Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids

A study was carried out on the characterisation and biological activities of Tinospora crispa extract with emphasis on alkaloids. Methanolic extraction, crude alkaloid fractionation and separation using different chromatographic techniques (open columns and preparative TLC) were used for isolation o...

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Main Author:	Azrulrizawati, Abd Hamid
Format:	Thesis
Language:	English
Published:	2013
Subjects:	TP Chemical technology
Online Access:	http://umpir.ump.edu.my/id/eprint/7288/1/Characterisation%20and%20biological%20activities%20of%20tinospora%20crispa%20%28menispermaceae%29%20extract%20with%20emphasis%20on%20alkaloids%20.pdf
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spelling	my-ump-ir.72882023-05-11T07:47:32Z Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids 2013-07 Azrulrizawati, Abd Hamid TP Chemical technology A study was carried out on the characterisation and biological activities of Tinospora crispa extract with emphasis on alkaloids. Methanolic extraction, crude alkaloid fractionation and separation using different chromatographic techniques (open columns and preparative TLC) were used for isolation of pure compounds. The structure of the isolated compounds were elucidated by spectroscopic methods such as UV, IR, 1D (H, C, DEPTQ), 2D (COSY, HMQC, HMBC) NMR, MS and also by comparison with the literature. Twelve compounds were isolated from these plants comprising eight alkaloids and four nonalkaloid compounds. Six of the alkaloid, viz., N formylannonaine,N-formylnornuciferine, lysicamine, magnoflorine, columbamine and dihydrodiscretamine previously isolated from T.crispa and other species the genus Tinospora. In addition, one known alkaloid, liriodenine was found for the first time in this study. A novel alkaloid, 4,13-dihydroxy-2,8,9 trimethoxydibenzo[a,g]quinolizinium was isolated and its structure was established by modern spectroscopic technique. A biosynthethic route to this alkaloid is proposed. Another new compound isolated was aliphatic amine, N,N-dimetylhexadecan-1-amine. Three types of bioactivity studies, viz., acetylcholinesterase inhibitory, radical scavenging and antimicrobial studies were carried out on isolated compounds containing nitrogen. The quaternary protoberberine alkaloids; columbamine and dihydrodiscretamine were found to be potent acetylcholinesterase inhibitors. Most of the isolated quaternary alkaloids showed moderately (IC> 500-800 μg/mL) radical scavenging activity. Oxaporphine alkaloids, lysicamine, liriodenine and aliphatic amine inhibited the growth of the Gram-positive bacteria, Staphylococcus aureus (+) and Enterococcus faecalis (+). Aliphatic amine also exhibited inhibitory activity against Gram-negative bacteria, Proteus vulgaris (-) and Psuedomonas aeurogenosa (-). Results of the present biological activity investigation further points to the potential of this plant species as a good source of new AChE inhibitors. The antioxidant and antimicrobial properties of different compounds support documented traditional use of T. crispa in wound healing and treatment of rheumatic, diarrhoea, ulcers, itches and wounds. 2013-07 Thesis http://umpir.ump.edu.my/id/eprint/7288/ http://umpir.ump.edu.my/id/eprint/7288/1/Characterisation%20and%20biological%20activities%20of%20tinospora%20crispa%20%28menispermaceae%29%20extract%20with%20emphasis%20on%20alkaloids%20.pdf pdf en public phd doctoral Universiti Malaysia Pahang Faculty of Industrial Sciences and Technology Mohd Yusof, Mashitah
institution	Universiti Malaysia Pahang Al-Sultan Abdullah
collection	UMPSA Institutional Repository
language	English
advisor	Mohd Yusof, Mashitah
topic	TP Chemical technology
spellingShingle	TP Chemical technology Azrulrizawati, Abd Hamid Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
description	A study was carried out on the characterisation and biological activities of Tinospora crispa extract with emphasis on alkaloids. Methanolic extraction, crude alkaloid fractionation and separation using different chromatographic techniques (open columns and preparative TLC) were used for isolation of pure compounds. The structure of the isolated compounds were elucidated by spectroscopic methods such as UV, IR, 1D (H, C, DEPTQ), 2D (COSY, HMQC, HMBC) NMR, MS and also by comparison with the literature. Twelve compounds were isolated from these plants comprising eight alkaloids and four nonalkaloid compounds. Six of the alkaloid, viz., N formylannonaine,N-formylnornuciferine, lysicamine, magnoflorine, columbamine and dihydrodiscretamine previously isolated from T.crispa and other species the genus Tinospora. In addition, one known alkaloid, liriodenine was found for the first time in this study. A novel alkaloid, 4,13-dihydroxy-2,8,9 trimethoxydibenzo[a,g]quinolizinium was isolated and its structure was established by modern spectroscopic technique. A biosynthethic route to this alkaloid is proposed. Another new compound isolated was aliphatic amine, N,N-dimetylhexadecan-1-amine. Three types of bioactivity studies, viz., acetylcholinesterase inhibitory, radical scavenging and antimicrobial studies were carried out on isolated compounds containing nitrogen. The quaternary protoberberine alkaloids; columbamine and dihydrodiscretamine were found to be potent acetylcholinesterase inhibitors. Most of the isolated quaternary alkaloids showed moderately (IC> 500-800 μg/mL) radical scavenging activity. Oxaporphine alkaloids, lysicamine, liriodenine and aliphatic amine inhibited the growth of the Gram-positive bacteria, Staphylococcus aureus (+) and Enterococcus faecalis (+). Aliphatic amine also exhibited inhibitory activity against Gram-negative bacteria, Proteus vulgaris (-) and Psuedomonas aeurogenosa (-). Results of the present biological activity investigation further points to the potential of this plant species as a good source of new AChE inhibitors. The antioxidant and antimicrobial properties of different compounds support documented traditional use of T. crispa in wound healing and treatment of rheumatic, diarrhoea, ulcers, itches and wounds.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Azrulrizawati, Abd Hamid
author_facet	Azrulrizawati, Abd Hamid
author_sort	Azrulrizawati, Abd Hamid
title	Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
title_short	Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
title_full	Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
title_fullStr	Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
title_full_unstemmed	Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids
title_sort	characterisation and biological activities of tinospora crispa (menispermaceae) extract with emphasis on alkaloids
granting_institution	Universiti Malaysia Pahang
granting_department	Faculty of Industrial Sciences and Technology
publishDate	2013
url	http://umpir.ump.edu.my/id/eprint/7288/1/Characterisation%20and%20biological%20activities%20of%20tinospora%20crispa%20%28menispermaceae%29%20extract%20with%20emphasis%20on%20alkaloids%20.pdf
_version_	1783731925074051072

Characterisation and Biological Activities of Tinospora Crispa (Menispermaceae) Extract with Emphasis on Alkaloids

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