cyanidin-3-o-beta-glucopyranoside and cyanidin-3-galactoside

The pigmented rice has been consumed in China, Japan, and Korea for a long time. It has been used for strengthening kidney function, treating anemia, promoting blood circulation, removing blood stasis, treating diabetes, and ameliorating sight in traditional Chinese medicine. The extracts from pigmented rice are used as natural food colorants in bread, ice cream, and liquor as well as functional food. The pigmented rice is mainly black, red, and dark purple rice, and contains a variety of flavones, tannin, phenolics, sterols, tocols, γ-oryzanols, amino acids, and essential oils. Anthocyanins are thought as major functional components of pigmented rice. Several anthocyanins have been isolated and identified from the pigmented rice, including cyanidin 3-glucoside, cyanidin 3-galactoside, cyanidin 3-rutinoside, cyanidin 3,5-diglucoside, malvidin 3-galactoside, peonidin 3-glucoside, and pelargonidin 3,5-diglucoside. This review provides up-to-date coverage of pigmented rice in regard to bioactive constituents, extraction and analytical methods, and bioactivities. Special attention is paid to the bioactivities including antioxidant and free radical scavenging, antitumor, antiatherosclerosis, hypoglycemic, and antiallergic activities.

Topics: Animals; Anthocyanins; Anti-Allergic Agents; Anticholesteremic Agents; Antineoplastic Agents; Antioxidants; China; Galactosides; Glucosides; Humans; Hypoglycemic Agents; Japan; Oryza; Phenols; Pigmentation; Plant Extracts; Republic of Korea

The inhibitory effects of dietary polyphenols against α-amylase have attracted great interest among researchers. The aim of this review is to give an overview of the research reports on the structure-activity relationship of polyphenols inhibiting α-amylase. The molecular structures that influence the inhibition are the following: (1) The hydroxylation of flavonoids improved the inhibitory effect on α-amylase; (2) Presence of an unsaturated 2,3-bond in conjugation with a 4-carbonyl group has been associated with stronger inhibition; (3) The glycosylation of flavonoids decreased the inhibitory effect on α-amylase depending on the conjugation site and the class of sugar moiety; (4) The methylation and methoxylation of flavonoids obviously weakened the inhibitory effect; (5) The galloylated catechins have higher inhibition than nongalloylated catechins; the catechol-type catechins were stronger than the pyrogallol-type catechins; the inhibition activities of the catechins with 2,3-trans structure were higher than those of the catechins with 2,3-cis structure; (6) Cyanidin-3-glucoside showed higher inhibition against than cyanidin and cyanidin-3-galactoside and cyanidin-3,5-diglucoside had no inhibitory activity; (7) Ellagitannins with β-galloyl groups at glucose C-1 positions have higher inhibitory effect than the α-galloyl and nongalloyl compounds and the molecular weight of ellagitannins is not an important element.

Topics: alpha-Amylases; Anthocyanins; Catechin; Coumaric Acids; Galactosides; Glucosides; Glycosylation; Humans; Hydrolyzable Tannins; Hydroxylation; Methylation; Molecular Structure; Polyphenols; Proanthocyanidins; Structure-Activity Relationship

Our previous research showed the antioxidant activity of anthocyanins extracted from. Acute renal injury model was initiated by 30 min clamping bilateral renal pedicle and followed by 24-hour reperfusion in C57Bl/6J mice. Four groups of mice were orally pretreated in 50 mg/g/12 h for two weeks with cyanidin-3-arabinoside, cyanidin-3-glucodise, and cyaniding-3-galactoside and anthocyanins (three-cyanidin mixture), respectively, sham-control group and the renal injury-untreated groups only with saline.. The model resulted in renal dysfunction with high serum creatinine, blood urea nitrogen, and changes in proinflammatory cytokines (TNF-ɑ, IL-1. the current study provided the first attempt to investigate the role of anthocyanins purified from

Topics: Animals; Anthocyanins; Antioxidants; Apoptosis; Arabinonucleosides; Body Weight; Caspase 9; Fruit; Galactosides; Inflammation; Kidney; Kidney Failure, Chronic; Lipid Peroxidation; Mice; Mice, Inbred C57BL; Oxidative Stress; Photinia; Reperfusion; Reperfusion Injury; Risk

1. Anthocyanins are a subgroup of flavonoids responsible for the blue, purple and red color of many fruits, flowers and leaves. Consumption of foods rich in anthocyanins is associated with a reduced risk of cardiovascular disease and cancer. Most food intervention studies employ once or twice per day dose schedules. 2. The current study demonstrated that plasma concentrations of cyanidin-3-galactoside and cyanidin-3-xyloside, the two major components of saskatoon berries, were significantly increased following three consecutive saskatoon berry supplements 4 hours apart. This accumulation is due to the residual concentrations of anthocyanins at the time of second and third supplements. 3. Accumulation was especially pronounced for peonidin-3-glucoside and peonidin-3-galactoside, the methylated metabolites of cyanidin-3-glucoside and cyanidin-3-galactoside, respectively. Little or no accumulation was observed for cyanidin-3-arabinoside and cyanidin-3-glucoside, two other components of saskatoon berries, possibly due to their short half-lives. 4. Thus, taking anthocyanin supplements with every meal would provide higher plasma concentrations for some anthocyanins and their metabolites than the once or twice-a-day dose regimens.

