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1.
J Agric Food Chem ; 72(28): 15755-15764, 2024 Jul 17.
Artigo em Inglês | MEDLINE | ID: mdl-38954802

RESUMO

Squalene has been proven to possess various bioactive functions that are widely present in vegetable oils. A more comprehensive understanding of the reaction behavior of squalene under oxidative conditions was achieved by studying its antioxidant capacity and thermal degradation products. The total singlet oxygen quenching rate constant (kr + kq) of squalene was 3.8 × 107 M-1 s-1, and both physical and chemical quenching mechanisms equally contribute to the overall singlet oxygen quenching. Fourteen degradation products of squalene were identified at 180 °C by using gas chromatography-mass spectrometry (GC-MS). Combining with DFT calculations, the thermal degradation pathway of squalene was proposed: the aldehydes, ketones, and alcohols, and epoxy compounds were formed by the homolytic cleavage of squalene hydroperoxides to form alkoxy radicals, followed by ß-scission of the alkoxyl radicals at adjacent C-C bonds or intramolecular cyclization.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Oxirredução , Oxigênio Singlete , Esqualeno , Esqualeno/química , Oxigênio Singlete/química , Cinética , Antioxidantes/química , Óleos de Plantas/química , Estrutura Molecular
2.
Food Res Int ; 186: 114372, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38729730

RESUMO

The oxidation and degradation of fats lead to a decrease in the nutritional value of food and pose safety concerns. Saturated fatty acids also hold a significant position in the field of lipid oxidation. In this study, the oxidation products of methyl palmitate were investigated by using gas chromatography mass spectrometry (GC-MS). Seven monohydroperoxides and 72 secondary oxidation products were detected. Combined with density functional theory (DFT) calculations, the formation mechanisms of oxidation products can be summarized into four stages. The initial stage involved the formation of monohydroperoxides and alkanes, followed by the subsequent stage involving methyl x-oxo(hydroxy)hexadecanoates. The third stage involved the formation of methyl ketones, carboxylic acids, and aldehydes, while the final stage involved lactones. Meanwhile, methyl ketones were the most abundant oxidation product, approximately 25 times more abundant than aldehydes; the calculated results agreed well with the experimental results. The establishment of a comprehensive thermal oxidation mechanism for palmitic acid provided a new foundation for future lipid oxidation analyses.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Oxirredução , Aldeídos/química , Aldeídos/análise , Palmitatos/química , Ácido Palmítico/química , Cetonas/química , Ácidos Carboxílicos/química
3.
Int J Food Microbiol ; 417: 110690, 2024 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-38581832

RESUMO

Soy sauce is a traditional condiment that undergoes microbial fermentation of various ingredients to achieve its desired color, scent, and flavor. Sporidiobolus pararoseus, which is a type of Rhodocerevisiae, shows promising potential as a source of lipids, carotenoids, and enzymes that can enrich the taste and color of soy sauce. However, there is currently a lack of systematic and comprehensive studies on the functions and mechanisms of action of S. pararoseus during soy sauce fermentation. In this review, it is well established that S. pararoseus produces lipids that are abundant in unsaturated fatty acids, particularly oleic acid, as well as various carotenoids, such as ß-carotene, torulene, and torularhodin. These pigments are synthesized through the mevalonic acid pathway and possess remarkable antioxidant properties, acting as natural colorants. The synthesis of carotenoids is stimulated by high salt concentrations, which induces oxidative stress caused by NaCl. This stress further activates crucial enzymes involved in carotenoid production, ultimately leading to pigment formation. Moreover, S. pararoseus can produce high-quality enzymes that aid in the efficient utilization of soy sauce substrates during fermentation. Furthermore, this review focused on the impact of S. pararoseus on the color and quality of soy sauce and comprehensively analyzed its characteristics and ingredients. Thus, this review serves as a basis for screening high-quality oleaginous red yeast strains and improving the quality of industrial soy sauce production through the wide application of S. pararoseus.


