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Evidence-Based Complementary and Alternative Medicine
Volume 2012, Article ID 908562, 12 pages
http://dx.doi.org/10.1155/2012/908562
Research Article

Hesperidin-3′-O-Methylether Is More Potent than Hesperidin in Phosphodiesterase Inhibition and Suppression of Ovalbumin-Induced Airway Hyperresponsiveness

1School of Respiratory Therapy, College of Medicine, Taipei Medical University, Taipei 110, Taiwan
2Department of Otolaryngology, Taipei Medical University Hospital, Taipei 110, Taiwan
3Department of Dermatology, Taipei Medical University Hospital, Taipei 110, Taiwan
4Department of Pharmacology, College of Medicine, Taipei Medical University, Taipei 110, Taiwan
5Department of Medical Technology, College of Medicine, Taipei Medical University, Taipei 110, Taiwan

Received 18 May 2012; Accepted 27 August 2012

Academic Editor: Wagner Vilegas

Copyright © 2012 You-Lan Yang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. M. E. Lee, J. Markowitz, J. O. Lee, and H. Lee, “Crystal structure of phosphodiesterase 4D and inhibitor complex,” FEBS Letters, vol. 530, no. 1–3, pp. 53–58, 2002. View at Publisher · View at Google Scholar · View at Scopus
  2. T. J. Torphy and L. B. Cieslinski, “Characterization and selective inhibition of cyclic nucleotide phosphodiesterase isozymes in canine tracheal smooth muscle,” Molecular Pharmacology, vol. 37, no. 2, pp. 206–214, 1990. View at Google Scholar · View at Scopus
  3. Z. Kapui, P. Schaeffer, E. G. Mikus et al., “Experimental studies on guanosine 3',5'-cyclic monophosphate levels and airway responsiveness of the novel phosphodiesterase type 5 inhibitor SR 265579 in guinea-pigs,” Arzneimittel-Forschung/Drug Research, vol. 49, no. 8, pp. 685–693, 1999. View at Google Scholar · View at Scopus
  4. J. de Boer, A. J. Philpott, R. G. M. Van Amsterdam, M. Shahid, J. Zaagsma, and C. D. Nicholson, “Human bronchial cyclic nucleotide phosphodiesterase isoenzymes: biochemical and pharmacological analysis using selective inhibitors,” British Journal of Pharmacology, vol. 106, no. 4, pp. 1028–1034, 1992. View at Google Scholar · View at Scopus
  5. P. J. Silver, L. T. Hamel, M. H. Perrone, R. G. Bentley, C. R. Bushover, and D. B. Evans, “Differential pharmacologic sensitivity of cyclic nucleotide phosphodiesterase isozymes isolated from cardiac muscle, arterial and airway smooth muscle,” European Journal of Pharmacology, vol. 150, no. 1-2, pp. 85–94, 1988. View at Google Scholar · View at Scopus
  6. E. Kim, H. O. Chun, S. H. Jung et al., “Improvement of therapeutic index of phosphodiesterase type IV inhibitors as anti-asthmatics,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 14, pp. 2355–2358, 2003. View at Publisher · View at Google Scholar · View at Scopus
  7. M. A. Giembycz, “Phosphodiesterase 4 inhibitors and the treatment of asthma: where are we now and where do we go from here?” Drugs, vol. 59, no. 2, pp. 193–212, 2000. View at Google Scholar · View at Scopus
  8. A. Robichaud, C. Savoie, P. B. Stamatiou et al., “Assessing the emetic potential of PDE4 inhibitors in rats,” British Journal of Pharmacology, vol. 135, no. 1, pp. 113–118, 2002. View at Google Scholar · View at Scopus
  9. A. Robichaud, P. B. Stamatiou, S. L. C. Jin et al., “Deletion of phosphodiesterase 4D in mice shortens α2-adrenoceptor-mediated anesthesia, a behavioral correlate of emesis,” Journal of Clinical Investigation, vol. 110, no. 7, pp. 1045–1052, 2002. View at Publisher · View at Google Scholar · View at Scopus
  10. W. C. Ko, C. M. Shih, Y. H. Lai, J. H. Chen, and H. L. Huang, “Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships,” Biochemical Pharmacology, vol. 68, no. 10, pp. 2087–2094, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. P. Knekt, J. Kumpulainen, R. Järvinen et al., “Flavonoid intake and risk of chronic diseases,” American Journal of Clinical Nutrition, vol. 76, no. 3, pp. 560–568, 2002. View at Google Scholar · View at Scopus
  12. K. Y. Yen, Pharmacology of Common Chinese Medicine (III), National Research Institute of Chinese Medicine, Taipei, Taiwan, 1971.
