Unsaturated lipid matrices protect plant sterols from degradation during heating treatment

Barriuso, Blanca; Astiasarán, Icíar; Ansorena, Diana

doi:10.1016/j.foodchem.2015.09.074

Cited by 26 publications

(18 citation statements)

References 39 publications

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“…Both the presence of an acyl moiety in the cholesteryl ester and its unsaturation affected the rate of cholesteryl molecule oxidation [30]. It has been shown that the presence of unsaturated fatty acids in a heated medium hindered phytosterol degradation [27]. Similar degradation levels to those found in our results were observed when stigmasterol was heated for 2 h at 180 °C in sunflower oil [31].…”

Section: Resultssupporting

confidence: 84%

“…When the influence of the degree of unsaturation of different lipid matrices (methyl esters of stearic, oleic, linoleic and linolenic acids) on a mixture of three plant sterols (campesterol, sitosterol and stigmasterol) at 180 °C for up to 3 h was performed, the kinetic constant value progressively decreased along with the degree of unsaturation [27]. Greater levels of unsaturation of the lipid matrix exhibited a protective effect against the degradation of plant sterols during heating, indicating that degradation of unsaturated fatty acids was easier than sterols [28].…”

Section: Resultsmentioning

confidence: 99%

“…When stigmasterol and cholesterol were heated in sunflower oil, 7α-hydroxy- and 7-keto- derivatives were the most abundant oxidation products [31]. When the same phytosterols were heated in fatty acid methyl ester medium for 3 h at 180 °C, the oxidation derivatives were formed at a much slower rate [27]. The protective effect of unsaturated fatty acids on the oxidation of sterols has been proposed by Barriuso et al [27].…”

Section: Resultsmentioning

confidence: 99%

“…When the same phytosterols were heated in fatty acid methyl ester medium for 3 h at 180 °C, the oxidation derivatives were formed at a much slower rate [27]. The protective effect of unsaturated fatty acids on the oxidation of sterols has been proposed by Barriuso et al [27]. …”

Section: Resultsmentioning

confidence: 99%

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Effect of Fatty Acid Unsaturation on Phytosteryl Ester Degradation

Raczyk

Kmiecik

Przybylski

et al. 2017

J Americ Oil Chem Soc

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This study examined the thermo-oxidative degradation of stigmasterol fatty acids esters. Stigmasterol stearate, oleate, linoleate and linolenate were synthesized by chemical esterification and their purity evaluated by 1H-NMR and GC–MS. The degradation of stigmasterol esters was examined after heating them at 60 and 180 °C for 1, 2, 4, 8 and 12 h. It was established that stigmasterol esters were prone to thermo-oxidative degradation, with time and temperature affecting the degree of degradation. The unsaturation of fatty acids affected the rate of stigmasteryl ester degradation. The kinetics of StS and StO degradation were similar and the additional double bonds in StL and StLn resulted in their faster decomposition. The esters degraded faster at 180 than at 60 °C. The sterol and fatty acid molecules degraded at different rates, such that the fatty acid moiety deteriorated faster than the sterol at both temperatures, independent of the time of heating and the level of unsaturation.

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Section: Resultssupporting

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Effect of Fatty Acid Unsaturation on Phytosteryl Ester Degradation

Raczyk

Kmiecik

Przybylski

et al. 2017

J Americ Oil Chem Soc

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“…Some studies show that sterols degrade slower in the presence of unsaturated fatty acids. Nevertheless, in a recent review, it has been mentioned that “the behavior of phytosterols under different degree of unsaturation of the surrounding lipids needs further investigation.” It was suggested that oxidation of unsaturated phytosterols may protect other compounds from their oxidation . Β‐sitosterol was found to have in vitro capacity to trap free radicals …”

Section: Introductionmentioning

confidence: 99%

Impact of Added Phytosteryl/Phytostanyl Fatty Acid Esters on Chemical Parameters of Margarines upon Heating and Pan‐Frying

