Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)

Chemical investigation of Artocarpus kemando and Artocarpus odoratissimus have resulted in the isolation of ten compounds, three of which are new. All the pure metabolites were purified by means of chromatographic method and their structures were determined from modern spectroscopic identificatio...

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Main Author:	Teo, Siow Hwa
Format:	Thesis
Language:	English English
Published:	2010
Subjects:	Botanical chemistry - Malaysia Biological chemistry Artocarpus - Malaysia
Online Access:	http://psasir.upm.edu.my/id/eprint/12431/1/FS_2010_13A.pdf
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id	my-upm-ir.12431
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spelling	my-upm-ir.124312013-05-27T07:52:12Z Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae) 2010-03 Teo, Siow Hwa Chemical investigation of Artocarpus kemando and Artocarpus odoratissimus have resulted in the isolation of ten compounds, three of which are new. All the pure metabolites were purified by means of chromatographic method and their structures were determined from modern spectroscopic identification such as one-dimensional nuclear magnetic resonance spectroscopy, two-dimensional nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet spectroscopy and mass spectrometry. The two new compounds successfully isolated from the crude extracts of stem bark of the Artocarpus kemando, are artomandin (161) and kemandonin (162). Besides this, two triterpenoids were identified to be 24-methylenecycloartanyl acetate (160) and β-Sitosterol (1), while four flavonoids were authenticated as cycloartobiloxanthone (8), artoindonesianin C (51), artonol B (73) and artochamin (95). On the other hand, studies on the stem bark crude extracts of Artocarpus odoratissimus yielded a triterpenoid, traxateryl acetate (163), and a new flavonoid, artosimmin (164). The biological studies on the crude extracts and pure compounds of Artocarpus species indicated both to have significant biological activity especially in the cytotoxic assay. Cytotoxic assay was performed using human promyelocytic leukemia, HL-60 and human breast adenocarcinoma, MCF-7 cell lines. All the stem bark extracts of Artocarpus species were found to show significant growth inhibition activities towards HL-60 cell line especially the chloroform, ethyl acetate and ethanol extracts of Artocarpus odoratissimus, which gave extremely low IC50 values of 3.2, 3.7 and 2.9 μg/ ml, respectively. Moreover, the MCF-7 cell line was found to be sensitive against the chloroform, ethyl acetate and ethanol extracts of Artocarpus odoratissimus with IC50 values of less than 30.0 μg/ ml. Artomandin (161) strongly inhibits the HL-60 and MCF-7 cell lines with IC50 values of 2.4 and 3.1 μg/ ml, respectively. Both cell lines also showed similar degree of susceptibility toward artosimmin (164) with IC50 values of 1.1 and 3.4 μg/ ml, respectively. However, the HL-60 cell line was found to be moderately susceptible toward cycloartobiloxanthone (8) and kemandonin (162) with IC50 values of 5.7 and 6.9 μg/ ml, respectively. Meanwhile, the MCF-7 cell line was also observed to be far less sensitive to cycloartobiloxanthone (8) and kemandonin (162), which exhibited medium cytotoxicity with the IC50 value of 13.4 and 13.1 μg/ ml, respectively. Antioxidant assays were also carried out on the crude extracts and pure compounds of the stem bark of Artocarpus kemando and Artocarpus odoratissimus using free radical DPPH scavenging test. The crude chloroform, ethanol and methanol extracts of Artocarpus kemando gave the strongest antioxidant capacity in the free radical DPPH tests with extremely low IC50 values of 27.1, 19.2 as well as 23.3 μg/ ml. artomandin (161) and artosimmin (164), showed the highest potential of scavenging effect towards the DPPH radical test with IC50 values of 38.0 and 32.1 μg/ ml, respectively. Meanwhile, cycloartobiloxanthone (8) revealed a lower DPPH scavenging effect with an IC50 value of 87.2 μg/ ml. Both artoindonesianin C (51) and artonol B (73) gave weak scavenging activity with IC50 values of more than 90.0 μg/ ml. Botanical chemistry - Malaysia Biological chemistry Artocarpus - Malaysia 2010-03 Thesis http://psasir.upm.edu.my/id/eprint/12431/ http://psasir.upm.edu.my/id/eprint/12431/1/FS_2010_13A.pdf application/pdf en public masters Universiti Putra Malaysia Botanical chemistry - Malaysia Biological chemistry Artocarpus - Malaysia Faculty Of Science English
