Formation and decomposition of stigmasterol hydroperoxides and secondary oxidation products during thermo‐oxidation

Kemmo, Suvi; Soupas, Laura; Lampi, Anna‐Maija; Piironen, Vieno

doi:10.1002/ejlt.200401112

Cited by 33 publications

(17 citation statements)

References 29 publications

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“…The total amount of polar oxidation products accounted thus only for 18% of the initial stigmasterol indicating that other types of products had to be formed. The polar oxides may have been suffered further reactions, such as polymerization (Kemmo, Soupas, Lampi & Piironen, 2005;Soupas et al, 2006) or dehydration, giving rise to other types of non polar products (Bortolomeazzi, De Zan, Pizzale & Lanfranco, 2000). These results are in agreement with those obtained by Lampi, Juntunen, Toivo and Piironen (2002), with a maximum content of polar oxidation products after 1 hour heating of stigmaterol at 180 ºC 7-ketostigmasterol was the only product whose content increased statistically during the whole course of the experiment.…”

Section: Effects Of Thermo-oxidation On Stigmasterol As Measured By Psupporting

confidence: 87%

Determination of non-polar and mid-polar monomeric oxidation products of stigmasterol during thermo-oxidation

et al. 2010

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Oxidation products of stigmasterol were characterized by their polarity and molecular size using solid phase extraction (SPE) and high performance size exclusion (HPSEC) methods. Monomeric oxides were studied further by GC-MS and GC-FID. The focus was on identifying and quantificating non-polar and mid-polar monomeric oxides after SPE fractionation. Commercial stigmasterol was subjected to 180 ºC up to 3 hours. Six oxidation products were identified by GC-MS in the nonpolar and mid-polar monomeric fractions, and they appeared already after the first hour of heating. Quantification by GC-FID showed an increase in the non-polar and mid-polar oxidation products during heating time, and their amounts reached values of 6.1 and 47.0 μg/mg of commercial stigmasterol, respectively. Polar oxidation products commonly measured reached a value of 193 μg/mg after 1 hour of heating, while after 3-hour heating, the amount was only 164 μg/mg. Since as much as 550 μg/mg of stigmasterol was decomposed, the monomeric products explained only partly the stigmasterol loss. Dimeric and polymeric products contributed to 165 µg/g of gap showing the importance of polymerization reactions at 180 ºC.2

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Section: Effects Of Thermo-oxidation On Stigmasterol As Measured By Psupporting

confidence: 87%

Determination of non-polar and mid-polar monomeric oxidation products of stigmasterol during thermo-oxidation

et al. 2010

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“…In this sense, Soupas et al (35) proposed 140 °C as the key temperature in the process, since sterols behaved differently below and above this temperature. At 175-180 °C, whereas Xu et al (30) found the maximum amount of COPs at similar times as in our experiment, some other works, (14,32,36) obtained that SOPs decreased only after 40, 60 and 90 min, respectively.…”

Section: Effect Of Heating Treatmentsupporting

confidence: 82%

“…Besides, instead of the ones we analyzed, other oxides could have been formed, such as 6-hydroxy, 20-hydroxy, 22-hydroxy, dienes, trienes… (29,36,63). Moreover, SOPs derived from cholesterol and stigmasterol could have decomposed to form oligomers, polymers and other compounds characteristic of advanced stages of oxidation (29,39), yielding an overall lower balance than for campesterol and sitosterol derived oxides.…”

Section: Effect Of the Type Of Sterolmentioning

confidence: 95%

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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“…Thus, it was concluded that 7-keto derivatives represent a simple, reliable marker of the extent of PS oxidation in food (Cercaci et al 2007). Although the distribution of POP may depend on the oxidation phase/status as well (Kemmo et al 2005), the 7-keto derivatives were the most abundant oxides.…”

Section: Impact Of Frying On the Total Amount Of Psmentioning

confidence: 98%

Oxidation of β-sitosterol and campesterol in sunflower oil upon deep- and pan-frying of French fries

Ramadan

2015

J Food Sci Technol

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Fried foods, both deep-fried and pan-fried, are enjoyed by people worldwide. Frying is one of the main factors leading to formation of phytosterols (PS) oxidation products (POP) in vegetable oils. The aim of this study was to measure the oxidation of β-sitosterol (24α-ethyl-5-cholesten-3β-ol) and campesterol (24α-methyl-5-cholesten-3β-ol) in commercial sunflower oil (SFO) during deepand pan-frying of French fries for different periods (30, 60, 120 and 240 min). The total amount of PS in SFO was 4732 μg/g, wherein the major PS were β-sitosterol and campesterol. The results of POP were confirmed by the GC-MS analysis that monitored the formation of oxides during frying. Upon frying, total PS content decreased whereas the highest decrease was measured after 240 min of frying. The oxidative stability (OS) of different sitosterol and campesterol during both frying methods was evaluated. In general, pan frying resulted in more PS oxidation than deep frying. β-Sitosterol oxides predominated while campesterol oxides were formed to a lesser extent. 7-Ketositosterol, followed by 7β-hydroxysitosterol, 5,6-epoxy derivatives and 7α-hydroxysitosterol were the main POP induced during frying. The proportion of 7-keto derivatives decreased during frying while the proportion of 7β-hydroxy derivatives increased. The formation of POP might be a limiting factor for frying in SFO for long periods.

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Formation and decomposition of stigmasterol hydroperoxides and secondary oxidation products during thermo‐oxidation

Cited by 33 publications

References 29 publications

Determination of non-polar and mid-polar monomeric oxidation products of stigmasterol during thermo-oxidation

Determination of non-polar and mid-polar monomeric oxidation products of stigmasterol during thermo-oxidation

Oxysterols formation: A review of a multifactorial process

Oxidation of β-sitosterol and campesterol in sunflower oil upon deep- and pan-frying of French fries

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