Abstract
Polyphenols, such as rosmarinic acid, are widely distributed natural products with relevant antioxidant activity. Oxidative stress plays an important role in the pathogenesis of a number of disorders. Here, we report on the synthesis and biological effects of the polyphenolic esters hydroxytyrosyl gallate ( 1), hydroxytyrosyl protocatechuate ( 2) and hydroxytyrosyl caffeate ( 3), structurally related to rosmarinic acid. The three compounds showed a greater free radical scavenging activity than their precursors and also than rosmarinic acid. Esters 1 and 3 significantly reduced thrombin-evoked platelet aggregation, which is likely mediated to the attenuation of thrombin-stimulated Ca 2+ release and entry. The three compounds reduced the ability of platelets to accumulate Ca 2+ in the intracellular stores, probably by enhancing the Ca 2+ leakage rate and reduced store-operated Ca 2+ entry in these cells. These observations suggest that the structurally-simplified analogs to rosmarinic acid, compounds 1 and 3, might be the base of therapeutic strategies to prevent thrombotic complications associated to platelet hyperaggregability due to oxidative stress.
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