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Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa

1
Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, Gambang Kuantan, Pahang 26300, Malaysia
2
Department of Pharmacy, King's College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 8WA, UK
*
Author to whom correspondence should be addressed.
Molecules 2014, 19(1), 1201-1211; https://doi.org/10.3390/molecules19011201
Received: 1 December 2013 / Revised: 14 January 2014 / Accepted: 15 January 2014 / Published: 20 January 2014
(This article belongs to the Section Natural Products 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. View Full-Text
Keywords: Tinospora crispa; Menispermaceae; ethnoremedy; anticholinesterase inhibitory activities; quaternary alkaloids; 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g] quinolizinium; dihydrodiscretamine; columbamine Tinospora crispa; Menispermaceae; ethnoremedy; anticholinesterase inhibitory activities; quaternary alkaloids; 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g] quinolizinium; dihydrodiscretamine; columbamine
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MDPI and ACS Style

Yusoff, M.; Hamid, H.; Houghton, P. Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa. Molecules 2014, 19, 1201-1211.

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