1,8-Cineol inhibits nuclear translocation of NF-κB p65 and NF-κB-dependent transcriptional activity

Biochimica et Biophysica Acta - Molecular Cell Research

Volumn 1833, Issue 12, 2013, Pages 2866-2878

  Greiner, Johannes F W ^a   Müller, Janine ^a   Zeuner, Marie Theres ^a   Hauser, Stefan ^a   Seidel, Thorsten ^a,c   Klenke, Christin ^b   Grunwald, Lena Marie ^a   Schomann, Timo ^a   Widera, Darius ^a   Sudhoff, Holger ^b   Kaltschmidt, Barbara ^a   Kaltschmidt, Christian ^a  

^a BIELEFELD UNIVERSITY   (Germany)

^b Kopf und Halschirurgie Klinikum Bielefeld   (Germany)

^c GEOPHYSICAL LABORATORY   (United States)

Author keywords

1,8 Cineol; Human cell lines; Inflammation; Inflammatory diseases; NF B; PBMCs

Indexed keywords

CINEOLE; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE P38; STRESS ACTIVATED PROTEIN KINASE 1; TRANSCRIPTION FACTOR RELA;

ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; FLUORESCENCE RESONANCE ENERGY TRANSFER; HELA CELL; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IMMUNOCYTOCHEMISTRY; PERIPHERAL BLOOD MONONUCLEAR CELL; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; QUANTITATIVE ANALYSIS; WESTERN BLOTTING;

EID: 84882772281     PISSN: 01674889     EISSN: 18792596     Source Type: Journal    
DOI: 10.1016/j.bbamcr.2013.07.001     Document Type: Article

References (73)

