SINTESIS ANALOG KURKUMIN MONOKETON BERBAHAN DASAR SINAMALDEHIDA DAN UJI AKTIVITASNYA SEBAGAI INHIBITOR ENZIM α-GLUKOSIDASE

Abstract

Telah dilakukan sintesis analog kurkumin monoketon sebagai senyawa target yang berbahan dasar sinamaldehida dan uji aktivitasnya sebagai inhibitor enzim α-glukosidase. Tahap sintesis melibatkan reaksi kondensasi aldol silang Claisen-Schmidt dengan variasi keton sehingga dihasilkan senyawa analog kurkumin monoketon. Pengujian aktivitas antidiabetes senyawa analog kurkumin dilakukan melalui inhibisi enzim α-glukosidase yang diisolasi dari beras lapuk (Oryza sativa). Tahapan awal penelitian ini yaitu analog kurkumin (2E,5E)-2,5-bis((E)-3-fenilalilidin) siklopentanon disintesis dengan mereaksikan sinamaldehid dan monoketon siklopentanon dalam pelarut etanol. Sintesis tersebut dilakukan dalam kondisi basa KOH dengan pengadukan pada suhu 52 °C selama 50 menit. Senyawa hasil sintesis dianalisis strukturnya menggunakan FTIR, direct inlet-MS, 1H- dan 13C-NMR. Tahap selanjutnya analog kurkumin hasil sintesis diuji aktivitasnya sebagai inhibitor enzim α-glukosidase. Hasil penelitian menunjukkan bahwa analog kurkumin monoketon hasil sintesis diperoleh rendemen sebesar 72,15%. Hasil berupa padatan berwana kuning dengan titik leleh sebesar 196,20–200,10 °C. Hasil uji inhibisi terhadap enzim α-glukosidase mengindikasi bahwa analog kurkumin memiliki aktivitas antidiabetik dan cukup berpotensi untuk menginhibisi enzim α-glukosidase dengan persentase inhibisi sebesar 70,71%. THE SYNTHESIS OF CURCUMINE ANALOGUE MONOCETONE FROM CINAMALDEHYDE AND ITS ACTIVITY TEST AS α-GLUCOCYDE ENZYME INHIBITOR The synthesis of curcumin analog monoketone as target compounds from cinnamaldehyde and inhibition assay against α-glucosidase enzyme had been performed. The stepwise of synthesis was performed by aldol condensation Claisen-Schmidt reaction and used ketone to give curcumin analog monoketone. The antidiabetic activity of curcumin analog was carried out by inhibition test against α-glucosidase enzyme isolated from rotten (Oryza sativa). The first step of synthesis (2E,5E)-2,5-bis((E)-3-phenylallylidene) cyclopentanone was started by reacting cinnamaldehyde and cyclopentanone as monoketone in etanol as solvent. The synthesis was carried out in base condition (KOH) by stirring at 52 °C for 50 minutes. The structures of product was identified by using FTIR, direct inlet-MS, 1H- and 13C-NMR. Futhermore, the activity of curcumin analog was tested against with α-glucosidase enzyme inhibition. The results show that the curcumin analog was yielded in 72.15% as yellow solid. The melting point of curcumin analog was at 196.20–200.10 °C. The inhibition against α-glucosidase enzyme indicated that the curcumin analog was potential to inhibit α-glucosidase enzyme with the highest activity by giving inhibtion percentage of about 70.71% at 2.5 mM.

Keywords

• analog kurkumin monoketon, sinamaldehida, α-glukosidase, antidiabetik