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Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl

Phytochemicals and bioactivities of the fruits and the leaves of Phaleria macrocarpa have been studied. Successive extraction of the dried fruits using cold extraction followed by fractionation and purification afforded two benzophenones identified as 2,6,4'-trihydroxy-4-methoxybenzophenone and...

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Main Author: Md. Othman, Siti Nur Atiqah
Format: Thesis
Language:English
Published: 2014
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QD Chemistry
Online Access:http://eprints.utm.my/id/eprint/48822/25/SitiNurAtiqahMdOthmanMFS2014.pdf
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spelling my.utm.488222020-06-24T03:35:05Z http://eprints.utm.my/id/eprint/48822/ Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl Md. Othman, Siti Nur Atiqah QD Chemistry Phytochemicals and bioactivities of the fruits and the leaves of Phaleria macrocarpa have been studied. Successive extraction of the dried fruits using cold extraction followed by fractionation and purification afforded two benzophenones identified as 2,6,4'-trihydroxy-4-methoxybenzophenone and 6,4'-dihydroxy-4-methoxybenzophenone-2-O-ß-D-glucopyranoside and two triterpenoids identified as 24-methylenecycloartan-3-one and 24-methyl-9,19-cyclolanost-25-en-3-ol. Meanwhile, cold extraction of the dried leaves followed by fractionation and purification yielded two sterols known as stigmasterol and ß-sitosterol. Fractionation and purification process were done using vacuum liquid chromatography and column chromatography, respectively. The structures of isolated compounds were elucidated on the basis of their spectral data including 1D and 2D Nuclear Magnetic Resonance (1H, 13C, DEPT, COSY, HMQC, HMBC), Infrared, Ultraviolet spectroscopies and mass spectrometry. The antibacterial activities of all crude extracts and isolated compounds were performed using disc diffusion method followed by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against two Gram-positive bacterial strains, Bacillus subtilis and Staphylococcus aureus together with two Gram-negative bacterial strains including Escherichia coli and Pseudomonas putida. The results have demonstrated that all extracts and isolated compounds exhibited weak activity against all tested bacteria with the MBC values exceeded 1000 µg/mL. Evaluation of antioxidant activity using 2,2-diphenyl-1-picrylhydydrazyl (DPPH) assay has revealed strong free radical scavenging properties of ethyl acetate and ethanol extracts from the fruits with SC50 of 14.00 and 19.97 µg/mL, respectively. The chloroform extract from the fruits and all extracts from the leaves exhibited moderate antioxidant activities with SC50 ranging between 58.07 – 94.10 µg/mL. Among the isolated compounds, 2,6,4'-trihydroxy-4-methoxy- benzophenone exhibited high free radical scavenging activity with SC50 of 29.73 µg/mL whereas the other isolated compounds were inactive against DPPH. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was carried out to evaluate the cytotoxic activity of crude extracts and isolated compounds. MTT assay of CHO, MCF-7, MDA-MB-231 and MDA-MB-468 cells were treated with all extracts and isolated compounds whereas the cell viability of 3T3, HeLa and HT-29 were treated by extracts of the fruits and two isolated benzophenones. The result has demonstrated good activity of dichloromethane extract from the leaves against MDA-MB-231 cell line (IC50 70 µg/mL) and moderate cytotoxic effect of ethanol extract from the fruits towards MDA-MB-468 and HT-29 cell lines with the same IC50 of 100 µg/mL. Chloroform extract from the fruits was found to have moderate cytotoxic properties against HT-29 cell line (IC50 100 µg/mL). All isolated compounds were found to have weak cytotoxic activity towards all tested cell lines. 2014-07 Thesis NonPeerReviewed application/pdf en http://eprints.utm.my/id/eprint/48822/25/SitiNurAtiqahMdOthmanMFS2014.pdf Md. Othman, Siti Nur Atiqah (2014) Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl. Masters thesis, Universiti Teknologi Malaysia, Faculty of Science. http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:83756
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Md. Othman, Siti Nur Atiqah
Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
description Phytochemicals and bioactivities of the fruits and the leaves of Phaleria macrocarpa have been studied. Successive extraction of the dried fruits using cold extraction followed by fractionation and purification afforded two benzophenones identified as 2,6,4'-trihydroxy-4-methoxybenzophenone and 6,4'-dihydroxy-4-methoxybenzophenone-2-O-ß-D-glucopyranoside and two triterpenoids identified as 24-methylenecycloartan-3-one and 24-methyl-9,19-cyclolanost-25-en-3-ol. Meanwhile, cold extraction of the dried leaves followed by fractionation and purification yielded two sterols known as stigmasterol and ß-sitosterol. Fractionation and purification process were done using vacuum liquid chromatography and column chromatography, respectively. The structures of isolated compounds were elucidated on the basis of their spectral data including 1D and 2D Nuclear Magnetic Resonance (1H, 13C, DEPT, COSY, HMQC, HMBC), Infrared, Ultraviolet spectroscopies and mass spectrometry. The antibacterial activities of all crude extracts and isolated compounds were performed using disc diffusion method followed by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against two Gram-positive bacterial strains, Bacillus subtilis and Staphylococcus aureus together with two Gram-negative bacterial strains including Escherichia coli and Pseudomonas putida. The results have demonstrated that all extracts and isolated compounds exhibited weak activity against all tested bacteria with the MBC values exceeded 1000 µg/mL. Evaluation of antioxidant activity using 2,2-diphenyl-1-picrylhydydrazyl (DPPH) assay has revealed strong free radical scavenging properties of ethyl acetate and ethanol extracts from the fruits with SC50 of 14.00 and 19.97 µg/mL, respectively. The chloroform extract from the fruits and all extracts from the leaves exhibited moderate antioxidant activities with SC50 ranging between 58.07 – 94.10 µg/mL. Among the isolated compounds, 2,6,4'-trihydroxy-4-methoxy- benzophenone exhibited high free radical scavenging activity with SC50 of 29.73 µg/mL whereas the other isolated compounds were inactive against DPPH. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was carried out to evaluate the cytotoxic activity of crude extracts and isolated compounds. MTT assay of CHO, MCF-7, MDA-MB-231 and MDA-MB-468 cells were treated with all extracts and isolated compounds whereas the cell viability of 3T3, HeLa and HT-29 were treated by extracts of the fruits and two isolated benzophenones. The result has demonstrated good activity of dichloromethane extract from the leaves against MDA-MB-231 cell line (IC50 70 µg/mL) and moderate cytotoxic effect of ethanol extract from the fruits towards MDA-MB-468 and HT-29 cell lines with the same IC50 of 100 µg/mL. Chloroform extract from the fruits was found to have moderate cytotoxic properties against HT-29 cell line (IC50 100 µg/mL). All isolated compounds were found to have weak cytotoxic activity towards all tested cell lines.
format Thesis
author Md. Othman, Siti Nur Atiqah
author_facet Md. Othman, Siti Nur Atiqah
author_sort Md. Othman, Siti Nur Atiqah
title Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
title_short Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
title_full Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
title_fullStr Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
title_full_unstemmed Chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
title_sort chemical constituents and bioactivities of the fruits and leaves of phaleria macrocarpa (scheff.) boerl
publishDate 2014
url http://eprints.utm.my/id/eprint/48822/25/SitiNurAtiqahMdOthmanMFS2014.pdf
http://eprints.utm.my/id/eprint/48822/
http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:83756
_version_ 1672610472401043456
score 13.211869

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