Abstract：
:Proanthocyanidins (PACs) are natural plant-derived polymers used in leather tanning, wood adhesives, water purification, and mud additives for oil drilling. Quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood and mimosa (Acacia mearnsii) bark extracts are the major industrial sources of PACs. These commercial extracts are often sulfited via treatment with sodium hydrogen sulfite to reduce their viscosity and increase their solubility in water. An ESI-MS investigation into the molecular composition of sulfited (cold-water-soluble) quebracho heartwood extract indicates that sulfitation of the PACs occurs via S(N)2 attack of a sulfite ion at both C-2 and C-4 of the constituent flavan-3-ol monomer extender units. Attack at C-2 leads to the opening of the pyran ring. This releases an additional electron-donating phenolic hydroxy group on the A-ring and renders the extract more nucleophilic and suitable for the manufacturing of adhesives. Attack at C-4 leads to interflavanyl bond fission and decrease of the PAC oligomer chain length. The introduction of sulfonic acid moieties at C-2 or C-4 increases the polarity and water solubility of the hot water soluble (unsulfited) extract and transforms it into a cold-water-soluble extract.
journal_name
Phytochemistryjournal_title
Phytochemistryauthors
Venter PB,Senekal ND,Amra-Jordaan M,Bonnet SL,Van der Westhuizen JHdoi
10.1016/j.phytochem.2012.01.027subject
Has Abstractpub_date
2012-06-01 00:00:00pages
156-69eissn
0031-9422issn
1873-3700pii
S0031-9422(12)00138-0journal_volume
78pub_type
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