Table of Contents Author Guidelines Submit a Manuscript
Evidence-Based Complementary and Alternative Medicine
Volume 2017, Article ID 4018724, 10 pages
https://doi.org/10.1155/2017/4018724
Research Article

Interactions of Desmethoxyyangonin, a Secondary Metabolite from Renealmia alpinia, with Human Monoamine Oxidase-A and Oxidase-B

1National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
2Department of Biomolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
3Programa de Ofidismo/Escorpionismo, Sede de Investigación Universitaria, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Torre 2, Laboratorio 631, Medellín, Colombia
4College of Pharmacy, University of South Carolina, Columbia, SC 29208, USA

Correspondence should be addressed to Babu L. Tekwani; ude.ssimelo@inawketb

Received 23 April 2017; Revised 24 June 2017; Accepted 17 July 2017; Published 24 August 2017

Academic Editor: Cheorl-Ho Kim

Copyright © 2017 Narayan D. Chaurasiya 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. T. E. Särkinen, M. F. Newman, P. J. M. Maas et al., “Recent oceanic long-distance dispersal and divergence in the amphi-Atlantic rain forest genus Renealmia L.f. (Zingiberaceae),” Molecular Phylogenetics and Evolution, vol. 44, no. 3, pp. 968–980, 2007. View at Publisher · View at Google Scholar · View at Scopus
  2. A. Antonelli and I. Sanmartín, “Why are there so many plant species in the Neotropics?” Taxon, vol. 60, no. 2, pp. 403–414, 2011. View at Google Scholar · View at Scopus
  3. D. A. Focho, W. T. Ndam, and B. A. Fonge, “Medicinal plants of Aguambu-Bamumbu in the Lebialem highlands, Southwest Province of Cameroon,” African Journal of Pharmacy and Pharmacology, vol. 3, no. 1, pp. 1–13, 2009. View at Google Scholar · View at Scopus
  4. M. H. K. Tchuendem, J. A. Mbah, A. Tsopmo et al., “Anti-plasmodial sesquiterpenoids from the African Renealmia cincinnata,” Phytochemistry, vol. 52, no. 6, pp. 1095–1099, 1999. View at Publisher · View at Google Scholar · View at Scopus
  5. R. R. B. Negrelle, “Renealmia l..f.: Botanical, pharmacological and agronomical aspects,” Revista Brasileira de Plantas Medicinais, vol. 17, no. 2, pp. 274–290, 2015. View at Publisher · View at Google Scholar · View at Scopus
  6. B. J. Cabanillas, A.-C. Le Lamer, D. Olagnier et al., “Leishmanicidal compounds and potent PPARγ activators from Renealmia thyrsoidea (Ruiz & Pav.) Poepp. & Endl,” Journal of Ethnopharmacology, vol. 157, pp. 149–155, 2014. View at Publisher · View at Google Scholar · View at Scopus
  7. W. Milliken and B. Albert, “The use of medicinal plants by the Yanomami Indians of Brazil,” Economic Botany, vol. 50, no. 1, pp. 10–25, 1996. View at Publisher · View at Google Scholar · View at Scopus
  8. M. J. Macía, “Renealmia alpinia (Rottb.) Maas (Zingiberaceae): an edible plant from Sierra Norte de Puebla (México),” Anales del Jardín Botánico de Madrid, vol. 60, no. 1, pp. 183–187, 2002. View at Publisher · View at Google Scholar
  9. C. Lans, T. Harper, K. Georges, and E. Bridgewater, “Medicinal and ethnoveterinary remedies of hunters in Trinidad,” BMC Complementary and Alternative Medicine, vol. 1, article 10, 17 pages, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. R. Otero, R. Fonnegra, S. L. Jiménez et al., “Snakebites and ethnobotany in the northwest region of Colombia. Part I: traditional use of plants,” Journal of Ethnopharmacology, vol. 71, no. 3, pp. 493–504, 2000. View at Publisher · View at Google Scholar · View at Scopus
  11. A. Camilo Patiño, D. María Benjumea, and J. Andrés Pereañez, “Inhibition of venom serine proteinase and metalloproteinase activities by Renealmia alpinia (Zingiberaceae) extracts: Comparison of wild and in vitro propagated plants,” Journal of Ethnopharmacology, vol. 149, no. 2, pp. 590–596, 2013. View at Publisher · View at Google Scholar · View at Scopus
