SINTESIS ANALOG KURKUMIN MONO-KETON BERBAHAN DASAR BENZALDEHIDA DAN UJI AKTIVITASNYA SEBAGAI INHIBITOR ENZIM α-AMILASE SERTA EFEK SINERGITAS DENGAN ASAM FERULAT

EKO RITO ENDARSYAH, Prof. Dr. Chairil Anwar; Drs. Bambang Purwono, M.Sc., Ph.D

2019 | Skripsi | S1 KIMIA

Sintesis analog kurkumin mono-keton berbahan dasar benzaldehida dan uji aktivitasnya sebagai inhibitor α-amilase serta efek sinergitas dengan asam ferulat telah dilakukan. Penelitian ini diawali dengan sistesis senyawa analog kurkumin melalui kondensasi Claisen-Schmidt dengan mereaksikan benzaldehid dengan aseton menghasilkan (1E,4E)-1,5-difenilpenta-1,4-dien-3-on (analog kurkumin AS) dan dengan sikloheksanon menghasilkan (2E,6E)-2,6-dibenzilidin sikloheksanon (analog kurkumin SH) menggunakan katalis kalium hidroksida 5% pada kondisi refluks selama 1 jam. Struktur senyawa hasil sintesis dielusidasikan dengan FTIR, Direct Inlet-MS, dan 1H-NMR. Senyawa analog kurkumin hasil sintesis diuji aktivitas penghambatannya terhadap enzim α-amilase dengan penentuan persentase inhibisi dan menggunakan akarbosa sebagai kontrol positif serta uji sinergitas dengan asam ferulat. Penentuan absorbansi menggunakan microplate reader pada panjang gelombang 550 nm. Hasil sintesis diperoleh senyawa analog kurkumin AS dan SH berupa padatan berwarna kuning dengan rendemen 79,48% dan 89,60%. Hasil uji inhibisi analog kurkumin AS dan analog kurkumin SH terhadap enzim α-amilase menunjukkan aktivitas inhibisi tertinggi pada konsentrasi 1 mM sebesar 47,23% dan 68,50%. Uji sinergitas analog kurkumin AS dengan asam ferulat menunjukkan inhibisi tertinggi sebesar 86,21% pada perbandingan konsentrasi (AS:AF) 1:2 dan analog kurkumin SH dengan asam ferulat menunjukkan inhibisi tertinggi sebesar 82,32% pada perbandingan konsentrasi (SH:AF) 4:1.

Synthesis of mono-ketone curcumin analogues from benzaldehyde and activity assay as inhibitor of α-amylase enzyme and synergism effect with ferulic acid have been successfully conducted. This research is firstly initiated by synthesizing of mono-ketone curcumin analogues from benzaldehyde and various ketones (acetone and cyclohexanone) through Claisen-Schmidt aldol condensation to form (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one (curcumin analogue AS) and (2E,6E)-2,6-dibenzylidenecyclohexanone (curcumin analogue SH) using alkaline catalyst such as potassium hydroxide 5% under reflux condition for an hour. The structures of the products were elucidated by FTIR Spectrophotometer, Direct Inlet-MS and 1H-NMR. Mono-ketone curcumin analogues were then evaluated for their activity assay towards inhibition of alpha amylase enzyme through determination of inhibition presentation and acarbose was used as positive control. The synergy assay with ferulic acid was also done with combination of certain mono-ketone curcumin analogues. The determination of length of absorbance using micro plate reader was observed on 550 nm. The results showed that curcumin analogue AS and SH was obtained as yellow solid with a yield of 79.48% and 89.60% respectively. The results of inhibition assay towards alpha amylase enzyme showed the highest activity of 1 mM concentration those were 47.23% and 68.50%, respectively. The synergy assay of mono-ketone curcumin analogue AS showed the highest inhibition of 86.21% with the concentration comparison (AS:FA) 1:2, while for mono-ketone curcumin analogue SH showed the highest inhibition of 82.32% with the concentration comparison (SH:FA) 4:1.

Kata Kunci : α-amilase , analog kurkumin, asam ferulat, sinergi