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Review
. 2017 May 6;18(5):992.
doi: 10.3390/ijms18050992.

Soft-MS and Computational Mapping of Oleuropein

Luigi Gentile  1   2 , Nicola A Uccella  3   4 , Ganapathy Sivakumar  5
Affiliations
Review

Soft-MS and Computational Mapping of Oleuropein

Luigi Gentile et al. Int J Mol Sci. .

Abstract

Olive oil and table olives are rich sources of biophenols, which provides a unique taste, aroma and potential health benefits. Specifically, green olive drupes are enriched with oleuropein, a bioactive biophenol secoiridoid. Olive oil contains hydrolytic derivatives such as hydroxytyrosol, oleacein and elenolate from oleuropein as well as tyrosol and oleocanthal from ligstroside. Biophenol secoiridoids are categorized by the presence of elenoic acid or its derivatives in their molecular structure. Medical studies suggest that olive biophenol secoiridoids could prevent cancer, obesity, osteoporosis, and neurodegeneration. Therefore, understanding the biomolecular dynamics of oleuropein can potentially improve olive-based functional foods and nutraceuticals. This review provides a critical assessment of oleuropein biomolecular mechanism and computational mapping that could contribute to nutrigenomics.

Keywords: biophenols; hydroxytyrosol; olive oil; secoiridoid; table olives; tyrosol; β-glucosidase.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Molecular structures of olive biophenol secoiridoids.
Figure 2
Figure 2
Negative ion ESI-MS/MS spectra of oleuropein [17].
Figure 3
Figure 3
Collision activated dissociations (CAD) dissociations of oleuropein pseudomolecular anion, m/z 539.
Figure 4
Figure 4
Polar hydrolytic sequence of oleuropein under basic catalysis, competing with radical processes.
Figure 5
Figure 5
Reaction dynamics for the oligomerization of oleuropein under autoxidation, where R = Oleoside.
Figure 6
Figure 6
Acid-catalyzed hydrolysis of oleuropein.
Figure 7
Figure 7
The cascade dynamics of oleuropein to hydroxytyrosil elenolate in concert under acid-catalyzed conditions.
Figure 8
Figure 8
Oleuropein orbital surfaces and energy levels for highest occupied molecular orbital (HOMO), HOMO-1, HOMO-2, and lowest unoccupied molecular orbital (LUMO), LUMO+1, LUMO+2 using ab initio calculation with the 6-311G(d,p) basis set. Isosurface of the HOMO and LUMO consists of two colors (green and pink), which represents the positive and negative isosurfaces. The choice of color for positive or negative part is arbitrary.
See this image and copyright information in PMC

References

    1. López de Las Hazas M.C., Piñol C., Macià A., Motilva M.J. Hydroxytyrosol and the colonic metabolites derived from virgin olive oil intake induce cell cycle arrest and apoptosis in colon cancer cells. J. Agric. Food Chem. 2017 doi: 10.1021/acs.jafc.6b04933. - DOI - PubMed
    1. Sivakumar G., Briccoli Bati C., Uccella N.A. HPLC-MS screening of the antioxidant profile of Italian olive cultivars. Chem. Nat. Compd. 2005;41:588–591. doi: 10.1007/s10600-005-0214-8. - DOI
    1. Sánchez de Medina V., Miho H., Melliou E., Magiatis P., Priego-Capote F., Luque de Castro M.D. Quantitative method for determination of oleocanthal and oleacein in virgin olive oils by liquid chromatography-tandem mass spectrometry. Talanta. 2017;162:24–31. doi: 10.1016/j.talanta.2016.09.056. - DOI - PubMed
    1. Fabiani R. Anti-cancer properties of olive oil secoiridoid phenols: A systematic review of in vivo studies. Food Funct. 2016;7:4145–4159. doi: 10.1039/C6FO00958A. - DOI - PubMed
    1. Ramírez E., Brenes M., García P., Medina E., Romero C. Oleuropein hydrolysis in natural green olives: Importance of the endogenous enzymes. Food Chem. 2016;206:204–209. doi: 10.1016/j.foodchem.2016.03.061. - DOI - PubMed

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