cyanidin-3-o-beta-glucopyranoside and cyanidin-3-sambubioside

This study aims to link morphological and physico-chemical parameters with maturity stages of Natal plum (Carissa macrocarpa), an edible southern African fruit. Harvesting via an integrative holistic approach is recommended for optimal quality and functional compounds. Fruits at dark green (M1), light green (M2), colour break or pink (M3), red (M4), dark red (M5) stages were harvested in 2016 and 2017 seasons. The principal component analysis illustrated the colour value a* (redness), fruit weight, size (length and width), sugars (glucose and fructose), ascorbic acid content, cyanidin derivatives (cyanidin-3-O-pyranoside, cyanidin 3-O-β-sambubioside, cyanidin-3-O-glucoside), naringenin 4'-O-glucoside, and antioxidant property (FRAP) were higher in the following order of maturity stages M5 > M4 > M3 > M2 > M1. Quercetin 3-O-rhamnosyl galactoside and glucoside were higher in green (h° higher) firm M1 to M3 stages. A strong correlation exists between fruit weight, size, a* value and cyanidin derivatives or naringenin 4'-O-glucoside or ascorbic acid content or antioxidant activity. Thus, the M4 and M5 stages of Natal plum can serve as functional food.

Topics: Anthocyanins; Antioxidants; Apocynaceae; Chromatography, High Pressure Liquid; Disaccharides; Fruit; Functional Food; Glucosides; Mass Spectrometry; Principal Component Analysis; Sugars

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 2 h at 37 °C, followed by pancreatin/bile salts for 2 h at 37 °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 3.76 mg cyanidin-3-glucoside equivalents/g fresh weight (FW). Gastric digestion had no significant effect on anthocyanins. However, intestinal digestion substantially decreased anthocyanins up to 1.70 mg/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.

Topics: Anthocyanins; Catechin; Digestion; Disaccharides; Fruit; Glucosides; Humans; Hydrogen-Ion Concentration; Pancreatin; Pepsin A; Rubus

Serum high-density lipoprotein-cholesterol (HDL-C) is a risk factor considered to be protective of atherosclerosis. However, atherosclerosis is an inflammatory disease and contributes to impairment in high-density lipoprotein (HDL) function, including reductions in HDL-C, HDL antioxidant and anti-inflammatory activities. Anthocyanins are polyphenols that have demonstrated antioxidant and anti-inflammatory properties. The objective of this study was to determine whether an anthocyanin-rich black elderberry extract (Sambucus nigra) (BEE) (13% anthocyanins) would protect against inflammation-related impairments in HDL function and atherosclerosis in apoE(-/-) mice, a mouse model of hyperlipidemia and HDL dysfunction. We fed an AIN-93M diet supplemented with 1.25% (w/w) BEE or control diet to 10 week old male apoE(-/-) mice for 6 weeks. The BEE fed to mice was rich in cyanidin 3-sambubioside (∼ 9.8% w/w) and cyanidin 3-glucoside (∼ 3.8% w/w). After 6 weeks, serum lipids did not differ significantly between groups, while aspartate transaminase (AST) and fasting glucose were reduced in BEE-fed mice. Hepatic and intestinal mRNA changes with BEE-feeding were consistent with an improvement in HDL function (Apoa1, Pon1, Saa1, Lcat, Clu) and a reduction in hepatic cholesterol levels (increased Ldlr and Hmgcr, reduced Cyp7a1). In BEE-fed mice, serum paraoxonase-1 (PON1) arylesterase activity was significantly higher. In addition, mice fed BEE had significantly lower serum chemokine (C-C motif) ligand 2 (CCL2) compared to control-fed mice. Notably, we observed significant reductions in total cholesterol content of the aorta of BEE-fed mice, indicating less atherosclerosis progression. This study suggests that black elderberry may have the potential to influence HDL dysfunction associated with chronic inflammation by impacting hepatic gene expression.

