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

authored by

Annik Fischer, Recep Gök, Tuba Esatbeyoglu

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).

Organisation(s)

Molecular Food Chemistry and Food Development
Institute of Food and One Health
Institute of Food Science and Human Nutrition

Type

Article

Journal

Molecules

Volume

ISSN

1420-3049

Publication date

30.12.2024

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Analytical Chemistry, Chemistry (miscellaneous), Molecular Medicine, Pharmaceutical Science, Drug Discovery, Physical and Theoretical Chemistry, Organic Chemistry

Electronic version(s)

https://doi.org/10.3390/molecules30010111 (Access: Open)