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Open AccessArticle

UV-Vis Spectroelectrochemistry of Oleuropein, Tyrosol, and p-Coumaric Acid Individually and in an Equimolar Combination. Differences in LC-ESI-MS2 Profiles of Oxidation Products and their Neuroprotective Properties

1
Univ Rennes, CNRS, ISCR–UMR 6226, 35043 Rennes, France
2
INRS-Centre Armand Frappier, Laval, QC H7V 1B7, Canada
3
INAF, Québec, QC G1V 0A6, Canada
*
Authors to whom correspondence should be addressed.
Biomolecules 2019, 9(12), 802; https://doi.org/10.3390/biom9120802
Received: 30 October 2019 / Revised: 22 November 2019 / Accepted: 24 November 2019 / Published: 28 November 2019
Major phenolic compounds from olive oil (ArOH-EVOO), oleuropein (Ole), tyrosol (Tyr), and p-coumaric acid (p-Cou), are known for their antioxidant and neuroprotective properties. We previously demonstrated that their combination could potentiate their antioxidant activity in vitro and in cellulo. To further our knowledge of their electron-transfer properties, Ole, Tyr, and p-Cou underwent a spectroelectrochemical study, performed either individually or in equimolar mixtures. Two mixtures (Mix and Mix-seq) were prepared in order to determine whether distinct molecules could arise from their simultaneous or sequential oxidation. The comparison of Liquid Chromatography–Electrospray Ionization–Tandem Mass Spectrometry (LC-ESI-MS2) profiles highlighted the presence of specific oxidized products found in the mixes. We hypothesized that they derived from the dimerization between Tyr and Ole or p-Cou, which have reacted either in their native or oxidized forms. Moreover, Ole regenerates when the Mix undergoes oxidation. Our study also showed significant neuroprotection by oxidized Ole and oxidized Mix against H2O2 toxicity on SK-N-SH cells, after 24 h of treatment with very low concentrations (1 and 5 nM). This suggests the putative relevant role of oxidized Ole products to protect or delay neuronal death.
Keywords: olive oil phenolic compounds; UV-Vis spectroelectrochemistry; LC/MS2; oxidation; electron transfer; neuroprotection olive oil phenolic compounds; UV-Vis spectroelectrochemistry; LC/MS2; oxidation; electron transfer; neuroprotection
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Lambert de Malezieu, M.; Ferron, S.; Sauvager, A.; Courtel, P.; Ramassamy, C.; Tomasi, S.; Abasq, M.-L. UV-Vis Spectroelectrochemistry of Oleuropein, Tyrosol, and p-Coumaric Acid Individually and in an Equimolar Combination. Differences in LC-ESI-MS2 Profiles of Oxidation Products and their Neuroprotective Properties. Biomolecules 2019, 9, 802.

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