A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins
This study systematically investigated the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical induced oxidation of all dimeric C4-C8 linked B-type procyanidins (PCs) B1–B4 to maximise the formation of the oxidation products using a Design of Experiments (DoE) approach. The C4<i>β</i>-C8 linked...
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2024-12-01
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| author | Annik Fischer Recep Gök Tuba Esatbeyoglu |
| author_facet | Annik Fischer Recep Gök Tuba Esatbeyoglu |
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| description | This study systematically investigated the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical induced oxidation of all dimeric C4-C8 linked B-type procyanidins (PCs) B1–B4 to maximise the formation of the oxidation products using a Design of Experiments (DoE) approach. The C4<i>β</i>-C8 linked B1 and B2 formed the A1 (<b>1</b>) and A2 (<b>2</b>) (<i>m</i>/<i>z</i> 575 [M-H]<sup>−</sup>) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4<i>α</i>-C8 linked dimers B3 and B4 yielded for each two main oxidation products with <i>m</i>/<i>z</i> 575 [M-H]<sup>−</sup>. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 (<b>3</b>) and B4 (<b>5</b>)), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (<b>5</b>); 360 min, 53.7 °C for B4 (<b>6</b>)). The formation rates were optimised to 47.4 ± 1.14% (A1; <b>1</b>), 27.5 ± 0.76% (A2; <b>2</b>), 48.6 ± 4.01% (<b>3</b>), 32.0 ± 1.14% (<b>4</b>), 45.0 ± 5.14% (<b>5</b>) and 60.2 ± 3.68% (<b>6</b>). |
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| spelling | doaj-art-a3d23d281fac4bed973910b2c9d932e92025-01-10T13:18:55ZengMDPI AGMolecules1420-30492024-12-0130111110.3390/molecules30010111A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type ProcyanidinsAnnik Fischer0Recep Gök1Tuba Esatbeyoglu2Department of Molecular Food Chemistry and Development, Institute of Food and One Health, Leibniz University Hannover, 30167 Hannover, GermanyInstitute of Food Chemistry, Technische Universität Braunschweig, 38106 Braunschweig, GermanyDepartment of Molecular Food Chemistry and Development, Institute of Food and One Health, Leibniz University Hannover, 30167 Hannover, GermanyThis study systematically investigated the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical induced oxidation of all dimeric C4-C8 linked B-type procyanidins (PCs) B1–B4 to maximise the formation of the oxidation products using a Design of Experiments (DoE) approach. The C4<i>β</i>-C8 linked B1 and B2 formed the A1 (<b>1</b>) and A2 (<b>2</b>) (<i>m</i>/<i>z</i> 575 [M-H]<sup>−</sup>) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4<i>α</i>-C8 linked dimers B3 and B4 yielded for each two main oxidation products with <i>m</i>/<i>z</i> 575 [M-H]<sup>−</sup>. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 (<b>3</b>) and B4 (<b>5</b>)), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (<b>5</b>); 360 min, 53.7 °C for B4 (<b>6</b>)). The formation rates were optimised to 47.4 ± 1.14% (A1; <b>1</b>), 27.5 ± 0.76% (A2; <b>2</b>), 48.6 ± 4.01% (<b>3</b>), 32.0 ± 1.14% (<b>4</b>), 45.0 ± 5.14% (<b>5</b>) and 60.2 ± 3.68% (<b>6</b>).https://www.mdpi.com/1420-3049/30/1/111proanthocyanidinpolyphenolA-type dimerB-type dimerDPPH (2,2-diphenyl-1-picrylhydrazyl) radicalquinone methide |
| spellingShingle | Annik Fischer Recep Gök Tuba Esatbeyoglu A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins Molecules proanthocyanidin polyphenol A-type dimer B-type dimer DPPH (2,2-diphenyl-1-picrylhydrazyl) radical quinone methide |
| title | A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins |
| title_full | A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins |
| title_fullStr | A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins |
| title_full_unstemmed | A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins |
| title_short | A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins |
| title_sort | design of experiments approach to the radical induced oxidation of dimeric c4 c8 linked b type procyanidins |
| topic | proanthocyanidin polyphenol A-type dimer B-type dimer DPPH (2,2-diphenyl-1-picrylhydrazyl) radical quinone methide |
| url | https://www.mdpi.com/1420-3049/30/1/111 |
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