FUROFURAN LIGNANS DERIVATES FROM LEAVES OF CRYPTOCARYA COSTATA AND THEIR BIOACTIVITY

• Main Author: Apriadi Putra, Adhan
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/68337
• Institution: Institut Teknologi Bandung

Indonesia is a rich country with biological resources spread throughout the Indonesian archipelago. One of the islands with a high level of diversity and endemicity is the island of Sulawesi. Biodiversity in Sulawesi has spread from lower plants to higher plants. One of the known rare plants found in Sulawesi is Cryptocarya costata, belonging to the Lauraceae family. Plants of the Cryptocarya genus from Indonesia are reported as one of the genera producing pyrone and flavonoid bioactive compounds. The secondary metabolites studies of C. costata have been carried out only on the bark, but have not been carried out on other tissues. It has been reported in the bark of four compounds of flavonoid groups from the chalcone and flavanone groups, namely 7-hydroxy-5,6-dimethoxyflavanone, didimocarpine, 2',4'-dihydroxy-5',6'-dimethoxycalcone and isodidimocarpine. These compounds have bioactivity against P-388 murine leukemia cells with IC50 values of 130±4.7, 84.1±1.1; 5.7±0.9 and 11.1±0.2 ?M, respectively. The chalcone and flavanone compounds from C. costata have the uniqueness of ring A, which is fully oxygenated and ring B is not oxygenated. In this research, secondary metabolites of Cryptocarya costata were isolated from leaves that had not been previously reported. Isolation of compounds from C. costata leaves was carried out in several steps, starting with maceration of leaf powder using acetone as solvent. Furthermore, the acetone extract was fractionated and purified by various chromatographic techniques, including vacuum liquid chromatography (VLC) and gravity column chromatography (GCC). The structure of isolated compounds was characterized by using spectroscopic data 1D-NMR (1H-NMR and 13C-NMR), 2D-NMR (HSQC and HMBC), and mass spectrometry. Furthermore, the isolated compounds were examined for cytotoxic properties against MCF-7 breast cancer cells and DU145 prostate cancer cells. In this study, four secondary metabolites of the furofuran lignan group, namely (+)-silvatesmin, silvatesmin diastereoisomer, CC-3, and CC-4 have been isolated from leaves of C. costata. Compounds CC-3 and CC-4 were suggested as new compounds. The four furofuran lignan compounds that have been isolated were the first type of compound reported from C. costata. So far, new groups of lignans have only been found from four species of Cryptocarya, two of which are furofuran lignan, from C. nitens and C. immpresinervia. The results of the bioactivity assay of the four compounds isolated against two cancer cells, MCF-7 and DU145, showed that only compounds CC-3 and CC-4 had moderate activity against MCF-7 breast cancer cells.