toxicol 44:616–25.
  • Hausen BM, Reichling J, Harkenthal M. (1999). Degradation products of monoterpenes are the sensitizing agents in tea tree oil. Am J Contact Dermat 10:68–77.
  • International Organisation for Standardisation (ISO) (1996). ISO 4730: Oil of melaleuca, terpinen-4-ol type (tea tree oil). Geneva: International Organisation for Standardisation.
  • Ishida T, Asakawa Y, Takemoto T, Aratani T. (1981). Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J Pharmaceut Sci 70:406–15.
  • Jappe U, Schnuch A, Uter W. (2005). Rosacea and contact allergy to cosmetics and topical medicaments — retrospective analysis of multicentre surveillance data 1995–2002. Contact Dermat 52:96–101.
  • Johansson S, Gimenez-Arnau E, Grotli M, Karlberg AT, Borje A. (2008). Carbon- and oxygen-centered radicals are equally important haptens of allylic hydroperoxides in allergic contact dermatitis. Chem Res Toxicol 21:1536–47.
  • Kleiner SM. (1995). The true nature of herbs. Phys Sportsmed 23:13–14.
  • Knight TE, Hausen BM. (1994). Melaleuca oil (tea tree oil) dermatitis. J Am Acad Dermatol 30:423–7.
  • Larsen W, Nakayama H, Fischer T, Elsner P, Frosch P, Burrows D, Jordan W, Shaw S, Wilkinson J, Marks J, Jr., Sugawara M, Nethercott M, Nethercott J. (2001). Fragrance contact dermatitis: a worldwide multicenter investigation (Part II). Contact Dermat 44:344–6.
  • Matsumoto T, Ishida T, Yoshida T, Terao H, Takeda Y, Asakawa Y. (1992). The enantioselective metabolism of p-cymene in rabbits. Chem Pharmaceut Bull 40:1721–6.
  • Meesters RJ, Duisken M, Hollender J. (2007). Study on the cytochrome P450-mediated oxidative metabolism of the terpene alcohol linalool: indication of biological epoxidation. Xenobiotica 37:604–17.
  • Meesters RJ, Duisken M, Jahnigen H, Hollender J. (2008). Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates. J Chromatograph B Analyt Tech Biomed Life Sci 875:444–50.
  • Miyazawa M, Shindo M. (2001). Biotransformation of 1,8-cineole by human liver microsomes. Natural Prod Lett 15:49–53.
  • Murray M, Reidy GF. (1990). Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents. Pharmacol Rev 42:85–101.
  • Nilsson AM, Gafvert E, Salvador L, Luthman K, Bruze M, Gruvberger B, Nilsson JL, Karlberg AT. (2001). Mechanism of the antigen formation of carvone and related alpha, beta-unsaturated ketones. Contact Dermat 44:347–56.
  • Nostro A, Blanco AR, Cannatelli MA, Enea V, Flamini G, Morelli I, Sudano Roccaro A, Alonzo V. (2004). Susceptibility of methicillin-resistant staphylococci to oregano essential oil, carvacrol and thymol. FEMS Microbiol Lett 230:191–5.
  • Papadopoulos CJ, Carson CF, Hammer KA, Riley TV. (2006). Susceptibility of pseudomonads to Melaleuca alternifolia (tea tree) oil and components. J Antimicrob Chemother 58:449–51.
  • Rastogi SC, Heydorn S, Johansen JD, Basketter DA. (2001). Fragrance chemicals in domestic and occupational products. Contact Dermat 45:221–5.
  • Rubel DM, Freeman S, Southwell IA. (1998). Tea tree oil allergy: what is the offending agent? Report of three cases of tea tree oil allergy and review of the literature. Australasian J Dermatol 39:244–7.
  • Rutherford T, Nixon R, Tam M, Tate B. (2007). Allergy to tea tree oil: retrospective review of 41 cases with positive patch tests over 4.5 years. Australasian J Dermatol 48:83–7.
  • Schelz Z, Molnar J, Hohmann J. (2006). Antimicrobial and antiplasmid activities of essential oils. Fitoterapia 77:279–85.
  • Skold M, Borje A, Harambasic E, Karlberg AT. (2004). Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization. Chem Res Toxicol 17:1697–705.
  • Southwell IA, Flynn TM, Degabriele R. (1980). Metabolism of alpha- and beta-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula. Xenobiotica 10:17–23.
  • Thomson KF, Wilkinson SM. (2000). Allergic contact dermatitis to plant extracts in patients with cosmetic dermatitis. Br J Dermatol 142:84–8.
  • Valero M, Salmeron MC. (2003). Antibacterial activity of 11 essential oils against Bacillus cereus in tyndallized carrot broth. Int J Food Microbiol 85:73–81.
  • Walde A, Ve B, Scheline RR, Monge P. (1983). p-Cymene metabolism in rats and guinea-pigs. Xenobiotica 13:503–12.
  • Woolf A. 1999. Essential oil poisoning. J Toxicol Clin Toxicol 37:721–7.
  • Wrighton SA, Brian WR, Sari MA, Iwasaki M, Guengerich FP, Raucy JL, Molowa DT, Vandenbranden M. (1990). Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol Pharmacol 38:207–13.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.