Resveratrol inhibits endothelin-1, a vascular tension regulator. We synthesized the resveratrol analogue 4,4'-dihydroxy-trans-stilbene with 2 hydroxyl groups in the 4 and 4' position to obtain a molecule more active than resveratrol (3,4',5-trihydroxy-trans-stilbene). The results demonstrate that 4,4'-dihydroxy-trans-stilbene led to a significant decrease in total endothelin-1 secretion and in endothelin-1 messenger RNA (mRNA) levels in human endothelial cells. In addition, resveratrol and its analogue decreased endothelin-converting enzyme-1 mRNA levels and further reduced the activity of the enzyme. 4,4'-dihydroxy-trans-stilbene was more active than resveratrol because the new molecule exerted greater activity at the level of endothelin synthesis and conversion, even at a lower concentration. Although 4,4'-dihydroxy-trans-stilbene and resveratrol inhibited formation of reactive oxygen species and lipid peroxidation, the treatment of cells with different oxidant agents did not modify the endothelin-1 release. This finding suggests that the inhibition of endothelin-1 secretion is independent of the antioxidant properties of the 2 compounds. On the basis of these results, the resveratrol analogue 4,4'-dihydroxy-trans-stilbene could be a promising chemopreventive agent against cardiovascular diseases.

Structure-Activity Relationship of Resveratrol and Its Analogue, 4,4 '-Dihydroxy-Trans-Stilbene, Toward the Endothelin Axis in Human Endothelial Cells / T., Coppa; M. C., Lazze; O., Cazzalini; P., Perucca; R., Pizzala; L., Bianchi; L. A., Stivala; Forti, Luca; C., Maccario; V., Vannini; M., Savio. - In: JOURNAL OF MEDICINAL FOOD. - ISSN 1096-620X. - ELETTRONICO. - 14(2011), pp. 1173-1180.

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