Journal of the Chemical Society Perkin Transactions 1 · 1983 · 34 citations · 0 references
Life SciencesBiochemistryBotanyDrug DiscoveryNatural Product BiosynthesisPlant BiochemistryPlant Natural Product BiosynthesisTannin ChemistryBark TanninsCondensation RateCondensed Tannin BiosynthesisCondensed TanninsTannin CompositionTannin Condensation ReactionsTannin PhytochemistryTannin-based Natural Products
The triflavanoid fraction from the bark extract of the black wattle (Acacia mearnsii) comprises five angular prorobinetinidins with their constituent robinetinidol units [4,6 : 4,8]-linked to both (+)-catechin and (+)-gallocatechin. Synthetic proof of structure is provided for three bi-[(–)-robinetinidol]-(+)-catechin diastereoisomers. The complete dominance of prorobinetinidins in the higher oligomeric fractions correlates with the faster condensation rate of the parent (+)-leucorobinetinidin with the nucleophilic substrates compared with competing (+)-leucofisetinidin.