Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents
Abstract 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-perf...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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BMC
2023-10-01
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| Series: | Genes and Environment |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s41021-023-00284-3 |
| _version_ | 1797451467967168512 |
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| author | Hiroshi Kasai Kazuaki Kawai |
| author_facet | Hiroshi Kasai Kazuaki Kawai |
| author_sort | Hiroshi Kasai |
| collection | DOAJ |
| description | Abstract 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,N2-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,N2-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. |
| first_indexed | 2024-03-09T14:55:06Z |
| format | Article |
| id | doaj.art-4bcef730027b4cb1836e5afe324b4d88 |
| institution | Directory Open Access Journal |
| issn | 1880-7062 |
| language | English |
| last_indexed | 2024-03-09T14:55:06Z |
| publishDate | 2023-10-01 |
| publisher | BMC |
| record_format | Article |
| series | Genes and Environment |
| spelling | doaj.art-4bcef730027b4cb1836e5afe324b4d882023-11-26T14:15:03ZengBMCGenes and Environment1880-70622023-10-0145111910.1186/s41021-023-00284-3Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agentsHiroshi Kasai0Kazuaki Kawai1Department of Environmental Oncology, Institute of Industrial Ecological Sciences, University of Occupational and Environmental HealthDepartment of Environmental Oncology, Institute of Industrial Ecological Sciences, University of Occupational and Environmental HealthAbstract 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,N2-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,N2-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.https://doi.org/10.1186/s41021-023-00284-31,N2-ethenoguanine2,4-heptadienalCooking oilGastrointestinal carcinogenesis |
| spellingShingle | Hiroshi Kasai Kazuaki Kawai Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents Genes and Environment 1,N2-ethenoguanine 2,4-heptadienal Cooking oil Gastrointestinal carcinogenesis |
| title | Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents |
| title_full | Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents |
| title_fullStr | Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents |
| title_full_unstemmed | Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents |
| title_short | Formation of the mutagenic DNA lesion 1,N2-ethenoguanine induced by heated cooking oil and identification of causative agents |
| title_sort | formation of the mutagenic dna lesion 1 n2 ethenoguanine induced by heated cooking oil and identification of causative agents |
| topic | 1,N2-ethenoguanine 2,4-heptadienal Cooking oil Gastrointestinal carcinogenesis |
| url | https://doi.org/10.1186/s41021-023-00284-3 |
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