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Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities

Phytochemical and biological studies were carried out on two species from the Guttiferae family, Cratoxylum arborescens and Cratoxylum glaucum. The chemical investigation discovered triterpenoids, quinones and xanthones. These compounds were isolated using common chromatographic techniques and were...

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Main Author: Sim, Wei Chung
Format: Thesis
Language:English
English
Published: 2010
Online Access:http://psasir.upm.edu.my/id/eprint/19578/1/FS_2010_27_F.pdf
http://psasir.upm.edu.my/id/eprint/19578/
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spelling my.upm.eprints.195782013-05-27T08:02:37Z http://psasir.upm.edu.my/id/eprint/19578/ Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities Sim, Wei Chung Phytochemical and biological studies were carried out on two species from the Guttiferae family, Cratoxylum arborescens and Cratoxylum glaucum. The chemical investigation discovered triterpenoids, quinones and xanthones. These compounds were isolated using common chromatographic techniques and were identified using modern spectroscopic techniques such as 1D and 2D NMR, MS, IR and UV. Cratoxylum arborescens (stem bark) afforded friedelin, stigmasterol, fuscaxanthone C and two anthraquinone, vismiaquinone and 3-geranyloxy-6-methyl- ,8-dihydroxyanthraquinone. Meanwhile, studies on Cratoxylum glaucum (stem bark)revealed the presence of three xanthones, α-mangostin, β-mangostin and fuscaxanthone C, along with an anthraquinone, 1,8-dihydroxy-3-methoxy- 6-methylanthraquinone, friedelin, β-sitosterol and betulinic acid. This is the first report of α-mangostin, β-mangostin and betulinic acid from Cratoxylum glaucum. The acetylation of fuscaxanthone C has successfully yielded dimethylmangostin acetate. Antioxidant properties of the crude extracts of these two species were tested using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method and compared to a well known antioxidant, ascorbic acid. The crude methanol extracts of both Cratoxylum arborescens and C. glaucum showed high antioxidant activities with low EC50 values of 10.40 and 7.48 ppm, respectively, and are comparable to that of ascorbic acid, 5.17 ppm. The crude chloroform extract of C. arborescens also gave good activity, with an EC50 value of 31.04 ppm. The total phenolic content of the methanol extracts of both species were measured using Folin-Ciocalteu method. The hexane and ethyl acetate extracts of Cratoxylum glaucum and the hexane and chloroform extracts of Cratoxylum arborescens demonstrated low IC50 values against the MCF7 cancer cell line. Meanwhile, the ethyl acetate and methanol extracts of Cratoxylum glaucum and all the extracts of Cratoxylum arborescens were active against HL-60 cancer cell line. The antibacterial activity test was also carried out using eight bacteria, namely,Bacillus cereus, Micrococcus luteus, Methicillin-Sensitive Staphylococcus Aureus (MSSA), Methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli,Klebsiella pneumonia, Pseudomonas aeruginosa and Enterobacter aerogenes.However, all the crude extracts gave only weak or no inhibition to these bacteria. The larvicidal tests were performed against the larvae of Aedes aegypti using the WHO (1981) standard procedures with slight modifications. All the extracts of Cratoxylum arborescens and C. glaucum were found to be inactive against the larvae of Aedes aegypti. 2010-09 Thesis NonPeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/19578/1/FS_2010_27_F.pdf Sim, Wei Chung (2010) Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities. Masters thesis, Universiti Putra Malaysia. English
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
English
description Phytochemical and biological studies were carried out on two species from the Guttiferae family, Cratoxylum arborescens and Cratoxylum glaucum. The chemical investigation discovered triterpenoids, quinones and xanthones. These compounds were isolated using common chromatographic techniques and were identified using modern spectroscopic techniques such as 1D and 2D NMR, MS, IR and UV. Cratoxylum arborescens (stem bark) afforded friedelin, stigmasterol, fuscaxanthone C and two anthraquinone, vismiaquinone and 3-geranyloxy-6-methyl- ,8-dihydroxyanthraquinone. Meanwhile, studies on Cratoxylum glaucum (stem bark)revealed the presence of three xanthones, α-mangostin, β-mangostin and fuscaxanthone C, along with an anthraquinone, 1,8-dihydroxy-3-methoxy- 6-methylanthraquinone, friedelin, β-sitosterol and betulinic acid. This is the first report of α-mangostin, β-mangostin and betulinic acid from Cratoxylum glaucum. The acetylation of fuscaxanthone C has successfully yielded dimethylmangostin acetate. Antioxidant properties of the crude extracts of these two species were tested using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method and compared to a well known antioxidant, ascorbic acid. The crude methanol extracts of both Cratoxylum arborescens and C. glaucum showed high antioxidant activities with low EC50 values of 10.40 and 7.48 ppm, respectively, and are comparable to that of ascorbic acid, 5.17 ppm. The crude chloroform extract of C. arborescens also gave good activity, with an EC50 value of 31.04 ppm. The total phenolic content of the methanol extracts of both species were measured using Folin-Ciocalteu method. The hexane and ethyl acetate extracts of Cratoxylum glaucum and the hexane and chloroform extracts of Cratoxylum arborescens demonstrated low IC50 values against the MCF7 cancer cell line. Meanwhile, the ethyl acetate and methanol extracts of Cratoxylum glaucum and all the extracts of Cratoxylum arborescens were active against HL-60 cancer cell line. The antibacterial activity test was also carried out using eight bacteria, namely,Bacillus cereus, Micrococcus luteus, Methicillin-Sensitive Staphylococcus Aureus (MSSA), Methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli,Klebsiella pneumonia, Pseudomonas aeruginosa and Enterobacter aerogenes.However, all the crude extracts gave only weak or no inhibition to these bacteria. The larvicidal tests were performed against the larvae of Aedes aegypti using the WHO (1981) standard procedures with slight modifications. All the extracts of Cratoxylum arborescens and C. glaucum were found to be inactive against the larvae of Aedes aegypti.
format Thesis
author Sim, Wei Chung
spellingShingle Sim, Wei Chung
Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
author_facet Sim, Wei Chung
author_sort Sim, Wei Chung
title Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
title_short Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
title_full Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
title_fullStr Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
title_full_unstemmed Secondary Metabolites from the Stem Bark of Geronggang (Cratoxylum arborescens (Vahl) Bl.)and Ketemau (Cratoxylum glaucum K.) and Their Biological Activities
title_sort secondary metabolites from the stem bark of geronggang (cratoxylum arborescens (vahl) bl.)and ketemau (cratoxylum glaucum k.) and their biological activities
publishDate 2010
url http://psasir.upm.edu.my/id/eprint/19578/1/FS_2010_27_F.pdf
http://psasir.upm.edu.my/id/eprint/19578/
_version_ 1643827078040125440
score 13.211869

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