Cyanidin-3-xylosylrutinoside

Phenolics Profile and Protective Effect on Injuried HUVEC Cells of Epicarp Extracts from Kadsura coccinea.[Pubmed:35206033]

Foods. 2022 Feb 16;11(4). pii: foods11040556.

This study evaluated the phenolics profile and the antioxidative properties of K. coccinea fruits epicarp. A total of 13 phenolic compounds (six phenolic acids, four anthocyanins, two flavonols, and one flavone) were identified by ultra performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spetrometry(UPLC-QTOF-MS/MS). Two anthocyanins, Cyanidin-3-xylosylrutinoside and cyanidin-3-rutinoside, comprise 30.89~74.76% and 13.90~46.17% of the total amount of anthocyanins in K. Coccinea. Cytoprotective effect results evidenced that pretreatment of Human umbilical vein endothelial cells(HUVECs) with Kadsura. coccinea fruits' epicarp phenolic extracts at the concentrations of 50-200 microg/mL improved the cell viability after exposure to H2O2 significantly, and inhibited malonaldehyde(MDA) and reactive oxygen species(ROS) overproduction, as well as enhancing the content of superoxide dismutase (SOD) and glutathione Reductase (GR. This study proved that K. coccinea is a natural resource of phenolics rich with potential antioxidant ability, which may be valuable for developing nutraceuticals and dietary supplements.

[Investigation of lignans and anthocyanins as the main biologically active polyphenols of Schizandra chinensis fruits].[Pubmed:30592884]

Vopr Pitan. 2018;87(3):79-87.

For the first time the content and composition of dibenzocyclooctadiene lignans and anthocyanins in 10 samples of Chinese magnolia-vine fruits (Schizandra chinensis) collected in the Moscow Region, Khabarovsk and Primorsky Krai were studied. The determination of the profile of lignans was carried out according to the our original HPLC technique with diode-array spectrophotometric and mass spectrometric detection. The validation of the methodology for linearity, accuracy and precision was carried out. 11 characteristic for Schizandra chinensis lignans were found in all samples. In dried fruits the main lignan was schisandrine, in fresh-frozen fruits - angeloylgomizin O. The total content of lignans in fresh-frozen fruits was 5.50 mg/g, in dried fruits - from 12.50 to 18.95 mg/g. Anthocyanins of Chinese magnolia-vine were mainly represented by cyanidin glycosides, among which Cyanidin-3-xylosylrutinoside was predominated. The total content of anthocyanins determined by pH-differential spectrophotometry was from 0.21 mg/g in fresh-frozen fruits to 0.35-0.72 mg/g in dried fruits. The results obtained can be used to identify and standardize the fruits of Chinese magnolia- vine and the products of their processing.

Stability of anthocyanins in bokbunja (Rubus occidentalis L.) under in vitro gastrointestinal digestion.[Pubmed:29934151]

Food Chem. 2018 Nov 30;267:157-162.

The stability of anthocyanins in bokbunja (Rubus occidentalis L.) extract was investigated using an in vitro simulated gastrointestinal digestion. Ethanolic extract from bokbunja was digested with pepsin/HCl for 2h at 37 degrees C, followed by pancreatin/bile salts for 2h at 37 degrees C. Four anthocyanins including cyanidin-3-glucoside, cyanidin-3-sambubioside, Cyanidin-3-xylosylrutinoside and cyanidin-rutinoside were identified in the bokbunja extract. The total anthocyanin content of bokbunja was 3.76mg cyanidin-3-glucoside equivalents/g fresh weight (FW). Gastric digestion had no significant effect on anthocyanins. However, intestinal digestion substantially decreased anthocyanins up to 1.70mg/g FW, corresponding to 45% of that in the bokbunja extract. This indicates that about half of anthocyanins can reach an intestinal tract. In addition, a new compound comprised of cyanidin-3-glucosdie, catechin and acetaldehyde in a separated study was observed after in vitro gastrointestinal digestion. This shows that anthocyanins could be transformed into other compounds with different biochemical properties.

Suppression of Proinflammatory and Prosurvival Biomarkers in Oral Cancer Patients Consuming a Black Raspberry Phytochemical-Rich Troche.[Pubmed:26701664]

Cancer Prev Res (Phila). 2016 Feb;9(2):159-71.

Black raspberries (BRB) demonstrate potent inhibition of aerodigestive tract carcinogenesis in animal models. However, translational clinical trials evaluating the ability of BRB phytochemicals to impact molecular biomarkers in the oral mucosa remain limited. The present phase 0 study addresses a fundamental question for oral cancer food-based prevention: Do BRB phytochemicals successfully reach the targeted oral tissues and reduce proinflammatory and antiapoptotic gene expression profiles? Patients with biopsy-confirmed oral squamous cell carcinomas (OSCC) administered oral troches containing freeze-dried BRB powder from the time of enrollment to the date of curative intent surgery (13.9 +/- 1.27 days). Transcriptional biomarkers were evaluated in patient-matched OSCCs and noninvolved high at-risk mucosa (HARM) for BRB-associated changes. Significant expression differences between baseline OSCC and HARM tissues were confirmed using a panel of genes commonly deregulated during oral carcinogenesis. Following BRB troche administration, the expression of prosurvival genes (AURKA, BIRC5, EGFR) and proinflammatory genes (NFKB1, PTGS2) were significantly reduced. There were no BRB-associated grade 3-4 toxicities or adverse events, and 79.2% (N = 30) of patients successfully completed the study with high levels of compliance (97.2%). The BRB phytochemicals cyanidin-3-rutinoside and Cyanidin-3-xylosylrutinoside were detected in all OSCC tissues analyzed, demonstrating that bioactive components were successfully reaching targeted OSCC tissues. We confirmed that hallmark antiapoptotic and proinflammatory molecular biomarkers were overexpressed in OSCCs and that their gene expression was significantly reduced following BRB troche administration. As these molecular biomarkers are fundamental to oral carcinogenesis and are modifiable, they may represent emerging biomarkers of molecular efficacy for BRB-mediated oral cancer chemoprevention.

