Insight into virgin olive oil secoiridoids characterization by high-resolution mass spectrometry and accurate mass measurements

Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC

“…The [M+H] + ion showed spontaneous loss of water already in MS 1 and further fragmentation of the resulting [M-H 2 O+H] + ion at m/z 287 gave only one intense fragment ion at m/z 121, representing protonated 4-vinylphenol. MS data of oleocanthal are scarce in the literature and first highresolution fragment ion spectra of two coexisting isoforms of the deacetoxy ligstroside aglycon were only very recently published(Vichi, Cortés-Francisco & Caixach, 2013).Considering differences in the used instrument types, our MS data are in good agreement to the literature data(Vichi, Cortés-Francisco & Caixach, 2013;Gutiérrez-Rosales, Ríos & Gómez-Rey, 2003).The 1 H and 13 C NMR analysis of the mixture of substances 3 and 4 indicated that both, E and Z isomers of oleocanthal were isolated in a ratio of 7:3. In addition, 2D measurements (HSQC, HMBC and COSY) of the mixture allowed a complete assignment of proton and carbon signals of both compounds and the determination of the configuration of 3 and the close contact of C-3 to the olefinic hydrogen.…”

Characterization of bioactive and nutraceutical compounds occurring in olive oil processing wastes

“…The extraction of secoiridoids from olive oil was performed using the procedure described by Vichi et al with some modifications. Briefly, 2.0 g of olive oil were diluted with 3.0 mL of hexane; after mixing, 500 μL of methanol/water mixture (60:40 v/v) were added and, after vortexing and sonication, centrifuged for 5 min at 4000 rpm (i.e., 2000 g ); the methanolic‐aqueous fraction was then collected.…”

“…Due to the presence of a remarkable number of phenols, flavonoids and secoiridoids, OMW poses the need to develop a rapid, sensitive and accurate analytical platform for their characterization. In contrast to the great number of published papers reporting typical analytical approaches mainly based on liquid chromatography coupled with electrospray ionization mass spectrometry (ESI‐MS), a very few reports describe the simple fingerprint by infusion ESI‐MS or atmospheric pressure chemical ionization (APCI)‐MS of low molecular weight (LMW) phenols and/or secoiridoids occurring in extracts of olive oils, olive leaves and OMW . Matrix‐assisted laser desorption/ionization (MALDI) time‐of‐flight mass spectrometry (TOF MS) represents a powerful technique for the determination of molecular weights of organic compounds .…”

“…Matrix‐assisted laser desorption/ionization (MALDI) time‐of‐flight mass spectrometry (TOF MS) represents a powerful technique for the determination of molecular weights of organic compounds . To the best of our knowledge, MALDI‐TOF MS has never been applied to secoiridoids and closely related by‐product analysis, which are usually examined via ESI‐MS in negative ion mode . The main advantages of MALDI such as rapidity, sensitivity, easy sample preparation, no need for analyte derivatization can be exploited for screening and high‐throughput analysis of olive oil by‐products.…”

Future perspectives in Orbitrap™-high-resolution mass spectrometry in food analysis: a review

“…Keckes et al, (2013) have obtained polyphenolic profiles of honey samples, with a simple sample preparation involving dilution in aqueous sodium chloride solution, extraction with ethyl acetate, evaporation and re-dissolving in methanol/water before injection into a UHPLC-LTQ-Orbitrap system. Thirty-one flavonoids and eleven non-flavonoids were measured, and employing principal component analysis (PCA) enabled classification based on botanical (floral) origin.Classification and determination of authenticity of olive oils is equally analytically challenging Vichi et al, (2013). have analysed crude polar extracts from virgin olive oils using both an Exactive™ and Q-Exactive™ focussing on secoiridoid compounds.…”