Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa

Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extrac...

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Main Authors:	M. M., Yusoff, Hazrulrizawati, Hamid, Houghtan, Peter
Format:	Article
Language:	English English
Published:	Multidisciplinary Digital Publishing Institute (MDPI) 2014
Subjects:	QD Chemistry
Online Access:	http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/1/Molecules_2014___Tinospora_Crispa.pdf http://umpir.ump.edu.my/id/eprint/4856/4/Anticholinesterase%20Inhibitory%20Activity%20of%20Quaternary%20Alkaloids%20from%20Tinospora%20crispa.pdf

id	ump-4856
recordtype	eprints
spelling	ump-48562018-07-27T03:20:47Z http://umpir.ump.edu.my/id/eprint/4856/ Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter QD Chemistry Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids—dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman’s method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure–activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition. Multidisciplinary Digital Publishing Institute (MDPI) 2014-01-20 Article PeerReviewed application/pdf en http://umpir.ump.edu.my/id/eprint/4856/1/Molecules_2014___Tinospora_Crispa.pdf application/pdf en http://umpir.ump.edu.my/id/eprint/4856/4/Anticholinesterase%20Inhibitory%20Activity%20of%20Quaternary%20Alkaloids%20from%20Tinospora%20crispa.pdf M. M., Yusoff and Hazrulrizawati, Hamid and Houghtan, Peter (2014) Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa. Molecules, 19 (1). pp. 1201-1211. ISSN 1420-3049 (print); 1420-3049 (online) http://dx.doi.org/10.3390/molecules19011201 DOI: 10.3390/molecules19011201
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Malaysia Pahang
building	UMP Institutional Repository
collection	Online Access
language	English English
topic	QD Chemistry
spellingShingle	QD Chemistry M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
description	Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids—dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman’s method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure–activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition.
format	Article
author	M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter
author_facet	M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter
author_sort	M. M., Yusoff
title	Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
title_short	Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
title_full	Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
title_fullStr	Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
title_full_unstemmed	Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa
title_sort	anticholinesterase inhibitory activity of quaternary alkaloids from tinospora crispa
publisher	Multidisciplinary Digital Publishing Institute (MDPI)
publishDate	2014
url	http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/ http://umpir.ump.edu.my/id/eprint/4856/1/Molecules_2014___Tinospora_Crispa.pdf http://umpir.ump.edu.my/id/eprint/4856/4/Anticholinesterase%20Inhibitory%20Activity%20of%20Quaternary%20Alkaloids%20from%20Tinospora%20crispa.pdf
first_indexed	2023-09-18T21:59:48Z
last_indexed	2023-09-18T21:59:48Z
_version_	1777414321682251776

Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa

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