37064-31-6Relevant articles and documents
Oxidation of Procyanidins with Various Degrees of Condensation: Influence on the Color-Deepening Phenomenon
Hibi, Yoshihide,Yanase, Emiko
, (2019)
Color deepening in red rice is a known phenomenon that occurs during postharvest storage. As procyanidins potentially causes this color deepening, we previously subjected synthetic procyanidin B3, a model procyanidin, to chemical oxidation and determined the structures of the products. To further elucidate the effects of various degrees of polymerization on color deepening, in this study we oxidized synthetic procyanidin C2. The intensity of the UV-vis absorption between 300 and 500 nm in the spectrum of the reaction mixture increased with increasing oxidation time. This absorption following the oxidation of procyanidin C2 was more intense than that of procyanidin B3. HPLC-ESI-MS of the oxidized reaction mixture revealed several new peaks that suggested the formation of products with new intramolecular rather than intermolecular bonds. The major product was structurally identified by comparison with the UPLC-ESI-MS/MS data for a synthetic procyanidin C2 oxide, independently prepared by condensing procyanidin B3 oxide and taxifolin.
Efficient stereoselective synthesis of proanthocyanidin trimers with TMSOTf-catalyzed intermolecular condensation
Saito, Akiko,Tanaka, Akira,Ubukata, Makoto,Nakajima, Noriyuki
, p. 1069 - 1073 (2007/10/03)
A stereoselective synthesis of seven benzylated proanthocyanidin trimers with TMSOTf-catalyzed condensation reaction is described. In particular, epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4?-8)-catechin trimer and epicatechin-(4?-8)-catechin-(4α-8)-epicatechin trimer derivatives were obtained in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (-)-epicatechin trimers derivatives gave four natural procyanidin trimers in good yields.
Extensive High-Resolution Reverse 2D NMR Analysis for the Structural Elucidation of Procyanidin Oligomers
Balas, Laurence,Vercauteren, Joseph
, p. 386 - 393 (2007/10/02)
The structures of the procyanidin dimers catechin-(4α-8)-catechin and catechin-(4α-6)-catechin were proved by spectroscopic means.To distinguish between the two possible interflavonoid linkages, it is necessary to assign all the quaternary aromatic carbon signals.How these assignments can be made through two-dimensional NMR spectroscopy is described. - Keywords: 2D NMR 1H NMR 13C NMR Structural analysis Proanthocyanidins Catechin dimers Tannins