Unsaturated fatty alcohol derivatives of olive oil phenolic compounds with potential low-density lipoprotein (LDL) antioxidant and antiobesity properties

Bruno Almeida Cotrim, Jesús Joglar, M. Jesús L. Rojas, Juan Manuel Decara Del Olmo, Manuel MacIas-González, Miguel Romero Cuevas, Montserrat Fitó, Daniel Muñoz-Aguayo, María Isabel Covas Planells, Magí Farré, Fernando Rodríguez De Fonseca, Rafael De La Torre

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

A new route for the synthesis of fatty alcohol derivatives of hydroxytyrosol and other olive oil phenolic compounds was developed to allow the preparation of unsaturated derivatives. The biological activity of synthesized compounds was evaluated. Most of the compounds presented a significant antioxidant activity on low-density lipoprotein (LDL) particles. The activity of the tested products was significantly influenced by the number and position of unsaturations as well as modifications on the polar head of the synthesized compounds. Some of them presented modulation of food intake in rats and, due to their molecular similarity with CB 1 endogenous ligands, the endocannabinoid system and PPAR-α were also evaluated as potential targets. The pharmacodynamics could not be totally explained by CB 1 and PPAR-α receptor interactions because only two of the four compounds with biological activity showed a CB 1 activity and all of them presented low PPAR-α affinity, not justifying its whole in vivo activity. The hydroxytyrosol linoleylether (7) increased LDL resistance to oxidation with a capacity similar to that of hydroxytyrosol and was the most active in vivo compound with a hypophagic effect comparable to that of oleoylethanolamine. We consider that this compound could be a good lead compound for future drug development in obesity treatments. © 2012 American Chemical Society.
Original languageEnglish
Pages (from-to)1067-1074
JournalJournal of Agricultural and Food Chemistry
Volume60
Issue number4
DOIs
Publication statusPublished - 1 Feb 2012

Keywords

  • CBν
  • ether
  • fatty alcohol
  • obesity
  • PPAR-α

Fingerprint Dive into the research topics of 'Unsaturated fatty alcohol derivatives of olive oil phenolic compounds with potential low-density lipoprotein (LDL) antioxidant and antiobesity properties'. Together they form a unique fingerprint.

  • Cite this

    Cotrim, B. A., Joglar, J., Rojas, M. J. L., Del Olmo, J. M. D., MacIas-González, M., Cuevas, M. R., Fitó, M., Muñoz-Aguayo, D., Covas Planells, M. I., Farré, M., Rodríguez De Fonseca, F., & De La Torre, R. (2012). Unsaturated fatty alcohol derivatives of olive oil phenolic compounds with potential low-density lipoprotein (LDL) antioxidant and antiobesity properties. Journal of Agricultural and Food Chemistry, 60(4), 1067-1074. https://doi.org/10.1021/jf203814r