Synthesis of Curcumin Analogues Monoketone from Cinnamaldehyde and their Inhibition Assay against Alpha-Glucosidase Enzyme

Abstract:

The synthesis of curcumin analogues monoketone as target compounds from cinnamaldehyde and inhibition assay against alpha-glucosidase enzyme had been performed. The stepwise of synthesis was performed by aldol condensation Claisen-Schmidt reaction andused ketones variation to give curcumin analogues monoketone. The antidiabetic activity of curcumin analogues was carried out by inhibition test against alpha-glucosidase enzyme isolated from rotten rice (Oryza sativa). The first step of synthesis was started by reacting cinnamaldehyde and monoketones such as acetone (curcumin analog A [(1E,3E,6E,8E)-1,9-diphenyl-1,3,6,8-nanotetraen-5-one]), cyclopentanone (curcumin analog B [(2E,5E)-2,5-bis ((E)-3-phenylallylidene) cyclopentanone], and cyclohexanone (curcumin analog C [(2E,6E)-2,6-bis [(E)-3-phenylallylidene] cyclohexanone]) in ethanol as solvent. The synthesis was carried out in base condition (KOH) by stirring at 52 °C for 50 minutes. The structures of all products were identified by using FTIR, direct inlet-MS, ¹H-and ¹³C-NMR. Futhermore, the activity of curcumin analogues was tested against with alpha-glucosidase enzyme inhibition. The results show that the curcumin analogues (A-C) were yielded in 85.57; 72.15; and 82.97%, respectively as yellow solid. The melting point of curcuminanalogues (A-C) were at 116.60-122.40; 196.20-200.10; and 142.30-148.10 °C, respectively. The inhibition of alpha-glucosidase enzyme indicated that the curcumin analog B was potential to inhibit alpha-glucosidase enzyme with the highest activity by giving inhibition percentage of about 70.71% at 2.5 mM.

• Periodical: Materials Science Forum (Volume 901)
• Pages: 110-117
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.901.110
• Online since: July 2017
• Authors: Yunia Mardianis*, Chairil Anwar, Winarto Haryadi
• Keywords: Antidiabetic, Cinnamaldehyde, Curcumin Analogs Monoketone, α-Glucosidase Enzyme

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