Topics: Alanine Transaminase; Animals; Anthocyanins; Apolipoprotein A-I; Apolipoproteins B; Aryldialkylphosphatase; Aspartate Aminotransferases; Biomarkers; Blood Glucose; Body Weight; Chemokine CCL2; Cholesterol, HDL; Chromatography, High Pressure Liquid; Disaccharides; Disease Models, Animal; Glucosides; Hyperlipidemias; Intestinal Mucosa; Intestines; Male; Mice; Mice, Knockout; Plant Extracts; Sambucus nigra; Thiobarbituric Acid Reactive Substances; Triglycerides

A healthy diet is an important factor in a healthy lifestyle that is becoming increasingly important in today's society. The fruits of European elder (Sambucus nigra L.) are a rich source of bioactive compounds like anthocyanins. In this study, dried and fresh fruits of four cultivated and six wild growing plants were investigated for their anthocyanin pattern and content as well as their bioactive compounds. After separation on HPTLC plates silica gel 60 F254 with a mixture of ethyl acetate, 2-butanone, formic acid and water, the plates were quantitatively evaluated by densitometry and also subjected to various (bio)assays to investigate the samples for compounds acting as radical-scavengers, antimicrobials, estrogens, and acetylcholinesterase or tyrosinase inhibitors. The mean contents for the two most abundant anthocyanins in European elderberries, confirmed by HPTLC-ESI-MS, ranged from 159 to 647mg/100g in fresh and from 166 to 2764mg/100g in dried fruits for cyanidin-3-sambubioside, and from 112 to 521mg/100g in fresh and 95 to 226mg/100g in dried fruits for cyanidin-3-glucoside. Additionally, the anthocyanin content was higher in berries of cultivars than of wild growing plants. The anthocyanins' radical scavenging activity and antimicrobial effect against Aliivibrio fischeri were confirmed. Further, a radical scavenging compound affecting A. fischeri and acting as acetylcholinesterase inhibitor was tentatively assigned by its protonated molecule at m/z 456 as either ursolic or oleanolic acid by HPTLC-ESI-MS. HPTLC hyphenated with bioassays and mass spectrometry was selected as method of choice for fingerprinting, pattern recognition, and bioprofiling of elderberry samples as well as quantitation and confirmation of bioactive compounds therein.

Topics: Acetylcholinesterase; Aliivibrio fischeri; Anthocyanins; Anti-Bacterial Agents; Antioxidants; Bacillus subtilis; Cholinesterase Inhibitors; Chromatography, Thin Layer; Disaccharides; Free Radical Scavengers; Fruit; Glucosides; Monophenol Monooxygenase; Plant Extracts; Sambucus; Spectrometry, Mass, Electrospray Ionization

A total of 19 different anthocyanins have been detected in four elderberry species and eight hybrids and quantified with the use of HPLC-MS(n). The profile and content levels of anthocyanins varied considerably among the analyzed elderberry species and hybrids. Cyanidin-3-O-sambubioside and cyanidin-3-O-glucoside were the most abundant anthocyanins in Sambucus nigra fruits. On the other hand, the prevalent anthocyanin in S. javanica hybrids was identified as cyanidin-3-(E)-p-coumaroyl-sambubioside-5-glucoside. The highest content of total analyzed anthocyanins (TAA) was determined in berries of the interspecific hybrid S. javanica × S. racemosa, followed by S. nigra, (S. javanica × S. nigra) × cv. Black Beauty, and (S. javanica × S. nigra) × S. cerulea. Berries of S. nigra var. viridis contained significantly lower levels of TAA. Our results provide novel information for nutritional research in addition to breeding programs, which strive to create new hybrids or cultivars with enhanced levels of bioactive components.

Topics: Anthocyanins; Antioxidants; Chromatography, High Pressure Liquid; Disaccharides; Fruit; Glucosides; Mass Spectrometry; Sambucus; Sambucus nigra