Monoterpenes Isolated from Minthostachys verticillata (Griseb.) Epling Essential Oil Modulates Immediate-Type Hypersensitivity Responses In Vitro and In Vivo

Abstract

In a previous work, we have demonstrated that Minthostachys verticillata essential oil has immunomodulatory effects in vitro on cells from allergic patients. Here we characterized main components of M. verticillata essential oil and also tested if these compounds modulate in vitro and in vivo the immediate-type allergic reaction.

Gas chromatography was used to identify main components of the essential oil. Pulegone (63.4 %), menthone (15.9 %), and limonene (2.1 %) were found as main classes. IL-13 levels were evaluated from lymphocytes cultures stimulated with allergen alone or combined with monoterpenes. All compounds stimulated cell proliferation but, interestingly, promoted a reduction of IL-13 values, limonene and the mixture of the three compounds being the most active. β-Hexosaminidase release was determined from basophils to which essential oil or monoterpenes were added. We observed that, whichever combination of monoterpenes was used, β-hexosaminidase release was diminished in all cases. Obtained values were even lower than those of antiallergic drug desloratadine. Essential oil and limonene inhibited mast cell activation and degranulation in the skin when testing passive cutaneous anaphylaxis, limonene being the most active.

In conclusion, limonene was the compound that showed the most potent immunomodulatory activity. This fact suggests that it constitutes a promising natural alternative for a novel treatment of allergic diseases.

Minthostachys verticillata - Lamiaceae - essential oil - monoterpenes - immediate-type allergicreaction

