Chromenone derivatives as monoamine oxidase inhibitors from marine-derived MAR4 clade Streptomyces sp. CNQ-031

Jong Min Oh, Chaeyoung Lee, Sang Jip Nam, Hoon Kim

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8 Scopus citations

Abstract

Three compounds were isolated from marine-derived Streptomyces sp. CNQ-031, and their inhibitory activities against monoamine oxidases (MAOs), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-secretase (BACE-1) were evaluated. Compound 1 (5,7-dihydroxy-2-isopropyl-4H-chromen-4-one) was a potent and selective inhibitor of MAO-A, with a 50% inhibitory concentration (IC50) of 2.70 μM and a selectivity index (SI) of 10.0 versus MAO-B. Compound 2 [5,7-dihydroxy-2-(1-methylpropyl)-4H-chromen-4-one] was a potent and low-selective inhibitor of MAO-B, with an IC50 of 3.42 μM and an SI value of 2.02 versus MAO-A. Compound 3 (1-methoxyphenazine) did not inhibit MAO-A or MAO-B. All three compounds showed little inhibitory activity against AChE, BChE, and BACE-1. The Ki value of compound 1 for MAO-A was 0.94 ± 0.28 μM, and the Ki values of compound 2 for MAO-A and MAO-B were 3.57 ± 0.60 and 1.89 ± 0.014 μM, respectively, with competitive inhibition. The 1-methylpropyl group in compound 2 increased the MAO-B inhibitory activity compared with the isopropyl group in compound 1. Inhibition of MAO-A and MAO-B by compounds 1 and 2 was recovered by dialysis experiments. These results suggest that compounds 1 and 2 are reversible, competitive inhibitors of MAOs and can be considered potential therapies for neurological disorders such as depression and Alzheimer’s disease.

Original languageEnglish
Pages (from-to)1022-1027
Number of pages6
JournalJournal of Microbiology and Biotechnology
Volume31
Issue number7
DOIs
StatePublished - 28 Jul 2021

Bibliographical note

Publisher Copyright:
Copyright© 2021 by The Korean Society for Microbiology and Biotechnology

Keywords

  • Chromenone derivatives
  • Monoamine oxidases
  • Reversible competitive inhibitors
  • Streptomyces sp. CNQ-031

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