SINTESIS TURUNAN EUGENOL DAN UJI INHIBISINYA TERHADAP ALFA-AMILASE

VICKA ANDINI, Prof. Dr. Chairil Anwar; Respati Tri Swasono, M.Phil., Ph.D.

2020 | Tesis | MAGISTER KIMIA

Senyawa 4-(2-bromopropil)-2-metoksifenol (turunan eugenol A), 4-(2-bromopropil)-1,2-dimetoksi benzena (turunan eugenol B), 4-(2-kloropropil)-2-metoksifenol (turunan eugenol C), dan 4-(2-kloropropil)-1,2-dimetoksi benzena (turunan eugenol D) telah berhasil disintesis. Sintesis turunan eugenol berlangsung melalui reaksi adisi Markovnikov dengan metode hidrobrominasi dan hidroklorinasi terhadap bahan dasar eugenol dan metileugenol masing-masing menggunakan HBr 47% dan HCl 37% yang dimediasi silika gel 60 dalam kondisi bebas pelarut organik pada suhu 5 ºC selama 1 jam. Reaksi dilanjutkan dalam suhu ruang selama 288 jam, kemudian campuran diekstraksi dan dihilangkan asam halida yang masih tersisa dengan larutan NaHCO3. Produk hasil sintesis dikarakterisasi menggunakan Kromatografi Lapis Tipis (KLT), Gas Chromatography-Mass Spectrophotometer (GC-MS), Fourier Transform Infrared (FTIR) Spectrophotometer, dan Nuclear Magnetic Resonance (NMR). Hasil penelitian diperoleh turunan eugenol A berupa cairan berwarna coklat kehitaman, turunan eugenol B berupa cairan berwarna kecoklatan, turunan eugenol C berupa cairan berwarna coklat kehitaman, dan turunan eugenol D berupa cairan berwarna kecoklatan dengan masing-masing persen hasil 78,27%, 76,68%, 94,17%, dan 76,63%. Uji inhibisi senyawa turunan eugenol A, B, C, dan D terhadap alfa-amilase telah dilakukan. Senyawa turunan eugenol A, B, dan C berpotensi sebagai inhibitor alfa-amilase. Aktivitas inhibisi tertinggi ditemukan pada senyawa A dan C dengan inhibisi pada konsentrasi 10 mM masing-masing 99,91 dan 99,38%, sedangkan aktivitas inhibisi tertinggi senyawa B diketahui sebesar 99,94% pada konsentrasi 12,5 mM.

Compounds of 4-(2-bromopropyl)-2-methoxyphenol (derivative of eugenol A), 4- (2-bromopropyl) -1,2-dimethoxy benzene (derivative of eugenol B), 4- (2-chloropropyl) -2-methoxyphenol (derivative of eugenol C), and 4- (2-chloropropyl) -1,2-dimethoxy benzene (derivative of eugenol D) have been successfully synthesized. Synthesis of eugenol derivatives has been performed through the Markovnikov addition reaction with the hydrobromination and hydrochlorination of eugenol and methyl eugenol compounds using 47% HBr and 37% HCl mediated by silica gel 60 under organic solvent-free conditions at 5 ºC for 1 hour. The reaction was continued at room temperature for 288 hours, then the mixture was extracted and removed halide acid residues with NaHCO3 solution. Synthesized products were characterized using Thin Layer Chromatography (TLC), Gas Chromatography-Mass Spectrophotometer (GC-MS), Fourier Transform Infrared (FTIR) Spectrophotometer, and Nuclear Magnetic Resonance (NMR). The results showed that the derivative of eugenol A obtained as a blackish-brown liquid, the derivative of eugenol B obtained as brown-colored liquid, the derivative of eugenol C obtained as blackish-brown liquid, and the derivative of eugenol D obtained as brownish-colored liquid with percen yield of 78.27%, 76.68%, 94.17%, and 76.63%, respectively. The result of the inhibition of eugenol A, B, C, and D derivatives against the alpha-amylase has been carried out. The derivatives of eugenol A, B, and C have the potential as an alpha-amylase inhibitor. The highest inhibitory activity at concentrations of 10 mM for compounds A and C were 99.91% and 99.38%, respectively, while the highest inhibitory activity of compound B is 99.94 % at a concentration of 12.5 mM.

Kata Kunci : eugenol, turunan, halogenasi, inhibisi, alfa-amilase