Planta Med 2012; 78 - PK12
DOI: 10.1055/s-0032-1321328

Methodology for the preparation of olive oil open ring secoiridoids

K Vougogiannopoulou 1, C Lemus 2, S Michel 1, AB Smith III 3, L Skaltsounis 2, B Deguin 1
  • 1Laboratoire de Pharmacognosie de l'Université Paris Descartes, Sorbonne Paris Cité, Faculté des Sciences Pharmaceutiques et Biologiques, U.M.R./C.N.R.S. 8638, 4, Avenue de l'Observatoire, F-75006 Paris
  • 2Department of Pharmacognosy, Faculty of Pharmacy, University of Athens, Zografou, 15771, Greece
  • 3Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104–6323, USA

Dedicated to the memory of Prof. François Tillequin.

Olive oil (OO) as an important component of the Mediterranean diet has been extensively studied and correlated with NSAID properties, simulating the ones of ibuprofen. The phenolic content of OO includes open ring secoiridoids such as oleacein (2), closely related to oleuropein (1). The latter is easily isolated from olive tree leaves and can be used as a natural synthon. Herein, it is proposed that the opening of the oleuropein secoiridoid ring can afford a series of secoiridoid dialdehydes similar to oleacein. This methodology can be expanded to various secoiridoid conjugates providing a tool for the synthesis of a number of analogues. Project was carried out under the scope of OLITEC (IAAP 230763).