TitleRapid Determination of Procyanidins Using MALDI-ToF/ToF Mass Spectrometry.
Publication TypeJournal Article
Year of Publication2018
AuthorsRush MD, Rue EA, Wong A, Kowalski P, Glinski JA, van Breemen RB
JournalJ Agric Food Chem
Date Published2018 Oct 31
KeywordsCatechin, Molecular Structure, Proanthocyanidins, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Although procyanidins constitute a unique class of polymeric plant secondary metabolites with a variety of biological properties including potent antioxidant activity, structure determination has been challenging, and structures of many complex procyanidins remain uncertain. To expedite the characterization of procyanidins, negative ion matrix-assisted laser desorption ionization high-energy collision-induced dissociation tandem time-of-flight (MALDI-ToF/ToF) mass spectra of 20 isolated procyanidins containing catechin and epicatechin subunits with degrees of polymerization up to five were obtained and evaluated. Structurally significant fragmentation pathways of singly charged, deprotonated molecules were identified representing quinone methide, heterocyclic ring fission, and retro-Diels-Alder fragmentation. The interpretation of the tandem mass spectra for sequencing A-type, B-type, mixed-type, linear, and branched procyanidins is explained using specific examples of each.

Alternate JournalJ. Agric. Food Chem.
PubMed ID30286291
PubMed Central IDPMC6296472
Grant ListF31 AT009039 / AT / NCCIH NIH HHS / United States
R01 AT007659 / AT / NCCIH NIH HHS / United States