Analysis of commercial proanthocyanidins. Part 3: The chemical composition of wattle (Acacia mearnsii) bark extract

Electrospray mass spectrometry combined with established synthetic- and phytochemistry perspectives established that wattle bark extract consists of angular oligomers based on catechin and gallocatechin as starter units and fisetinidol and predominantly robinetinidol as extender units. [Display omit...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2012-11, Vol.83, p.153-167
Main Authors: Venter, Pieter B., Senekal, Nadine D., Kemp, Gabré, Amra-Jordaan, Maryam, Khan, Pir, Bonnet, Susan L., van der Westhuizen, Jan H.
Format: Article
Language:English
Subjects:
Acacia - chemistry
Acacia mearnsii
acid tolerance
bark
catechin
chemical composition
Condensed Tannins
Electrospray Mass Spectrometry
epigallocatechin
hydrolysis
mass spectrometry
Molecular Structure
Natural Polymer
Plant Bark - chemistry
Plant Extracts - chemistry
polymers
Proanthocyanidins
Proanthocyanidins - analysis
Stereoisomerism
Wattle Bark Extract
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Summary:Electrospray mass spectrometry combined with established synthetic- and phytochemistry perspectives established that wattle bark extract consists of angular oligomers based on catechin and gallocatechin as starter units and fisetinidol and predominantly robinetinidol as extender units. [Display omitted] ► Mass spectrometry investigation of the composition of wattle bark proanthocyanidins. ► Wattle bark proanthocyanidins consist predominantly of dimers and trimers. ► The starter units are angularly bonded catechin or gallocatechin. ► The extender units are the 5-deoxy flavan-3-ols, fisetinidol and robinetinidol. ► A rapid method to distinguish commercial quebracho and wattle tannin extracts. Wattle (Acacia mearnsii) bark extract is an important renewable industrial source of natural polymers for leather tanning and adhesive manufacturing. The wattle bark proanthocyanidin oligomers have 5-deoxy extender units that render the interflavanyl bonds resistant to acid catalysed hydrolysis and their composition cannot be determined via conventional thiolysis. We combined established phyto- and synthetic chemistry perspectives with an electrospray mass spectrometry investigation to establish that the flavan-3-ol based oligomers consist of a starter unit which is either catechin or gallocatechin, angularly bonded to fisetinidol or predominantly robinetinidol extender units.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2012.07.012