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-C8 linked B1 and B2 formed the A1 () and A2 () (/ 575 [M-H]) with an ether bridge between C2u-O-C7t as expected. Interestingly, the oxidation of the C4-C8 linked dimers B3 and B4 yielded for each two main oxidation products with / 575 [M-H]. One of them required only a short reaction time (10.0 min, 25.0 °C for B3 () and B4 ()), whereas the other was maximally formed at a longer time and higher temperature (314 min and 75.0 °C for B3 (); 360 min, 53.7 °C for B4 ()). The formation rates were optimised to 47.4 ± 1.14% (A1; ), 27.5 ± 0.76% (A2; ), 48.6 ± 4.01% (), 32.0 ± 1.14% (), 45.0 ± 5.14% () and 60.2 ± 3.68% ().
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| http://dx.doi.org/10.3390/molecules30010111 | DOI Listing |
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