Synthesis of Phenyl Cinnamate and 4-Phenylchroman-2-one and Cytotoxicity Activity Test Against HeLa Cervical Cancer Cells
| Main Authors: | ERNAWATI, TENI, FAIRUSI, DILA |
|---|---|
| Format: | Article info application/pdf eJournal |
| Bahasa: | ind |
| Terbitan: |
Fakultas Farmasi Universitas Indonesia
, 2013
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| Online Access: |
http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/221 http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/221/156 |
Daftar Isi:
- Cinnamic acid is a derivative of methyl cinnamate; it is included in the shikimic acid pathway derivatives. Cinnamic acid and its natural analogue are known as a cancer treatment for several centuries.Synthesis of phenyl cinnamic and 4-phenilkroman-2-on derived from methyl cinnamate had been done by using acid as a catalyst. Methyl cinnamic was first converted into cinnamic acid via hydrolysis reaction with alkaline. After that, cinnamic acid was chlorinated by using thionyl chloride and phenol reagent to produce fenil-sinamat. Esterification reaction was carried out by using an acid catalyst p-toluen sulfonic acid and phenol resulting 4-phenilkroman-2-on. We obtained the products for the synthesis of cinnamic acid, cinnamic phenyl and 4-fenilkroman-2-on, with yields respectively of 83.6%, 14.71%, and 16.18%.Cytotoxicity test using the brine shrimp lethality test (BSLT) was conducted on both cinnamic phenyl compound and 4-phenilkroman-2-on compound. LC50 values obtained for both compounds respectively were 223.87 ppm and 112.72 ppm. The results of MTT cytotoxicity assay method for cervical cancer HeLa cells (ATCC CCL2) using phenyl cinnamic and 4-phenilkroman-2-on were found that the percentage of inhibition obtained is over 50%.
- Asam sinamat merupakan turunan dari metil sinamat, yang termasuk dalam jalur turunan asam shikimat. Asam sinamat dan analog alaminya dikenal dalam pengobatan kanker selama beberapa abad. Sintesis fenil sinamat dan 4-fenilkroman-2-on telah dilakukan dari metil sinamat dengan menggunakan katalis asam. Senyawa metil sinamat terlebih dahulu dikonversi menjadi asam sinamat melalui reaksi hidrolisis dengan basa. Selanjutnya asam sinamat diklorinasi menggunakan tionil klorida dan fenol dan menghasilkan fenil sinamat. Reaksi esterifikasi dengan fenol menggunakan katalis asam p-toluen sulfonat menghasilkan senyawa 4-fenilkroman-2-on. Dari peneitian ini diperoleh rendemen hasil sintesis asam sinamat, fenil sinamat dan 4-fenilkroman-2-on masing-masing adalah 83,6%, 14,71% dan 16,18%. Uji sitotoksisitas senyawa fenil sinamat dan 4-fenilkroman-2-on menggunakan metode brine shrimp lethality test (BSLT) diperoleh nilai LC50 masing-masing sebesar 223,87 dan 112,72 ppm. Hasil uji fenil sinamat dan 4-fenilkroman-2-on terhadap sel kanker serviks HeLa (ATCC CCL2) dengan metode MTT didapatkan persentase inhibisi masing-masing adalah di atas 50%.