Characterization of phenolic and secoiridoid aglycons present in virgin olive oil by gas chromatography-chemical ionization mass spectrometry

Angerosa, Franca; d’Alessandro, Nicola; Corana, Federica; Mellerio, G.

doi:10.1016/0021-9673(95)01375-x

Cited by 122 publications

(95 citation statements)

References 17 publications

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“…The main phenolic compounds in virgin olive oil are secoiridoid derivatives of 2-(3,4-dihydroxyphenyl)ethanol (3,4-DHPEA) and 2-(4-hydroxyphenyl)-ethanol (p-HPEA) that occur as either simple phenols or esterified with elenolic acid to form, respectively, oleuropein and its derivative demethyloleuropein, and ligstroside, their aglycones 3,4-DHPEA-EA and p-HPEA-EA (Figure 1) (Bendini et al, 2007;Suárez et al, 2009). The aglyconic form of oleuropein and ligstroside, 3,4-DHPEA-EA and p-HPEA-EA respectively, were reported for the first time by Montedoro et al, who also assigned their chemical structures, later confirmed by other (Montedoro et al, 1992;Angerosa et al, 1996;Owen et al, 2000). 3,4-DHPEA-EA and p-HPEA-EA, associated to the intense sensory of bitterness and pungency respectively attribute in VOO (Gutierrez-Rosales et al, 2003), is endowed with numerous beneficial effects on human health (Servili et al, 2004;Bendini et al, 2007;Esti et al, 1998;Della Ragione et al, 2000;Paiva-Martins et al, 2001;Fabiani et al, 2002;Carasco-Pancorbo et al, 2005;Artajo et al, 2006;Fabiani et al, 2006;Fabiani et al, 2008;Paiva-Martins et al, 2009).…”

Section: Introductionmentioning

confidence: 89%

Oleuropein an Olive Oil Compound in Acute and Chronic Inflammation Models: Facts and Perspectives

Britti¹,

Impellizzeri²,

Procopio³

et al. 2012

Olive Germplasm - The Olive Cultivation, Table Olive and Olive Oil Industry in Italy

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Section: Introductionmentioning

confidence: 89%

Oleuropein an Olive Oil Compound in Acute and Chronic Inflammation Models: Facts and Perspectives

Britti¹,

Impellizzeri²,

Procopio³

et al. 2012

Olive Germplasm - The Olive Cultivation, Table Olive and Olive Oil Industry in Italy

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“…1). Furthermore, the presence of two lignans, pinoresinol (8) and 1-acetoxypinoresinol (9), has been reported [10,11]. Phenyl acids ( [4] and references cited therein) and flavones [12,13] are further classes of phenolics identified in VOO; however, they occur in very low amounts in VOO in comparison with secoiridoid derivatives [8,14].…”

Section: Phenolic Compounds In Virgin Olive Oilmentioning

confidence: 98%

“…Breakdown products of two major phenolic constituents of the olive fruit (Olea europea L.), oleuropein and ligstroside, form the major part of the phenolic fraction. Both simple phenols -hydroxytyrosol (1), tyrosol (2), hydroxytyrosol acetate (3; [6]), tyrosol acetate [7] -and secoiridoid aglycones -the open dialdehydic forms of decarboxymethyl aglycone of oleuropein (4) and ligstroside (5; [8]) and monoaldehydic closed forms of oleuropein (6; [8]) and ligstroside aglycones (7; [7,9]) -appertain to this group (numbers refer to Fig. 1).…”

Section: Phenolic Compounds In Virgin Olive Oilmentioning

confidence: 99%

Comparability and reliability of different techniques for the determination of phenolic compounds in virgin olive oil

Hrnčiřík

Fritsche

2004

Euro J Lipid Sci & Tech

130

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Phenolic compounds represent a unique and functional part of the polar fraction of virgin olive oils. Many different approaches for the analysis of these compounds have been published, which has led to ambiguous results that are difficult to compare. In order to explain the controversial data reported in the literature, extraction techniques (solid-phase extraction, SPE, and liquid-liquid extraction, LLE), methods of analysis (HPLC and colorimetric assay) and quantification methods have been re-investigated with genuine olive oil phenols. The optimized LLE system led to high recovery of the nine major olive oil phenolics (93%) and, in addition, was at least as good as the SPE technique in view of costs, solvent and sample consumption, and analysis time. SPE was shown to be problematic because of the selectivity towards the individual phenolics, particularly the aglycone-type ones. The proposed LLE/HPLC method was compared with the traditional colorimetric assay (Folin-Ciocalteu method) by analyzing 23 samples of virgin olive oils. A strong correlation between both methods has been found, suggesting that the colorimetric assay is reasonably valid for a rough prediction of the total phenolic content. In the literature, the level of phenolics is expressed in several different units (reference compound equivalents in case of colorimetric measurements and ppm in HPLC measurements). As these units can differ in orders of magnitude, it is necessary to convert the data to a common base before comparing or combining them.

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“…Identification and quantitation, based traditionally on HPLC (with different detectors, such as UV, fluorescence, coulometric electrode array detection, amperometric detector) [144][145][146][147][148][149][150], GC-FID [151][152][153][154] and, more recently CE-UV, can be aided today by MS and NMR, which is a focus of the present review.…”

Section: New Analytical Approaches To Characterization Of the Phenolimentioning

confidence: 99%

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

et al. 2007

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Among vegetable oils, virgin olive oil (VOO) has nutritional and sensory characteristics that to make it unique and a basic component of the Mediterranean diet. The importance of VOO is mainly attributed both to its high content of oleic acid a balanced contribution quantity of polyunsaturated fatty acids and its richness in phenolic compounds, which act as natural antioxidants and may contribute to the prevention of several human diseases. The polar phenolic compounds of VOO belong to different classes: phenolic acids, phenyl ethyl alcohols, hydroxy-isochromans, flavonoids, lignans and secoiridoids. This latter family of compounds is characteristic of Oleaceae plants and secoiridoids are the main compounds of the phenolic fraction. Many agronomical and technological factors can affect the presence of phenols in VOO. Its shelf life is higher than other vegetable oils, mainly due to the presence of phenolic molecules having a catechol group, such as hydroxytyrosol and its secoiridoid derivatives. Several assays have been used to establish the antioxidant activity of these isolated phenolic compounds. Typical sensory gustative properties of VOO, such as bitterness and pungency, have been attributed to secoiridoid molecules. Considering the importance of the phenolic fraction of VOO,

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Characterization of phenolic and secoiridoid aglycons present in virgin olive oil by gas chromatography-chemical ionization mass spectrometry

Cited by 122 publications

References 17 publications

Oleuropein an Olive Oil Compound in Acute and Chronic Inflammation Models: Facts and Perspectives

Oleuropein an Olive Oil Compound in Acute and Chronic Inflammation Models: Facts and Perspectives

Comparability and reliability of different techniques for the determination of phenolic compounds in virgin olive oil

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

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