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脂类结构影响二十二碳六烯酸和二十碳五烯酸在模拟消化体系中的消化和氧化行为。

Lipid Structure Influences the Digestion and Oxidation Behavior of Docosahexaenoic and Eicosapentaenoic Acids in the Simulated Digestion System.

机构信息

Food Sciences, Department of Life Technologies, University of Turku, FI-20014 Turku, Finland.

Faculty of Pharmaceutical Sciences, University of Iceland, IS-107 Reykjavík, Iceland.

出版信息

J Agric Food Chem. 2023 Jul 5;71(26):10087-10096. doi: 10.1021/acs.jafc.3c02207. Epub 2023 Jun 20.

DOI:10.1021/acs.jafc.3c02207
PMID:37338276
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10326875/
Abstract

Omega-3 fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are essential for human health but prone to oxidation. While esterification location is known to influence the stability of omega-3 in triacylglycerols (TAGs) in oxidation trials, their oxidative behavior in the gastrointestinal tract is unknown. Synthesized ABA- and AAB-type TAGs containing DHA and EPA were submitted to static digestion for the first time. Tridocosahexaenoin and DHA as ethyl esters were similarly digested. Digesta were analyzed by gas chromatography, liquid chromatography-mass spectrometry, and nuclear magnetic resonance spectroscopy. Besides the formation of di- and monoacylglycerols, degradation of hydroperoxides was detected in ABA- and AAB-type TAGs, whereas oxygenated species increased in tridocosahexaenoin. Ethyl esters were mainly unaffected. EPA was expectedly less susceptible to oxidation prior to and during the digestion process, particularly in -2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.

摘要

ω-3 脂肪酸,如二十碳五烯酸(EPA)和二十二碳六烯酸(DHA),对人体健康至关重要,但容易氧化。酯化位置已知会影响三酰基甘油(TAGs)中 ω-3 的稳定性在氧化试验中,但它们在胃肠道中的氧化行为尚不清楚。首次提交了含有 DHA 和 EPA 的 ABA-和 AAB 型 TAG 进行静态消化。三 docosahexaenoin 和 DHA 乙酯也进行了类似的消化。通过气相色谱、液相色谱-质谱和核磁共振波谱分析消化产物。除了二酰基和单酰基甘油的形成外,在 ABA-和 AAB 型 TAG 中检测到氢过氧化物的降解,而三 docosahexaenoin 中的氧化物种增加。乙酯主要不受影响。在消化过程之前和期间,EPA 预期不易氧化,尤其是在 -2 位置。这些结果与作为补充剂或成分使用的定制 ω-3 结构的生产有关。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/31676f9fbb1f/jf3c02207_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/dfb15559af0d/jf3c02207_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/cd537f4a0ad3/jf3c02207_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/b5834daeb355/jf3c02207_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/50defd59542b/jf3c02207_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/31676f9fbb1f/jf3c02207_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/dfb15559af0d/jf3c02207_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/cd537f4a0ad3/jf3c02207_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/b5834daeb355/jf3c02207_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/50defd59542b/jf3c02207_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83cc/10326875/31676f9fbb1f/jf3c02207_0006.jpg

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2
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Food Chem. 2023 Feb 15;402:134271. doi: 10.1016/j.foodchem.2022.134271. Epub 2022 Sep 15.
3
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Foods. 2024 Feb 7;13(4):513. doi: 10.3390/foods13040513.
膳食中的三酰甘油氢过氧化物不会被吸收,但它会在胃肠道中诱导其他三酰甘油氢过氧化物的形成。
Redox Biol. 2022 Nov;57:102471. doi: 10.1016/j.redox.2022.102471. Epub 2022 Sep 14.
4
Oxidative stability, oxidation pattern and α-tocopherol response of docosahexaenoic acid (DHA, 22:6n-3)-containing triacylglycerols and ethyl esters.含二十二碳六烯酸(DHA,22:6n-3)的三酰甘油和乙酯的氧化稳定性、氧化模式及α-生育酚反应
Food Chem. 2022 Sep 1;387:132882. doi: 10.1016/j.foodchem.2022.132882. Epub 2022 Apr 3.
5
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6
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7
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9
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10
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Nat Protoc. 2019 Apr;14(4):991-1014. doi: 10.1038/s41596-018-0119-1. Epub 2019 Mar 18.