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SINTESIS ANALOG KURKUMIN MONOKETON BERBAHAN DASAR Para-DIMETILAMINOBENZALDEHIDA DENGAN SIKLOHEKSANON DAN UJI AKTIVITASNYA SEBAGAI INHIBITOR ENZIM Alfa-AMILASE

Dea Meima Monet, Dr. Endang Astuti, M.Si. ; Dr. Winarto Haryadi, M.Si

2022 | Skripsi | S1 KIMIA

Sintesis analog kurkumin monoketon berbahan dasar para-dimetilaminobenzaldehida dengan sikloheksanon dan uji aktivitasnya sebagai inhibitor enzim alfa-amilase telah berhasil dilakukan. Sintesis ini dilakukan dengan tujuan untuk memperoleh senyawa analog kurkumin dari para-dimetilaminobenzaldehida dengan sikloheksanon, mengetahui aktivitas penghambatan senyawa analog kurkumin hasil sintesis terhadap enzim alfa-amilase, dan tipe inhibitornya. Sintesis analog kurkumin dilakukan dengan mereaksikan para-dimetilaminobenzaldehida dengan sikloheksanon menggunakan pelarut etanol dan katalis KOH 5 % yang dilakukan dengan metode refluks selama 50 menit pada suhu 50 ºC. Hasil sintesis dikarakterisasi menggunakan FTIR, Direct Inlet-MS (DI-MS), 1H-NMR, dan 13C- NMR. Senyawa analog kurkumin yang diperoleh kemudian diuji aktivitas inhibisinya terhadap enzim alfa-amilase serta ditentukan tipe inhibitornya. Uji aktivitas inhibisi terhadap enzim αlfa-amilase dilakukan juga pada akarbosa sebagai pembanding. Produk hasil sintesis kurkumin yang diperoleh yaitu (2E,5E)-2,5-bis(4-(dimetilamino)benzilidin)sikloheksanon dengan rendemen 53,33 %. Senyawa analog kurkumin menunjukkan aktivitas inhibisi tertinggi sebesar 96,56 % pada konsentrasi 0,500 mM, sedangkan senyawa akarbosa menunjukkan aktivitas inhibisi tertinggi sebesar 90,19 % pada konsentrasi 1,000 mM. Hasil ini menunjukkan senyawa analog kurkumin memiliki aktivitas inhibisi terhadap enzim alfa-amilase yang lebih baik dibanding akarbosa. Berdasarkan hasil penentuan nilai KM dan Vmaks maka diketahui tipe inhibitor analog kurkumin hasil sintesis dan akarbosa berupa tipe inhibitor unkompetitif.

A synthesis of monoketone curcumin analogue from para-dimethylaminobenzaldehyde with cyclohexanone and its activity test as inhibitor of alpha-amylase enzyme has been done. The aims of the synthesis are to obtain curcumin analogue compound from para-dimethylaminobenzaldehyde by reaction with cyclohexanone, to know the inhibition type and activity of curcumin analogue on alpha-amylase. The synthesis was initiated by reacting para-dimethylaminobenzaldehyde with cyclohexanone using ethanol as a solvent in the presence of KOH 5 % catalyst by reflux method for 50 min at 50 ºC. The product was characterized using FTIR, Direct Inlet-MS, 1H- NMR, and 13C-NMR. Inhibiton assay against alpha-amylase enzyme was performed towards product of analogue curcumin synthesis and type of inhibitor was investigated. Inhibition assay against alpha-amylase enzyme was carried out towards acarbose as a comparison. The curcumin synthesis product obtained was (2E,5E)-2,5-bis(4-dimethylamino)benzylidine)cyclohexanone with 53.33 % yield. Curcumin analogue has a highest inhibiton 96.56 % at 0.500 mM, while acarbose has a highest inhibition 90.19 % at 1.00 mM. This results showed that curcumin analogue has better inhibition assay against alpha-amylase enzyme than acarbose. The determination of KM and Vmax showed that the inhibitor type of curcumin analogue product and acarbose are uncompetitive.

Kata Kunci : akarbosa, analog kurkumin, para-dimetilaminobenzaldehida, enzim alfa-amilase

  1. S1-2022-381076-abstract.pdf  
  2. S1-2022-381076-bibliography.pdf  
  3. S1-2022-381076-tableofcontent.pdf  
  4. S1-2022-381076-title.pdf