A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins

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Original languageEnglish
Article number111
JournalMolecules
Volume30
Issue number1
Publication statusPublished - 30 Dec 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).

Keywords

    A-type dimer, B-type dimer, DPPH (2,2-diphenyl-1-picrylhydrazyl) radical, oxidation, polyphenol, proanthocyanidin, quinone methide, synthesis

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A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins. / Fischer, Annik; Gök, Recep; Esatbeyoglu, Tuba.
In: Molecules, Vol. 30, No. 1, 111, 30.12.2024.

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title = "A Design of Experiments Approach to the Radical-Induced Oxidation of Dimeric C4-C8 Linked B-Type Procyanidins",
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).",
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author = "Annik Fischer and Recep G{\"o}k and Tuba Esatbeyoglu",
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year = "2024",
month = dec,
day = "30",
doi = "10.3390/molecules30010111",
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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 -

By the same author(s)