Synthesis of Curcumin Derivatives (2.5-Bis((E)-4-Hydroxy-3-Methoxy Benzylidine) Cyclopenta-1-On) from Vanillin and Its Activity Test Against Α-Glucosidase Enzymes

Rahma Diyan Martha*  -  STIKes Karya Putra Bangsa Tulungagung, East Java, Indonesia
Danar Danar  -  Universitas Negeri Malang, Indonesia
Rini Retnosari  -  Universiti Kebangsaan Malaysia, Malaysia

(*) Corresponding Author

Synthesis of curcumin analogs (2.5-Bis((E)-4-Hydroxy-3-Methoxy Benzylidine) Cyclopenta-1-On) based on Claisen-Schmidt condensation using an acid catalyst and inhibition of glucosidase enzyme was carried out. The antidiabetic activity of curcumin analogs was carried out by the use of α-glucosidase enzyme from moldy rice (Oryza sativa). The curcumin analogs were synthesized by reacting the vanillin with cyclopentanone.  The structure of all products was confirmed by FTIR, GC-MS, 1H-13C-NMR spectrometers, and the activity enzyme. The results showed the curcumin analogs were yielded in 52.27%, respectively as yellowish-green solid. The inhibition test of the α-glucosidase enzyme showed that the curcumin analogs were the potential to inhibit the α-glucosidase enzyme with an inhibition percentage of about 94.26% in 5 mM.

Keywords: vanillin; cyclopentanone; curcumin; α-glucosidase enzymes

  1. Debjit, B. et al. (2009) ‘Role of the community pharmacist in management and prevention diabetic foot ulcer and infections’, Journal of Chemical and Pharmaceutical Research, 1, pp. 38–53.
  2. Du, Z. Y. et al. (2006) ‘α-Glucosidase inhibition of natural curcuminoids and curcumin analogs’, European Journal of Medicinal Chemistry, 41(2), pp. 213–218. doi: 10.1016/j.ejmech.2005.10.012.
  3. Kita, A. et al. (1991) ‘Substrate specificity and subsite affinities of crystalline α-glucosidase from Aspergillus niger’, Agricultural and Biological Chemistry, 55(9), pp. 2327–2335. doi: 10.1080/00021369.1991.10870952.
  4. Konatham, S., Kumar, P. and Pharma, J. A. (2010) ‘Synthesis and Screening of Antidiabetic Activity of Some Novel Curcumin Analog’, International Journal of pharma and bio sciences, 1(2), pp. 1–12.
  5. Lam, S. H. et al. (2008) ‘α-Glucosidase inhibitors from the seeds of Syagrus romanzoffiana’, Phytochemistry, 69(5), pp. 1173–1178. doi: 10.1016/j.phytochem.2007.12.004.
  6. Lee, S. L. et al. (2005) ‘Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs’, Bioorganic and Medicinal Chemistry, 13(22), pp. 6175–6181. doi: 10.1016/j.bmc.2005.06.058.
  7. Liang, R. et al. (2009) ‘Synthesis of wheat straw-g-poly(acrylic acid) superabsorbent composites and release of urea from it’, Carbohydrate Polymers, 77(2), pp. 181–187. doi: 10.1016/j.carbpol.2008.12.018.
  8. Nampoothiri, S. V. et al. (2011) ‘In vitro antioxidant and inhibitory potential of Terminalia bellerica and Emblica officinalis fruits against LDL oxidation and key enzymes linked to type 2 diabetes’, Food and Chemical Toxicology, 49(1), pp. 125–131. doi: 10.1016/j.fct.2010.10.006.
  9. Ren, S. et al. (2011) ‘Two flavanone compounds from litchi (Litchi chinensis Sonn.) seeds, one previously unreported, and appraisal of their α-glucosidase inhibitory activities’, Food Chemistry, 127(4), pp. 1760–1763. doi: 10.1016/j.foodchem.2011.02.054.
  10. Rinasih, I. (1998) ‘Sintesis Senyawa 3, 4 Dimetoksi Benzaldehida dari Vanilin Dalam Suasana Basa’.
  11. Scopes, R. (2013) ‘Protein purification: principles and practice’, Springer Science & Business Media. New York, 178(1).
  12. Vessal, M., Hemmati, M. and Vasei, M. (2003) ‘Antidiabetic effects of quercetin in streptozocin-induced diabetic rats’, Comparative Biochemistry and Physiology - C Toxicology and Pharmacology, 135(3), pp. 357–364. doi: 10.1016/S1532-0456(03)00140-6.

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WJC: Walisongo Journal of Chemistry
Published by the Department of Chemistry
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