  12. I. Gómez-Betancur, J. A. Pereañez, A. C. Patiño, and D. Benjumea, “Inhibitory effect of pinostrobin from Renealmia alpinia, on the enzymatic and biological activities of a PLA2,” International Journal of Biological Macromolecules, vol. 89, pp. 35–42, 2016. View at Publisher · View at Google Scholar · View at Scopus
  13. I. Gómez-Betancur, D. Benjumea, A. Patiño, N. Jiménez, and E. Osorio, “Inhibition of the toxic effects of Bothrops asper venom by pinostrobin, a flavanone isolated from Renealmia alpinia (Rottb.) MAAS,” Journal of Ethnopharmacology, vol. 155, no. 3, pp. 1609–1615, 2014. View at Publisher · View at Google Scholar · View at Scopus
  14. I. Gómez-Betancur, N. Cortés, D. Benjumea, E. Osorio, F. León, and S. J. Cutler, “Antinociceptive activity of extracts and secondary metabolites from wild growing and micropropagated plants of Renealmia alpinia,” Journal of Ethnopharmacology, vol. 165, pp. 191–197, 2015. View at Publisher · View at Google Scholar
  15. T.-W. Chou, J.-H. Feng, C.-C. Huang et al., “A plant kavalactone desmethoxyyangonin prevents inflammation and fulminant hepatitis in mice,” PLoS ONE, vol. 8, no. 10, Article ID e77626, 2013. View at Publisher · View at Google Scholar · View at Scopus
  16. N. Gökhan-Kelekçi, S. Yabanoǧlu, E. Küpeli et al., “A new therapeutic approach in Alzheimer disease: Some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics,” Bioorganic and Medicinal Chemistry, vol. 15, no. 17, pp. 5775–5786, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. J. G. Villarinho, K. D. V. Pinheiro, F. D. V. Pinheiro et al., “The antinociceptive effect of reversible monoamine oxidase-A inhibitors in a mouse neuropathic pain model,” Progress in Neuro-Psychopharmacology and Biological Psychiatry, vol. 44, pp. 136–142, 2013. View at Publisher · View at Google Scholar · View at Scopus
  18. W. Liu, A. Rabinovich, Y. Nash et al., “Anti-inflammatory and protective effects of MT-031, a novel multitarget MAO-A and AChE/BuChE inhibitor in scopolamine mouse model and inflammatory cells,” Neuropharmacology, vol. 113, pp. 445–456, 2017. View at Publisher · View at Google Scholar · View at Scopus
  19. N. D. Chaurasiya, V. Gogineni, K. M. Elokely et al., “Isolation of acacetin from Calea urticifolia with inhibitory properties against human monoamine oxidase-A and -B,” Journal of Natural Products, vol. 79, no. 10, pp. 2538–2544, 2016. View at Publisher · View at Google Scholar · View at Scopus
  20. S. Parikh, S. Hanscom, P. Gagne, C. Crespi, and C. Patten, “A Fluorescent-based, high-throughput assay for detecting inhibitors of human,” Tech. Rep. S02T081R2, BD Biosciences Discovery Labware, Woburn, Mass, USA, 2002. View at Google Scholar
  21. S.-Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara, “Structure of human monoamine oxidase A at 2.2-Å resolution: The control of opening the entry for substrates/inhibitors,” Proceedings of the National Academy of Sciences of the United States of America, vol. 105, no. 15, pp. 5739–5744, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. C. Binda, M. Li, F. Hubálek, N. Restelli, D. E. Edmondson, and A. Mattevi, “Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures,” Proceedings of the National Academy of Sciences of the United States of America, vol. 100, no. 17, pp. 9750–9755, 2003. View at Publisher · View at Google Scholar · View at Scopus
  23. G. Madhavi Sastry, M. Adzhigirey, T. Day, R. Annabhimoju, and W. Sherman, “Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments,” Journal of Computer-Aided Molecular Design, vol. 27, no. 3, pp. 221–234, 2013. View at Publisher · View at Google Scholar · View at Scopus
