Inflammation Research

, Volume 44, Issue 9, pp 372–375 | Cite as

Effects of indole-3-acetic acid on croton oil- and arachidonic acid-induced mouse ear edema

  • L. H. Jones
  • D. S. P. Abdalla
  • J. C. Freitas
Original Research Papers

Abstract

The indole-3-acetic acid (IAA) is a plant growth hormone (auxin) being considered as a tryptophan metabolite in animals. The main purpose of this work was to verify IAA's topical anti-inflammatory action using croton oil- or arachidonic acid-induced mouse ear edema, in comparison to known anti-inflammatory agents. IAA antioxidant activity was also verified by measuring the inhibition of brain homogenate lipid peroxidation with the thiobarbituric acid reactive substances (TBARS) test. IAA inhibited the action of both croton oil- and arachidonic acid-induced edema in a dose-dependent manner (4.0 µmoles IAA inhibited 75.8% in croton oil and 82.5% in arachidonic acid induced ear edema). Both IAA (5.3 mM) and indomethacin (8.0 mM) inhibited TBARS formation. Data suggest that IAA exhibits antiinflammatory effect possibly by its antioxidant activity.

Keywords

Indole-3-acetic acid Mouse ear edema Antioxidants Croton oil Arachidonic acid 

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References

  1. [1]
    Artígas FC, Martinez E, Tusell JM, Sunol C, Gelpì E. On the metabolic origin of plasmatic indole-3-acetic acid in the rat. Biochem Pharmacol 1983;32:3251–4.Google Scholar
  2. [2]
    Mills MH, Finlay DC, Haddad PR. Determination of melatonin and monoamines in rat pineal using reverse-phase ion-interaction chromatography with fluorescence detection. J Chromatogr 1991;564:93–102.Google Scholar
  3. [3]
    Kogl F, Haagen-smit AJ, Erxleben H. Vegetable growth substances. XII. The occurrence of auxins in the human and animal organism. Z Physiol Chem 1933;220:137–61.Google Scholar
  4. [4]
    Kogl F, Haagen-smit AJ, Erxleben H. Plant growth substances. XI. A new auxin (“heteroauxin”) from urine. Z Physiol Chem 1934a;228:90–105.Google Scholar
  5. [5]
    Martinez E, Artigas F, Sunol C, Tusell JM, Gelpì E. Liquid-chromatographic determination of indole-3-acetic acid and 5-hydroxyindolil-3-acetic acid in human plasma. Clin Chem 1983;29:1354–57.Google Scholar
  6. [6]
    Warsh JJ, Chan PW, Godse DD, Coscina DV, Stancer HC. Gas chromatography-mass fragmentographic determination of indole-3-acetic acid in rat brain. J Neurochem 1977;29:955–58.Google Scholar
  7. [7]
    Tussell JM, Artigas F, Sunol C, Martinez E, Gelpi E. Comparison of high-performance liquid chromatography and gas chromatography-mass spectrometry for the analysis of indole-3-acetic acid in brain tissue. J Chromatogr 1984;306:338–44.Google Scholar
  8. [8]
    Bertilsson L, Palmér L. Indole-3-acetic acid in human cerebrospinal fluid: identification and quantification by mass fragmentography. Science 1972;117:74–6.Google Scholar
  9. [9]
    Young SN, Anderson GM, Purdy WC. Indoleamine metabolism in rat brain studied through measurements of tryptophan, 5-hydroxyindoleacetic acid, and indoleacetic acid in cerebrospinal fluid. J Neurochem 1980a;34:309–15.Google Scholar
  10. [10]
    Young SN, Anderson GM, Gauthier S, Purdy WC. The origin of indoleacetic acid and indolepropionic acid in rat and human cerebrospinal fluid. J Neurochem 1980b;34:1087–92.Google Scholar
  11. [11]
    Gordon SA, Buess E. Observations on the physiology and radiation response of auxin formation by animal tissues. Ann NY Acad Sci 1967;144:136–45.Google Scholar
  12. [12]
    Ichimura H, Yamaki T. Indole-3-acetic acid in animal embryos. Sci Pap Coll Gen Educ Univ Tokyo (Biol) 1975;25:43–8Google Scholar
  13. [13]
    Weissbach H, King W, Sjoerdsma A, Udenfriend S. Formation of indole-3-acetic acid and tryptamine in animals. A method for estimation of indole-3-acetic acid in tissues. J Biol Chem 1959;234:81–6.Google Scholar
  14. [14]
    Cadenas E, Simic MG, Sies H. Antioxidant activity of 5-hydroxytryptophan, 5-hydroxyindole, and dopa against microsomal lipid peroxidation and its dependence on vitamin E. Free Rad Res Commun 1989;6:11–17.Google Scholar
  15. [15]
    Christen S, Peterhans E, Stocker R. Antioxidant activities of some tryptophan metabolites: possible implication for inflammatory diseases. Proc Natl Acad Sci 1990;87:2506–10.Google Scholar
  16. [16]
