490-46-0Relevant articles and documents
Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects.
Hatano, Tsutomu,Miyatake, Haruka,Natsume, Midori,Osakabe, Naomi,Takizawa, Toshio,Ito, Hideyuki,Yoshida, Takashi
, p. 749 - 758 (2002)
Purification of polar fractions from cacao liquor extracts gave 17 phenolics including four new compounds. The new compounds were characterized as a C-glycosidic flavan, an O-glycoside of a dimeric and two O-glycosides of trimeric A-linked proanthocyanidins, on the basis of spectroscopic data. Isolated polyphenols showed inhibitory effects on nicotinamide adenine dinucleotide phosphate-dependent lipid peroxidation in microsomes and on the autoxidation of linoleic acid. These effects were attributed to the radical-scavenging activity in the peroxidation chain reactions, based on the findings that the cacao polyphenols effectively scavenged the 1,1-diphenyl-2-picrylhydrazyl radical.
TWO PROANTHOCYANIDINS FROM THE BARK OF DALBERGIA MONETARIA
Nunes, Domingos S.,Haag, Armin,Bestmann, Hans-Juergen
, p. 2183 - 2186 (1989)
Key Word Index - Dalbergia monetaria; Leguminosae-Papilionoideae; proanthocyanidin dimers.Abstract - In a chemical investigation of the bark of Dalbergia moneteria the two new proanthocyanidins (2R,3R,4R)-3,3',4',7-tetrahydroxyflavan-(4β->8)-epicatechin and (2R,3R,4R)-3,4',7-trihydroxyflavan-(4β->8)-epicatechin were isolated.
Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities
Choongo, Kennedy,Ishikawa, Yoshinobu,Kikuchi, Takashi,Munsimbwe, Linous,Murata, Toshihiro,Shirakura, Izumi,Suganuma, Keisuke
, p. 91 - 104 (2022/01/20)
Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5–9), and 17 known compounds (3, 4, and 10–24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual charact
Proanthocyanidin Tetramers and Pentamers from Cinnamomum verum Bark and Their Dentin Biomodification Bioactivities
Jing, Shu-Xi,Alania, Yvette,Reis, Mariana,McAlpine, James B.,Chen, Shao-Nong,Bedran-Russo, Ana K.,Pauli, Guido F.
, p. 391 - 404 (2022/02/16)
To enable the further exploration of structure-activity relationships (SARs) of proanthocyanidins (PACs) with dentin biomodification abilities, Cinnamomum verum was selected for scaled-up purification of mixed A-/B-type, medium-size PAC oligomers. Sequential purification by centrifugal partition chromatography (CPC), Sephadex LH-20, and semiprep HPLC chromatography yielded four underivatized tetrameric (5-8) and two pentameric (9-10) PACs. Their unambiguous structural characterization involved extensive spectral and chemical degradation approaches to show that epicatechin units are connected by plant-specific combinations of doubly linked A- and singly linked B-type interflavanyl bonds. The biomechanical properties (via dynamic mechanical analysis) and physicochemical structure (via infrared spectroscopy) were assessed to evaluate the biomodification potency of PAC-treated collagen in a preclinical dentin model. This study revealed that (4→8) versus (4→6) bonds in PAC interflavan linkages have limited influence on biomechanical outcomes of dentin. By exhibiting a 25-fold increase in the complex modulus of treated dentin compared to control, aesculitannin E (5) was found to be the most potent PAC known to date for enhancing the mechanical properties of dentin in this preclinical model.