Isolation and characterization of a secoiridoid derivative from two-phase olive waste (alperujo)

© 2015 American Chemical Society. A secoiridoid derivative was isolated from the ethyl acetate extract of two-phase olive waste (alperujo). The structure of this compound was fully characterized as s-trans-(E)-3-(1-oxobut-2-en-2-yl)glutaric acid. The spectroscopic data, including one- and two-dimensional nuclear magnetic resonance, mass spectrometry, infrared analysis, and ultraviolet spectrum, were showed. The origin of this compound has not been previously studied, although it most likely results from the breakdown of the oleuropein (or ligstroside) secoiridoid skeleton via oxidation and decarboxylation of the dialdehydic form of elenolic acid, with this transformation being enhanced by extraction of phenolics with ethyl acetate. In addition, the bactericidal activity of (E)-3-(1-oxobut-2-en-2-yl)glutaric acid and extracts containing it was evaluated against two phytopatoghenic microorganisms Pseudomonas syringae and Agrobacterium tumefaciens.Funding was received from the Spanish Ministry of Economy and Competitiveness and co-funded by the European Social Fund (ESF) (Project AGL2013-48291-R). Guillermo Rodríguez-Gutiérrez (Contract RYC-2012-10456 ) thanks the “Ramón y Cajal” program, and Fátima Rubio-Senent (JAE-Pre104) thanks the Spanish National Research Council (CSIC) program, for providing financial support, both co-funded by the ESF.Peer Reviewe