Transformations and antioxidative activities of lignans and stilbenes at high temperatures

Patrik Runeberg; Dmitry Ryabukhin; Lucas Lagerquist; Jani Rahkila; Patrik Eklund

doi:10.1016/j.foodchem.2022.134641

Transformations and antioxidative activities of lignans and stilbenes at high temperatures

Patrik Runeberg, Dmitry Ryabukhin, Lucas Lagerquist, Jani Rahkila, Patrik Eklund^*

^*Corresponding author for this work

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

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Abstract

Thermal transformations of polyphenols from the lignan and stilbene families were investigated at temperatures ranging from 200 °C to 250 °C, in polyethylene glycol (PEG-400), dimethylformamide (DMF) and in sunflower oil (SO). The polyphenols showed varying degrees of thermal stabilities and in some cases intramolecular transformations were observed. The formed products were isolated and characterized. Oligomerization of the polyphenols at thermo-oxidative conditions was also investigated. Finally, the antioxidative activity of the polyphenols against thermo-oxidative degradation α-linoleic acid was investigated at 200 °C. The results suggested that the studied substrates retained their antioxidative properties at elevated temperatures, with stilbenes showing most efficient protection against thermo-oxidative degradation of polyunsaturated fatty acids.

Original language	English
Article number	134641
Journal	Food Chemistry
Volume	404, part B
DOIs	https://doi.org/10.1016/j.foodchem.2022.134641
Publication status	Published - 15 Mar 2023
MoE publication type	A1 Journal article-refereed

Keywords

7-Hydroxy-secoisolariciresinol (PubChem CID: 44566585)
7-Hydroxymatairesinol (PubChem CID: 10948757)
Antioxidants
Cyclolariciresinol (PubChem CID: 4177125)
Lariciresinol (PubChem CID: 332427)
Lignans
Matairesinol (PubChem CID:119205)
Pinosylvin (PubChem CID: 5280457)
Pinosylvin Monomethyl Ether (PubChem CID: 5281719)
Polyphenols
Resveratrol (PubChem CID: 445154)
Secoisolariciresinol (PubChem CID: 65373)
Stilbenes
Thermal transformation
α-Conidenrin (PubChem CID: 457194)

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10.1016/j.foodchem.2022.134641Licence: CC BY

1-s2.0-S0308814622026036-mainFinal published version, 1.17 MBLicence: CC BY

https://urn.fi/URN:NBN:fi-fe2023050139655

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title = "Transformations and antioxidative activities of lignans and stilbenes at high temperatures",

abstract = "Thermal transformations of polyphenols from the lignan and stilbene families were investigated at temperatures ranging from 200 °C to 250 °C, in polyethylene glycol (PEG-400), dimethylformamide (DMF) and in sunflower oil (SO). The polyphenols showed varying degrees of thermal stabilities and in some cases intramolecular transformations were observed. The formed products were isolated and characterized. Oligomerization of the polyphenols at thermo-oxidative conditions was also investigated. Finally, the antioxidative activity of the polyphenols against thermo-oxidative degradation α-linoleic acid was investigated at 200 °C. The results suggested that the studied substrates retained their antioxidative properties at elevated temperatures, with stilbenes showing most efficient protection against thermo-oxidative degradation of polyunsaturated fatty acids.",

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author = "Patrik Runeberg and Dmitry Ryabukhin and Lucas Lagerquist and Jani Rahkila and Patrik Eklund",

note = "Publisher Copyright: {\textcopyright} 2022 The Author(s)",

year = "2023",

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doi = "10.1016/j.foodchem.2022.134641",

language = "English",

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T1 - Transformations and antioxidative activities of lignans and stilbenes at high temperatures

AU - Runeberg, Patrik

AU - Ryabukhin, Dmitry

AU - Lagerquist, Lucas

AU - Rahkila, Jani

AU - Eklund, Patrik

PY - 2023/3/15

Y1 - 2023/3/15

N2 - Thermal transformations of polyphenols from the lignan and stilbene families were investigated at temperatures ranging from 200 °C to 250 °C, in polyethylene glycol (PEG-400), dimethylformamide (DMF) and in sunflower oil (SO). The polyphenols showed varying degrees of thermal stabilities and in some cases intramolecular transformations were observed. The formed products were isolated and characterized. Oligomerization of the polyphenols at thermo-oxidative conditions was also investigated. Finally, the antioxidative activity of the polyphenols against thermo-oxidative degradation α-linoleic acid was investigated at 200 °C. The results suggested that the studied substrates retained their antioxidative properties at elevated temperatures, with stilbenes showing most efficient protection against thermo-oxidative degradation of polyunsaturated fatty acids.

AB - Thermal transformations of polyphenols from the lignan and stilbene families were investigated at temperatures ranging from 200 °C to 250 °C, in polyethylene glycol (PEG-400), dimethylformamide (DMF) and in sunflower oil (SO). The polyphenols showed varying degrees of thermal stabilities and in some cases intramolecular transformations were observed. The formed products were isolated and characterized. Oligomerization of the polyphenols at thermo-oxidative conditions was also investigated. Finally, the antioxidative activity of the polyphenols against thermo-oxidative degradation α-linoleic acid was investigated at 200 °C. The results suggested that the studied substrates retained their antioxidative properties at elevated temperatures, with stilbenes showing most efficient protection against thermo-oxidative degradation of polyunsaturated fatty acids.

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KW - Secoisolariciresinol (PubChem CID: 65373)

KW - Stilbenes

KW - Thermal transformation

KW - α-Conidenrin (PubChem CID: 457194)

KW - Thermal transformationPolyphenolsLignansStilbenesAntioxidants

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VL - 404, part B

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Transformations and antioxidative activities of lignans and stilbenes at high temperatures

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Keywords

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