Assuntos
Basidiomycota , Carotenoides , Fermentação , Alimentos de Soja , Alimentos de Soja/microbiologia , Basidiomycota/metabolismo , Carotenoides/metabolismo , Microbiologia de Alimentos , Antioxidantes/metabolismo
4.
J Agric Food Chem ; 72(11): 5757-5765, 2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38445360

RESUMO

Thermal stability and antioxidant ability of γ-oryzanol in oil have been widely studied. However, further research is needed to explore its thermal degradation products and degradation pathways. The thermal degradation products of γ-oryzanol in stripped soybean oil were identified and quantified by employing high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) during heating at 180 °C. The results revealed that γ-oryzanol undergoes ester bond cleavage to form trans-ferulic acid and free sterols, and trans-ferulic acid generated intermediate compound 4-vinylguaiacol, which ultimately generated vanillin. Analysis of kinetic and thermodynamic parameters revealed the thermal stability ranking of the four components of γ-oryzanol as follows: CampFA > CAFA > 24MCAFA > SitoFA. Furthermore, γ-oryzanol exhibited superior antioxidant activity at lower temperatures. The results of this study provide a theoretical basis for a better understanding of the thermal stability and antioxidant properties of γ-oryzanol in oil under thermal oxidation conditions.


Assuntos
Antioxidantes , Ácidos Cumáricos , Fenilpropionatos , Antioxidantes/química , Oxirredução , Fenilpropionatos/química , Estresse Oxidativo
5.
J Agric Food Chem ; 72(1): 704-714, 2024 Jan 10.
Artigo em Inglês | MEDLINE | ID: mdl-38131267

RESUMO

The impact of the oxidation of linoleic acid cannot be overlooked in daily food consumption. This study used gas chromatography-mass spectrometry (GC-MS) to identify both nonvolatile oxidation products and volatile oxidation products of methyl linoleic acid at 180 °C and density function theory to investigate oxidation mechanisms. An analysis of nonvolatile oxidation products revealed the presence of three primary oxidation products. The three primary oxidation products were identified as hydroperoxides, peroxide-linked dimers, and heterocyclic compounds in a ratio of 2.70:1:3.69 (mmol/mmol/mmol). The volatile components of secondary oxidation products were found including aldehydes (40.77%), alkanes (19.89%), alcohols (9.02%), furans (6.11%), epoxides (0.46%), and acids (2.50%). DFT calculation proved that the secondary oxidation products mainly came from peroxides (77%). Finally, we look forward to our research contributing positively to lipid autoxidation and human health.


Assuntos
Aldeídos , Ácido Linoleico , Humanos , Temperatura , Oxirredução , Cromatografia Gasosa-Espectrometria de Massas , Aldeídos/química , Ácidos Linoleicos
6.
Foods ; 13(1)2023 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-38201057

RESUMO

Resveratrol (3,5,4'-trihydroxystilbene), a naturally occurring polyphenol that is widely utilized in functional food due to its antioxidant, anti-inflammatory, anti-cancer and anti-aging properties. In the present study, the antioxidant capacity and oxidation products of resveratrol in soybean oil were investigated. The antioxidant activity of resveratrol was evaluated by employing various in vitro antioxidant assays such as DPPH scavenging activities, ferric reducing abilities (FRAP) and oxygen radical absorbance capacity (ORAC). Furthermore, monitoring the peroxide value and the acid value of soybean oil with the addition of 200-1000 µg/g of resveratrol at 60 and 180 °C. It was found that when the concentration of resveratrol in soybean oil was 600 µg/g, the antioxidant capacity was most effective. Resveratrol and its thermal degradation products were identified using liquid chromatography-mass spectrometry (LC-MS) and gas chromatography-mass spectrometry (GC-MS). There were seven nonvolatile oxidation products with mass-to-charge ratios of 138.03, 171.04, 185.10, 157.03, 436.13, 244.07 and 306.09 kg/C and two volatile oxidation products with mass-to-charge ratios of 100.05 and 158.13 kg/C were identified. The research findings may provide essential information for the development of resveratrol as functional oils in future.

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