Journal of Microbiology and Biotechnology

  • 제27권2호
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  • Pages.316-320
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  • 2017
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  • 1017-7825(pISSN)
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  • 1738-8872(eISSN)
한국미생물·생명공학회 (The Korean Society for Microbiology and Biotechnology)
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Potent Selective Inhibition of Monoamine Oxidase A by Alternariol Monomethyl Ether Isolated from Alternaria brassicae

  • Lee, Hyun Woo (Department of Pharmacy and Research Institute of Life Pharmaceutical Sciences, Sunchon National University) ;
  • Kim, Yeon Ji (Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Nam, Sang-Jip (Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Kim, Hoon (Department of Pharmacy and Research Institute of Life Pharmaceutical Sciences, Sunchon National University)
  • 투고 : 2016.10.21
  • 심사 : 2016.11.04
  • 발행 : 2017.02.28
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초록

Alternariol monomethyl ether (AME), a dibenzopyrone derivative, was isolated from Alternaria brassicae along with altertoxin II (ATX-II). The compounds were tested for the inhibitory activity of monoamine oxidase (MAO), which catalyzes neurotransmitting monoamines. AME was found to be a highly potent and selective inhibitor of human MAO-A with an $IC_{50}$ value of $1.71{\mu}M$; however, it was found to be ineffective for MAO-B inhibition. ATX-II was not effective for the inhibition of either MAO-A or MAO-B. The inhibition of MAO-A using AME was apparently instantaneous. MAO-A activity was almost completely recovered after the dilution of the inhibited enzyme with an excess amount of AME, suggesting AME is a reversible inhibitor. AME showed mixed inhibition for MAO-A in Lineweaver-Burk plots with a $K_i$ value of $0.34{\mu}M$. The findings of this study suggest that microbial metabolites and dibenzopyrone could be potent MAO inhibitors. In addition, AME could be a useful lead compound for developing reversible MAO-A inhibitors to treat depression, Parkinson's disease, and Alzheimer's disease.

