ISOLATION, TRANSFORMATION REACTION, AND CYTOTOXICITY ASSAY OF BIFLAVONOID FROM AGATHIS DAMMARA LEAVES (ARAUCARIACEAE)
Cancer is the second leading cause of death worldwide, with the number of deaths reaching 9.6 million people in 2018. Research on anticancer drugs from natural products is growing rapidly, considering that anticancer drugs still have side effects. One group of natural compounds that is known t...
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| Format: | Final Project |
| Language: | Indonesia |
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| Online Access: | https://digilib.itb.ac.id/gdl/view/81551 |
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| Institution: | Institut Teknologi Bandung |
| Language: | Indonesia |
| Summary: | Cancer is the second leading cause of death worldwide, with the number of deaths reaching
9.6 million people in 2018. Research on anticancer drugs from natural products is growing
rapidly, considering that anticancer drugs still have side effects. One group of natural
compounds that is known to have anticancer potential is biflavonoids. The biflavonoid
group has been reported from the genus Agathis. One of the Agathis genus which is
endemic to Indonesia, is Agathis dammara. A study of biflavonoids from the leaves and
twigs of A. dammara from Cikole has successfully isolated 15 biflavonoid compounds,
seven of which have been reported to inhibit the BACE-1 enzyme as an anti Alzheimer.
Next, research on biflavonoids from the non-polar to semi-polar fraction of A. dammara
leaves from Bandung has also been reported. The compounds that have been isolated are
7,4',7'',4'''-tetra-O-methylcupressuflavone (3) , and 7,4',7''-tri-O-methylcupressuflavone (2),
and one new compound is 4',7 '',4'''-tri-O-methylcupressuflavone (6). However, the
biflavonoid from the semi-polar to polar fraction of the leaves of A. dammara (Bandung)
and the study of their cytotoxic activity have not been reported. In addition, in nature,
prenylated biflavonoids exist and studies of their bioactivity are limited. Therefore, the
objective of this research was to continue the isolation, transformation reaction, and
characterization of bioflavonoids from semi-polar to polar fractions of the leaves of A.
dammara growing in Bandung. The biflavonoid isolation was carried out using
chromatographic techniques such as vacuum liquid chromatography (VLC), gravity
column chromatography (GCC), and radial chromatography (RC). In this research, two
biflavonoids were successfully isolated, identified as 7,4',7''-tri-O-methylcupressuflavone
(59.6 mg) and 7-mono-O-methylcupressuflavone (13.4 mg). The compound 7-mono-Omethylcupressuflavone (7) was isolated for the first time from the species A. dammara.
Then, the main compound was transformed through a prenylation reaction, and a pure
product was obtained, which was a new compound, namely 4'''-O-prenyl-7,4',7”-tri-Omethylcupressuflavone (28) with a yield of 69.4 %. Meanwhile, the results of the
cytotoxicity assay against murine leukemia P-388 cells showed that the acetone extract of
A. dammara leaves was active with an IC50 value of 5,52 µg/mL. Two of isolated
compounds, labelled as compounds 2 and 7 indicated that the values of IC50 >100 µg/mL
and 6,23 µg/mL, respectively. Additionally, the compounds from transformation reaction
(28) has result an IC50 values 23,06 µg/mL. |
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