1. Balunas M.J., Kinghorn A.D. Drug discovery from medicinal plants. Life Sci. 2005, 78:431-441.
2. Juergens U.R., Dethlefsen U., Steinkamp G., Gillissen A., Repges R., Vetter H. Anti-inflammatory activity of 1.8-cineol (eucalyptol) in bronchial asthma: a double-blind placebo-controlled trial. Respir. Med. 2003, 97:250-256.
3. Yuan G., Wahlqvist M.L., He G., Yang M., Li D. Natural products and anti-inflammatory activity. Asia Pac. J. Clin. Nutr. 2006, 15:143-152.
4. McGilevery C., Reed J. Aroma Therapy 1993, Ultimate Editions, London.
5. Zhou J.Y., Wang X.F., Tang F.D., Lu G.H., Wang Y., Bian R.L. Inhibitory effect of 1,8-cineol (eucalyptol) on Egr-1 expression in lipopolysaccharide-stimulated THP-1 cells. Acta Pharmacol. Sin. 2007, 28:908-912.
6. Worth H., Schacher C., Dethlefsen U. Concomitant therapy with cineole (eucalyptole) reduces exacerbations in COPD: a placebo-controlled double-blind trial. Respir. Res. 2009, 10:69.
7. Cloez M.S. Étude chimique de l'eucalyptol. Comptes Rendus 1870, 70:687-690.
8. Kovar K.A., Gropper B., Friess D., Ammon H.P. Blood levels of 1,8-cineole and locomotor activity of mice after inhalation and oral administration of rosemary oil. Planta Med. 1987, 53:315-318.
9. Andrade-Neto M., Alencar J.W., Cunha A.H., Silveira E.R. Volatile constituents of Psidium pohlianum Berg, and Psidium guyanensis Pers. J. Essent. Oil Res. 1994, 6:299-300.
10. Leão Lana E.J., da Silva Rocha K.A., Kozhevnikov I.V., Gusevskaya E.V. Synthesis of 1,8-cineole and 1,4-cineole by isomerization of α-terpineol catalyzed by heteropoly acid. J. Mol. Catal. A Chem. 2006, 259:99-102.
11. Santos F.A., Rao V.S. Antiinflammatory and antinociceptive effects of 1,8-cineole a terpenoid oxide present in many plant essential oils. Phytother. Res. 2000, 14:240-244.
12. Abdon A.P., Leal-Cardoso J.H., Coelho-de-Souza A.N., Morais S.M., Santos C.F. Antinociceptive effects of the essential oil of Croton nepetaefolius on mice. Braz. J. Med. Biol. Res. 2002, 35:1215-1219.
13. Santos F.A., Rao V.S. 1,8-Cineol, a food flavoring agent, prevents ethanol-induced gastric injury in rats. Dig. Dis. Sci. 2001, 46:331-337.
14. Santos F.A., Silva R.M., Tome A.R., Rao V.S., Pompeu M.M., Teixeira M.J., De Freitas L.A., De Souza V.L. 1,8-Cineole protects against liver failure in an in-vivo murine model of endotoxemic shock. J. Pharm. Pharmacol. 2001, 53:505-511.
15. Santos F.A., Silva R.M., Campos A.R., De Araujo R.P., Lima Junior R.C., Rao V.S. 1,8-Cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis. Food Chem. Toxicol. 2004, 42:579-584.
16. Inoue K., Takano H., Shiga A., Fujita Y., Makino H., Yanagisawa R., Ichinose T., Kato Y., Yamada T., Yoshikawa T. Effects of volatile constituents of a rosemary extract on allergic airway inflammation related to house dust mite allergen in mice. Int. J. Mol. Med. 2005, 16:315-319.
17. Mulyaningsih S., Sporer F., Reichling J., Wink M. Antibacterial activity of essential oils from eucalyptus and of selected components against multidrug-resistant bacterial pathogens. Pharm. Biol. 2011, 49:893-899.
18. Djenane D., Yanguela J., Amrouche T., Boubrit S., Boussad N., Roncales P. Chemical composition and antimicrobial effects of essential oils of Eucalyptus globulus, Myrtus communis and Satureja hortensis against Escherichia coli O157:H7 and Staphylococcus aureus in minced beef. Food Sci. Technol. Int. 2011, 17:505-515.
19. Juergens U.R., Stober M., Vetter H. Inhibition of cytokine production and arachidonic acid metabolism by eucalyptol (1.8-cineole) in human blood monocytes in vitro. Eur. J. Med. Res. 1998, 3:508-510.
20. Bastos V.P., Gomes A.S., Lima F.J., Brito T.S., Soares P.M., Pinho J.P., Silva C.S., Santos A.A., Souza M.H., Magalhaes P.J. Inhaled 1,8-cineole reduces inflammatory parameters in airways of ovalbumin-challenged Guinea pigs. Basic Clin. Pharmacol. Toxicol. 2011, 108:34-39.
