Proanthocyanidin Dimers and Trimers from <i>Vitis vinifera</i> Provide Diverse Structural Motifs for the Evaluation of Dentin Biomodification.

ABSTRACT: Aimed at exploring the dentin biomodification potential of proanthocyanidins (PACs) for the development of dental biomaterials, this study reports the phytochemical and dental evaluation of nine B-type PACs from grape seed extract (GSE). Out of seven isolated dimers (1-7), four new compounds (2, 3, 5, and 6) involved relatively rare ent-catechin or ent-epicatechin monomeric flavan-3-ol units. Low-temperature NMR analyses conducted along with phloroglucinolysis and electronic circular dichroism enabled unequivocal structural characterization and stereochemical assignment. Additionally, one known (8) and one new (9) B-type trimer were characterized. Differential ¹³C NMR chemical shifts (Δδ) were used to determin

SUBMITTER: Phansalkar RS 

PROVIDER: S-EPMC6899061 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature