Haykal, Muhammad Nazhif (2018) Retrosintesis Dan Sintesis Senyawa Kiral 1-(3- metoksi-4-hidroksi)fenil-2-propilmetanoat Dan Aktivitas Proapoptosisnya Terhadap Sel Kanker Serviks. Sarjana thesis, Universitas Brawijaya.
Abstract
Telah dilakukan retrosintesis dan sintesis senyawa kiral ester eugenol, 1- (3-metoksi, 4-hidroksi)fenil-2-propilmetanoat, dan uji aktivitas proapoptosisnya terhadap sel kanker serviks. Starting material dalam sintesis adalah eugenol yang diisolasi dari minyak cengkeh perdagangan melalui distillasi fraksinasi dengan vakum menghasilkan rendemen 70,66% dan kemurnian 100%. Analisis retrosintesis menghasilkan sinton bermuatan negatif dari gugus karboksilat dan sinton postitif dari gugus alkena. Sintesis ester eugenol dilakukan dengan prinsip reaksi adisi-esterifikasi melalui reaksi antara eugenol dengan asam format dengan perbandingan mol 1:27 dan lama reaksi 11 jam. Analisis data GC-MS terhadap hasil sintesis menunjukkan ester eugenol dihasilkan dengan kemurnian 92,42% dengan persen yield sebesar 93,34%. Data spektra UV dari ester eugenol menunjukkan adanya gugus karbonil ester yang ditunjukkan oleh serapan pada maks = 290 nm serta data spektra Infrared pada daerah 1714,60 cm-1 (gugus karbonil), 1193,65 cm-1 (gugus C-O-C ester) dan hilangnya serapan pada daerah 914,20 cm-1 dan 995,20 cm-1 yang menunjukkan hilangnya ikatan rangkap gugus vinil dalam struktur eugenol. Spektra massa menunjukkan ion molekul pada m/z 210 sesuai dengan berat molekul ester eugenol. Selanjutnya dilakukan penyiapan penanaman media kultur sel HeLa untuk uji antiproliferatif kanker serviks. Konsentrasi pelarut DMSO yang sesuai dengan senyawa aktif maupun sel kultur adalah 1%. Hasil pengamatan cytogram menunjukkan nilai LC50 dari ester eugenol berada di bawah 0,01% sedangkan eugenol di atas 0,01% yang menunjukkan kemampuan apoptosis ester eugenol lebih tinggi daripada eugenol terhadap sel kanker serviks. Nilai LC50 ester eugenol didapatkan pada konsentrasi 48,73 ppm yang menunjukkan potensinya dapat dimanfaatkan sebagai bahan obat kanker serviks berbasis bahan alam.
English Abstract
Retrosynthesis and synthesis of chiral compounds of eugenol ester, 1- (3- methoxy, 4-hydroxy)phenyl-2-propyl ethanoate, and their proapoptotic activity test have been performed against cervical cancer cells. Starting material used in the synthesis is eugenol, which is isolated from traded clove oil by fractionation distillation with vacuum, produces 70.66% yield and 100% purity. The retrosynthesis analysis produces negatively charged syringes of carboxylate and post official groups from the alkene group. The eugenol ester synthesis was carried out by the principle of esterification-addition reactions through the reaction between eugenol and formic acid with a mole ratio of 1:27 and a reaction time of 11 hours. Analysis of GC-MS data on synthesis results showed eugenol ester with purity of 92.42% and a yield percentage of 93.34%. The UV spectra data of the eugenol esters showed the presence of carbonyl ester groups exhibited by uptake at max = 290 nm and Infrared spectral data at 1714,60 cm-1 (carbonyl), 1193,65 cm-1 (COC ester). There is also absorption loss in the 914.20 cm-1 and 995.20 cm-1 regions, indicating the loss of the double bond of the vinyl group in the eugenol structure. The mass spectra show molecular ions at m/z 210 corresponding to the molecular weight of the eugenol ester. Furthermore, there is preparation to plant HeLa cell culture media for an antiproliferative test of cervical cancer. The concentration of DMSO solvent corresponding to the active compound and culture cell is 1%. The result of cytogram observation showed that LC50 value of eugenol ester was below 0.01%, while eugenol above 0.01%, showed that eugenol ester apoptosis ability was higher than eugenol against cervical cancer cells. The LC50 value of ester eugenol was obtained at a concentration of 48.73 ppm, indicating its potential to be utilized as an ingredient of cervical cancer drug based on the natural product.
Other obstract
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| Item Type: | Thesis (Sarjana) |
|---|---|
| Identification Number: | SKR/FK/2018/15/051803001 |
| Uncontrolled Keywords: | Eugenol, ester eugenol, kanker serviks, apoptosis, Eugenol, eugenol ester, anti-cervical cancer, apoptosis |
| Subjects: | 600 Technology (Applied sciences) > 616 Diseases > 616.9 Other disease > 616.99 Tumors and miscellaneous communicable diseases > 616.994 Cancers |
| Divisions: | Fakultas Kedokteran > Pendidikan Dokter |
| Depositing User: | Nur Cholis |
| Date Deposited: | 26 May 2020 23:58 |
| Last Modified: | 21 Oct 2021 03:32 |
| URI: | http://repository.ub.ac.id/id/eprint/168129 |
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