  13. D. Wei, X. Ci, X. Chu, M. Wei, S. Hua, and X. Deng, “Hesperidin suppresses ovalbumin-induced airway inflammation in a mouse allergic asthma model,” Inflammation, pp. 1–8, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. W. C. Ko, M. C. Chen, S. H. Wang, Y. H. Lai, J. H. Chen, and C. N. Lin, “3-O-methylquercetin more selectively inhibits phosphodiesterase subtype 3,” Planta Medica, vol. 69, no. 4, pp. 310–315, 2003. View at Publisher · View at Google Scholar · View at Scopus
  15. W. J. Thompson and M. M. Appleman, “Multiple cyclic nucleotide phosphodiesterase activities from rat brain,” Biochemistry, vol. 10, no. 2, pp. 311–316, 1971. View at Google Scholar · View at Scopus
  16. H. S. Ahn, W. Crim, M. Romano, E. Sybertz, and B. Pitts, “Effects of selective inhibitors on cyclic nucleotide phosphodiesterase of rabbit aorta,” Biochemical Pharmacology, vol. 38, no. 19, pp. 3331–3339, 1989. View at Publisher · View at Google Scholar · View at Scopus
  17. T. Podzuweit, P. Nennstiel, and A. Muller, “Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine,” Cellular Signalling, vol. 7, no. 7, pp. 733–738, 1995. View at Publisher · View at Google Scholar · View at Scopus
  18. S. A. Harrison, D. H. Reifsnyder, and B. Gallis, “Isolation and characterization of bovine cardiac muscle cGMP-inhibited phosphodiesterase: a receptor for new cardiotonic drugs,” Molecular Pharmacology, vol. 29, no. 5, pp. 506–514, 1986. View at Google Scholar · View at Scopus
  19. M. L. Reeves, B. K. Leigh, and P. J. England, “The identification of a new cyclic nucleotide phosphodiesterase activity in human and guinea-pig cardiac ventricle. Implications for the mechanism of action of selective phosphodiesterase inhibitors,” Biochemical Journal, vol. 241, no. 2, pp. 535–541, 1987. View at Google Scholar · View at Scopus
  20. P. G. Gillespie and J. A. Beavo, “Inhibition and stimulation of photoreceptor phosphodiesterases by dipyridamole and M and B 22,948,” Molecular Pharmacology, vol. 36, no. 5, pp. 773–781, 1989. View at Google Scholar · View at Scopus
  21. H. H. Schneider, R. Schmiechen, M. Brezinski, and J. Seidler, “Stereospecific binding of the antidepressant rolipram to brain protein structures,” European Journal of Pharmacology, vol. 127, no. 1-2, pp. 105–115, 1986. View at Google Scholar · View at Scopus
  22. Y. Zhao, H. T. Zhang, and J. M. O'Donnell, “Inhibitor binding to type 4 phosphodiesterase (PDE4) assessed using [3H]piclamilast and [3H]rolipram,” Journal of Pharmacology and Experimental Therapeutics, vol. 305, no. 2, pp. 565–572, 2003. View at Publisher · View at Google Scholar · View at Scopus
  23. A. Kanehiro, T. Ikemura, M. J. Mäkelä et al., “Inhibition of phosphodiesterase 4 attenuates airway hyperresponsiveness and airway inflammation in a model of secondary allergen challenge,” American Journal of Respiratory and Critical Care Medicine, vol. 163, no. 1, pp. 173–184, 2001. View at Google Scholar · View at Scopus
  24. E. Hamelmann, J. Schwarze, K. Takeda et al., “Noninvasive measurement of airway responsiveness in allergic mice using barometric plethysmography,” American Journal of Respiratory and Critical Care Medicine, vol. 156, no. 3, pp. 766–775, 1997. View at Google Scholar · View at Scopus
  25. G. E. Winterrowd and J. E. Chin, “Flow cytometric detection of antigen-specific cytokine responses in lung T cells in a murine model of pulmonary inflammation,” Journal of Immunological Methods, vol. 226, no. 1-2, pp. 105–118, 1999. View at Publisher · View at Google Scholar · View at Scopus
