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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Multidisciplinary Digital Publishing Institute (MDPI)
2014
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| Online Access: | 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 |
| _version_ | 1848817477940674560 |
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| author | M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter |
| author_facet | M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter |
| author_sort | M. M., Yusoff |
| building | UMP Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-15T01:22:24Z |
| format | Article |
| id | ump-4856 |
| institution | Universiti Malaysia Pahang |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-15T01:22:24Z |
| publishDate | 2014 |
| publisher | Multidisciplinary Digital Publishing Institute (MDPI) |
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| 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). (Published) http://dx.doi.org/10.3390/molecules19011201 DOI: 10.3390/molecules19011201 |
| spellingShingle | QD Chemistry M. M., Yusoff Hazrulrizawati, Hamid Houghtan, Peter Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa |
| title | 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_short | Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa |
| title_sort | anticholinesterase inhibitory activity of quaternary alkaloids from tinospora crispa |
| topic | QD Chemistry |
| 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 |