cyanidin-3-o-beta-glucopyranoside and delphinidin-3-rutinoside

Anthocyanin-rich fractions isolated from blackcurrant (Ribes nigrum L.) including delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were enzymatically acylated with lauric acid. All the four anthocyanins were successfully monoacylated, and their relative proportions did not affect the conversion yield. The acylation occurred at the 6″-OH position of the glucosides and at the rhamnose 4‴-OH of the rutinosides. The rutinoside moieties of the anthocyanins were successfully acylated for the first time, and the corresponding acylation sites were verified by NMR analysis. The acylation enhanced the lipophilicity. The hydrophilic anthocyanin rutinosides were more lipophilic after acylation. Introducing lauric acid into the anthocyanins significantly improved the thermostability and capacity to inhibit lipid peroxidation and maintained UV-vis absorbance and antioxidant activity. This research provides important insights into acylation of mixed anthocyanins with different glycosyl moieties.

Topics: Acylation; Anthocyanins; Antioxidants; Glucosides; Lipid Peroxidation; Magnetic Resonance Spectroscopy; Ribes; Tandem Mass Spectrometry

The objectives of this study were to compare the anti-inflammatory effects of anthocyanins from blueberry (BBA), blackberry (BKA), and blackcurrant (BCA) and to determine the relationship between their antioxidant capacity and anti-inflammatory effect in macrophages. Major anthocyanins in BBA, BKA and BCA were malvidin-3-glucoside (16%), cyanidin-3-glucoside (98%) and delphinidin-3-rutinoside (44%), respectively. BKA showed higher total antioxidant capacity than BBA and BCA. RAW 264.7 macrophages were incubated with 0-20 μg/ml of BBA, BKA and BCA, and subsequently activated by lipopolysaccharide (LPS) to measure proinflammatory cytokine production. Interleukin 1β (IL-1β) messenger RNA (mRNA) levels were significantly decreased by all berry anthocyanins at 10 μg/ml or higher. Tumor necrosis factor α (TNFα) mRNA levels and secretion were also significantly decreased in LPS-treated macrophages. The levels of the repression were comparable for all berry anthocyanins. LPS-induced nuclear factor κB (NF-κB) p65 translocation to the nucleus was markedly attenuated by all of the berry anthocyanins. In bone marrow-derived macrophages (BMMs) from nuclear factor E2-related factor 2 wild-type (Nrf2(+/+)) mice, BBA, BKA and BCA significantly decreased cellular reactive oxygen species (ROS) levels with a concomitant decrease in IL-1β mRNA levels upon LPS stimulation. However, in the BMM from Nrf2(-/-) mice, the anthocyanin fractions were able to significantly decrease IL-1β mRNA despite the fact that ROS levels were not significantly affected. In conclusion, BBA, BKA and BCA exert their anti-inflammatory effects in macrophages, at least in part, by inhibiting nuclear translocation of NF-κB independent of the NRF2-mediated pathways.

Topics: Animals; Anthocyanins; Blueberry Plants; Glucosides; Inflammation; Inflammation Mediators; Lipopolysaccharides; Macrophages; Mice; NF-E2-Related Factor 2; NF-kappa B; Protein Transport; Ribes; Rubus; Tumor Necrosis Factor-alpha

Host- and bacteria-derived proteinases are considered to play critical roles in periodontitis progression. This study investigated the ability of a blackcurrant extract and its major anthocyanins (cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside and delphinidin-3-O-rutinoside) to inhibit the activity of matrix metalloproteinases (MMPs), neutrophil elastase and periodontopathogen (Porphyromonas gingivalis, Tannerella forsythia and Treponema denticola) proteinases.. Enzyme inhibition was detected using fluorometric and colorimetric assays after incubating blackcurrant extract and its major anthocyanins (at concentrations of 6.25, 12.5, 25 and 50 μg/mL) with MMPs, elastase or bacterial proteinases, along with their specific substrates. Substrate degradation was recorded every hour for up to 4 h.. The blackcurrant extract (50 μg/mL) inhibited all proteinases tested. MMP-1 and MMP-9 were significantly inhibited by pure anthocyanins at concentrations ranging from 6.25 to 50 μg/mL. Elastase activity was inhibited by cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside in the range of 6.25-50 μg/mL and by delphinidin-3-O-rutinoside at 50 μg/mL. P. gingivalis, T. forsythia and T. denticola proteinases were also significantly inhibited by pure anthocyanins. In all cases, enzyme inhibition was time-dependent.. Our study showed that a blackcurrant extract and its major anthocyanins were able to inhibit the activity of host- and bacteria-derived proteinases. This suggests that such natural compounds may represent promising agents for use in adjunctive treatments for periodontitis.

Topics: Anthocyanins; Bacterial Proteins; Bacteroides; Glucosides; Humans; Leukocyte Elastase; Matrix Metalloproteinase 1; Matrix Metalloproteinase Inhibitors; Plant Extracts; Porphyromonas gingivalis; Protease Inhibitors; Proteolysis; Ribes; Treponema denticola

Fifteen anthocyanin structures are reported from an extract of black currant berries (Ribes nigrum L.). These are the 3-O-glucosides and the 3-O-rutinosides of pelargonidin, cyanidin, peonidin, delphinidin, petunidin, and malvidin, cyanidin 3-O-arabinoside, and the 3-O-(6' '-p-coumaroylglucoside)s of cyanidin and delphinidin. The anthocyanins were characterized by means of size exclusion chromatography, high-performance liquid chromatography, UV-visible spectroscopy, and electrospray mass spectrometry. The four main pigments (the 3-O-glucosides and the 3-O-rutinosides of delphinidin and cyanidin) made up >97% of the total anthocyanin content. The minor pigments were enriched from the extract by successive partition against ethyl acetate and by gel fractionation. These chromatographic steps were successfully used to isolate the acylated anthocyanins from the ethyl acetate layer and to separate cyanidin 3-O-arabinoside from the mixture of anthocyanins. The amounts of anthocyanin rutinosides were found to be higher than the amount of the corresponding glucosides for all detected pigments having the same aglycon moiety.

Topics: Anthocyanins; Chromatography, Gel; Chromatography, High Pressure Liquid; Glucosides; Magnoliopsida; Mass Spectrometry; Pigments, Biological