The Inhibition of Uric Acid Formation Catalyzed by Xanthine Oxidase Properties of the Alkyl Caffeates and Cardol

Xanthine oxidase inhibitors may serve as therapeutic agents for hyperuricaemia and/or oxidative stress. From our continuing investigation, we proposed that some inhibitors for reactions catalyzed by xanthine oxidase consisted of a head portion and a tail portion and that each portion had different functions for inhibition. In a previous study on the effect of alkyl gallates on the uric acid formation catalyzed by xanthine oxidase it was shown that the alkyl chain length needs to be longer than C6 to exert inhibitory activity. In the current study, compounds having different head portions, alkyl caffeates, alkyl protocatechuates, alkyl 3,5-dihydroxybenzoates, 3,4- dihydroxyphenylalkanoates and 3,5-dihydroxyphenylalkanoates were prepared, and their effects on the uric acid formation were examined. A series of alkyl caffeates (C1-C10) was demonstrated effective in inhibiting the uric acid formation, and the inhibitory activity increased by increasing the alkyl chain length. However, none of the other compounds was effective in inhibiting the uric acid formation. These results indicate that head portions in these compounds are important for the inhibition of uric acid formation and require further a specific structural feature to elicit the inhibitory activity.