Curcumin Analogs as Potent Aldose Reductase Inhibitors

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Abstract
In the present study, curcuminoids isolated fromcurcuma longawere demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6‐bis(3,4‐dihydroxybenzylidene)cyclohexanone (A2), 2,5‐bis(3,4‐dihydroxybenzylidene)cyclopentanone (B2), 1,5‐bis(3,4‐dihydroxyphenyl)‐1,4‐pentadiene‐3‐one (C2), and 3,5‐bis(3,4‐dihydroxybenzylidene)‐4‐piperidone (D2) showed remarkably potent inhibitory effects on aldose reductase with IC50of 2.9 μM, 2.6 μM, 3.4 μM, and 4.9 μM, respectively. The structure‐activity relationship revealed that the curcumin analogs withortho‐dihydroxyl groups could form a more tight affinity with aldose reductase to exert more potential inhibitory activities.