Kinetics of 25‐hydroperoxycholesterol formation during photo‐oxidation of crystalline cholesterol

Medina-Meza, Ilce Gabriela; Rodríguez‐Estrada, Maria Teresa; Lercker, Giovanni; Barnaba, Carlo; Garcı́a, Hugo S.

doi:10.1002/jsfa.6455

Cited by 9 publications

(4 citation statements)

References 30 publications

(98 reference statements)

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“…It is worth to note that 7-keto is an end-product of cholesterol oxidation and is derived from further oxidation of 7-hydroxyl epimers. Similarly, triol is the end-product of 5,6-epoxides, and 25-OH is the most important derivative of cholesterol oxidation in its side chain (Medina-Meza, Rodriguez-Estrada, Garcia, & Lercker, 2012; Medina-Meza, Rodríguez-Estrada, García, & Lercker, 2012; Medina-Meza, Rodriguez-Estrada, Lercker, Barnaba, & García, 2014) The ANOVA-based heatmap in Figure 1B is helpful to identify characteristics of abundance that are predominant in the powder vs. liquid presentation. At the same time, Figure 1B suggests a potential subclassification based on a more specific lipid and oxidative signature.…”

Section: Resultsmentioning

confidence: 99%

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Lipidomics and Dietary Assessment of Infant Formulas Reveal High Intakes of Major Cholesterol Oxidative Product (7-ketocholesterol)

Kilvington

Barnaba

Rajasekaran

et al. 2020

Preprint

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Approximately two-thirds of US infants receive infant formula (IF) as a primary or sole nutritional source during the first six months of life. IF is available in a variety of commercial presentations, although from a manufacturing standpoint, they can be categorized in powder-(PIF) or liquid-(LIF) based formulations. Herein, thirty commercial IFs were analyzed in their oxidative and non-oxidative lipidomics profiles. Results show that LIFs have a characteristic lipidomic fingerprint, enriched in an oxidated form of cholesterol, and a lower load of phytosterols. We identified 7-ketocholesterol – a major end-product of cholesterol oxidation – as a potential biomarker of IF manufacturing. Our data allowed re-classification of IF based on their metabolomic fingerprint, resulting in three groups assigned with low-to-high oxidative status. Finally, we modeled the dietary intake for cholesterol, sterols, and 7-ketocholesterol in the first year of life. The database provided in this study will be instrumental for scientists interested in infant nutrition, to establish bases for epidemiological studies aimed to find connections between nutrition and diet-associated diseases, such as sitosterolemia.

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Section: Resultsmentioning

confidence: 99%

“…Medina-Meza, Rodriguez-Estrada, Garcia, & Lercker, 2012;Medina-Meza, Rodríguez-Estrada, García, & Lercker, 2012;Medina-Meza, Rodriguez-Estrada, Lercker, Barnaba, & García, 2014) The ANOVA-based heatmap in several COPs, which potentially masks the fact that only 7-keto and triol are spiking in the Volcano plot.…”

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confidence: 99%

Lipidomics and Dietary Assessment of Infant Formulas Reveal High Intakes of Major Cholesterol Oxidative Product (7-ketocholesterol)

Kilvington

Barnaba

Rajasekaran

et al. 2020

Preprint

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“…However, appreciable amounts of cholesterol in fish are prone to oxidation during the preparation and production of processed fish [39,40]. Many studies have shown that polyunsaturated fatty acids in fish are extremely susceptible to COP formation during fish processing [41,42]. Results can vary if different cooking methods are applied to all food samples.…”

Section: Discussionmentioning

confidence: 99%

Quantification of Cooking Method Effect on COP Content in Meat Types Using Triple Quadrupole GC-MS/MS

et al. 2020

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A diet containing cholesterol is an essential component of biological function; however, cholesterol oxidation products (COPs) remain a major public health concern. This study investigated the effects of cooking methods (boiling and frying) on the production levels of COPs in processed foods. Samples, as represented by minced beef, chicken sausages, and fish fillets, were subjected to different cooking methods followed by COP extraction using a saponification method. Then, six common COPs, 5α-cholest, α-epoxy, β-epoxy, 25-HC, triol, and 7-keto, were quantified by triple quadrupole gas chromatography–mass spectrometry (GS-MS/MS). A significantly high number of COPs were detected in minced meat, of which 7-keto and triol were detected as major oxidation products, followed by chicken sausages and fish fillets (p ≤ 0.05). Compared to boiling, frying generated significantly more COPs, specifically triol (0.001–0.004 mg/kg) and 7-keto (0.001–0.200 mg/kg), in all samples. Interestingly, cholesterol level was found to be slightly (but not significantly) decreased in heat-treated samples due to oxidation during cooking, producing a higher number of COPs. Notably, the fish fillets were found to produce the fewest COPs due to the presence of a low amount of cholesterol and unsaturated fatty acids. In conclusion, adapting boiling as a way of cooking and choosing the right type of meat could serve to reduce COPs in processed foods.

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“…However, according to a large number of studies, these techniques, besides the thermal preparation for consumption, lead to oxidative degradation of cholesterol. These studies have shown a relationship between the presence of polyunsaturated fatty acids and the formation of cholesterol oxides during the processing of fish (Osada and others ; Ohshima and others ; Shozen and others ; Lee and others ; Saldanha and Bragagnolo ; Oliveira and Lira ; Sancho and others ; Cardenia and others ; Medina‐Meza and others ). Polyunsaturated fatty acids are extremely susceptible to oxidation even under mild environmental conditions, forming free radicals that will accelerate the lipid chain oxidation processes (Frankel ), yielding COPs.…”

Section: Cholesterol Oxidation Products In Processed Fishmentioning

confidence: 97%

Cholesterol Oxidation in Fish and Fish Products

Dantas

Sampaio

Ferreira

et al. 2015

Journal of Food Science

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Fish and fish products are important from a nutritional point of view due to the presence of high biological value proteins and the high content of polyunsaturated fatty acids, especially those of the n-3 series, and above all eicosapentaenoic acid and docosahexaenoic acid. However, these important food products also contain significant amounts of cholesterol. Although cholesterol participates in essential functions in the human body, it is unstable, especially in the presence of light, oxygen, radiation, and high temperatures that can cause the formation of cholesterol oxidation products or cholesterol oxides, which are prejudicial to human health. Fish processing involves high and low temperatures, as well as other methods for microbiological control, which increases shelf life and consequently added value; however, such processes favor the formation of cholesterol oxidation products. This review brings together data on the formation of cholesterol oxides during the preparation and processing of fish into food products which are recognized and recommended for their nutritional properties.

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Kinetics of 25‐hydroperoxycholesterol formation during photo‐oxidation of crystalline cholesterol

Abstract: The results of this work confirm that cholesterol in the crystalline state involves different oxidation patterns as compared to cholesterol in solution. Moreover, the numerical fit proved that hydroperoxidation is the rate-limiting step in 25-OH formation.

Cited by 9 publications

References 30 publications

Lipidomics and Dietary Assessment of Infant Formulas Reveal High Intakes of Major Cholesterol Oxidative Product (7-ketocholesterol)

Lipidomics and Dietary Assessment of Infant Formulas Reveal High Intakes of Major Cholesterol Oxidative Product (7-ketocholesterol)

Quantification of Cooking Method Effect on COP Content in Meat Types Using Triple Quadrupole GC-MS/MS

Cholesterol Oxidation in Fish and Fish Products

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