Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 57, Issue 23, Pages 11161-11167Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf9033305
Keywords
Oleuropein; hydroxytyrosol; COX-1 and COX-2 Inhibitor; lanthanoid triflates; Lewis acid catalyst; molecular modeling
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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.
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