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Synthesis of some esters of cinnamic acid and evaluation of their in vitro antidiabetic and antioxidant properties
Abstract
Purpose: To synthesize various ester derivatives of cinnamic acid and to evaluate their in vitro antidiabetic and antioxidant properties.
Methods: Esters of cinnamic acid were synthesized by refluxing the parent compound (cinnamic acid) with different alcohols using concentrated sulphuric acid as a catalyst. Physicochemical analyses (solubility, boiling point, refractive index) and spectrophotometric analyses (ultraviolet-visible spectroscopy (UV-VIS), Fourier-transform infrared spectroscopy (FT-IR) and gas chromatography-mass spectroscopy (GC-MS)) were carried out on the synthesized products. The antioxidant inhibitory property, uptake of glucose by yeast, and haemoglobin glycosylation of the synthesized products were also evaluated using standard methods.
Results: The identities of methylcinnamate, ethylcinnamate, propylcinnamate, 2-propylcinnamate, butylcinnamate and 2-butylcinnamate were confirmed, at m/z ratios of (131,103,77 and M+ of162), (131,103,77 and M+ of 176), (147,103,77and M+ of 190), (147,103,77 and M+ of 204), (143, 103, 77 and M+ of 190), and finally (147,103,77 and M+ of 204) respectively. FT-IR results revealed the following important bonds for the synthesized compounds: C=O, C-C, C-O, C=H, C-H and adjacent H. The results for glucose uptake by yeast and of haemoglobin glycosylation test indicate that all the products facilitated the transport and detachment of glucose at varying concentrations, respectively. The DPPH scavenging activity of propylcinnamate, 2-butylcinnamate and methylcinnamate with the absorbance of 63.06, 56.85 and 53.06 at 50 μg/mL - 250 μg/mL, respectively, recorded the highest values when compared with the control (ascorbic acid).
Conclusion: The results reveal that the six ester derivatives of cinnamic acid exhibit a certain degree of antidiabetic activity by facilitating the uptake of glucose by yeast and reducing glycation of haemoglobin; thus, showing a reasonable level of inhibition against free radicals.