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
topic	Botanical chemistry - Malaysia Biological chemistry Artocarpus - Malaysia
spellingShingle	Botanical chemistry - Malaysia Biological chemistry Artocarpus - Malaysia Teo, Siow Hwa Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
description	Chemical investigation of Artocarpus kemando and Artocarpus odoratissimus have resulted in the isolation of ten compounds, three of which are new. All the pure metabolites were purified by means of chromatographic method and their structures were determined from modern spectroscopic identification such as one-dimensional nuclear magnetic resonance spectroscopy, two-dimensional nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet spectroscopy and mass spectrometry. The two new compounds successfully isolated from the crude extracts of stem bark of the Artocarpus kemando, are artomandin (161) and kemandonin (162). Besides this, two triterpenoids were identified to be 24-methylenecycloartanyl acetate (160) and β-Sitosterol (1), while four flavonoids were authenticated as cycloartobiloxanthone (8), artoindonesianin C (51), artonol B (73) and artochamin (95). On the other hand, studies on the stem bark crude extracts of Artocarpus odoratissimus yielded a triterpenoid, traxateryl acetate (163), and a new flavonoid, artosimmin (164). The biological studies on the crude extracts and pure compounds of Artocarpus species indicated both to have significant biological activity especially in the cytotoxic assay. Cytotoxic assay was performed using human promyelocytic leukemia, HL-60 and human breast adenocarcinoma, MCF-7 cell lines. All the stem bark extracts of Artocarpus species were found to show significant growth inhibition activities towards HL-60 cell line especially the chloroform, ethyl acetate and ethanol extracts of Artocarpus odoratissimus, which gave extremely low IC50 values of 3.2, 3.7 and 2.9 μg/ ml, respectively. Moreover, the MCF-7 cell line was found to be sensitive against the chloroform, ethyl acetate and ethanol extracts of Artocarpus odoratissimus with IC50 values of less than 30.0 μg/ ml. Artomandin (161) strongly inhibits the HL-60 and MCF-7 cell lines with IC50 values of 2.4 and 3.1 μg/ ml, respectively. Both cell lines also showed similar degree of susceptibility toward artosimmin (164) with IC50 values of 1.1 and 3.4 μg/ ml, respectively. However, the HL-60 cell line was found to be moderately susceptible toward cycloartobiloxanthone (8) and kemandonin (162) with IC50 values of 5.7 and 6.9 μg/ ml, respectively. Meanwhile, the MCF-7 cell line was also observed to be far less sensitive to cycloartobiloxanthone (8) and kemandonin (162), which exhibited medium cytotoxicity with the IC50 value of 13.4 and 13.1 μg/ ml, respectively. Antioxidant assays were also carried out on the crude extracts and pure compounds of the stem bark of Artocarpus kemando and Artocarpus odoratissimus using free radical DPPH scavenging test. The crude chloroform, ethanol and methanol extracts of Artocarpus kemando gave the strongest antioxidant capacity in the free radical DPPH tests with extremely low IC50 values of 27.1, 19.2 as well as 23.3 μg/ ml. artomandin (161) and artosimmin (164), showed the highest potential of scavenging effect towards the DPPH radical test with IC50 values of 38.0 and 32.1 μg/ ml, respectively. Meanwhile, cycloartobiloxanthone (8) revealed a lower DPPH scavenging effect with an IC50 value of 87.2 μg/ ml. Both artoindonesianin C (51) and artonol B (73) gave weak scavenging activity with IC50 values of more than 90.0 μg/ ml.
format	Thesis
qualification_level	Master's degree
author	Teo, Siow Hwa
author_facet	Teo, Siow Hwa
author_sort	Teo, Siow Hwa
title	Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
title_short	Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
title_full	Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
title_fullStr	Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
title_full_unstemmed	Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)
title_sort	phytochemistry and biological activities of artocarpus kemando miq. (pudau) and artocarpus odoratissimus blanco (terap) (moraceae)
granting_institution	Universiti Putra Malaysia
granting_department	Faculty Of Science
publishDate	2010
url	http://psasir.upm.edu.my/id/eprint/12431/1/FS_2010_13A.pdf
_version_	1747811364748918784

Phytochemistry And Biological Activities Of Artocarpus Kemando Miq. (Pudau) And Artocarpus Odoratissimus Blanco (Terap) (Moraceae)

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