    Northover BJ. The action of anti-inflammatory compounds in mice with peritonitis. J Pathol Bacterial 1964;87:395–404.Google Scholar
  17. [17]
    Giusti P, Carrara M, Cima L, Borin G. Antinociceptive effect of some carboxypeptidase a inhibitors in comparison with d-phenylalanine. Eur J Pharmacol 1985;116:287–92.Google Scholar
  18. [18]
    Therman E, Seppala M. Indole-3-acetic acid as protective substance against X-rays. Physiol Plant 1959;12:716–9.Google Scholar
  19. [19]
    White RH. Indole-3-acetic acid and 2-(indol-3-ylmethyl)indol-3-yl acetic acid in the thermophilic archaebacteriumSulfolobus acidocaldarius J Bacterial 1987;169:5859–60.Google Scholar
  20. [20]
    Simchowitz L, Mehta J, Spilberg I. Chemotatic factor-induced generation of superoxide radicals by human neutrophils. Arthritis Rheum 1979;22:755–63.Google Scholar
  21. [21]
    Van Zyl A, Louw A. Inhibition of peroxidase activity by some non-steroidal anti-inflammatory drugs. Biochem Pharmacol 1979;28:2753–9.Google Scholar
  22. [22]
    Bonta IL, Parnham MJ, Biol MI, Vincent JE, Bragt PC. Antirheumatic drugs: present deadlock and new vistas. Progress Med Chem 1980;17:231–2.Google Scholar
  23. [23]
    Pekoe G, Van Dyke K, Peden D, Mengoli H, English D. Antioxidation theory of non-steroidal anti-inflammatory drugs based upon the inhibition of luminol-enhanced chemiluminescence from the myeloperoxidase reaction. Agents Action 1982;12:371–6.Google Scholar
  24. [24]
    Aruoma OI, Halliwell B. The iron-binding and hydroxyl radical scavenging action of anti-inflammatory drugs. Xenobiot 1988;18:459–70.Google Scholar
  25. [25]
    Sagar PS, Das UN, Koratkar R, Ramesh G, Padma M, Kumar GS. Cytotoxic action of cis-unsaturated fatty acids on human cervical carcinoma (HeLa) cells: relationship to free radicals and lipid peroxidation and its modulation by calmodulin antagonists. Cancer Lett 1992;63:189–98.Google Scholar
  26. [26]
    Kohn HI, Liversedge M. On a new aerobic metabolite whose production by brain is inhibited by apomorphine, emetine, ergotamine, epinephrine and menadione. J Pharmacol Exp Ther 1944;82:292–300.Google Scholar
  27. [27]
    Winterbourn CC, Gutteridge JM, Halliwell B. Doxorubicin-dependent lipid peroxidation at low partial pressures of O2. J Free Radical Biol Med 1985;1:43–9.Google Scholar
  28. [28]
    Bresnick E, Bailey G, Bonney RJ, Wighiman P. Phospholipase activity in skin after application of phorbol esters and 3-methylcholanthrene. Carcinogen 1981;2:1119–22.Google Scholar
  29. [29]
    Kondoh H, Sato Y, Kanoh H. Arachidonic acid metabolism in cultured mouse keratinocytes. J Invest Dermatol 1985;85:64–9.Google Scholar
  30. [30]
    McColl SR, Hurst NP, Cleland LG. Modulation by phorbol myristate acetate of arachidonic acid release and leukotriene synthesis by human polymorphonuclear leukocytes stimulated withA23187. Biochem Biophys Res Commun 1986;141:399–404.Google Scholar
  31. [31]
    Ashendel GL, Boutwell RK. Prostaglandin E and F levels in mouse epidermis are increased by tumour promoting phorbol esters. Biochem Biophys Res Commun 1979;90:623–7.Google Scholar
  32. [32]
    Furstenberger G, Marks F. Early prostaglandin E synthesis is an obligatory event in the induction of cell proliferation in mouse epidermis in vivo by phorbol ester TPA. Biochem Biophys Res Commun 1980;92:749–56.Google Scholar
  33. [33]
    Inoue H, Mori T, Shibata S, Koshihara Y. Modulation by glycyrrhetinic acid derivatives of TPA-induced mouse ear oedema. Br J Pharmacol 1989;96:204–10.Google Scholar
  34. [34]
    Tonelli G, Thibault L, Ringler I. A bio-assay for the concomitant assessment of the antiphlogistic and thymolytic activities of topically applied corticoids. Endocrinol 1965;77:625–34.Google Scholar
  35. [35]
    Bird J, Kim HP, Lee HJ. Topical anti-inflammatory activity of esters of steroid 21-oic acids. Steroids 1986;47:35–40.Google Scholar
  36. [36]
    Freitas JC, Blankeimeir LA, Jacobs RS. In vitro inactivation of the neurotoxic action of beta-bungarotoxin for marine natural product, manoalide. Experientia 1984;40:864–5.Google Scholar
  37. [37]
    Van Arman CG. Anti-inflammatory drugs. Clin Pharmacol Ther 1974;16:900–4.Google Scholar
  38. [38]
    Swingle KF, Reiter MJ, Schwartzmiller DH. Comparison of croton oil and cantharidin induced inflammations of the mouse ear and their modification by topically applied drugs. Arch Int Pharmacodyn 1981;254:168–78.Google Scholar
