September 2016 SPSFAM Book

9/13/2016

Structures of PACs

Mixtures of oligomers and polymers composed of flavan-3-ols

Flavan-3-ols

OH Oligomeric and polymeric PACs

3’

B

1

8

2’

O OH

2

OH

A

3 4 5 C

1’

OH

6

OH

OH OH

O OH

(+)-Catechin

Extension units

n-2

OH

OH

OH

O OH

OH

Terminal unit

OH

OH

 DP: degree of polymerization   Oligomers: DP 2‐10  Polymers: DP ＞ 10  Epicatechin is the primary constituent monomer in cranberry PACs

(-)-Epicatechin

3

Cranberry PACs are unique

B-type procyanidins in other

A-type procyanidins in Cranberries

fruits

 95% of cranberry PAC oligomers contain 1 or more A-type bonds.  26% of cranberry PAC oligomers contain 2 or more A-type bonds.

2