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HPLC-HDX-HRMS partial identification of a series of tetrameric and pentameric cyclic procyanidins and prodelphinidins in wine extracts.

A solid phase extraction method was applied for the identification of a series of unconventional crown (macrocyclic) B-type proanthocyanidin tetramers (m/z 1169.2557, 1185.2507, 1201.2456, 1217.2405) and pentamers (m/z 1457.3191, 1473.3140, 1489.3090, 1505.3039, 1521.2988) containing (epi)catechins only (procyanidins) or (epi)catechins and (epi)gallocatechins (prodelphinidins). These compounds were identified in red wine by HPLC-HRMS coupled with on-line hydrogen/deuterium exchange (HDX) after purification with a C18 SPE phase from the original wine sample. The number and type of monomer units present in each procyanidin and prodelphinidin are discussed based on the experimental measured masses, their retention time distribution among observed isomers, MS/MS fragmentations and the HDX-induced shift of the theoretical monoisotopic mass. The elution in reverse-phase HPLC shifted to lower retention times when the ratio of (epi)gallocatechin units in these molecules increased with respect to the content of (epi)catechin units, as a consequence of the increase of polarity.