Raczyk

Bonte²,

Matthäus³

et al. 2017

Euro J Lipid Sci & Tech

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The effect of the thermal treatment on chemical parameters of margarines enriched with phytosteryl fatty acid esters is evaluated. Sterols, fatty acids, polar and volatile compounds, dimers, trimers, tocopherols, 3‐MCPD and glycidyl esters are analyzed applying GPC‐RI, GC‐FID, GC‐MS, and HPLC. Additionally, a Rancimat test is performed to compare the oxidative stability of margarines. This study shows that margarines with and without added phytosteryl esters are both stable at a mild temperature of 60 °C over a period of at least 7 days. On the other side after 15 min of pan‐frying at 180 °C a degradation of unsaturated fatty acids (14–47%), phytosterols (31–49%), and vitamin‐E‐active compounds (71–100%) is found. The supplementation of margarines with phytosteryl fatty acid esters have no effect on their oxidative stability during pan‐frying characterized by Rancimat test and total polar compounds. Volatile, degradation products of fatty acids as well as phytosterols, are found after pan‐frying. The composition of volatiles after pan‐frying significantly differed depends on the presence of additional PSE in margarines. For the first time, it is shown that pan‐frying with margarines over a period of 15 min results in a remarkable formation of 3‐MCPD esters while the increase of glycidyl esters is only very moderate. Practical Application: Based on this study results additional phytosteryl esters do not have antioxidative properties on margarines upon pan‐frying. What is more, they are not stable during pan‐frying at 180 °C. A significant amount of nutritionals as phytosterols, vitamin E active compounds, unsaturated fatty acids are degraded within 15 min and other undesired compounds as dimers, trimers, 3‐MCPD esters are formed. According to the research, heating at a high temperature over longer time should not be applied to this kind of product to avoid oxidation of valuable constituents and formation of degradation products. Volatile compounds which were found are characteristic for fatty acids and phytosterols degradation and can be used as indicators of margarines oxidation. The research presents chemical changes in margarines with and without additional phytosteryl/phytostanyl fatty acid esters. In the graphical abstract compounds which naturally occur in those margarines are presented and compounds which are formed after thermo‐oxidative degradation during pan‐frying.

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Application of small angle X‐ray scattering in exploring the effect of edible oils with different unsaturation FAs on bioaccessibility of stigmasterol oleate

Wang,

Wang

et al. 2023

J Sci Food Agric

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BACKGROUNDPhytosterol can improve its lipid solubility, lipophilic/hydrophilic balance and bioaccessibility by esterification with fatty acids, which increases its practical application range in the food industry. In the present study, small angle X‐ray scattering combined with the pH‐stat in vitro digestion model was applied to continuously monitor the molecular structure evolution of mixed micelles during digestion and investigate the effect of three edible oils (olive oil with 72.41 ± 0.57% oleic, sunflower seed oil with 63.45 ± 0.78% linoleic, refined linseed oil with 51.74 ± 0.34% linolenic) on bioaccessibility of stigmasterol oleate in vitro.RESULTSThe release degree and rate of fatty acids in the three edible oil systems (kOO+ST‐OA = 0.0501, kSO+ST−OA = 0.0357, kLO+ST‐OA = 0.0323) was compared. The three different edible oils had similar impact on the formation of dietary mixed micelles during the simulatedin vitro digestion of stigmasterol oleate, although there were significant differences in molecular morphology and composition of mixed micelles. The results showed that the vesicles formed by linoleic oil (SO system) or linolenic oil (LO system) were easy to dissociate. The largest average number and diameter of vesicles (5.55 × 1016 cm−3 and 2230.75 Å), the most stable vesicle structure and the fastest fatty acid release rate were observed in the OO system.CONCLUSIONCompared to linoleic (SO system) or linolenic (LO system), the oleic (OO system) could facilitate the transformation of micelles to vesicles and maintain the stability of its membrane, significantly promotin the dissolution of stigmasterol and improving bioaccessibility. © 2023 Society of Chemical Industry.

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Unsaturated lipid matrices protect plant sterols from degradation during heating treatment

Cited by 26 publications

References 39 publications

Effect of Fatty Acid Unsaturation on Phytosteryl Ester Degradation

Effect of Fatty Acid Unsaturation on Phytosteryl Ester Degradation

Impact of Added Phytosteryl/Phytostanyl Fatty Acid Esters on Chemical Parameters of Margarines upon Heating and Pan‐Frying

Application of small angle X‐ray scattering in exploring the effect of edible oils with different unsaturation FAs on bioaccessibility of stigmasterol oleate

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