PYRONE DERIVATIVES OF CRYPTOCARYA PULCHRINERVIA LEAVES AND THEIR CYTOTOXIC ACTIVITY AGAINST MURINE LEUKEMIA P-388 CELLS

• Main Author: Abdurrahman, Syawal
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/38220
• Institution: Institut Teknologi Bandung

Cryptocarya genus locally known as "medang" is a genus having high evolution rank in Lauraceae family. This genus spreads over tropical and subtropical regions, including Indonesia. Cryptocarya has economic values since its wood has been used as building materials and pulps. This plant has also been used as traditional medicines, such as to cure headaches and fever. Literature study showed that the main secondary metabolites in this genus are alkaloids, ?-pyrones and flavonoids. These secondary metabolites have diverse bioactivities, such as anticancer, antimalarial, antiinflammatory and antimicrobial. In addition, other secondary metabolites are also known, i.e. stilbenes, lignans, coumarins, terpenoids, steroids and carboxylic acid derivatives. Up to know, only 26 species Cryptocarya Indonesia have been studied for their phytochemicals and bioactivities. Nevertheless, the study of phytochemical and bioactivity of secondary metabolites of C. pulchrinervia species has not been reported yet. Therefore, this study aimed was to isolate the secondary metabolites of leaves of C. pulchrinervia and to examine the bioactivity of extracts and isolated compounds against murine leukemia cells P-388. Isolation of secondary metabolites has been conducted with a series of separation methods include maceration using methanol, separation of chlorophyl and partition with ethyl acetate. Ethyl acetate extract was then separated and purified using vacuum liquid chromatography technique, gravity column chromatography, and radial chromatography. In this research, seven pure compounds have been obtained and three of which have been characterized based on spectroscopic data of IR and NMR (1H, 13C, HSQC, HMBC and TOCSY). Those three compounds werw suggested as Piron derivative, namely CP-1, CP-2 and CP-3 that were proposed as new compounds. Biogenesis of Piron follows a common path that merging acetate malonate and shikimate pathway. The acetyl-CoA is reacted with malonyl- CoA to form polyketides. The addition of cinnamoyl-CoA to polyketides is occurred to get aromatic ring. Then, the secondary reactions (reduction, addition, cyclization and dehydration) take place to produce CP-1, CP-2 and CP-3. Test cytotoxic assay against murine leukemia cells P-388 showed that methanol and ethyl acetate extract were inactive with IC50 values of 38.61 and 46.25 µg/mL, respectively. However, two compounds, CP-1 and CP-2, were active with each IC50 values of of 3.04 and 3.03 µg/mL Meanwhile. CP-3 was inactive with IC50 29,35 µg/mL. Therefore, compounds CP-1 and CP-2 can be suggessted to be the lead compound fot anticancer. In addition, the structure and activity relationship has been discussed and it can be proposed that the addition of carbonyl group and hydroxyl group on the side chain can increase the cytotoxic against murine leukemia P-388 and the oxygenation on aromatic ring can decrease the cytotoxic against murine leukemia P-388.