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참고문헌

  1. Ramsay RR. 2012. Monoamine oxidases: the biochemistry of the proteins as targets in medicinal chemistry and drug discovery. Curr. Top. Med. Chem. 12: 2189-2209. https://doi.org/10.2174/156802612805219978
  2. Orhan IE. 2016. Potential of natural products of herbal origin as monoamine oxidase inhibitors. Curr. Pharm. Des. 22: 268-276.
  3. Yamada M, Yasuhara H. 2004. Clinical pharmacology of MAO inhibitors: safety and future. Neurotoxicology 25: 215-221. https://doi.org/10.1016/S0161-813X(03)00097-4
  4. Youdim MB, Edmondson D, Tipton KF. 2006. The therapeutic potential of monoamine oxidase inhibitors. Nat. Rev. Neurosci. 7: 295-309. https://doi.org/10.1038/nrn1883
  5. Mostert S, Petzer A, Petzer JP. 2015. Indanones as highpotency reversible inhibitors of monoamine oxidase. ChemMedChem. 10: 862-873. https://doi.org/10.1002/cmdc.201500059
  6. Abdelhafez OM, Amin KM, Ali HI, Abdalla MM, Batran RZ. 2012. Synthesis of new 7-oxycoumarin derivatives as potent and selective monoamine oxidase A inhibitors. J. Med. Chem. 55: 10424-10436. https://doi.org/10.1021/jm301014y
  7. Fowler JS, Logan J, Azzaro AJ, Fielding RM, Zhu W, Poshusta AK, et al. 2010. Reversible inhibitors of monoamine oxidase-A (RIMAs): robust, reversible inhibition of human brain MAOA by CX157. Neuropsychopharmacology 35: 623-631. https://doi.org/10.1038/npp.2009.167
  8. Gentili F, Pizzinat N, Ordener C, Marchal-Victorion S, Maurel A, Hofmann R, et al. 2006. 3-[5-(4,5-Dihydro-1Himidazol-2-yl)-furan-2-yl]phenylamine (amifuraline), a promising reversible and selective peripheral MAO-A inhibitor. J. Med. Chem. 49: 5578-5586. https://doi.org/10.1021/jm060605r
  9. Kim H, Sablin SO, Ramsay RR. 1997. Inhibition of monoamine oxidase A by ${\beta}$-carboline derivatives. Arch. Biochem. Biophys. 337: 137-142. https://doi.org/10.1006/abbi.1996.9771
  10. Mattsson C, Svensson P, Sonesson C. 2014. A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors. Eur. J. Med. Chem. 73: 177-186. https://doi.org/10.1016/j.ejmech.2013.11.035
  11. Berlin I, Zimmer R, Thiede HM, Payan C, Hergueta T, Robin L, Puech AJ. 1990. Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects. Br. J. Clin. Pharmacol. 30: 805-816. https://doi.org/10.1111/j.1365-2125.1990.tb05445.x
  12. Dolle F, Valette H, Bramoulle Y, Guenther I, Fuseau C, Coulon C, et al. 2003. Synthesis and in vivo imaging properties of [11C]befloxatone: a novel highly potent positron emission tomography ligand for mono-amine oxidase-A. Bioorg. Med. Chem. Lett. 13: 1771-1775 https://doi.org/10.1016/S0960-894X(03)00215-4
  13. Lotufo-Neto F, Trivedi M, Thase ME. 1999. Meta-analysis of the reversible inhibitors of monoamine oxidase type A moclobemide and brofaromine for the treatment of depression. Neuropsychopharmacology 20: 226-247. https://doi.org/10.1016/S0893-133X(98)00075-X
  14. Carradori S, D'Ascenzio M, Chimenti P, Secci D, Bolasco A. 2014. Selective MAO-B inhibitors: a lesson from natural products. Mol. Divers. 18: 219-243. https://doi.org/10.1007/s11030-013-9490-6
  15. Mathew B, Suresh J, Mathew GE, Parasuraman R, Abdulla N. 2014. Plant secondary metabolites - potent inhibitors of monoamine oxidase isoforms. Cent. Nerv. Syst. Agents Med. Chem. 14: 28-33. https://doi.org/10.2174/1871524914666140826111930
  16. Vina D, Serra S, Lamela M, Delogu G. 2012. Herbal natural products as a source of monoamine oxidase inhibitors: a review. Curr. Top. Med. Chem. 12: 2131-2144. https://doi.org/10.2174/156802612805219996
  17. Lee HW, Jung WK, Kim HJ, Jeong YS, Nam SJ, Kang H, Kim H. 2015. Inhibition of monoamine oxidase by anithiactins from Streptomyces sp. J. Microbiol. Biotechnol. 25: 1425-1428. https://doi.org/10.4014/jmb.1505.05020
  18. Lee IK, Yun BS, Oh S, Kim YH, Lee MK, Yoo ID. 1999. 5-Methylmellein and nectriapyrone, two new monoamine oxidase inhibitors. Med. Sci. Res. 27: 463-465.
  19. Marin S, Ramos AJ, Cano-Sancho G, Sanchis V. 2013. Mycotoxins: occurrence, toxicology, and exposure assessment. Food Chem. Toxicol. 60: 218-237. https://doi.org/10.1016/j.fct.2013.07.047
  20. Ostry V. 2008. Alternaria mycotoxins: an overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs. World Mycotoxin J. 1: 175-188. https://doi.org/10.3920/WMJ2008.x013
  21. Scott PM, Zhao W, Feng S, Lau BP. 2012. Alternaria toxins alternariol and alternariol monomethyl ether in grain foods in Canada. Mycotoxin Res. 28: 261-266. https://doi.org/10.1007/s12550-012-0141-z
  22. Zhang SY, Li ZL, Bai J, Wang Y, Zhang LM, Wu X, Hua HM. 2012. A new perylenequinone from a halotolerant fungus, Alternaria sp. M6. Chin. J. Nat. Med. 10: 68-71.
  23. Schwarz C, Tiessen C, Kreutzer M, Stark T, Hofmann T, Marko D. 2012. Characterization of a genetoxic impact compound in Alternaria alternata infected rice as altertoxin II. Arch. Toxicol. 86: 1911-1925. https://doi.org/10.1007/s00204-012-0958-4
  24. Lee HW, Ryu HW, Kang MG, Park D, Oh SR, Kim H. 2016. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorg. Med. Chem. Lett. 26: 4714-4719 https://doi.org/10.1016/j.bmcl.2016.08.044
  25. Legoabe LJ, Petzer A, Petzer JP. 2012. Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives. Eur. J. Med. Chem. 49: 343-353. https://doi.org/10.1016/j.ejmech.2012.01.037
  26. Petzer A, Harvey BH, Petzer JP. 2014. The interactions of azure B, a metabolite of methylene blue, with acetylcholinesterase and butyrylcholinesterase. Toxicol. Appl. Pharmacol. 274: 488-493. https://doi.org/10.1016/j.taap.2013.10.014
  27. Petzer A, Pienaar A, Petzer JP. 2013. The inhibition of monoamine oxidase by esomeprazole. Drug Res. (Stuttg.). 63: 462-467. https://doi.org/10.1055/s-0033-1345163

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