Sintesis Analog Kurkumin dari Turunan Benzaldehida dan Monoketon serta Uji Aktivitas dan Efek Sinergisitasnya dengan Asam Ferulat sebagai Inhibitor Alfa-Amilase

KHOIROTUN NAFILLAH, Prof. Dr. Chairil Anwar ; Dr. Muhammad Idham Darussalam M, M.Sc

2019 | Tesis | MAGISTER KIMIA

Sintesis senyawa analog kurkumin berbahan dasar veratraldehida dan p-anisaldehida, dan uji inhibisi enzim �±-amilase serta sinergisitasnya dengan asam ferulat telah dilakukan. Penelitian ini bertujuan untuk mensintesis senyawa analog kurkumin, mengetahui aktivitas dan efek sinergisitas dengan asam ferulat sebagai inhibitor enzim �±-amilase dengan pengujian secara in vitro. Tahap sintesis melibatkan kondensasi Claisen-Schmidt dari aldehida aromatik (veratraldehida dan p-anisaldehida) dengan monoketon (sikloheksanon dan siklopentanon) menggunakan katalis kalium hidroksida 8% dalam pelarut etanol, menghasilkan senyawa analog kurkumin (1-4) berwarna kuning dengan rendemen berturut-turut sebesar 26,39; 31,13; 18,42; dan 31,87%. Elusidasi struktur terhadap semua produk dilakukan dengan spektrometer FTIR, Direct Inlet-MS, 1H- dan 13C-NMR. Uji aktivitas inhibisi senyawa analog kurkumin terhadap enzim �±-amilase dan sinergisitasnya dengan asam ferulat menggunakan iodin sebagai reagen dan diukur absorbansinya pada panjang gelombang 568 nm dengan spektrofotometer UV-vis menunjukkan % inhibisi masing-masing senyawa analog kurkumin (1-4) pada konsentrasi 1 mM sebesar 58,17; 33,03; 22,95; dan 91,50%. Analog kurkumin menunjukkan efek sinergisitas dengan asam ferulat pada perbandingan konsentrasi senyawa analog kurkumin dan asam ferulat (1:8) untuk analog kurkumin 1 dan 2 dengan aktivitas inhibisi enzim �±-amilase sebesar 98,65 dan 99,23%, dan pada perbandingan konsentrasi (1:4) untuk analog kurkumin 3 dan 4 sebesar 98,37 dan 99,14%.

Synthesis of curcumin analogs from veratraldehyde and p-anisaldehyde and their inhibition test towards �±-amylase enzyme and their synergism effect with ferulic acid (FA) have been performed. The synthesis involves Claisen-Schimdt condensation from aromatic aldehyde (veratraldehyde and p-anisaldehyde) with monoketones (cyclohexanone and cyclopentanone) using potassium hydroxide as catalyst in ethanol, to produce curcumin analogs (1-4) as yellow solid in 26.39; 31.13; 18.42; and 31.87% yield, respectively. Structure elucidation of all products was carried out by means of FTIR, Direct Inlet-MS, 1H- and 13C-NMR spectrometers. The inhibitory activity test of the curcumin analogs compound against �±-amylase enzyme and their synergism with ferulic acid used iodine as a reagent. The inhibition percentage was calculated using the quantized absorbance obtained from UV-vis spectrophotometer at wavelength of 568 nm. The assay of curcumin analogs (1-4) towards �±-amylase showed inhibition percentage of 58.17; 33.03; 22.95; and 91.50% at concentration 1 mM. The result showed that the curcumin analogs displayed synergism effect with ferulic acid towards �±-amylase. The curcumin analogs 1 and 2 demonstrated potential inhibition with % inhibition of 98.65 and 99.23%, respectively, at concentration curcumin : FA of 1:8. In addition, the curcumin analogs 3 and 4 showed the inhibition percentage of 98.37 and 99.14%, respectively, at the concentration ratio of curcumin and FA of 1:4.

Kata Kunci : analog kurkumin, veratraldehida, p-anisaldehida, enzim �±lfa-amilase, asam ferulat