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Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents
BACKGROUND: The DNA-damaging compounds in heated cooking oil were identified as guanosine adducts. Heated vegetable oil was subjected to deep-frying conditions at 170 °C for 45 min, reacted with isopropylidene guanosine (ipG) at pH 7.4, and the resulting compounds were separated by high-performance...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
BioMed Central
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599067/ https://www.ncbi.nlm.nih.gov/pubmed/37880746 http://dx.doi.org/10.1186/s41021-023-00284-3 |
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author | Kasai, Hiroshi Kawai, Kazuaki |
author_facet | Kasai, Hiroshi Kawai, Kazuaki |
author_sort | Kasai, Hiroshi |
collection | PubMed |
description | BACKGROUND: The DNA-damaging compounds in heated cooking oil were identified as guanosine adducts. Heated vegetable oil was subjected to deep-frying conditions at 170 °C for 45 min, reacted with isopropylidene guanosine (ipG) at pH 7.4, and the resulting compounds were separated by high-performance liquid chromatography (HPLC). RESULTS: Two adducts, 8-hydroxy-ipG and 1,N(2)-etheno-ipG, were identified in the reaction mixture. One of the major components in heated cooking oil, 2,4-heptadienal (HDE), efficiently produced etheno-ipG from ipG in the presence of tBuOOH. An oxidized HDE solution was fractionated using HPLC to identify causative agents, and each fraction was tested for etheno-ipG formation. In addition to the known lipid peroxidation product, 4,5-epoxy-2-heptenal, two unknown polar components with potent etheno-ipG formation activity were discovered. Based on Mass and UV spectra, their structures were identified as 6-oxo- and 6-hydroxy-2,4-HDE. Similarly, 6-oxo- and 6-hydroxy-2,4- decadienal (DDE) were formed from 2,4-DDE. Significant amounts of 6-oxo- and 6-hydroxy-2,4-alkadienal were detected in the heated cooking oil. These compounds induced the formation of 1,N(2)-ethenoguanine in nucleosides and DNA, especially in the presence of tBuOOH. Moreover, the formation of 6-oxo- and 6-OH-HDE from 2,4-HDE was accelerated in the presence of hemin and tBuOOH. CONCLUSION: The results suggest that these compounds are not only generated during the oil heating process but also produced from 2,4-alkadienal through digestion under normal physiological conditions, especially after ingesting heme- and alkyl-OOH-containing diets. Moreover, these compounds can be formed within cells under oxidative stress, potentially linking them to gastrointestinal carcinogenesis. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s41021-023-00284-3. |
format | Online Article Text |
id | pubmed-10599067 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | BioMed Central |
record_format | MEDLINE/PubMed |
spelling | pubmed-105990672023-10-26 Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents Kasai, Hiroshi Kawai, Kazuaki Genes Environ Research BACKGROUND: The DNA-damaging compounds in heated cooking oil were identified as guanosine adducts. Heated vegetable oil was subjected to deep-frying conditions at 170 °C for 45 min, reacted with isopropylidene guanosine (ipG) at pH 7.4, and the resulting compounds were separated by high-performance liquid chromatography (HPLC). RESULTS: Two adducts, 8-hydroxy-ipG and 1,N(2)-etheno-ipG, were identified in the reaction mixture. One of the major components in heated cooking oil, 2,4-heptadienal (HDE), efficiently produced etheno-ipG from ipG in the presence of tBuOOH. An oxidized HDE solution was fractionated using HPLC to identify causative agents, and each fraction was tested for etheno-ipG formation. In addition to the known lipid peroxidation product, 4,5-epoxy-2-heptenal, two unknown polar components with potent etheno-ipG formation activity were discovered. Based on Mass and UV spectra, their structures were identified as 6-oxo- and 6-hydroxy-2,4-HDE. Similarly, 6-oxo- and 6-hydroxy-2,4- decadienal (DDE) were formed from 2,4-DDE. Significant amounts of 6-oxo- and 6-hydroxy-2,4-alkadienal were detected in the heated cooking oil. These compounds induced the formation of 1,N(2)-ethenoguanine in nucleosides and DNA, especially in the presence of tBuOOH. Moreover, the formation of 6-oxo- and 6-OH-HDE from 2,4-HDE was accelerated in the presence of hemin and tBuOOH. CONCLUSION: The results suggest that these compounds are not only generated during the oil heating process but also produced from 2,4-alkadienal through digestion under normal physiological conditions, especially after ingesting heme- and alkyl-OOH-containing diets. Moreover, these compounds can be formed within cells under oxidative stress, potentially linking them to gastrointestinal carcinogenesis. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s41021-023-00284-3. BioMed Central 2023-10-25 /pmc/articles/PMC10599067/ /pubmed/37880746 http://dx.doi.org/10.1186/s41021-023-00284-3 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/ (https://creativecommons.org/publicdomain/zero/1.0/) ) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Kasai, Hiroshi Kawai, Kazuaki Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title | Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title_full | Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title_fullStr | Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title_full_unstemmed | Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title_short | Formation of the mutagenic DNA lesion 1,N(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
title_sort | formation of the mutagenic dna lesion 1,n(2)-ethenoguanine induced by heated cooking oil and identification of causative agents |
topic | Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599067/ https://www.ncbi.nlm.nih.gov/pubmed/37880746 http://dx.doi.org/10.1186/s41021-023-00284-3 |
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