FLAVANOID FROM LEAVES OF MACARANGA MAPPA (EUPHORBIACEAE) AND ITS CYTOTOXIC AND ANTIOXIDANT ACTIVITIES

• Main Author: Aulia
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/34590
• Institution: Institut Teknologi Bandung

Macaranga, or locally known as “mahang-mahangan”, is one of the large genera of the family Euphorbiaceae, consisting about 300 species with a relatively wide distribution, ranging from Africa and Madagascar in the west to the tropical regions of Asia, northern Australia, and islands in the eastern Pacific. Of the total 300 species, 125 of them are in Indonesia. Phytochemical investigation on this genus is relatively new and still limited. However from the reported data it shows unique chemical structures on their phenolic derivatives, especially the flavonoid and stilben compounds. Phytochemical investigation revealed that Macaranga plants produce chalcone, dihydrochalcone, flavanone, flavonol, flavanonol, isoflavonoid, and stilbene derivatives. Characteristics and the uniqueness of these compounds occur as a result of the attachment of terpenoid substituents, identified as prenyl (C5), geranyl (C10), farnesyl (C15), and labdanyl (C20) groups, on various positions of aromatic rings. The compounds of Macaranga showed a variety of activities, including as antioxidants, COX inhibitors, cytotoxicities, and as plant growth regulators. M. mappa is one of species growing in Indonesia. Until now, only one compound has been isolated from M. Mappa, resulted compound prenylated stilbenoid with a very high cytotoxic activity (IC50 < 10 ?M) against some human cancer cells, including breast cancers (MDA-MDB) and ovarian (SK-OV and SKVLB). Therefore, further studies of this species open up opportunities for discovery of prenylated phenolic derivatives which expected having cytotoxic activity against cancer cells. The objectivites of this research is for phytochemical investigation of Indonesian M. mappa, tested the antioxidant and cytotoxic activity, and the structure-activity relationship study of the isolated compounds were evaluated for their antioxidant and cytotoxic activity. Isolation of phenolic compounds from leaves of M. mappa involved a number of laboratory works, including extraction using aseton solvent, fractination, and purification using various chromatographic techniques. The molecular structures of the isolated compounds were determined based on spectroscopic data, including UV, MS, 1D and 2D NMR. Cytotoxic test was carried out againts murine leukemia P- 388 cell according to the method of MTT assay, while antioxidant properties were evaluated according to DPPH methods. In this research, three flavonoid compounds have successfully isolated and characterized as nimfaeol C (15), apigenin (40), and luteolin (41). In antioxidant assay, the acetone extract showed weak activity with IC50 2,94 ?g/mL. Meanwhile the isolated compound, luteolin (41) and nimfaeol C (15) showed a stronger antioxidant activity than positive control (ascorbic acid, IC50 2,17 µg/mL or 12,33 ?M) with IC50 1,73 dan 2,13 µg/mL, respectively (equivalent to 6,05 dan 4,33 µM). But apigenin (40) have weaker activity with IC50 3,51 µg/mL (13 µM). However, that three compounds can be categorized as a powerful antioxidant. In cytotoxicity assay toward murine leukemia P-388 cell, the acetone extract is active with IC50 3,7 ?g/mL, more active than nimfaeol C (15) and apigenin (40) with IC50 6.4 and 22.5 µg/mL, respectively, and less active than luteolin (41) with IC50 of 2.3 µg/mL. Luteolin (41) showed a highly active cytotoxic activity with IC50 8.04 ?M, whereas nimfaeol C (15) and apigenin (40) showed moderate activity and inactivity with IC50 13 and 83.33 ?M, respectively. Overall it can be concluded that orto- dihydroxy group at C-3’ and C-4’ (ring B) has an important role in increasing activity of antioxidant and cytotoxicity assay. Reduction of hydroxyl group at C- 3’ showed a decrease in activity, as shown by apigenin (40).