  39. [39]
    Tubaro A, Dri P, Melato M, Mulas G, Bianchi P, Del Negro P, Della Loggia R. In the croton oil ear test the effects of non steroidal antiinflammatory drugs (NSAIDs) are dependent on the dose of the irritant. Agents Actions 1986;19:371–3.Google Scholar
  40. [40]
    Griffiths RJ, Wood BE, Ll S, Blackham A. Pharmacological modification of 12-o-tetradecanoylphorbol-13-acetate induced inflammation and epidermal cell proliferation in mouse skin. Agents Actions 1988;25:344–51.Google Scholar
  41. [41]
    Young JM, Wagner BM, Spires DA. Tachyphylaxis in 12-o-tetradecanoyl phorbol acetate and arachidonic acid-induced ear edema. J Invest Dermatol 1983;80:48–52.Google Scholar
  42. [42]
    Blackham A, Griffiths RJ, Hallam C, Mann J, Mitchell PD, Norris AA, et al. FPL 62064, a topically active 5-lipoxygenase/cyclooxygenase inhibitor. Agents Actions 1990;30:432–42.Google Scholar
  43. [43]
    Milne MD, Crawford MA, Girão CB, Loughridge L. The excretion of indolylacetic acid and related indolic acids in man and the rat. Clin Sci 1960;19:165–79.Google Scholar
  44. [44]
    Erspamer V. Observations on the fate of indolalkylamines in the organism. J Physiol 1955;127:118–33.Google Scholar
  45. [45]
    Gordon SA, Fry RJM, Barr S. Origin of urinary auxin in the germfree and conventional mouse. Am J Physiol 1972;222:399–403.Google Scholar
  46. [46]
    Opas EE, Bonney RJ, Humes JL. Prostaglandin and leukotriene synthesis in mouse ears inflamed by arachidonic acid. J Invest Dermatol 1985;84:253–6.Google Scholar
  47. [47]
    Carlson RP, O'Neill-Davis L, Chang J, Lewis AJ. Modulation of mouse ear edema by cyclooxygenase and lipoxygenase inhibitors and other pharmacologic agents. Agents Actions 1985;17:197–204.Google Scholar
  48. [48]
    Pignat W, Kienzle R, Bottcher I. How specific is the arachidonic acid-induced mouse ear oedema for lipoxigenase (LO)- and cyclooxigenase (CO)-inhibitors? Agents Actions 1986;19:368–70.Google Scholar
  49. [49]
    Crummey A, Herper GP, Boyle EA, Mengan FR. Inhibition of arachidonic acid-induced ear oedema as a model for assessing topical anti-inflammatory compounds. Agents Actions 1987;20:69–76.Google Scholar
  50. [50]
    Emerit I, Levy A, Cerutti P. Suppression of tumor promoter phorbolymristate acetate-induced chromosome breakage by antioxidants and inhibitors of arachidonic acid metabolism. Mutat Res 1983;110:327–35.Google Scholar
  51. [51]
    Kamimura M. Antiinflammatory activity of vitamin E. J Vitaminol 1972;18:204–9.Google Scholar
  52. [52]
    Nakadate T, Yamamoto S, Aizu E, Kato R. Effects of flavonoids and antioxidants on 12-o-tetradecanoyl-phorbol-13-acetate-caused epidermal ornithine decarboxylase induction and tumor promotion in relation to lipoxygenase inhibition by these compounds. GANN 1984;75:214–22.Google Scholar
  53. [53]
    Levy L. The antiinflammatory action of some compounds with antioxidant properties. Inflamm 1976;1:333–45.Google Scholar
  54. [54]
    Niki E, Takahashi M, Komuro E. Antioxidant activity of vitamin E in lipossomal membrane. Chem Lett 1986;9:1573–6.Google Scholar
  55. [55]
    Palozza P, Krinsky NI. The inhibition of radical-initiated peroxidation of microsomal lipids by both a-tocopherol and b-carotene. Free Radical Biol & Med 1991;11:407–14.Google Scholar
  56. [56]
    Pulla Reddy AC, Lokesh BR. Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat liver microsomes. Moll Cell Biochem 1992;111:117–24.Google Scholar
  57. [57]
    Emerit I, Cerutti PA. Tumour promoter phorbol-12-myristate-13-acetate induces chromosomal damage via indirect action. Nature 1981;293:144–6.Google Scholar
  58. [58]
    Birnboim HC. Factors which affect DNA strand breakage in human leucocytes exposed to a tumor promoter, phorbol myristate acetate. Can J Physiol Pharmacol 1982;60:1359–66.Google Scholar

Copyright information

© Birkhäuser Verlag 1995

Authors and Affiliations

  • L. H. Jones
    • 1
  • D. S. P. Abdalla
    • 2
  • J. C. Freitas
    • 1
  1. 1.Department of Physiology, Biosciences InstituteUniversity of São Paulo, Rua do MatãoSão PauloBrazil
  2. 2.Department of Clinical and Toxicological Analyses, Pharmaceutical Sciences FacultyUniversity of São PauloBrazil

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