References

• 1 Pettipher R. The roles of the prostaglandin D2 receptors DP1 and CRTH2 in promoting allergic responses.  Br J Pharmacol. 2008;  153 191-199
• 2 Schwartz L B, Lewis R A, Seldin D, Austen K F. Acid hydrolases and tryptase from secretory granules of dispersed human lung mast cells.  J Immunol. 1981;  4 1290-1294
• 3 Schroeder J T, MacGlashan Jr. D W, Lichtenstein L M. Human basophils: mediator release and cytokine production.  Adv Immunol. 2001;  77 93-122
• 4 Gauchat J F, Henchoz S, Mazzei G. Induction of human IgE synthesis in B cells by mast cells and basophils.  Nature. 1993;  365 340-343
• 5 Barnes P J. Allergy Review Series VII: Intracellular signaling and regulation of allergic reactions. Molecular mechanisms of corticosteroids in allergic diseases.  Allergy. 2001;  56 928-936
• 6 Winiski A, Wang S, Schwendinger B, Stuetz A. Inhibition of T-cell activation in vitro in human peripheral blood mononuclear cells by pimecrolimus and glucocorticosteroids and combinations thereof.  Exp Dermatol. 2007;  16 699-704
• 7 De Feo V. Medicinal and magical plants in the northern Peruvian Andes.  Fitoterapia. 1992;  63 417-440
• 8 Primo V, Rovera M, Zanón S, Oliva M, Demo M, Daghero J, Sabini L. Determinación de la actividad antibacteriana y antiviral del aceite esencial de Minthostachys verticillata (Griseb.) Epling.  Rev Argentina Microbiol. 2001;  33 113-117
• 9 Cariddi L N, Panero A, Demo M S, Grosso M, Zygadlo J, Sabini L I, Maldonado A M. Inhibition of immediate-type allergic reaction by Minthostachys verticillata (Griseb.) Epling essential oil.  J Essent Oil Res. 2007;  19 190-196
• 10 Cariddi L, Moser M, Andrada M C, Demo M S, Zygadlo J A, Sabini L I, Maldonado A M. The effect of Minthostachys verticillata essential oil on the immune response of patients allergic to dust mites.  BLACPMA. 2009;  8 224-233
• 11 Senatore F. Volatile constituents of Minthostachys setosa (Briq.) Epling. (Lamiaceae) from Perú.  Flavour Fragr J. 1998;  13 263-265
• 12 Zygadlo J, Maestri D, Lamarque A, Guzmán C, Velasco-Negueruela A, Pérez-Alonso M, García-Vallejos M, Grosso N. Essential oil variability of Minthostachys verticillata.  Biochem Syst Ecol. 1996;  24 319-323
• 13 Julius M, Simpson E, Herzemberg L. A rapid method for the isolation of functional thymus-derived murine lymphocytes.  Eur J Immunol. 1973;  3 645-649
• 14 Tuchscherer M, Kanitz E, Otten W, Tuchscherer A. Effects of prenatal stress on cellular and humoral immune responses in neonatal pigs.  Vet Immunol Immunopathol. 2002;  86 195-203
• 15 Ly N P, Li Y, Sredl D L, Perkins D L, Finn P W, Weiss S T, Gold D R. Elevated allergen-induced IL-13 secretion predicts IgE elevation in children ages 2–5 years.  J Clin Immunol. 2005;  25 314-319
• 16 Grinstein M, Simkin G, Alonso M R, Helvani R, Mathov E. Test de degranulación de basófilos humanos como un método in vitro para el diagnóstico y prevención de reacciones adversas a drogas.  Rev Argentina Astma Alergia Inmunol. 1986;  3 765-786
• 17 Shibata H, Yagi T. Rate assay of N-acetyl-β-D-hexosaminidase with 4-nitrophenyl N-acetyl-beta-D-glucosaminide as an artificial substrate.  Clin Chim Acta. 1996;  251 53-64
• 18 Na H J, Jeong H J, Bae J, Kim Y B, Park S T, Yun Y G, Kim H M. Tongkyutang inhibits mast cell-dependent allergic reactions and inflammatory cytokines secretion.  Clin Chim Acta. 2002;  319 35-41
• 19 Lindner I, Meier C, Url A, Unger H, Grassauer A, Prieschl-Grassauer E, Doerfler P. Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation.  BMC Immunology. advance online publication 21 May 2010 ;  DOI: 10.1186/1471-2172-11-24
• 20 Dalle Carbonare M, Del Giudice E, Stecca A, Colavito D, Fabris M, D'Arrigo A, Bernardini D, Dam M, Leon A. A saturated N-acylethanolamine other than N-palmitoyl ethanolamine with anti-inflammatory properties: a neglected story.  J Neuroendocrinol. 2008;  20 26-34
• 21 Katayama S, Shionoya H, Ohtake S. New method for extraction of extravasated dye in the skin and the influence of fasting stress on passive cutaneous anaphylaxis in guinea pigs and rats.  Microbiol Immunol. 1978;  22 89-101
• 22 De Feo V, Ricciardi A, Biscardi D, Senatore F. Chemical composition and antimicrobial screening of the essential oil of Minthostachys verticillata (Griseb.) Eppl. Lamiaceae.  J Essent Oil Res. 1998;  10 61-65
• 23 Fish S C, Donaldson D D, Goldman S J, Williams C M, Kasaian M T. IgE generation and mast cell effector function in mice deficient in IL-4 and IL-13.  J Immunol. 2005;  74 7716-7724
• 24 Zhao Y, Yang J, Gao Y D, Guo W. Th17 immunity in patients with allergic asthma.  Int Arch Allergy Immunol. 2010;  151 297-307
• 25 Ko E, Rho S, Lee E, Seo Y, Cho C, Lee Y, Min B, Shin M, Hong M, Bae H. Traditional Korean medicine (SCRT) modulate Th1/Th2 specific cytokine production in mice CD4+ T cell.  J Ethnopharmacol. 2004;  92 121-128
• 26 Yoshikawa M, Nakamura S, Kato Y, Matsuhira K, Matsuda H. Medicinal flowers. XIV. New acylated oleanane-type triterpene oligoglycosides with antiallergic activity from flower buds of chinese tea plant (Camellia sinensis).  Chem Pharm Bull. 2007;  55 598-605
• 27 Rafias S, Pascual-Pascual M, Martínez-Granero I, Pascual-Castroviejo L. Efecto de los corticoides en el tratamiento de la distrofia muscular de Duchenne.  An Pediatr. 2002;  57 518-523
• 28 Hirota R, Roger N, Nakamura H, Song H S, Sawamura M, Suganuma N. Anti-inflammatory effects of limonene from yuzu (Citrus junos Tanaka) essential oil on eosinophils.  J Food Sci. 2010;  75 87-92
• 29 Yoon W, Lee N, Hyun C. Limonene suppresses lipopolisacharides-induced production of nitric oxide, prostaglandin E₂ and pro-inflammatory cytokines in RAW 264.7 macrophages.  J Oleo Sci. 2010;  59 415-421
• 30 Keinan E, Alt A, Amir G, Bentur L, Bibi H, Shoseyov D. Natural ozone scavenger prevents asthma in sensitized rats.  Bioorg Med Chem. 2005;  13 557-562
• 31 Rabi T, Bishayee A. d-Limonene sensitizes docetaxel-induced cytotoxicity in human prostate cancer cells: Generation of reactive oxygen species and induction of apoptosis.  J Carcinogen. 2009;  8 1-9
• 32 Sun J. D-limonene: safety and clinical applications.  Altern Med Rev. 2007;  12 259-264