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Proanthocyanidin (Molecule of the Month for November 2020)



Proanthocyanidins are a class of polyphenols found in many plants, most notably apples, cranberries maritime pine bark and that of most other pine species, cinnamon, aronia fruit, blueberry, cocoa beans, grape seed, grape skin (procyanidins and prodelphinidins),and red wines of Vitis vinifera (the European wine grape). Cocoa beans contain the highest concentrations. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees.

A 2017 systematic review showed that cranberry products significantly reduced the incidence of Urinary tract infections, UTIs, indicating that cranberry products may be effective particularly for individuals with recurrent infections. In 2019, the American Urological Association released guidelines stating that a moderate level of evidence supports the use of cranberry products containing PACs for possible prevention from recurrent UTIs.

Formal Chemical Name (IUPAC)
(15R)-2-(3,4-dihydroxyphenyl)-8-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol

References

https://en.wikipedia.org/wiki/Proanthocyanidin

Picture of Proanthocyanidin 3D model

click on the picture of  Proanthocyanidin above to interact
with the 3D model of the
Proanthocyanidin structure
(this will open a new browser window)

Picture of Proanthocyanidin

C30 H24 O13



Update by Karl Harrison
(Molecule of the Month for November 2020 )

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