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Record W2054844583 · doi:10.1002/jms.456

Tandem mass spectrometry of the B‐type procyanidins in wine and B‐type dehydrodicatechins in an autoxidation mixture of (+)‐catechin and (−)‐epicatechin

2003· article· en· W2054844583 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueJournal of Mass Spectrometry · 2003
Typearticle
Languageen
FieldMedicine
TopicTea Polyphenols and Effects
Canadian institutionsBrock University
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryAutoxidationTandem mass spectrometryMass spectrometryTrimerCatechinDimerChromatographyProanthocyanidinWineDissociation (chemistry)StereochemistryOrganic chemistryPolyphenolAntioxidant

Abstract

fetched live from OpenAlex

We describe the characterization of the B-type procyanidins in wine and the B-type dehydrodicatechins (dimeric flavan-3-ols) obtained for the autoxidation of (+)-catechin and (-)-epicatechin by tandem mass spectrometry (MS/MS) coupled to reversed-phase high-performance liquid chromatography (HPLC). The MS/MS analysis demonstrates that the interesting major fragments derive from the dissociations of the C-ring on the catechin or epicatechin unit, such as retro-Diels-Alder reactions. The two kinds of dimers give completely different fragmentations because of the striking effect of the C-C interflavan linkage (IFL). For the natural dimers in wine, a catechin or epicatechin unit linking to the C-4 position stabilizes the product ions by forming a large pi-pi hyperconjugated system, whereas a similar pi-pi system is formed within dehydrodicatechin B through the C-C IFL. Thus dissociation in MS/MS experiments was inhibited. Apparently, the fragmentations of the dimers differ from that of the monomer, which is very important in the study of the gas-phase ion behaviour of the polymeric flavan-3-ols. In addition, two specific fragment ions at m/z 451 for native dimers and at m/z 393 for autoxidation species in HPLC/MS/MS were found to be very useful for analysing mixtures of B-type procyanidins and B-type dehydrodicatechins in food and beverages.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Observational · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.352
Threshold uncertainty score0.675

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.002
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.011
GPT teacher head0.263
Teacher spread0.251 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it