Electrospray ionisation tandem mass spectrometric investigation of phenylpropanoids and secoiridoids from solid olive residue

Abstract

This work is focused on the recovery and structural characterisation of bioactive compounds from SOR (solid olive residue), a low cost and widely available by-product in the Mediterranean basin. In the light of the interesting biological activities attributed both to secoiridoid and phenylpropanoids, the aim of this work was to carry out a systematic tandem mass spectrometric study for the identification and characterisation of these two class of compounds extracted from SOR derived from Coratina, a cultivar widely diffused in the south of Italy. Five phenylpropanoids, in addition to verbascoside, and two new secoiridoids were identified.

LC‐DAD/ESI‐MS/MS study of phenolic compounds in ash (Fraxinus excelsior L. and F. americana L.) heartwood. Effect of toasting intensity at cooperage

“…The first expulsion of the feruloyl unit was in agreement with the position of the feruloyl moiety at the terminal rhamnose unit. These results are in accordance with the fragmentation pattern described in the literature [27] for eukovoside, reported in solid olive residue. Phenylethanoids detected in leaves, bark and phloem of Fraxinus showed as caffeoyl esters, [11] and to the best of our knowledge, this is the first report on the occurrence of ferulic acid derivatives.…”

“…Product ion spectra of these peaks are in agreement with the loss of a water molecule, and the presence of a caffeic acid moiety and its descarboxylated product, and the presence of a hexose molecule, in accordance with the literature data. [27,29] The molecular mass of peak 53 was 30 Da higher than the verbascoside, suggesting the presence of a methoxyl group. Ions observed in the MS 2 analysis of the deprotonated molecule showed typical fragmentation pathways with a methoxyl group substituted in the b position.…”

“…Peaks 9, 11,13,15,22,26,27,32,33,34,36,38,39,46,48, 50, 52, 54 and 55 were identified as dilignols or oligolignols, using literature data for UV/Vis absorbance and mass spectra when standards were not available. Among them, different class of dilignols and oligolignols were identified.…”

“…This dilignol was the major component in the acetone extract from thermally modified F. excelsior wood, [15] after 4 h at 200 C in a nitrogen atmosphere and under pressure. It can therefore be considered thermally very stable, which facilitate its use as a food additive, a nutraceutical or a drug, since these families of compounds have been the subject of many papers in recent years, [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] due to their important biological activity. [39] Unfortunately, we found very little data in regard to their response to thermal treatments that could be used in the food or pharmaceutical industry.…”

Phenolic Molecules in Virgin Olive Oils: a Survey of Their Sensory Properties, Health Effects, Antioxidant Activity and Analytical Methods. An Overview of the Last Decade Alessandra

“…Table 2 provides an overview of methodologies based on LC-tandem mass spectrometry used for the analysis of phenolic compounds in olive oil. The table does not include several publications in which the analysis of olive fruit, leaves, pulp and pomace, olive tree wood, as well as olive oil waste waters were carried out by using HPLC-MS [14,49,156,[161][162][163][164][165][166][167][168]. Other important issues are the presence of phenolic metabolites of VOO in the human low density lipoprotein fraction [169][170].…”