Liquid chromatography mass spectrometry for plant sterol oxide determination in complex mixtures

Kemmo, Suvi; Ollilainen, Velimatti; Lampi, Anna‐Maija; Piironen, Vieno

doi:10.1007/s00217-007-0661-5

Cited by 18 publications

(14 citation statements)

References 28 publications

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“…Nevertheless, according to Cercaci et al Regarding stigmasterol, the double bond present in C22 could lead to the idea of a greater oxidation of this compound, however, these bonds in the side chain do not affect its reactivity (60,64). Therefore, it is not surprising that, in this work, stigmasterol was the less oxidized sterol.…”

Section: Effect Of the Type Of Sterolmentioning

confidence: 56%

Oxysterols formation: A review of a multifactorial process

Barriuso

Ansorena

Astiasarán

2017

The Journal of Steroid Biochemistry and Molecular Biology

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Highlights1-Heating sterols at 180 °C produced a high extent of oxidation.2-The presence and unsaturation degree of the surrounding lipids protected sterols from oxidation.3-Plant aqueous extracts protected cholesterol from oxidation.4-Greater amounts of campesterol-derived oxidation products were observed, followed by sitosterol, cholesterol and stigmasterol.5-In 5 out of 7 of our studies, 7-keto derivatives were the most abundant oxysterols formed. AbstractDietary sterols are nutritionally interesting compounds which can suffer oxidation reactions. In the case of plant sterols, they are being widely used for food enrichment due to their hypocholesterolemic properties. Besides, cholesterol and plant sterols oxidation products are associated with the development of cardiovascular and neurodegenerative diseases, among others. Therefore, the evaluation of the particular factors affecting sterol degradation and oxysterols formation in foods is of major importance. The present work summarizes the main results obtained in experiments which aimed to study four aspects in this context: the effect of the heating treatment, the unsaturation degree of the surrounding lipids, the presence of antioxidants on sterols degradation, and at last, oxides formation. The use of model systems allowed the isolation of some of these effects resulting in more accurate data. Thus, these results could be applied in real conditions.

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Section: Effect Of the Type Of Sterolmentioning

confidence: 56%

Oxysterols formation: A review of a multifactorial process

Barriuso

Ansorena

Astiasarán

2017

The Journal of Steroid Biochemistry and Molecular Biology

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“…Overall, fragmentation of monomer ions indicates the presence of two oxygen molecules, indicative of sterol oxides. Kemmo et al [24,25] also established similar fragmentation and type of ions during the analysis of different types of sterol oxides.…”

Section: Sterol Monomer Fractionmentioning

confidence: 90%

“…In this way, oligomers up to tetramers of triolein with and without additional oxygen atoms were observed. A similar technique was applied for the separation and identification of cholesterol and phytosterol oxides [24,25]. In this paper we present for the first time to our knowledge, the mass spectra of phytosterol oligomers and proposing fragmentation of these molecules.…”

Section: Introductionmentioning

confidence: 99%

Sitosterol Thermo‐oxidative Degradation Leads to the Formation of Dimers, Trimers and Oligomers: A Study Using Combined Size Exclusion Chromatography/Mass Spectrometry

Rudzińska

Przybylski

Zhao

et al. 2010

Lipids

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Phytosterols are recognized as functional food components with cholesterol reducing properties in humans. The formation of phytosterol oligomers as a result of the thermo-oxidative degradation of sitosterol is shown to occur. The existence of oligomers is demonstrated by size exclusion chromatography (SEC) and confirmed by combined SEC-atmospheric pressure chemical ionization mass spectrometry (SEC/APCI-MS). A speculative structure for the sitosterol dimer with 3,7' linkage is proposed consistent with data from tandem mass spectrometry and exact mass measurements. Higher molecular weight species arising from the formation of trimers or higher oligomers are seen in the mass spectra. Fragments of sitosterol formed by thermo-oxidative processes are also shown to oligomerize and their common structural characteristics are demonstrated by tandem mass spectrometry. The results presented provide evidence for the possible formation of oligomeric species involving sterols in addition to those known for acylglycerides in vegetable oils subjected to extreme oxidative stress such as in frying.

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“…Clariana et al [67] found this technique better than CG-FID in a study performed with pork meat. Due to the necessity of a derivatization process and the impossibility of analysing thermolabile molecules, some liquid chromatography methods have been recently developed [68][69][70]. However, liquid chromatography shows lower resolution than gas chromatography, and the best way to overcome this problem is coupling it to a mass spectrometer detector, which in this case is quite complex and still has not been well solved.…”

Section: Chromatographymentioning

confidence: 99%

A review of analytical methods measuring lipid oxidation status in foods: a challenging task

Barriuso

Astiasarán

Ansorena

2012

Eur Food Res Technol

276

220

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Lipid oxidation analysis in food samples is a relevant topic since compounds generated in the process are related to undesirable sensory and biological effects. As the process is complex and depends on the type of lipid substrate, oxidation agents and environmental factors, proper measurement of lipid oxidation remains a challenging task. A great variety of methodologies have been developed and implemented so far, both for determining primary oxidation products and secondary oxidation products. Most common methods and classical procedures are described, including peroxide value, TBARS analysis and chromatography. Some other methodologies such as chemiluminescence, fluorescence emission, Raman spectroscopy, infrared spectroscopy or magnetic resonance, provide interesting and promising results, so attention must be paid to these alternative techniques in the area of food lipid oxidation analysis.

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Liquid chromatography mass spectrometry for plant sterol oxide determination in complex mixtures

Cited by 18 publications

References 28 publications

Oxysterols formation: A review of a multifactorial process

Oxysterols formation: A review of a multifactorial process

Sitosterol Thermo‐oxidative Degradation Leads to the Formation of Dimers, Trimers and Oligomers: A Study Using Combined Size Exclusion Chromatography/Mass Spectrometry

A review of analytical methods measuring lipid oxidation status in foods: a challenging task

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