58546-60-4Relevant academic research and scientific papers
Synthesis, biological evaluation, and molecular modeling of oleuropein and its semisynthetic derivatives as cyclooxygenase inhibitors
Procopio, Antonio,Alcaro, Stefano,Nardi, Monica,Oliverio, Manuela,Ortuso, Francesco,Sacchetta, Paolo,Pieragostino, Damiana,Sindona, Giovanni
experimental part, p. 11161 - 11167 (2010/07/13)
Oleuropein, the main phenolic compound in virgin olive oil, and several of its derivatives such as oleuropein aglycone, hydroxytyrosol, and their respective acetylated lipophilic forms were obtained by simple and environmentally friendly semisynthetic protocols. The same molecules were then tested in vitro and in vivo, comparing their intriguing anti-COX-1 and anti-COX-2 properties to those of well-known anti-inflammatory drugs such as ibuprofen and celecoxib. Finally, molecular modeling experiments displaying the most probable binding modes within the classical binding clefts of the enzymes suggest the heme moiety as a potential alternative target. 2009 American Chemical Society.
CHEMICAL-CATALYTIC METHOD FOR THE PERACYLATION OF OLEUROPEIN AND ITS PRODUCTS OF HYDROLYSIS
-
Page/Page column 9, (2009/01/20)
The method, object of the present invention, concerns the peracylation of oleuropein and its products of hydrolysis: The method makes use of the excellent properties as Lewis acid catalysts of halides and tryphilates of lanthanides (III). The component is placed to react, in the presence of catalytic quantities of Lewis acid, directly with an acylating agent containing at least one acylic group R, where R is H, an alkylic radical of 1-31 atoms of linear or branched carbon, an alkenylic radical containing up to 31 atoms of carbon or an arylic group. The procedures for the extraction and the successive hydrolysis of the oleuropein for the synthesis of its aglycon and the hydroxytyrosol, resolve the problems tied to the quantitative yield of the products and to the use of highly-toxic and expensive catalysts. Furthermore, the innovative and inventive contribution is given by the peracylation of the oleuropein and its products of synthesis, aglycon and hydroxytyrosol, that supply a new class of molecule, biologically active as anti-oxidants and anti-inflammatory ones. The proven anti-oxidant activity of oleuropein and its derivates leads to the hypothesis that they could also act as protectors against oxidative stress at the level of the central nervous system, one of the causal factors of Parkinson's disease. The molecules examined are all good protectors against oxidative stress and the greater efficiency of the peracylated derivatives is presumably due to their greater lipophilicity and the possibility of penetrating the cellular membrane.
