Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis

Sook Yee Liew; Kooi Yeong Khaw; Vikneswaran Murugaiyah; Chung Yeng Looi; Yi Li Wong; Mohd Rais Mustafa; Marc Litaudon; Khalijah Awang

doi:10.1016/j.phymed.2014.11.003

Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis

Sook Yee Liew, Kooi Yeong Khaw, Vikneswaran Murugaiyah, Chung Yeng Looi, Yi Li Wong, Mohd Rais Mustafa, Marc Litaudon, Khalijah Awang

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

49 Citations (Scopus)

Abstract

Nine monoterpenoid indole alkaloids; naucletine (1), angustidine (2), nauclefine (3), angustine (4), naucline (5), angustoline (6), harmane (7), 3,14-dihydroangustoline (8), strictosamide (9) and one quinoline alkaloid glycoside; pumiloside (10) from Nauclea officinalis were tested for cholinesterase inhibitory activity. All the alkaloids except for pumiloside (10) showed strong to weak BChE inhibitory effect with IC₅₀ values ranging between 1.02-168.55 μM. Angustidine (2), nauclefine (3), angustine (4), angustoline (6) and harmane (7) showed higher BChE inhibiting potency compared to galanthamine. Angustidine (2) was the most potent inhibitor towards both AChE and BChE. Molecular docking (MD) studies showed that angustidine (2) docked deep into the bottom gorge of hBChE and formed hydrogen bonding with Ser 198 and His 438. Kinetic study of angustidine (2) on BChE suggested a mixed inhibition mode with an inhibition constant (Ki) of 6.12 μM.

Original language	English
Pages (from-to)	45-48
Number of pages	4
Journal	Phytomedicine
Volume	22
Issue number	1
DOIs	https://doi.org/10.1016/j.phymed.2014.11.003
Publication status	Published - 9 Aug 2015
Externally published	Yes

Keywords

Angustidine
Cholinesterase
Kinetic study
Molecular docking
Nauclea officinalis

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10.1016/j.phymed.2014.11.003

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title = "Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis",

abstract = "Nine monoterpenoid indole alkaloids; naucletine (1), angustidine (2), nauclefine (3), angustine (4), naucline (5), angustoline (6), harmane (7), 3,14-dihydroangustoline (8), strictosamide (9) and one quinoline alkaloid glycoside; pumiloside (10) from Nauclea officinalis were tested for cholinesterase inhibitory activity. All the alkaloids except for pumiloside (10) showed strong to weak BChE inhibitory effect with IC50 values ranging between 1.02-168.55 μM. Angustidine (2), nauclefine (3), angustine (4), angustoline (6) and harmane (7) showed higher BChE inhibiting potency compared to galanthamine. Angustidine (2) was the most potent inhibitor towards both AChE and BChE. Molecular docking (MD) studies showed that angustidine (2) docked deep into the bottom gorge of hBChE and formed hydrogen bonding with Ser 198 and His 438. Kinetic study of angustidine (2) on BChE suggested a mixed inhibition mode with an inhibition constant (Ki) of 6.12 μM.",

keywords = "Angustidine, Cholinesterase, Kinetic study, Molecular docking, Nauclea officinalis",

author = "Liew, {Sook Yee} and Khaw, {Kooi Yeong} and Vikneswaran Murugaiyah and Looi, {Chung Yeng} and Wong, {Yi Li} and Mustafa, {Mohd Rais} and Marc Litaudon and Khalijah Awang",

note = "Funding Information: This work was supported by University of Malaya research grants (UM.C/625/1/HIR/MOHE/SC/37 and PV050/2012A) and Centre National de la Recherche Scientifique (CNRS) grant (57-02-03-1007). The authors thank D.M. Nor and R. Syamsir for collection of plant material and T. L. Eng for botanical identification. The plant collection was carried out within the framework of an official agreement between the CNRS and the University of Malaya (Malaysia). Publisher Copyright: {\textcopyright} 2014 Elsevier GmbH. Copyright: Copyright 2015 Elsevier B.V., All rights reserved.",

year = "2015",

month = aug,

day = "9",

doi = "10.1016/j.phymed.2014.11.003",

language = "English",

volume = "22",

pages = "45--48",

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T1 - Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis

AU - Liew, Sook Yee

AU - Khaw, Kooi Yeong

AU - Murugaiyah, Vikneswaran

AU - Looi, Chung Yeng

AU - Wong, Yi Li

AU - Mustafa, Mohd Rais

AU - Litaudon, Marc

AU - Awang, Khalijah

N1 - Funding Information: This work was supported by University of Malaya research grants (UM.C/625/1/HIR/MOHE/SC/37 and PV050/2012A) and Centre National de la Recherche Scientifique (CNRS) grant (57-02-03-1007). The authors thank D.M. Nor and R. Syamsir for collection of plant material and T. L. Eng for botanical identification. The plant collection was carried out within the framework of an official agreement between the CNRS and the University of Malaya (Malaysia). Publisher Copyright: © 2014 Elsevier GmbH. Copyright: Copyright 2015 Elsevier B.V., All rights reserved.

PY - 2015/8/9

Y1 - 2015/8/9

N2 - Nine monoterpenoid indole alkaloids; naucletine (1), angustidine (2), nauclefine (3), angustine (4), naucline (5), angustoline (6), harmane (7), 3,14-dihydroangustoline (8), strictosamide (9) and one quinoline alkaloid glycoside; pumiloside (10) from Nauclea officinalis were tested for cholinesterase inhibitory activity. All the alkaloids except for pumiloside (10) showed strong to weak BChE inhibitory effect with IC50 values ranging between 1.02-168.55 μM. Angustidine (2), nauclefine (3), angustine (4), angustoline (6) and harmane (7) showed higher BChE inhibiting potency compared to galanthamine. Angustidine (2) was the most potent inhibitor towards both AChE and BChE. Molecular docking (MD) studies showed that angustidine (2) docked deep into the bottom gorge of hBChE and formed hydrogen bonding with Ser 198 and His 438. Kinetic study of angustidine (2) on BChE suggested a mixed inhibition mode with an inhibition constant (Ki) of 6.12 μM.

AB - Nine monoterpenoid indole alkaloids; naucletine (1), angustidine (2), nauclefine (3), angustine (4), naucline (5), angustoline (6), harmane (7), 3,14-dihydroangustoline (8), strictosamide (9) and one quinoline alkaloid glycoside; pumiloside (10) from Nauclea officinalis were tested for cholinesterase inhibitory activity. All the alkaloids except for pumiloside (10) showed strong to weak BChE inhibitory effect with IC50 values ranging between 1.02-168.55 μM. Angustidine (2), nauclefine (3), angustine (4), angustoline (6) and harmane (7) showed higher BChE inhibiting potency compared to galanthamine. Angustidine (2) was the most potent inhibitor towards both AChE and BChE. Molecular docking (MD) studies showed that angustidine (2) docked deep into the bottom gorge of hBChE and formed hydrogen bonding with Ser 198 and His 438. Kinetic study of angustidine (2) on BChE suggested a mixed inhibition mode with an inhibition constant (Ki) of 6.12 μM.

KW - Angustidine

KW - Cholinesterase

KW - Kinetic study

KW - Molecular docking

KW - Nauclea officinalis

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SN - 0944-7113

VL - 22

SP - 45

EP - 48

JO - Phytomedicine

JF - Phytomedicine

IS - 1

ER -

Natural indole butyrylcholinesterase inhibitors from Nauclea officinalis

Abstract

Keywords

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