Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis

Kaempferia angustifolia, K rotunda (Zingiberaceae), Spennacoce articularis and S. exilis (Rubiaceae) were chosen since they have long been used traditionally in medicinal treatment. In this research, isolation and separation work had been carried out using various solvents and chromatographic met...

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Main Author:	Neoh, Bee Keat
Format:	Thesis
Language:	English English
Published:	2006
Subjects:	Chromatographic analysis Zingiberaceae Rubiaceae
Online Access:	http://psasir.upm.edu.my/id/eprint/6288/1/FS_2006_12.pdf
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id	my-upm-ir.6288
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spelling	my-upm-ir.62882023-10-20T07:10:51Z Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis 2006-01 Neoh, Bee Keat Kaempferia angustifolia, K rotunda (Zingiberaceae), Spennacoce articularis and S. exilis (Rubiaceae) were chosen since they have long been used traditionally in medicinal treatment. In this research, isolation and separation work had been carried out using various solvents and chromatographic methods. The structure of these compounds were determined by using spectroscopic methods such as ineared (IR), nuclear magnetic resonance ('H, 13C and 2D- NMR), mass spectrometry (MS) and by comparison with the data reported previously. The crude extracts and some of the isolated compounds were subjected to the biological activity test: antioxidant, antimicrobial tests, cytotoxic screening and larvicidal activity.Extracts fiom Kaempferia angush~oliah ave yielded a new compound angustifolienol (58), together with seven other compounds; crotepoxide (33), p-sitosterol (a), boesenboxide (M), 2'-hydroxy-4, 4', 6'-trimethoxychalcone (Xi), 6-methylzeylenol (59), and sucrose (60), and zeylenol(35). Frationation of extracts fiom K. rotunda has yielded five pure compounds; crotepoxide (33), tetracosanoic acid (61), benzoic acid (62), stigmasterol (45) and p-sitosterol (44). Both tetracosanoic acid (61) and benzoic acid (62) are new to species. Extracts fiom S. art'iculm's gave two pure compounds, identified as ursolic acid (63) and stigmasterol (45). While the extracts from S. exilis gave four compounds, benzo[g]isoquinoline-5,IOdione (64), stigmasterol (49, hexadecanoic acid (65) and ursolic acid (63). Phytochemical studies on later species had never been reported before. Acetylations of new compound, angustifolienol (58) gave two derivatives, triacetoxyangustifolienol (66) and diacetoxyangustifolienol (67). Both are new compounds, and have never been reported previously either as natural product or synthesized compounds. The major constituents of the essential oil of K. angustifolia was DL- camphor (20.57 %), while the major constituent of K. rotunda was benzyl benzoate (49.84 %). The major constituent of the essential oil of S. articularis was phytol(10.31 %), while the major constituent of S. exilis was oleic acid (20.9 %).Cytotoxic screening showed that all the crude extracts of K angustiijolia and K. rotunab were not cytotoxic against HL-60 cell line. However, pure compounds of K. angu~hyolia showed strong activity. All crude extracts of S. articularis and S. exilis (except hexane extract of S. exilis) and ursolic acid (63) were strongly cytotoxic towards HL-60 and MCF-7 cell lines. All extracts and most of the pure compounds were subjected to four strains of microbes (MRSA, Pseudomonas aeruginosa, Salmonella typhimurium and Bacillus subtilis) in the antimicrobial test. Pet. ether extracts fiom Kaempferia species, all extracts fiom S. exilis and boesenboxide (34) were active towards some microbes. In antioxidant assay, K rotunda was more active than Kaempferia angustiyolia while both Spennacoce species were moderately active. Besides that, some of the compounds from Kaempferia angustzyolia were subjected to the antioxidant assay and showed stronger antioxidant activity than a- tocopherol. In addition, all plants also showed moderate to low larvicidal activity. Chromatographic analysis Zingiberaceae Rubiaceae 2006-01 Thesis http://psasir.upm.edu.my/id/eprint/6288/ http://psasir.upm.edu.my/id/eprint/6288/1/FS_2006_12.pdf text en public doctoral Universiti Putra Malaysia Chromatographic analysis Zingiberaceae Rubiaceae Science Sukari, Mohd Aspollah English
