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

doi:10.1007/s12272-001-1212-7

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

Department of Biosystems and Biotechnology

Research output: Contribution to journal › Article › peer-review

44 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 language	English
Pages (from-to)	679-683
Number of pages	5
Journal	Archives of pharmacal research
Volume	31
Issue number	6
DOIs	https://doi.org/10.1007/s12272-001-1212-7
Publication status	Published - 2008 Jun

Keywords

Methylpiperate
Monoamine oxidase inhibitor
Piper longum
Piperaceae

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery
Organic Chemistry

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10.1007/s12272-001-1212-7

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title = "Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase",

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.",

keywords = "Methylpiperate, Monoamine oxidase inhibitor, Piper longum, Piperaceae",

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

note = "Funding Information: This work was supported by the research grant of the Chungbuk National University in 2006. We are grateful to Korea Basic Science Institute for mass, 1Hand 13C-NMR spectral measurements.",

year = "2008",

month = jun,

doi = "10.1007/s12272-001-1212-7",

language = "English",

volume = "31",

pages = "679--683",

journal = "Archives of Pharmacal Research",

issn = "0253-6269",

publisher = "Pharmaceutical Society of Korea",

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TY - JOUR

T1 - Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase

AU - Lee, Seon A.

AU - Hwang, Ji Sang

AU - Han, Xiang Hua

AU - Lee, Chul

AU - Lee, Min Hee

AU - Choe, Sang Gil

AU - Hong, Seong Su

AU - Lee, Dongho

AU - Lee, Myung Koo

AU - Hwang, Bang Yeon

N1 - Funding Information: This work was supported by the research grant of the Chungbuk National University in 2006. We are grateful to Korea Basic Science Institute for mass, 1Hand 13C-NMR spectral measurements.

PY - 2008/6

Y1 - 2008/6

N2 - 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.

AB - 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.

KW - Methylpiperate

KW - Monoamine oxidase inhibitor

KW - Piper longum

KW - Piperaceae

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JO - Archives of Pharmacal Research

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IS - 6

ER -

Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase

Abstract

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