21. Salminen A., Lehtonen M., Suuronen T., Kaarniranta K., Huuskonen J. Terpenoids: natural inhibitors of NF-kappaB signaling with anti-inflammatory and anticancer potential. Cell. Mol. Life Sci. 2008, 65:2979-2999.
22. Jeong H.J., Koo H.N., Na H.J., Kim M.S., Hong S.H., Eom J.W., Kim K.S., Shin T.Y., Kim H.M. Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells. Cytokine 2002, 18:252-259.
23. Kim S.W., Choi S.C., Choi E.Y., Kim K.S., Oh J.M., Lee H.J., Oh H.M., Kim S., Oh B.S., Kimm K.C., Lee M.H., Seo G.S., Kim T.H., Oh H.C., Woo W.H., Kim Y.S., Pae H.O., Park D.S., Chung H.T., Jun C.D. Catalposide, a compound isolated from catalpa ovata, attenuates induction of intestinal epithelial proinflammatory gene expression and reduces the severity of trinitrobenzene sulfonic acid-induced colitis in mice. Inflamm. Bowel Dis. 2004, 10:564-572.
24. Koo H.J., Song Y.S., Kim H.J., Lee Y.H., Hong S.M., Kim S.J., Kim B.C., Jin C., Lim C.J., Park E.H. Antiinflammatory effects of genipin, an active principle of gardenia. Eur. J. Pharmacol. 2004, 495:201-208.
25. Ichida M., Finkel T. Ras regulates NFAT3 activity in cardiac myocytes. J. Biol. Chem. 2001, 276:3524-3530.
26. Bachelerie F., Alcami J., Arenzana-Seisdedos F., Virelizier J.L. HIV enhancer activity perpetuated by NF-kappa B induction on infection of monocytes. Nature 1991, 350:709-712.
27. Schneider C.A., Rasband W.S., Eliceiri K.W. NIH Image to ImageJ: 25years of image analysis. Nat. Methods 2012, 9:671-675.
28. Wolf A., Akrap N., Marg B., Galliardt H., Heiligentag M., Humpert F., Sauer M., Kaltschmidt B., Kaltschmidt C., Seidel T. Elements of transcriptional machinery are compatible among plants and mammals. PLoS One 2013, 8:e53737.
29. Schmitz M.L., Baeuerle P.A. The p65 subunit is responsible for the strong transcription activating potential of NF-kappa B. EMBO J. 1991, 10:3805-3817.
30. Barnes P.J., Karin M. Nuclear factor-kappaB: a pivotal transcription factor in chronic inflammatory diseases. N. Engl. J. Med. 1997, 336:1066-1071.
31. Baldwin A.J. The NF-kappa B and I kappa B proteins: new discoveries and insights. Annu. Rev. Immunol. 1996, 14:649-683.
32. Kanno T., Franzoso G., Siebenlist U. Human T-cell leukemia virus type I Tax-protein-mediated activation of NF-kappa B from p100 (NF-kappa B2)-inhibited cytoplasmic reservoirs. Proc. Natl. Acad. Sci. U. S. A. 1994, 91:12634-12638.
33. Sen R., Baltimore D. Inducibility of kappa immunoglobulin enhancer-binding protein Nf-kappa B by a posttranslational mechanism. Cell 1986, 47:921-928.
34. Poltorak A., He X., Smirnova I., Liu M.Y., Van Huffel C., Du X., Birdwell D., Alejos E., Silva M., Galanos C., Freudenberg M., Ricciardi-Castagnoli P., Layton B., Beutler B. Defective LPS signaling in C3H/HeJ and C57BL/10ScCr mice: mutations in Tlr4 gene. Science 1998, 282:2085-2088.
35. Akira S., Takeda K. Toll-like receptor signalling. Nat. Rev. Immunol. 2004, 4:499-511.
36. Aupperle K.R., Bennett B.L., Boyle D.L., Tak P.P., Manning A.M., Firestein G.S. NF-kappa B regulation by I kappa B kinase in primary fibroblast-like synoviocytes. J. Immunol. 1999, 163:427-433.
37. Marok R., Winyard P.G., Coumbe A., Kus M.L., Gaffney K., Blades S., Mapp P.I., Morris C.J., Blake D.R., Kaltschmidt C., Baeuerle P.A. Activation of the transcription factor nuclear factor-kappaB in human inflamed synovial tissue. Arthritis Rheum. 1996, 39:583-591.
38. Lawrence T., Gilroy D.W., Colville-Nash P.R., Willoughby D.A. Possible new role for NF-kappaB in the resolution of inflammation. Nat. Med. 2001, 7:1291-1297.
39. Tak P.P., Firestein G.S. NF-kappaB: a key role in inflammatory diseases. J. Clin. Invest. 2001, 107:7-11.
