Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase

Hua Han Xiang; Su Hong Seong; Dongho Lee; Joon Lee Jung; Soon Lee Moon; Dong Cheul Moon; Kun Han; Ki Wan Oh; Koo Lee Myung; Seup Ro Jai; Yeon Hwang Bang

doi:10.1007/bf02980210

Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase

Hua Han Xiang, Su Hong Seong, Dongho Lee, Joon Lee Jung, Soon Lee Moon, Dong Cheul Moon, Kun Han, Ki Wan Oh, Koo Lee Myung, Seup Ro Jai, Yeon Hwang Bang

Department of Biosystems and Biotechnology

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

14 Citations (Scopus)

Abstract

1-Methyl-2-undecyl-4(1H)-quinolone (1) was previously isolated as a selective MAO-B inhibitor from the Evodiae Fructus. Further bioassay-guided purification led to the identification of five known quinolone alkaloids, 1-methyl-2-nonyl-4(1H)-quinolone (2), 1-methyl-2-[(Z)-6-undecenyl]-4(1H)- quinolone (3), evocarpine (4), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)- quinolone (5), and dihydroevocarpine (6). All the isolates showed more potent inhibitory effects against MAO-B compared to MAO-A. The most MAO-B selective compound 5 among the isolates inhibited MAO-B in a competitive manner, according to kinetic analyses by Lineweaver-Burk reciprocal plots.

Original language	English
Pages (from-to)	397-401
Number of pages	5
Journal	Archives of pharmacal research
Volume	30
Issue number	4
DOIs	https://doi.org/10.1007/bf02980210
Publication status	Published - 2007 Apr 30

Keywords

Evodia rutaecarpa
Evodiae fructus
Monoamine oxidase inhibitor
Quinolone alkaloid
Rutaceae

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery
Organic Chemistry

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10.1007/bf02980210

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title = "Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase",

abstract = "1-Methyl-2-undecyl-4(1H)-quinolone (1) was previously isolated as a selective MAO-B inhibitor from the Evodiae Fructus. Further bioassay-guided purification led to the identification of five known quinolone alkaloids, 1-methyl-2-nonyl-4(1H)-quinolone (2), 1-methyl-2-[(Z)-6-undecenyl]-4(1H)- quinolone (3), evocarpine (4), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)- quinolone (5), and dihydroevocarpine (6). All the isolates showed more potent inhibitory effects against MAO-B compared to MAO-A. The most MAO-B selective compound 5 among the isolates inhibited MAO-B in a competitive manner, according to kinetic analyses by Lineweaver-Burk reciprocal plots.",

keywords = "Evodia rutaecarpa, Evodiae fructus, Monoamine oxidase inhibitor, Quinolone alkaloid, Rutaceae",

author = "Xiang, {Hua Han} and Seong, {Su Hong} and Dongho Lee and Jung, {Joon Lee} and Moon, {Soon Lee} and Moon, {Dong Cheul} and Kun Han and Oh, {Ki Wan} and Myung, {Koo Lee} and Jai, {Seup Ro} and Bang, {Yeon Hwang}",

note = "Funding Information: This work was supported by the Regional Research Centers Program of the Ministry of Education & Human Resources Development in Korea. The authors are grateful to the Korea Basic Science Institute, Daejeon, Korea, for NMR and mass spectral measurements.",

year = "2007",

month = apr,

day = "30",

doi = "10.1007/bf02980210",

language = "English",

volume = "30",

pages = "397--401",

journal = "Archives of Pharmacal Research",

issn = "0253-6269",

publisher = "Pharmaceutical Society of Korea",

number = "4",

}

TY - JOUR

T1 - Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase

AU - Xiang, Hua Han

AU - Seong, Su Hong

AU - Lee, Dongho

AU - Jung, Joon Lee

AU - Moon, Soon Lee

AU - Moon, Dong Cheul

AU - Han, Kun

AU - Oh, Ki Wan

AU - Myung, Koo Lee

AU - Jai, Seup Ro

AU - Bang, Yeon Hwang

N1 - Funding Information: This work was supported by the Regional Research Centers Program of the Ministry of Education & Human Resources Development in Korea. The authors are grateful to the Korea Basic Science Institute, Daejeon, Korea, for NMR and mass spectral measurements.

PY - 2007/4/30

Y1 - 2007/4/30

N2 - 1-Methyl-2-undecyl-4(1H)-quinolone (1) was previously isolated as a selective MAO-B inhibitor from the Evodiae Fructus. Further bioassay-guided purification led to the identification of five known quinolone alkaloids, 1-methyl-2-nonyl-4(1H)-quinolone (2), 1-methyl-2-[(Z)-6-undecenyl]-4(1H)- quinolone (3), evocarpine (4), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)- quinolone (5), and dihydroevocarpine (6). All the isolates showed more potent inhibitory effects against MAO-B compared to MAO-A. The most MAO-B selective compound 5 among the isolates inhibited MAO-B in a competitive manner, according to kinetic analyses by Lineweaver-Burk reciprocal plots.

AB - 1-Methyl-2-undecyl-4(1H)-quinolone (1) was previously isolated as a selective MAO-B inhibitor from the Evodiae Fructus. Further bioassay-guided purification led to the identification of five known quinolone alkaloids, 1-methyl-2-nonyl-4(1H)-quinolone (2), 1-methyl-2-[(Z)-6-undecenyl]-4(1H)- quinolone (3), evocarpine (4), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)- quinolone (5), and dihydroevocarpine (6). All the isolates showed more potent inhibitory effects against MAO-B compared to MAO-A. The most MAO-B selective compound 5 among the isolates inhibited MAO-B in a competitive manner, according to kinetic analyses by Lineweaver-Burk reciprocal plots.

KW - Evodia rutaecarpa

KW - Evodiae fructus

KW - Monoamine oxidase inhibitor

KW - Quinolone alkaloid

KW - Rutaceae

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U2 - 10.1007/bf02980210

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M3 - Article

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SN - 0253-6269

VL - 30

SP - 397

EP - 401

JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

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ER -

Quinolone alkaloids from evodiae fructus and their inhibitory effects on monoamine oxidase

Abstract

Keywords

ASJC Scopus subject areas

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