A-type proanthocyanidin

Source: Wikipedia, the free encyclopedia.

A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, polyphenols, condensed tannins, and OPCs. Proanthocyanidins were first popularized by French scientist Jacques Masquelier.[1]

Distribution in plants

Schematic chemical structure of an A type proanthocyanidin dimer

A-type linkage is a less common feature in proanthocyanidins with both 4β→8 (

B-type) and 2β→O→7 interflavanoid bonds.[2]

A-type proanthocyanidin

cocoa liquor.[3]

Dimers

Other A-type proanthocyanidins can be found in cranberries,[2] cinnamon,[4] peanut skins[5][6] and Geranium niveum.[7]

Chemistry

retro-Diels-Alder (RDA) fission, benzofuran-forming fission (BFF) and quinone methide fission (QM).[9]

Metabolism

The metabolism of type-A proanthocyanidins is significant since a large number of metabolites are detected in urine and feces soon after ingestion of foods rich in polymers, indicating rapid elimination and absence of

phenolic acids with no known biological role.[10]

Research

In vitro, A-type proanthocyanidins isolated from

epithelial cells, whereas B-type proanthocyanidins from grape exhibited minor activity.[11] In humans, a 2014 review indicated there was insufficient clinical evidence that cranberry type-A proanthocyanidins are effective in lowering the risk of urinary tract infections (UTIs),[12] while a 2023 review concluded that long-term consumption of cranberry products may reduce the risk of UTIs in certain groups.[13]

References

  1. PMID 10767669. Archived from the original
    (PDF) on 4 November 2009. Retrieved 22 September 2009.
  2. ^
    PMID 17182824
    .
  3. PMID 11909632
    .
  4. PMID 22101466
    .
  5. doi:10.1016/j.jff.2014.10.034
    .
  6. doi:10.1016/S0031-9422(98)00736-5
    .
  7. PMID 10346950
    .
  8. doi:10.1016/S0040-4039(99)02097-3
    .
  9. PMID 18416438
    .
  10. PMID 22383303
    .
  11. PMID 16055161
    .
  12. doi:10.2903/j.efsa.2014.3657
    .
  13. PMID 37068952
    .
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