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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| Format: | Thesis |
| Language: | English English |
| Published: |
2010
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| Online Access: | http://psasir.upm.edu.my/id/eprint/12431/1/FS_2010_13A.pdf http://psasir.upm.edu.my/id/eprint/12431/ |
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| Summary: | 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. |
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