Phytochemical and bioactivity studies of Callicarpa maingayi K. & G

Callicarpa maingayi, which is known in Malaysia as “tampang besi” belongs to Lamiaceae family. The plants of the genus Callicarpa have been used to treat various ailments, such as malaria, skin cancer, indigestion, dropsy, stomach disorders and rheumatism. The stem bark of Callicarpa maingayi was ex...

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Main Author:	Mohammed Othman Asiri, Sumayyah
Format:	Thesis
Language:	English
Published:	2012
Subjects:	Phytochemicals Lamiaceae
Online Access:	http://psasir.upm.edu.my/id/eprint/32025/1/IB%202012%2013R.pdf
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spelling	my-upm-ir.320252015-01-20T03:27:35Z Phytochemical and bioactivity studies of Callicarpa maingayi K. & G 2012-02 Mohammed Othman Asiri, Sumayyah Callicarpa maingayi, which is known in Malaysia as “tampang besi” belongs to Lamiaceae family. The plants of the genus Callicarpa have been used to treat various ailments, such as malaria, skin cancer, indigestion, dropsy, stomach disorders and rheumatism. The stem bark of Callicarpa maingayi was exhaustively extracted using methanol-water (8:2). The crude extract was successively fractionated using n-hexane, chloroform and ethyl acetate. Separation, isolation and purification of compounds were done using solvent-solvent partitioning and chromatographic techniques such as High Performance Liquid chromatography (HPLC), as well as normal phase, reverse phase and Sephadex LH-20 column chromatography. From the hexane extract, three known compounds were isolated, namely palmitic acid(91), tetracosanoic acid (92) and a mixture of stigmasterol and β-sitosterol (93). The investigation on the chloroform extract led to the isolation of two new naphthoquinone, (+)-callicarpaquinone-A (97), callicarpaquinone-B (96), along with known avicequinone-C (95), which was isolated from the first time from Callicarpa species, and 3β-hydroxy-lup-20(29)-en-28-oic-acid (94). From the ethyl acetate extract, three known compounds (+)-paulownin (98), (-)-wodeshiol (99), which were isolated for the first time from Callicarpa species together with β- sitosterol-β-D-glucopyranoside (100). The extracts and isolated compounds were screened in vitro for anticholinesterase and cytotoxic activities using Ellman's and MTT (3-(4,5-dimethylthiazole-2-yl)-2,5- diphenyltetrazolium bromide) methods. The hexane, chloroform and ethyl acetate extracts were inactive against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50 values of > 100 μM, but were found to exhibit significant cytotoxicity against liver cancer (HepG2) and breast cancer (MCF-7) cell lines with IC50 values ranging from 12.5 to 25.0 μg/mL. The isolated compounds, (+)-callicarpaquinone-A (97), callicarpaquinone-B (96), avicequinone-C (95), (+)-paulownin (98) and (-)-wodeshiol (99) were inactive against AChE with IC50 values of > 100 μM. However, they were active against the MCF-7 breast cancer cell line with IC50 values of 25.0, 1.9, 2.3, 14.0 and 14.0 μM, respectively. The structures of the isolated compounds were elucidated using spectroscopic techniques including UV, IR, MS, 1H NMR, 13C NMR, DEPT, HMBC and1H-1H COSY. Phytochemicals Lamiaceae 2012-02 Thesis http://psasir.upm.edu.my/id/eprint/32025/ http://psasir.upm.edu.my/id/eprint/32025/1/IB%202012%2013R.pdf application/pdf en public masters Universiti Putra Malaysia Phytochemicals Lamiaceae Institute of Bioscience
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English
topic	Phytochemicals Lamiaceae
spellingShingle	Phytochemicals Lamiaceae Mohammed Othman Asiri, Sumayyah Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
description	Callicarpa maingayi, which is known in Malaysia as “tampang besi” belongs to Lamiaceae family. The plants of the genus Callicarpa have been used to treat various ailments, such as malaria, skin cancer, indigestion, dropsy, stomach disorders and rheumatism. The stem bark of Callicarpa maingayi was exhaustively extracted using methanol-water (8:2). The crude extract was successively fractionated using n-hexane, chloroform and ethyl acetate. Separation, isolation and purification of compounds were done using solvent-solvent partitioning and chromatographic techniques such as High Performance Liquid chromatography (HPLC), as well as normal phase, reverse phase and Sephadex LH-20 column chromatography. From the hexane extract, three known compounds were isolated, namely palmitic acid(91), tetracosanoic acid (92) and a mixture of stigmasterol and β-sitosterol (93). The investigation on the chloroform extract led to the isolation of two new naphthoquinone, (+)-callicarpaquinone-A (97), callicarpaquinone-B (96), along with known avicequinone-C (95), which was isolated from the first time from Callicarpa species, and 3β-hydroxy-lup-20(29)-en-28-oic-acid (94). From the ethyl acetate extract, three known compounds (+)-paulownin (98), (-)-wodeshiol (99), which were isolated for the first time from Callicarpa species together with β- sitosterol-β-D-glucopyranoside (100). The extracts and isolated compounds were screened in vitro for anticholinesterase and cytotoxic activities using Ellman's and MTT (3-(4,5-dimethylthiazole-2-yl)-2,5- diphenyltetrazolium bromide) methods. The hexane, chloroform and ethyl acetate extracts were inactive against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with IC50 values of > 100 μM, but were found to exhibit significant cytotoxicity against liver cancer (HepG2) and breast cancer (MCF-7) cell lines with IC50 values ranging from 12.5 to 25.0 μg/mL. The isolated compounds, (+)-callicarpaquinone-A (97), callicarpaquinone-B (96), avicequinone-C (95), (+)-paulownin (98) and (-)-wodeshiol (99) were inactive against AChE with IC50 values of > 100 μM. However, they were active against the MCF-7 breast cancer cell line with IC50 values of 25.0, 1.9, 2.3, 14.0 and 14.0 μM, respectively. The structures of the isolated compounds were elucidated using spectroscopic techniques including UV, IR, MS, 1H NMR, 13C NMR, DEPT, HMBC and1H-1H COSY.
format	Thesis
qualification_level	Master's degree
author	Mohammed Othman Asiri, Sumayyah
author_facet	Mohammed Othman Asiri, Sumayyah
author_sort	Mohammed Othman Asiri, Sumayyah
title	Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
title_short	Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
title_full	Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
title_fullStr	Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
title_full_unstemmed	Phytochemical and bioactivity studies of Callicarpa maingayi K. & G
title_sort	phytochemical and bioactivity studies of callicarpa maingayi k. & g
granting_institution	Universiti Putra Malaysia
granting_department	Institute of Bioscience
publishDate	2012
url	http://psasir.upm.edu.my/id/eprint/32025/1/IB%202012%2013R.pdf
_version_	1747811643447836672

Phytochemical and bioactivity studies of Callicarpa maingayi K. & G

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