Rutin is a plant extract that belongs to the flavonoid group of compounds. Many studies showed that Rutin has a potential pharmacological uses such as an antioxidant, anti-inflammatory, antihypertensive activities. Rutin is widely used as medicinal product and food supplement and marketed in different pharmaceutical dosage formulations. However, the absorption of rutin from the gastrointestinal tract is low and hence has low plasma bioavailability due to its low solubility. In this study, we aim to improve the water solubility and consequently its bioavailability by synthesizing different derivatives of rutin prodrugs.
Methodology: Decaacetylated ester of rutin was first synthesized. Then selective partial deacetylation was performed to produce the hexaacetylated ester of rutin. Water solubility of the new derivative as well as its dissolution was compared to rutin. An evaluation of the antioxidant activity of the hexaacetylated derivative was tested using DPPH reduction method. Moreover, A UV-Visible spectrophotometric method was developed and validated for the analysis of a tablet formulation of the newly synthesized derivative.
Results: The hexaacetylated ester derivative of rutin was successfully synthesized as confirmed by NMR. Moreover, the water solubility and the dissolution profile was approximately two fold increased compared to that of the original rutin. Water solubility for the partially acetylated product has been increased from 0.07 to 0.15 mg /ml and its dissolution increase from 22% to 37.5% compared to the original rutin. Moreover, the antioxidant activity results showed that the newly synthesized derivative preserved the antioxidant activity of the original rutin.
Conclusion: An improvement on the poor solubility of rutin was achieved by selective acetylation of some of OH groups of rutin. The tablet formulation of the partially acetylated ester derivative of rutin gave a better dissolution over the already marketed rutin tablets.