  26. B. N. Melgert, D. S. Postma, M. Geerlings et al., “Short-term smoke exposure attenuates ovalbumin-induced airway inflammation in allergic mice,” American Journal of Respiratory Cell and Molecular Biology, vol. 30, no. 6, pp. 880–885, 2004. View at Publisher · View at Google Scholar · View at Scopus
  27. W. W. Busse and R. F. Lemanske, “Asthma,” New England Journal of Medicine, vol. 344, no. 5, pp. 350–362, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. H. Revets, G. Pynaert, J. Grooten, and P. De Baetselier, “Lipoprotein I, a TLR2/4 ligand modulates Th2-driven allergic immune responses,” Journal of Immunology, vol. 174, no. 2, pp. 1097–1103, 2005. View at Google Scholar · View at Scopus
  29. A. Vojdani and J. Erde, “Regulatory T cells, a potent immunoregulatory target for CAM researchers: the ultimate antagonist (I),” Evidence-based Complementary and Alternative Medicine, vol. 3, no. 1, pp. 25–30, 2006. View at Publisher · View at Google Scholar · View at Scopus
  30. D. J. Cher and T. R. Mosmann, “Two types of murine helper T cell clone. II. Delayed-type hypersensitivity is mediated by Th1 clones,” Journal of Immunology, vol. 138, no. 11, pp. 3688–3694, 1987. View at Google Scholar · View at Scopus
  31. V. D. Bokkenheuser, C. H. L. Shackleton, and J. Winter, “Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans,” Biochemical Journal, vol. 248, no. 3, pp. 953–956, 1987. View at Google Scholar · View at Scopus
  32. Y. L. Yang, H. T. Hsu, K. H. Wang et al., “Hesperetin-7,3'-O-dimethylether selectively inhibits phosphodiesterase 4 and effectively suppresses ovalbumin-induced airway hyperresponsiveness with a high therapeutic ratio,” Journal of Biomedical Science, vol. 18, no. 1, p. 84, 2011. View at Publisher · View at Google Scholar
  33. S. Y. Namgoong, K. H. Son, H. W. Chang, S. S. Kang, and H. P. Kim, “Effects of naturally occurring flavonoids on mitogen-induced lymphocyte proliferation and mixed lymphocyte culture,” Life Sciences, vol. 54, no. 5, pp. 313–320, 1994. View at Publisher · View at Google Scholar · View at Scopus
  34. C. Taube, C. Duez, Z. H. Cui et al., “The role of IL-13 in established allergic airway disease,” Journal of Immunology, vol. 169, no. 11, pp. 6482–6489, 2002. View at Google Scholar · View at Scopus
  35. B. B. Vargaftig and M. Singer, “Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13,” American Journal of Respiratory Cell and Molecular Biology, vol. 28, no. 4, pp. 410–419, 2003. View at Publisher · View at Google Scholar · View at Scopus
  36. J. Tucker, C. H. Fanta et al., “Integrative inflammation pharmacology: asthma,” in Principles of Pharmacology the Pathophysiologic Basis of Drug Therapy, D. E. Golan, Ed., pp. 695–705, Lippincott Williams & Wilkins, Philadelphia, Pa, USA, 2005. View at Google Scholar
  37. P. S. Foster, S. P. Hogan, A. J. Ramsay, K. I. Matthaei, and I. G. Young, “Interleukin 5 deficiency abolishes eosinophilia, airways hyperreactivity, and lung damage in a mouse asthma model,” Journal of Experimental Medicine, vol. 183, no. 1, pp. 195–201, 1996. View at Publisher · View at Google Scholar · View at Scopus
  38. E. Clayton, G. Bardi, S. E. Bell et al., “A crucial role for the p110δ subunit of phosphatidylinositol 3-kinase in B cell development and activation,” Journal of Experimental Medicine, vol. 196, no. 6, pp. 753–763, 2002. View at Publisher · View at Google Scholar · View at Scopus
