Isolation and Identification of procyanidins in Aronia Melanocarpa Using NMR, LC-IT-TOF/MS/MS and MALDI-TOF MS

Abstract

Aronia melanocarpa berries procyanidins (Amps) were divided in three fractions: ethyl acetate phase extract of Amps (E-Amps), aqueous phase extract of Amps (W-Amps), and methanol phase extract of Amps (M-Amps). Flavan-3-ol monomers and oligomeric procyanidins were isolated from E-Amps using Sephadex LH-20 column chromatography and reversed-phase preparative HPLC. 1 H and 13 C NMR analyses indicated five flavan-3-ol monomers and oligomeric procyanidins: (+)-catechin, (-)-epicatechin, procyanidin B2 [EC-(4β→8)-EC], procyanidin B1 [EC-(4β→8)-C], and procyanidin C1 [EC-(4β→8)-EC-(4β→8)-EC]. MALDI-TOF-MS analysis demonstrated that the structure units of polymeric Amps, which were linked by B-type bonds, contained only catechin and epicatechin. In addition, the degree of polymerization was from pentamer to twenty-two polymer. Five flavan-3-ol monomers and oligomeric procyanidins had strong antioxidant activities. The DPPH and ABTS free-radical scavenging capacities followed the order: flavan-3-ol monomers > dimeric procyanidins > trimeric procyanidins > ascorbic acid. However, FRAP values increased with a degree of polymerization.

Screening For α-Amylase Inhibitory Activity Of Crataegus And Rubus Genera In Syria, Isolation And Identification Of The Active Principle

“…A correlation between the protons of the methylene group at position 4 to the carbons C2, C5, C3 and C10 is to be seen in the HMBC spectrum. This information proves the binding of the benzene ring B to C2 and the distribution of the protons of the ring C. These results were similar to those reported in the literature [16][17][18].…”

Black chokeberry (Aronia melanocarpa L.) polyphenols attenuate obesity-induced colonic inflammation by regulating gut microbiota and the TLR4/NF-κB signaling pathway in high fat diet-fed rats

“…BCPs were extracted in accordance with our previous research. 25 BCP extracts contained (+)-catechin, (−)-epicatechin, chlorogenic acid, cis -tiliroside, procyanidin B1, procyanidin B2, procyanidin C1, cyanidin-3-galactoside chloride, cyanidin 3-monoarabinoside, cyanidin 3-xyloside and cyanidin 3- O -glucoside chloride, which were detected and quantified by LC-MS/MS. The result are shown in ESI Table S1 †…”

“…Cell viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. 18 The cells were inoculated in a 96-well plate (5 × 10 4 per well) and cultured at 37 °C for 24 h when the cells grow to the exponential growth phase and the cells were treated with different concentrations (25,50,100,200, 400 μg mL −1 , respectively) of samples, while the Con group was treated with the medium for 24 h. Then, 100 μL of MTT solution (1 mg mL −1 ) was added to each well and cultured for another 4 h. Formazan crystals were diluted with 150 μL dimethyl sulfoxide (DMSO). The plate was determined at 570 nm wavelength and read on a microplate reader (Thermo Multiskan FC, SH, CHINA).…”