Comparison of traditional and commercial vinegars based on metabolite profiling and antioxidant activity.[Pubmed:25293630]

J Microbiol Biotechnol. 2015 Feb;25(2):217-26.

Metabolite profiles of seven commercial vinegars and two traditional vinegars were performed by gas chromatography time-of-flight mass spectrometry with multivariate statistical analysis. During alcohol fermentation, yeast, nuruk, and koji were used as sugars for nutrients and as fermentation substrates. Commercial and traditional vinegars were significantly separated in the principal component analysis and orthogonal partial least square discriminant analysis. Six sugars and sugar alcohols, three organic acids, and two other components were selected as different metabolites. Target analysis by ultra-performance liquid chromatography quadruple-time-of-flight mass spectrometry and liquid chromatographyion trap-mass spectrometry/mass spectrometry were used to detect several metabolites having antioxidant activity, such as Cyanidin-3-xylosylrutinoside, cyanidin-3-rutinoside, and quercetin, which were mainly detected in Rural Korean Black raspberry vinegar (RKB). These metabolites contributed to the highest antioxidant activity measured in RKB among the nine vinegars. This study revealed that MS-based metabolite profiling was useful in helping to understand the metabolite differences between commercial and traditional vinegars and to evaluate the association between active compounds of vinegar and antioxidant activity.

Optimization of ultrasound-assisted extraction of anthocyanins in red raspberries and identification of anthocyanins in extract using high-performance liquid chromatography-mass spectrometry.[Pubmed:17321780]

Ultrason Sonochem. 2007 Sep;14(6):767-78.

Anthocyanins (Acys) are naturally occurring compounds that impart color to fruit, vegetables and plants. The extraction of Acys from red raspberry (Rubus idaeus L. var. Heritage) by ultrasound-assisted process (UAP) was studied. A central composite rotate design (CCRD) was used to obtain the optimal conditions of ultrasound-assisted extraction (UAE), and the effects of operating conditions, such as the ratio of solvents to materials, ultrasonic power and extraction time, on the extraction yield of Acys were studied through response surface methodology (RSM). The optimized conditions of UAE were as follows: ratio of solvents to materials was 4:1 (ml/g), extraction time was 200s, and ultrasonic power was 400 W. Under these conditions 34.5 mg of Acys from 100g of fresh fruits (T(Acy), expressed as cyanidin-3-glucoside), approximately 78.13% of the total red pigments, could be obtained by UAE. The Acys compositions of extracts were identified by high-performance liquid chromatography-mass spectrometry (HPLC-MS), 12 kinds of Acys had been detected and eight kinds of Acys were characterized. Result indicated that cyanidin-3-sophoroside, cyanidin-3-(2(G)-glucosylrutinoside), cyanidin-3-sambubioside, cyanidin-3-rutinoside, Cyanidin-3-xylosylrutinoside, cyanidin-3-(2(G)-glucosylrutinoside), and cyanidin-3-rutinoside were main components in extracts. In addition, in comparison with the conventional solvent extraction, UAE is more efficient and rapid to extract Acys from red raspberry, due to the strong disruption of fruit tissue structure under ultrasonic acoustic cavitation, which had been observed with the scanning electron microscopy (SEM). However, the Acys compositions in extracts by both methods were similar, which were investigated using HPLC profile.

Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days.[Pubmed:16172180]

J Clin Pharmacol. 2005 Oct;45(10):1153-64.

Eleven subjects completed a clinical trial to determine the safety/tolerability of freeze-dried black raspberries (BRB) and to measure, in plasma and urine, specific anthocyanins-cyanidin-3-glucoside, cyanidin-3-sambubioside, cyanidin-3-rutinoside, and Cyanidin-3-xylosylrutinoside, as well as ellagic acid. Subjects were fed 45 g of freeze-dried BRB daily for 7 days. Blood samples were collected predose on days 1 and 7 and at 10 time points postdose. Urine was collected for 12 hours predose on days 1 and 7 and at three 4-hour intervals postdose. Maximum concentrations of anthocyanins and ellagic acid in plasma occurred at 1 to 2 hours, and maximum quantities in urine appeared from 0 to 4 hours. Overall, less than 1% of these compounds were absorbed and excreted in urine. None of the pharmacokinetic parameters changed significantly between days 1 and 7. In conclusion, 45 g of freeze-dried BRB daily are well tolerated and result in quantifiable anthocyanins and ellagic acid in plasma and urine.