40. Gasparini C., Feldmann M. NF-kappaB as a target for modulating inflammatory responses. Curr. Pharm. Des. 2012, 18:5735-5745.
41. Widera D., Mikenberg I., Elvers M., Kaltschmidt C., Kaltschmidt B. Tumor necrosis factor alpha triggers proliferation of adult neural stem cells via IKK/NF-kappaB signaling. BMC Neurosci. 2006, 7:64.
42. Widera D., Kaus A., Kaltschmidt C., Kaltschmidt B. Neural stem cells, inflammation and NF-kappaB: basic principle of maintenance and repair or origin of brain tumours?. J. Cell. Mol. Med. 2008, 12:459-470.
43. Ngkelo A., Meja K., Yeadon M., Adcock I., Kirkham P.A. LPS induced inflammatory responses in human peripheral blood mononuclear cells is mediated through NOX4 and Gialpha dependent PI-3kinase signalling. J. Inflamm. (Lond.) 2012, 9:1.
44. Chun E., Lee S.H., Lee S.Y., Shim E.J., Cho S.H., Min K.U., Kim Y.Y., Park H.W. Toll-like receptor expression on peripheral blood mononuclear cells in asthmatics; implications for asthma management. J. Clin. Immunol. 2010, 30:459-464.
45. Lieb K., Kaltschmidt C., Kaltschmidt B., Baeuerle P.A., Berger M., Bauer J., Fiebich B.L. Interleukin-1 beta uses common and distinct signaling pathways for induction of the interleukin-6 and tumor necrosis factor alpha genes in the human astrocytoma cell line U373. J. Neurochem. 1996, 66:1496-1503.
46. Lieb K., Fiebich B.L., Schaller H., Berger M., Bauer J. Interleukin-1 beta and tumor necrosis factor-alpha induce expression of alpha 1-antichymotrypsin in human astrocytoma cells by activation of nuclear factor-kappa B. J. Neurochem. 1996, 67:2039-2044.
47. Kutuk O., Basaga H. Aspirin prevents apoptosis and NF-kappaB activation induced by H2O2 in hela cells. Free Radic. Res. 2003, 37:1267-1276.
48. Schwamborn J., Lindecke A., Elvers M., Horejschi V., Kerick M., Rafigh M., Pfeiffer J., Prullage M., Kaltschmidt B., Kaltschmidt C. Microarray analysis of tumor necrosis factor alpha induced gene expression in U373 human glioblastoma cells. BMC Genomics 2003, 4:46.
49. Dvorak Z., Vrzal R., Maurel P., Ulrichova J. Differential effects of selected natural compounds with anti-inflammatory activity on the glucocorticoid receptor and NF-kappaB in HeLa cells. Chem. Biol. Interact. 2006, 159:117-128.
50. Carpenter S., Wochal P., Dunne A., O'Neill L.A. Toll-like receptor 3 (TLR3) signaling requires TLR4 Interactor with leucine-rich REPeats (TRIL). J. Biol. Chem. 2011, 286:38795-38804.
51. McCoy C.E., Carpenter S., Palsson-McDermott E.M., Gearing L.J., O'Neill L.A. Glucocorticoids inhibit IRF3 phosphorylation in response to Toll-like receptor-3 and -4 by targeting TBK1 activation. J. Biol. Chem. 2008, 283:14277-14285.
52. Werner J., Decarlo C.A., Escott N., Zehbe I., Ulanova M. Expression of integrins and Toll-like receptors in cervical cancer: effect of infectious agents. Innate Immun. 2012, 18:55-69.
53. Chang J.H., Park J.Y., Kim S.K. Dependence on p38 MAPK signalling in the up-regulation of TLR2, TLR4 and TLR9 gene expression in Trichomonas vaginalis-treated HeLa cells. Immunology 2006, 118:164-170.
54. Wyllie D.H., Kiss-Toth E., Visintin A., Smith S.C., Boussouf S., Segal D.M., Duff G.W., Dower S.K. Evidence for an accessory protein function for Toll-like receptor 1 in anti-bacterial responses. J. Immunol. 2000, 165:7125-7132.
55. Visintin A., Halmen K.A., Khan N., Monks B.G., Golenbock D.T., Lien E. MD-2 expression is not required for cell surface targeting of Toll-like receptor 4 (TLR4). J. Leukoc. Biol. 2006, 80:1584-1592.
56. Nagai Y., Akashi S., Nagafuku M., Ogata M., Iwakura Y., Akira S., Kitamura T., Kosugi A., Kimoto M., Miyake K. Essential role of MD-2 in LPS responsiveness and TLR4 distribution. Nat. Immunol. 2002, 3:667-672.
57. Yoo C.G., Lee S., Lee C.T., Kim Y.W., Han S.K., Shim Y.S. Effect of acetylsalicylic acid on endogenous I kappa B kinase activity in lung epithelial cells. Am. J. Physiol. Lung Cell. Mol. Physiol. 2001, 280:L3-L9.
58. Hehner S.P., Heinrich M., Bork P.M., Vogt M., Ratter F., Lehmann V., Schulze-Osthoff K., Droge W., Schmitz M.L. Sesquiterpene lactones specifically inhibit activation of NF-kappa B by preventing the degradation of I kappa B-alpha and I kappa B-beta. J. Biol. Chem. 1998, 273:1288-1297.
59. Bork P.M., Bacher S., Schmitz M.L., Kaspers U., Heinrich M. Hypericin as a non-antioxidant inhibitor of NF-kappa B. Planta Med. 1999, 65:297-300.
60. Calzado M.A., Ludi K.S., Fiebich B., Ben-Neriah Y., Bacher S., Munoz E., Ballero M., Prosperini S., Appendino G., Schmitz M.L. Inhibition of NF-kappaB activation and expression of inflammatory mediators by polyacetylene spiroketals from Plagius flosculosus. Biochim. Biophys. Acta 2005, 1729:88-93.
61. Moussaieff A., Shohami E., Kashman Y., Fride E., Schmitz M.L., Renner F., Fiebich B.L., Munoz E., Ben-Neriah Y., Mechoulam R. Incensole acetate, a novel anti-inflammatory compound isolated from Boswellia resin, inhibits nuclear factor-kappa B activation. Mol. Pharmacol. 2007, 72:1657-1664.
62. Riehemann K., Behnke B., Schulze-Osthoff K. Plant extracts from stinging nettle (Urtica dioica), an antirheumatic remedy, inhibit the proinflammatory transcription factor NF-kappaB. FEBS Lett. 1999, 442:89-94.
63. Zhou J.Y., Tang F.D., Mao G.G., Bian R.L. Effect of alpha-pinene on nuclear translocation of NF-kappa B in THP-1 cells. Acta Pharmacol. Sin. 2004, 25:480-484.
64. Galvez M., Martin-Cordero C., Ayuso M.J. Iridoids as DNA topoisomerase I poisons. J. Enzyme Inhib. Med. Chem. 2005, 20:389-392.
65. Berchtold C.M., Chen K.S., Miyamoto S., Gould M.N. Perillyl alcohol inhibits a calcium-dependent constitutive nuclear factor-kappaB pathway. Cancer Res. 2005, 65:8558-8566.
66. Juergens U.R., Engelen T., Racke K., Stober M., Gillissen A., Vetter H. Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Pulm. Pharmacol. Ther. 2004, 17:281-287.
67. Trinh H.T., Lee I.A., Hyun Y.J., Kim D.H. Artemisia princeps Pamp. Essential oil and its constituents eucalyptol and alpha-terpineol ameliorate bacterial vaginosis and vulvovaginal candidiasis in mice by inhibiting bacterial growth and NF-kappaB activation. Planta Med. 2011, 77:1996-2002.
68. Lima P.R., de Melo T.S., Carvalho K.M., de Oliveira I.B., Arruda B.R., de Castro Brito G.A., Rao V.S., Santos F.A. 1,8-cineole (eucalyptol) ameliorates cerulein-induced acute pancreatitis via modulation of cytokines, oxidative stress and NF-kappaB activity in mice. Life Sci. 2013, 92:1195-1201.
69. Moteki H., Hibasami H., Yamada Y., Katsuzaki H., Imai K., Komiya T. Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line. Oncol. Rep. 2002, 9:757-760.
70. Bellas R.E., Lee J.S., Sonenshein G.E. Expression of a constitutive NF-kappa B-like activity is essential for proliferation of cultured bovine vascular smooth muscle cells. J. Clin. Invest. 1995, 96:2521-2527.
71. Brantley D.M., Chen C.L., Muraoka R.S., Bushdid P.B., Bradberry J.L., Kittrell F., Medina D., Matrisian L.M., Kerr L.D., Yull F.E. Nuclear factor-kappaB (NF-kappaB) regulates proliferation and branching in mouse mammary epithelium. Mol. Biol. Cell 2001, 12:1445-1455.
72. Bharti A.C., Donato N., Singh S., Aggarwal B.B. Curcumin (diferuloylmethane) down-regulates the constitutive activation of nuclear factor-kappa B and IkappaBalpha kinase in human multiple myeloma cells, leading to suppression of proliferation and induction of apoptosis. Blood 2003, 101:1053-1062.
73. Biswas D.K., Shi Q., Baily S., Strickland I., Ghosh S., Pardee A.B., Iglehart J.D. NF-kappa B activation in human breast cancer specimens and its role in cell proliferation and apoptosis. Proc. Natl. Acad. Sci. U. S. A. 2004, 101:10137-10142.