SINTESIS DAN UJI INHIBISI ENZIM ALFA GLUKOSIDASE PADA ANALOG KURKUMIN DARI VANILIN DAN BROMOVANILIN

RAHMA DIYAN MARTHA, Dra. Tutik Dwi Wahyuningsih, M.Si, Ph.D; Dr.Chairil Anwar

2016 | Tesis | S2 Ilmu Kimia

Telah disintesis analog kurkumin (1-4) serta uji inhibisi enzim α-glukosidase nya. Analog kurkumin disintesis melalui reaksi kondensasi aldol silang Claisen-Schmidt dari bahan dasar vanillin dan bromovanilin hasil dari brominasi vanillin menggunakan katalis asam. Uji aktivitas antidiabetik analog kurkumin (1-4) dilakukan terhadap enzim α-glukosidase yang diperoleh dari beras lapuk (Oryza sativa). Brominasi terhadap vanillin dilakukan dengan menggunakan KBrO3 dan HBr dalam kondisi asam. Analog kurkumin (1,2) disintesis masing-masing dengan mereaksikan vanillin dengan sikloheksanon dan siklopentanon, sedangkan analog kurkumin (3,4) disintesis masing-masing dengan mereaksikan bromovanilin dengan sikloheksanon dan siklopentanon. Sintesis tersebut dilakukan dalam kondisi asam HCl dengan pengadukan pada suhu kamar selama 2 jam dan didiamkan selama 2 hari. Hasil yang diperoleh dianalisis strukturnya dengan spektrometer FTIR, GC-MS, 1H- dan 13C-NMR. Analog kurkumin hasil sintesis kemudian diuji aktifitasnya sebagai inhibitor enzim α-glukosidase. Hasil penelitian menunjukkan bahwa reaksi brominasi vanillin menghasilkan 5-bromovanilin yang berupa padatan putih dengan rendemen 79,00%. Hasil sintesis analog kurkumin (1-4) berupa padatan berwarna hijau kekuningan dengan rendemen masing-masing 53,00; 52,27; 42,74 dan 41,56%. Hasil uji inhibisi terhadap enzim α-glukosidase menunjukkan bahwa kurkumin 2 cukup potensial untuk menginhibisi enzim α-glukosidase dengan persen inhibisi 94,26% pada konsentrasi senyawa 5 mM.

The syntheses and α-glucosidase enzyme inhibition test of curcumin analogues (1-4) had been performed. The curcumin analogues were synthesized based on Claisen-Schmidt condensation from vanillin and bromovanillin,the product of vanillin bromination by using acid catalyst. The antidiabetic activity of curcumin analogues(1-4) was carried out by the use of α-glucosidase enzyme from moldy rice (Oryza sativa). The bromination of vanillin was performed using KBrO3 and HBr in acidic condition. The curcumin analogues (1,2) were synthesized by reacting the vanillin with cyclohexanone and cyclopentanone, while curcumin analogues (3,4) were synthesized by reacting bromovanillin with cyclohexanone and cyclopentanone. The synthesis was carried out in acidic condition (HCl) by stirring at room temperature for 2 hours and allowed to settle for 2 days. The structure of all products were confirmed by FTIR, GC-MS, 1H- and 13C-NMR spectrometersand the activity of curcumin analogues were examined with α-glucosidase enzyme inhibitor. The results showed that the bromination of vanillin produced 5-bromovanillin as white solid with 79.00% yield and the curcumin analogues (1-4) were yielded in 53.00, 52.27, 42.72 and 41.56%, respectively as yellowish green solid. The inhibition test of α-glucosidase enzyme showed that the curcumin 2 was potential to inhibit the α-glucosidase enzyme with inhibition percentage about 94.26% at 5 mM.

Kata Kunci : Vanilin, Bromovanilin, Kurkumin, Analog kurkumin, Enzimα-glukosidase