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

Gabriele Beltrame; Eija Ahonen; Annelie Damerau; Haraldur G. Gudmundsson; Gudmundur G. Haraldsson; Kaisa M. Linderborg

doi:10.1021/acs.jafc.3c02207

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

Gabriele Beltrame, Eija Ahonen, Annelie Damerau, Haraldur G. Gudmundsson, Gudmundur G. Haraldsson, Kaisa M. Linderborg^*

^*Corresponding author for this work

Faculty of Physical Sciences

Research output: Contribution to journal › Article › peer-review

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 in vitro 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 sn-2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.

Original language	English
Pages (from-to)	10087-10096
Number of pages	10
Journal	Journal of Agricultural and Food Chemistry
Volume	71
Issue number	26
DOIs	https://doi.org/10.1021/acs.jafc.3c02207
Publication status	Published - 20 Jun 2023

Bibliographical note

Funding Information:
A personal financial grant to Gabriele Beltrame from the Niemi Foundation is acknowledged. Personal financial grants to Annelie Damerau from the Finnish Cultural Foundation and to Eija Ahonen from the Niemi Foundation, the Finnish Cultural Foundation, and the Finnish Food Research Foundation are acknowledged. This work was carried out as part of the project “Omics of oxidation─Solutions for better quality of docosahexaenoic and eicosa-pentaenoic acids” funded by the Academy of Finland (grant number 315274, PI Kaisa Linderborg).

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.

Other keywords

DHA
EPA
ethyl ester
in vitro digestion
oxidation
TAG enantiomers
Gas Chromatography-Mass Spectrometry
Humans
Esters
Triglycerides
Digestion
Eicosapentaenoic Acid
Docosahexaenoic Acids
Fatty Acids, Omega-3

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10.1021/acs.jafc.3c02207

Cite this

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title = "Lipid Structure Influences the Digestion and Oxidation Behavior of Docosahexaenoic and Eicosapentaenoic Acids in the Simulated Digestion System",

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 in vitro 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 sn-2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.",

keywords = "DHA, EPA, ethyl ester, in vitro digestion, oxidation, TAG enantiomers, Gas Chromatography-Mass Spectrometry, Humans, Esters, Triglycerides, Digestion, Eicosapentaenoic Acid, Docosahexaenoic Acids, Fatty Acids, Omega-3",

author = "Gabriele Beltrame and Eija Ahonen and Annelie Damerau and Gudmundsson, {Haraldur G.} and Haraldsson, {Gudmundur G.} and Linderborg, {Kaisa M.}",

note = "Funding Information: A personal financial grant to Gabriele Beltrame from the Niemi Foundation is acknowledged. Personal financial grants to Annelie Damerau from the Finnish Cultural Foundation and to Eija Ahonen from the Niemi Foundation, the Finnish Cultural Foundation, and the Finnish Food Research Foundation are acknowledged. This work was carried out as part of the project “Omics of oxidation─Solutions for better quality of docosahexaenoic and eicosa-pentaenoic acids” funded by the Academy of Finland (grant number 315274, PI Kaisa Linderborg). Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

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doi = "10.1021/acs.jafc.3c02207",

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AU - Damerau, Annelie

AU - Gudmundsson, Haraldur G.

AU - Haraldsson, Gudmundur G.

AU - Linderborg, Kaisa M.

N1 - Funding Information: A personal financial grant to Gabriele Beltrame from the Niemi Foundation is acknowledged. Personal financial grants to Annelie Damerau from the Finnish Cultural Foundation and to Eija Ahonen from the Niemi Foundation, the Finnish Cultural Foundation, and the Finnish Food Research Foundation are acknowledged. This work was carried out as part of the project “Omics of oxidation─Solutions for better quality of docosahexaenoic and eicosa-pentaenoic acids” funded by the Academy of Finland (grant number 315274, PI Kaisa Linderborg). Publisher Copyright: © 2023 The Authors. Published by American Chemical Society.

PY - 2023/6/20

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N2 - 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 in vitro 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 sn-2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.

AB - 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 in vitro 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 sn-2. These results are relevant for the production of tailored omega-3 structures to be used as supplements or ingredients.

KW - DHA

KW - EPA

KW - ethyl ester

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KW - oxidation

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KW - Gas Chromatography-Mass Spectrometry

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KW - Esters

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KW - Eicosapentaenoic Acid

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KW - Fatty Acids, Omega-3

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AN - SCOPUS:85164237351

SN - 0021-8561

VL - 71

SP - 10087

EP - 10096

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 26

ER -

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

Abstract

Bibliographical note

Other keywords

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