PROCYANIDIN TRIMERS POSSESSING A DOUBLY LINKED STRUCTURE FROM AESCULUS HIPPOCASTANUM

Article abstract of DOI:10.1016/0031-9422(94)00637-9

Following tentative HPLC peak identification by UV/CRD absorbance ratios, structural examination of the phenolic metabolites of the fruit shells of Aesculus hippocastanum has led to the isolation and characterization of the uncommon procyanidin trimers, epicatechin-(4β,8;2β,7)-catechin-(4β,8)-epicatechin, epicatechin-(4α,8)-epicatechin-(4β,8;2β,7)-epicatechin, epicatechin-(4β,8)-epicatechin-(4β,8;2β,7)-epicatechin and epicatechin-(4β,8;2β,7)-epicatechin-(4α,8)-ent-epicatechin, possessing doubly linked units, associated with epicatechin-(4β,6)-epicatechin-(4β,6)-epicatechin.Amongst these, the first two mentioned compounds represent novel natural metabolites. the structures were determined by analysis of spectral data (1H NMR, FAB-mass spectrometry, CD) and chemical degradation. - Key words: Aesculus hippocastanum; Hippocastanaceae; fruit shells, proanthocyanidins; A-types; trimers; structure elucidation; chemical degradation.