Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities

Anaxagorea javanica Blume (synonym A. scortechinii King) or locally known as ‘bunga pompun’, ‘kekapur’, ‘larak lecek’, ‘akar angin’, ‘kinchong’ or ‘atis’ is an endermic plant in Malaysia. The plant belongs to Annonaceae family and is traditionally used for the treatment after childbirth. Phytochemi...

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Main Author:	Husain, Khairana
Format:	Thesis
Language:	English English
Published:	2008
Subjects:	Plant cells and tissues
Online Access:	http://psasir.upm.edu.my/id/eprint/7197/1/IB_2008_11a.pdf
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spelling	my-upm-ir.71972013-05-27T07:34:00Z Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities 2008-12 Husain, Khairana Anaxagorea javanica Blume (synonym A. scortechinii King) or locally known as ‘bunga pompun’, ‘kekapur’, ‘larak lecek’, ‘akar angin’, ‘kinchong’ or ‘atis’ is an endermic plant in Malaysia. The plant belongs to Annonaceae family and is traditionally used for the treatment after childbirth. Phytochemical investigation on the bark and root of this plant yielded seventeen pure compounds, comprising steroids, fatty acids, simple phenolics, alkaloids, flavonoids and sesquiterpenes. In total, seven alkaloids were isolated, out of which two new derivatives of copyrine alkaloid were 4,11-dimethoxyeupolauridine (87) and 2-methoxy-3-hydroxyeupolauridine (88) in addition to four known compounds, eupolauridine (22), 11- methoxyeupolauridine (86), sampangine (95) and 3-methoxysampangine (96). Another known alkaloid came from oxoaporphine was lysicamine (91). The isolation of copyrine and oxoaporphine alkaloids was a first time from the genus. Other known compounds isolated, included a mixture of β-sitosterol (49) and stigmasterol (94), quercetin (46), 7α-hydroxystigmasterol (92), 7-oxostigmasterol (93), 4-hydroxybutanamide (95), tetradecanoic acid (96), syringic aldehyde (97) and 2,3-dihydroxy-1-(4’-hydroxy-3’,5’-dimethoxyphenyl)-1-propanone (98). A novel sesquiterpene identified as 2,2,9-trimethyl-5-methylene-12-oxa-bicyclo[6.3.1]dodecane-4,9-diol (85) (nordine) was also isolated. All structures were elucidated by spectroscopic techniques and by comparison with data available from literature. Studies on the biological activities related to inflammation were conducted using nitric oxide (NO) and 5-lipoxygenase (5-LOX) inhibitory assay as a priminary screening as well as antioxidant assay. The results showed that both hexane and dichloromethane extracts from the barks possessed weak inhibition on NO production at the highest concentration of 200 μg/ml without cytotoxic effect. Meanwhile, inhibition of lipoxygenase activity was shown only by methanolic and acetone extracts from roots at 100 μg/ml with an IC50 of 48.21 and 63.87 μg/ml, respectively. However, all the crude extracts from barks and roots are poor radical scavenger inhibitors. Further in vitro investigation on the selected pure compounds showed that only sampangine (89) and 3- methoxysampangine (90) significantly inhibited NO production with IC50 values of 18.17 and 32.25 μg/ml, respectively, at the highest concentration of 25 μg/ml tested. Plant cells and tissues 2008-12 Thesis http://psasir.upm.edu.my/id/eprint/7197/ http://psasir.upm.edu.my/id/eprint/7197/1/IB_2008_11a.pdf application/pdf en public phd doctoral Universiti Putra Malaysia Plant cells and tissues Institute Bioscience English
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
topic	Plant cells and tissues
spellingShingle	Plant cells and tissues Husain, Khairana Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
description	Anaxagorea javanica Blume (synonym A. scortechinii King) or locally known as ‘bunga pompun’, ‘kekapur’, ‘larak lecek’, ‘akar angin’, ‘kinchong’ or ‘atis’ is an endermic plant in Malaysia. The plant belongs to Annonaceae family and is traditionally used for the treatment after childbirth. Phytochemical investigation on the bark and root of this plant yielded seventeen pure compounds, comprising steroids, fatty acids, simple phenolics, alkaloids, flavonoids and sesquiterpenes. In total, seven alkaloids were isolated, out of which two new derivatives of copyrine alkaloid were 4,11-dimethoxyeupolauridine (87) and 2-methoxy-3-hydroxyeupolauridine (88) in addition to four known compounds, eupolauridine (22), 11- methoxyeupolauridine (86), sampangine (95) and 3-methoxysampangine (96). Another known alkaloid came from oxoaporphine was lysicamine (91). The isolation of copyrine and oxoaporphine alkaloids was a first time from the genus. Other known compounds isolated, included a mixture of β-sitosterol (49) and stigmasterol (94), quercetin (46), 7α-hydroxystigmasterol (92), 7-oxostigmasterol (93), 4-hydroxybutanamide (95), tetradecanoic acid (96), syringic aldehyde (97) and 2,3-dihydroxy-1-(4’-hydroxy-3’,5’-dimethoxyphenyl)-1-propanone (98). A novel sesquiterpene identified as 2,2,9-trimethyl-5-methylene-12-oxa-bicyclo[6.3.1]dodecane-4,9-diol (85) (nordine) was also isolated. All structures were elucidated by spectroscopic techniques and by comparison with data available from literature. Studies on the biological activities related to inflammation were conducted using nitric oxide (NO) and 5-lipoxygenase (5-LOX) inhibitory assay as a priminary screening as well as antioxidant assay. The results showed that both hexane and dichloromethane extracts from the barks possessed weak inhibition on NO production at the highest concentration of 200 μg/ml without cytotoxic effect. Meanwhile, inhibition of lipoxygenase activity was shown only by methanolic and acetone extracts from roots at 100 μg/ml with an IC50 of 48.21 and 63.87 μg/ml, respectively. However, all the crude extracts from barks and roots are poor radical scavenger inhibitors. Further in vitro investigation on the selected pure compounds showed that only sampangine (89) and 3- methoxysampangine (90) significantly inhibited NO production with IC50 values of 18.17 and 32.25 μg/ml, respectively, at the highest concentration of 25 μg/ml tested.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Husain, Khairana
author_facet	Husain, Khairana
author_sort	Husain, Khairana
title	Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
title_short	Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
title_full	Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
title_fullStr	Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
title_full_unstemmed	Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities
title_sort	chemical constituents of anaxagorea javanica and their antioxidant and anti-inflammatory activities
granting_institution	Universiti Putra Malaysia
granting_department	Institute Bioscience
publishDate	2008
url	http://psasir.upm.edu.my/id/eprint/7197/1/IB_2008_11a.pdf
_version_	1747810671735603200

Chemical Constituents of Anaxagorea Javanica and Their Antioxidant and Anti-Inflammatory Activities

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