Major Project

Draft II_Major Project

Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside

Parvathy et al. (2009) conducted to prepare curcumin-β-diglucoside as a curcumin prodrug and to determine water solubility, antioxidant, antimutagenic and antibacterial activities of its by comparing with curcumin. Curcumin is a natural compound in turmeric, which has various pharmacological activities. However, curcumin has a low oral bioavailability because of its low water solubility and instability in aqueous and basic solutions. The use of a prodrug approach as a chemical and biochemical stabilization to overcome various barriers which can increase water solubility and stability. Curcumin-β-diglucoside was synthesized by glycosylation of curcumin at the phenolic hydroxyl group. Evaluation of water solubility found that curcumin-β-diglucoside was soluble in water at 10 mg/ml concentration, whereas curcumin was insoluble in water. The antioxidant activity showed that radical scavenging values of curcumin-β-diglucoside and curcumin were 50% and 41%, respectively. The antimutagenicity by protection the mutagenicity of sodium azide to Salmonella typhimurium demonstrated that the both of curcumin-β-diglucoside and curcumin afforded high activity. The antibacterials activity in Staphylococcus aureus and Escherichia coli found that curcumin-β-diglucosides had antibacterials activitiy with minimum inhibitory concentration (MIC) 0.051 and 0.469 µM, respectively, whereas, curcumin had antibacterials activitiy with MIC 0.081 and 0.611 µM, respectively. These activities between curcumin-β-diglucoside and curcumin were not significantly different. The researchers suggested that conjugation of the phenolic hydroxyl group of curcumin with sugar moiety improved only the water solubility of curcumin but does not affect its antioxidant, antimutagenic and antibacterial activities.

        This study provides scientific evidence to synthesis curcumin-β-diglucoside as a curcumin prodrug for improve the problems of curcumin. However, there are some limitations.

1)               The researchers did not explained method and analysis of solubility in the water of curcumin and curcumin prodrug.

2)               This study did not investigate the stability property. Curcumin-β-diglucoside should be determined stability property in aqueous and basic solution, which is an important problem of curcumin bioavailability (Zhang et al., 2011).

3)               This study investigated the activities of curcumin prodrug by using in vtro model may render of not significance in the results because prodrug refers to a pharmacologically inactive compound that is transformed by enzymes such as esterase, phosphatase and carboxylase in the mammalian system into an active substance by either chemical or metabolic process (Hosokawa, 2008). Therefoer, this study should be investigated the activities of curcumin prodrug by using in vivo model too.

The strength of this study is that synthesis of curcumin prodrug by conjugation of the phenolic hydroxyl group of curcumin with sugar, which had a solubility property and non-toxicity. Effects of curcumin prodrug determine by comparing with curcumin, which is the  parent compound. Moreover, this study is the clearly the methodology for synthesis and analysis of curcumin prodrug.

References

            Hosokawa, M. (2008). Structure and catalytic properties of carboxlyesterase isozymes                           involved in metabolic activation of prodrugs. Molecules, 13, 412-431.

Parvathy, K. S., Negi, P. S., & Srinivas, P. (2009). Antioxidant, antimutagenic and antibacterial activities of curcumin-β-diglucoside. Food Chemistry, 115, 523-530.

Zhang, F., Koh, G. Y., Jeansonne, D. P., Hollingsworth, J., Russo, P. S., Vicente, G., Stout, R. W., & Liu, Z. (2011). A novel solubility-enhanced curcumin formulation showing stability and maintainance of anticancer activity. Journal of pharmaceutical sciences, 100(7), 2778-2789.