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
advisor	Sukari, Mohd Aspollah
topic	Chromatographic analysis Zingiberaceae Rubiaceae
spellingShingle	Chromatographic analysis Zingiberaceae Rubiaceae Neoh, Bee Keat Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
description	Kaempferia angustifolia, K rotunda (Zingiberaceae), Spennacoce articularis and S. exilis (Rubiaceae) were chosen since they have long been used traditionally in medicinal treatment. In this research, isolation and separation work had been carried out using various solvents and chromatographic methods. The structure of these compounds were determined by using spectroscopic methods such as ineared (IR), nuclear magnetic resonance ('H, 13C and 2D- NMR), mass spectrometry (MS) and by comparison with the data reported previously. The crude extracts and some of the isolated compounds were subjected to the biological activity test: antioxidant, antimicrobial tests, cytotoxic screening and larvicidal activity.Extracts fiom Kaempferia angush~oliah ave yielded a new compound angustifolienol (58), together with seven other compounds; crotepoxide (33), p-sitosterol (a), boesenboxide (M), 2'-hydroxy-4, 4', 6'-trimethoxychalcone (Xi), 6-methylzeylenol (59), and sucrose (60), and zeylenol(35). Frationation of extracts fiom K. rotunda has yielded five pure compounds; crotepoxide (33), tetracosanoic acid (61), benzoic acid (62), stigmasterol (45) and p-sitosterol (44). Both tetracosanoic acid (61) and benzoic acid (62) are new to species. Extracts fiom S. art'iculm's gave two pure compounds, identified as ursolic acid (63) and stigmasterol (45). While the extracts from S. exilis gave four compounds, benzo[g]isoquinoline-5,IOdione (64), stigmasterol (49, hexadecanoic acid (65) and ursolic acid (63). Phytochemical studies on later species had never been reported before. Acetylations of new compound, angustifolienol (58) gave two derivatives, triacetoxyangustifolienol (66) and diacetoxyangustifolienol (67). Both are new compounds, and have never been reported previously either as natural product or synthesized compounds. The major constituents of the essential oil of K. angustifolia was DL- camphor (20.57 %), while the major constituent of K. rotunda was benzyl benzoate (49.84 %). The major constituent of the essential oil of S. articularis was phytol(10.31 %), while the major constituent of S. exilis was oleic acid (20.9 %).Cytotoxic screening showed that all the crude extracts of K angustiijolia and K. rotunab were not cytotoxic against HL-60 cell line. However, pure compounds of K. angu~hyolia showed strong activity. All crude extracts of S. articularis and S. exilis (except hexane extract of S. exilis) and ursolic acid (63) were strongly cytotoxic towards HL-60 and MCF-7 cell lines. All extracts and most of the pure compounds were subjected to four strains of microbes (MRSA, Pseudomonas aeruginosa, Salmonella typhimurium and Bacillus subtilis) in the antimicrobial test. Pet. ether extracts fiom Kaempferia species, all extracts fiom S. exilis and boesenboxide (34) were active towards some microbes. In antioxidant assay, K rotunda was more active than Kaempferia angustiyolia while both Spennacoce species were moderately active. Besides that, some of the compounds from Kaempferia angustzyolia were subjected to the antioxidant assay and showed stronger antioxidant activity than a- tocopherol. In addition, all plants also showed moderate to low larvicidal activity.
format	Thesis
qualification_level	Doctorate
author	Neoh, Bee Keat
author_facet	Neoh, Bee Keat
author_sort	Neoh, Bee Keat
title	Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
title_short	Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
title_full	Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
title_fullStr	Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
title_full_unstemmed	Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis
title_sort	chemical constituents and biological activity of kaempferia angustifolia, k. rotunda,spermacoce articularis and s. exilis
granting_institution	Universiti Putra Malaysia
granting_department	Science
publishDate	2006
url	http://psasir.upm.edu.my/id/eprint/6288/1/FS_2006_12.pdf
_version_	1783725721527517184

Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis

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