130519-75-4Relevant articles and documents
Oligomeric Flavonoids. Part 16. Novel Prorobinetinidins and the First A-Type Proanthocyanidin with a 5-Deoxy A- and 3,4-cis-C-Ring from the Maiden Investigation of Commercial Wattle Bark Extract
Cronje, Annemarie,Steynberg, Jan P.,Brandt, E. Vincent,Young, Desmond A.,Ferreira, Daneel
, p. 2467 - 2478 (2007/10/02)
Structural examination of the phenolic metabolites of commercially used wattle bark extract reveals the presence of a range of novel flavonoids comprising (-)-epirobinetinidol 1, the first C-methyl proanthocyanidin, (-)-fisetinidol-(4α,8)-6-methyl-(+)-catechin 3, the first prorobinetinidins with 3,4-cis-C-ring configurations 7 and 9, and the unique A-type prorobinetinidin 11 representing the first entry amongst this class of oligoflavonoids exhibiting a 5-deoxy A- and a 3,4-cis-C-ring.They are accompanied by a range of functionalized prorobinetinidin-type tetrahydropyranochromenes 20, 23, 25 and 28 and the trimeric 'isomerization-intermediate' 32, all exhibiting the characteristic structural features that are essential for the use of 'Mimosa' exctract in cold-setting adhesives and leather-tanning applications.In addition, evidence demonstrating that the dynamic A-E conformational equilibrium of flavan-3-ol moieties in condenced tannins may be influenced by external factors is presented.