  24. “Schrödinger Suite 2015-3 Protein Preparation Wizard; Epik version 3.3, Schrödinger,” Impact version 6.8, Schrödinger, LLC, New York, NY, USA, 2015; Prime version 4.1, Schrödinger, LLC, New York, NY, USA, 2015.
  25. J. L. Banks, H. S. Beard, Y. Cao et al., “Integrated Modeling Program, Applied Chemical Theory (IMPACT),” Journal of Computational Chemistry, vol. 26, no. 16, pp. 1752–1780, 2005. View at Publisher · View at Google Scholar · View at Scopus
  26. W. L. Jorgensen and J. Tirado-Rives, “The OPLS [optimized potentials for liquid simulations] potential functions for proteins, energy minimizations for crystals of cyclic peptides and crambin,” Journal of the American Chemical Society, vol. 110, no. 6, pp. 1657–1666, 1988. View at Publisher · View at Google Scholar · View at Scopus
  27. G. A. Kaminski, R. A. Friesner, J. Tirado-Rives, and W. L. Jorgensen, “Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides,” Journal of Physical Chemistry B, vol. 105, no. 28, pp. 6474–6487, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. D. Shivakumar, J. Williams, Y. Wu, W. Damm, J. Shelley, and W. Sherman, “Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the opls force field,” Journal of Chemical Theory and Computation, vol. 6, no. 5, pp. 1509–1519, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. Glide, version 6.8, Schrödinger, LLC, New York, NY, USA, 2015.
  30. LigPrep, version 3.5, Schrödinger, LLC, New York, NY, USA, 2015.
  31. C. Mulakala and V. N. Viswanadhan, “Could MM-GBSA be accurate enough for calculation of absolute protein/ligand binding free energies?” Journal of Molecular Graphics and Modelling, vol. 46, pp. 41–51, 2013. View at Publisher · View at Google Scholar · View at Scopus
  32. Prime, Schrödinger, LLC, New York, NY, USA, 2014.
  33. S. Carradori, M. D'Ascenzio, P. Chimenti, D. Secci, and A. Bolasco, “Selective MAO-B inhibitors: A lesson from natural products,” Molecular Diversity, vol. 18, no. 1, pp. 219–243, 2014. View at Publisher · View at Google Scholar · View at Scopus
  34. A. R. Bilia, S. Gallori, and F. F. Vincieri, “Kava-kava and anxiety: Growing knowledge about the efficacy and safety,” Life Sciences, vol. 70, no. 22, pp. 2581–2597, 2002. View at Publisher · View at Google Scholar · View at Scopus
  35. H. C. Chua, E. T. H. Christensen, K. Hoestgaard-Jensen et al., “Kavain, the major constituent of the anxiolytic kava extract, potentiates gabaa receptors: Functional characteristics and molecular mechanism,” PLoS ONE, vol. 11, no. 6, Article ID e0157700, 2016. View at Publisher · View at Google Scholar · View at Scopus
  36. R. Uebelhack, L. Franke, and H.-J. Schewe, “Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum forster (kava-kava),” Pharmacopsychiatry, vol. 31, no. 5, pp. 187–192, 1998. View at Publisher · View at Google Scholar · View at Scopus
  37. S. Sällström Baum, R. Hill, and H. Rommelspacher, “Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats,” Progress in Neuro-Psychopharmacology and Biological Psychiatry, vol. 22, no. 7, pp. 1105–1120, 1998. View at Publisher · View at Google Scholar · View at Scopus
  38. Y.-M. Tzeng and M.-J. Lee, “Neuroprotective properties of kavalactones,” Neural Regeneration Research, vol. 10, no. 6, pp. 875–877, 2015. View at Publisher · View at Google Scholar · View at Scopus
  39. J. Baell and M. A. Walters, “Chemistry: chemical con artists foil drug discovery,” Nature, vol. 513, no. 7519, pp. 481–483, 2014. View at Publisher · View at Google Scholar · View at Scopus
  40. J. B. Baell, “Feeling nature's pains: natural products, natural product drugs, and pan assay interference compounds (PAINS),” Journal of Natural Products, vol. 79, no. 3, pp. 616–628, 2016. View at Publisher · View at Google Scholar · View at Scopus