Details
| Originalsprache | Englisch |
|---|---|
| Aufsatznummer | 111 |
| Fachzeitschrift | Molecules |
| Jahrgang | 30 |
| Ausgabenummer | 1 |
| Publikationsstatus | Veröffentlicht - 30 Dez. 2024 |
Abstract
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 C4β-C8 linked B1 and B2 formed the A1 (1) and A2 (2) (m/z 575 [M-H] −) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4α-C8 linked dimers B3 and B4 yielded for each two main oxidation products with m/z 575 [M-H] −. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 (3) and B4 (5)), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (5); 360 min, 53.7 °C for B4 (6)). The formation rates were optimised to 47.4 ± 1.14% (A1; 1), 27.5 ± 0.76% (A2; 2), 48.6 ± 4.01% (3), 32.0 ± 1.14% (4), 45.0 ± 5.14% (5) and 60.2 ± 3.68% (6).
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Analytische Chemie
- Chemie (insg.)
- Chemie (sonstige)
- Biochemie, Genetik und Molekularbiologie (insg.)
- Molekularmedizin
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Pharmazeutische Wissenschaften
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Wirkstoffforschung
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: Molecules, Jahrgang 30, Nr. 1, 111, 30.12.2024.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins
AU - Fischer, Annik
AU - Gök, Recep
AU - Esatbeyoglu, Tuba
N1 - Publisher Copyright: © 2024 by the authors.
PY - 2024/12/30
Y1 - 2024/12/30
N2 - 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 C4β-C8 linked B1 and B2 formed the A1 (1) and A2 (2) (m/z 575 [M-H] −) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4α-C8 linked dimers B3 and B4 yielded for each two main oxidation products with m/z 575 [M-H] −. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 (3) and B4 (5)), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (5); 360 min, 53.7 °C for B4 (6)). The formation rates were optimised to 47.4 ± 1.14% (A1; 1), 27.5 ± 0.76% (A2; 2), 48.6 ± 4.01% (3), 32.0 ± 1.14% (4), 45.0 ± 5.14% (5) and 60.2 ± 3.68% (6).
AB - 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 C4β-C8 linked B1 and B2 formed the A1 (1) and A2 (2) (m/z 575 [M-H] −) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4α-C8 linked dimers B3 and B4 yielded for each two main oxidation products with m/z 575 [M-H] −. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 (3) and B4 (5)), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (5); 360 min, 53.7 °C for B4 (6)). The formation rates were optimised to 47.4 ± 1.14% (A1; 1), 27.5 ± 0.76% (A2; 2), 48.6 ± 4.01% (3), 32.0 ± 1.14% (4), 45.0 ± 5.14% (5) and 60.2 ± 3.68% (6).
KW - A-type dimer
KW - B-type dimer
KW - DPPH (2,2-diphenyl-1-picrylhydrazyl) radical
KW - oxidation
KW - polyphenol
KW - proanthocyanidin
KW - quinone methide
KW - synthesis
UR - http://www.scopus.com/inward/record.url?scp=85214464627&partnerID=8YFLogxK
U2 - 10.3390/molecules30010111
DO - 10.3390/molecules30010111
M3 - Article
VL - 30
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 1
M1 - 111
ER -