  39. K. Okkenhaug, A. Bilancio, G. Farjot et al., “Impaired B and T cell antigen receptor signaling in p110δ PI 3-kinase mutant mice,” Science, vol. 297, no. 5583, pp. 1031–1034, 2002. View at Publisher · View at Google Scholar · View at Scopus
  40. K. S. Lee, H. K. Lee, J. S. Hayflick, Y. C. Lee, and K. D. Puri, “Inhibition of phosphoinositide 3-kinase δ attenuates allergic airway inflammation and hyperresponsiveness in murine asthma model,” FASEB Journal, vol. 20, no. 3, pp. 455–465, 2006. View at Publisher · View at Google Scholar · View at Scopus
  41. C. L. Emson, S. E. Bell, A. Jones, W. Wisden, and A. N. J. McKenzie, “Interleukin (IL)-4-independent induction of immunoglobulin (Ig)E, and perturbation of T cell development in transgenic mice expressing IL-13,” Journal of Experimental Medicine, vol. 188, no. 2, pp. 399–404, 1998. View at Publisher · View at Google Scholar · View at Scopus
  42. C. M. Snapper, K. B. Marcu, and P. Zelazowski, “The immunoglobulin class switch: beyond 'accessibility',” Immunity, vol. 6, no. 3, pp. 217–223, 1997. View at Publisher · View at Google Scholar · View at Scopus
  43. J. Stavnezer, “Molecular processes that regulate class switching,” Current Topics in Microbiology and Immunology, vol. 245, pp. 127–168, 1999. View at Google Scholar · View at Scopus
  44. J. J. Haddad, S. C. Land, W. O. Tarnow-Mordi, M. Zembala, D. Kowalczyk, and R. Lauterbach, “Immunopharmacological potential of selective phosphodiesterase inhibition. I. Differential regulation of lipopolysaccharide-mediated proinflammatory cytokine (interleukin-6 and tumor necrosis factor-α) biosynthesis in alveolar epithelial cells,” Journal of Pharmacology and Experimental Therapeutics, vol. 300, no. 2, pp. 559–566, 2002. View at Google Scholar
  45. J. J. Haddad, S. C. Land, W. O. Tarnow-Mordi, M. Zembala, D. Kowalczyk, and R. Lauterbach, “Immunopharmacological potential of selective phosphodiesterase inhibition. II. Evidence for the involvement of an inhibitory-κB/nuclear factor-κB-sensitive pathway in alveolar epithelial cells,” Journal of Pharmacology and Experimental Therapeutics, vol. 300, no. 2, pp. 567–576, 2002. View at Publisher · View at Google Scholar · View at Scopus
  46. D. P. Westfall, W. T. Gerthoffer, and R. C. Webb, “Vasodilators and nitric oxide synthasein,” in Human Pharmacology Molecular to Clinical, T. M. Brody, J. Larner, and K. P. Minneman, Eds., pp. 239–247, Mosby, St. Louis, Mo, USA, 1998. View at Google Scholar
  47. C. H. Shih, L. H. Lin, H. T. Hsu et al., “Hesperetin, a selective phosphodiesterase 4 inhibitor, effectively suppresses ovalbumin-induced airway hyperresponsiveness without influencing xylazine/ketamine-induced anesthesia,” Evidence-Based Complementary and Alternative Medicine, vol. 2012, Article ID 472897, 10 pages, 2012. View at Publisher · View at Google Scholar
  48. A. Robichaud, C. Savoie, P. B. Stamatiou, F. D. Tattersall, and C. C. Chan, “PDE4 inhibitors induce emesis in ferrets via a noradrenergic pathway,” Neuropharmacology, vol. 40, no. 2, pp. 262–269, 2001. View at Publisher · View at Google Scholar · View at Scopus
  49. S. L. Jin, W. Richter, and M. Conti, “Insights into the physiological functions of PDE4 from knockout mice,” in Cyclic Nucleotide Phosphodiesterases in Health and Disease, J. A. Beavo, S. H. Francis, and M. D. Houslay, Eds., pp. 323–346, CRC Press, Boca Raton, Fla, USA, 2007. View at Google Scholar