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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doaj-a6e5534990bb423484cf54d74855ab422020-11-24T22:20:45ZengMDPI AGMolecules1420-30492014-01-011911201121110.3390/molecules19011201molecules19011201Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispaMashitah Yusoff0Hazrulrizawati Hamid1Peter Houghton2Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, Gambang Kuantan, Pahang 26300, MalaysiaFaculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, Gambang Kuantan, Pahang 26300, MalaysiaDepartment of Pharmacy, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 8WA, UKQuaternary 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.http://www.mdpi.com/1420-3049/19/1/1201Tinospora crispaMenispermaceaeethnoremedyanticholinesterase inhibitory activitiesquaternary alkaloids4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g] quinoliziniumdihydrodiscretaminecolumbamine |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Mashitah Yusoff Hazrulrizawati Hamid Peter Houghton |
spellingShingle |
Mashitah Yusoff Hazrulrizawati Hamid Peter Houghton Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa Molecules Tinospora crispa Menispermaceae ethnoremedy anticholinesterase inhibitory activities quaternary alkaloids 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g] quinolizinium dihydrodiscretamine columbamine |
author_facet |
Mashitah Yusoff Hazrulrizawati Hamid Peter Houghton |
author_sort |
Mashitah 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 |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2014-01-01 |
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. |
topic |
Tinospora crispa Menispermaceae ethnoremedy anticholinesterase inhibitory activities quaternary alkaloids 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g] quinolizinium dihydrodiscretamine columbamine |
url |
http://www.mdpi.com/1420-3049/19/1/1201 |
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