Topics: Anthocyanins; Dietary Supplements; Galactosides; Glucosides; Humans; Plasma; Rosaceae

The effect of microwave and heat pretreatment on the content and composition of anthocyanins, phenolics, and the antioxidant capacity of hawthorn drink were studied. Nine anthocyanins were isolated by chromatographic separation from the Zirou hawthorn source and their structure identified using HPLC-DAD-ESI/MS analysis. Heat and microwave pretreatments had a significant impact on the relative contents of hawthorn anthocyanins, such as cyanidin-3-galactoside (82.9% and 76.9%, respectively) and cyanidin-3-glucoside (9.2% and 11.5%, respectively). Pretreatment had no significant effect on pH, total soluble solid or total acid. More anthocyanins remained after heat treatment than after microwaving (0.745mg/100mL), and were 52.4% higher than the control group after storage for 7days. The colour density of the heat treated group was higher than the control group (24.5%) after 12days of fermentation. The main antioxidant capacities of the hawthorn drinks came from total polyphenolics rather than total anthocyanins or total flavonoids.

Topics: Anthocyanins; Antioxidants; Crataegus; Fermentation; Galactosides; Glucosides; Mass Spectrometry; Phenols; Plant Extracts

Endoplasmic reticulum (ER) stress is associated with insulin resistance and diabetic cardiovascular complications, and mechanism or remedy for ER stress remains to be determined. The results of the present study demonstrated that the levels of ER stress or unfolded protein response (UPR) markers, the intensity of thioflavin T (ThT) fluorescence and the abundances of GRP78/94, XBP-1 and CHOP proteins were elevated in cardiovascular tissue of diabetic leptin receptor-deficient (db/db) mice. Cyanidin-3-glucoside (C3G) and cyanidin-3-galactoside (C3Ga) are major anthocyanins in Saskatoon berry (SB) powder. The administration of 5% SB powder for 4 weeks attenuated ThT fluorescence and the UPR markers in hearts and aortae of wild-type and db/db mice. Treatment with glycated low-density lipoprotein (gLDL) increased ThT intensity in human umbilical vein endothelial cells (ECs). Elevated UPR markers were detected in gLDL-treated EC compared to control cultures. The involvement of ER stress in gLDL-treated EC was supported by that the addition of 4-phenyl butyrate acid (a known ER stress antagonist) inhibited gLDL-induced increases in ER stress or UPR markers. C3G at 30 μM or C3Ga at 100 μM reached their maximal inhibition on gLDL-induced increases in ThT, GRP78/94, XBP-1 and CHOP in EC. The results demonstrated that ER stress was enhanced in cardiovascular tissue of db/db mice or gLDL-treated EC. SB powder or cyanidin glycans prevented the abnormal increases in ER stress and UPR markers in cardiovascular tissue of diabetic db/db mice or gLDL-treated EC.

Topics: Animals; Anthocyanins; Benzothiazoles; Diabetes Mellitus, Experimental; Endoplasmic Reticulum Chaperone BiP; Endoplasmic Reticulum Stress; Endothelium, Vascular; Galactosides; Glucosides; Heart; Humans; Lipoproteins, LDL; Male; Mice, Inbred C57BL; Powders; Protective Agents; Rosaceae; Thiazoles; Transcription Factor CHOP; Unfolded Protein Response; X-Box Binding Protein 1

Total phenolic content, total antioxidant activity of Myrobalan plum (Prunus cerasifera Ehrh.) and anthocyanin content in peel were analyzed in this article. In addition, ultra-performance liquid chromatography with photodiode array detection and electrospray ionization tandem mass spectrometry were used to determine anthocyanin composition of this fruit. The range of total phenolic content of the tested samples was 1.34 to 6.11 g/kg fresh weight (FW), and anthocyanin content in fruit peel of Myrobalan plum was from 1.93 to 19.86 g/kg peel. Ferric reducing antioxidant power values varied from 11.20 to 44.83 μmol Trolox equivalent/g FW. Four main kinds of anthocyanins in purple Myrobalan plum were detected while 6 kinds in red ones.. The article showed the anthocyanin composition, phenolic content, and antioxidant activities of wild Myrobalan plum. The purple Myrobalan plum could be developed as a resource of fruit drinks because of its high antioxidant activity and the peel could be used as the resource to extract natural pigments.

Topics: Acetylation; Anthocyanins; Antioxidants; China; Chromatography, High Pressure Liquid; Endangered Species; Fruit; Galactosides; Glucosides; Pigmentation; Plant Extracts; Prunus; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry