Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase

Seon A. Lee, Ji Sang Hwang, Xiang Hua Han, Chul Lee, Min Hee Lee, Sang Gil Choe, Seong Su Hong, Dongho Lee, Myung Koo Lee, Bang Yeon Hwang

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

We have previously reported that piperine, a known piperidine alkaloid from Piper longum, competitively inhibited mouse brain MAO-A and MAO-B activities. Piperine also showed in vivo antidepressant-like activity against the tail suspension test. In the present study, we further expanded on the identification of MAO inhibitors from the fruit of P. longum. Activity-guided fractionation of a methylene chloride soluble extract led to the isolation of three known piperine-related compounds, methylpiperate (1), guineensine (2), and piperlonguminine (3). Of these, methylpiperate (1) and guineensine (2) showed significant MAO inhibitory activities with IC50 values of 3.6 and 139.2 μM, respectively. Furthermore, methylpiperate (1) exhibited a selective inhibitory effect against MAO-B (IC50 value: 1.6 μM) than MAO-A (IC50 value: 27.1 μM). The kinetic study using the Lineweaver-Burk plots analysis suggested that methylpiperate (1) competitively inhibits MAO-A and MAO-B activities with the Ki values of 23.5 and 1.3 μM, respectively.

Original languageEnglish
Pages (from-to)679-683
Number of pages5
JournalArchives of pharmacal research
Volume31
Issue number6
DOIs
Publication statusPublished - 2008 Jun

Keywords

  • Methylpiperate
  • Monoamine oxidase inhibitor
  • Piper longum
  • Piperaceae

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery
  • Organic Chemistry

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    Lee, S. A., Hwang, J. S., Han, X. H., Lee, C., Lee, M. H., Choe, S. G., Hong, S. S., Lee, D., Lee, M. K., & Hwang, B. Y. (2008). Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase. Archives of pharmacal research, 31(6), 679-683. https://doi.org/10.1007/s12272-001-1212-7