• Title/Summary/Keyword: cyanidin-3-O-glucoside

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Simultaneous analysis of anthocyanins and flavonols in various flower colors of Rhododendron schlippenbachii (royal azalea)

  • Oh, Soo-Min;Chun, Jin-Hyuk;Lee, Min-Ki;Kim, Jung-Bong;Kim, Sun-Ju
    • Korean Journal of Agricultural Science
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    • v.44 no.1
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    • pp.104-113
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    • 2017
  • Anthocyanins contained in Rhododendron schlippenbachii (royal azalea) are expressed in a variety of colors and affect flower colors. R. schlippenbachii flowers of seven colors (white, red group: pink, deep pink, red, purple group: light purple, purple, deep purple) were collected from the garden around KT&G building in the college of agriculture and life science. Seven types of anthocyanins [cyanidin 3-O-diglucoside, cyanidin 3-O-arabinoside-5-O-glucoside, cyanidin 3-O-galactoside, peonidin 3-O-arabinoside-5-O-glucoside, cyanidin 3-O-glucoside, cyanidin 3-O-(6"-O-malonyl) arabinoside, cyanidin 3-O-(6"-O-coumaroyl) glucoside] turned out to be from the cyanidin and peonidin series in R. schlippenbachii flowers. Also, seven types of flavonols [azaleatin 3-O-glucoside, azaleatin 3-O-arabinoside, azaleatin 3-O-rhamnoside, quercetin 3-O-galacatoside, quercetin 3-O-glucoside, quercetin 3-O-arabinoside, quercetin 3-O-rhamnoside] were identified in R. schlippenbachii flowers. Total anthocyanin amounts decreased in R. schlippenbachii flowers in the following order: 'deep pink' (8.07) > 'red' (6.37) > 'pink' (5.35) > 'deep purple' (0.78) > 'purple' (0.43) > 'light purple' ($0.22mg{\cdot}g^{-1}$ dry weight, DW) > 'white' (not detected). Total flavonol amounts decreased in the following order: 'pink' (97.78) > 'deep pink' (63.79) > 'deep purple' (61.98) > 'white' (57.58) > 'light purple' (47.06) > 'purple' (46.76) > 'red' ($7.60mg{\cdot}g^{-1}$ dry weight, DW). This study provided the quantitative and qualitative information for the variation of anthocyanin and flavonol compounds in R. schlippenbachii flowers. Furthermore, this information can contribute to the identification of anthocyanin and flavonol compounds in other Rhododendron flowers.

Isolation of Anthocyanin from Black Rice (Heugjinjubyeo) and Screening of its Antioxidant Activities (흑미(현진주벼)유래 안토시아닌의 항산화능 탐색)

  • Park, Young-Sam;Kim, Sun-Joong;Chang, Hyo-Ihl
    • Microbiology and Biotechnology Letters
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    • v.36 no.1
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    • pp.55-60
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    • 2008
  • Colored rices are a hulled grains having red or purple pigments in bran. Especially black rice (Heugjinjubyeo) is considered to be a healthy food in Asia. Black rice is of great interesting because of the possible biological activity with their anthocyanins. Anthocyanins are water-soluble plant pigments and representatives of flavonoids. The anthocyanins in black rice include cyanidin 3-O-glucoside, peonidin 3-O-glucoside, malvidin 3-O-glucoside, pelagonidin 3-O-glucoside and delphinidin 3-O-glucoside. In this study, anthocyanins in a black rice were analyzed quantitatively and qualitatively with HPLC and UV-Vis spectrophotometer. The anthocyanins contained approximately 95% of cyanidin-3-O-glucoside and 5% of peonidin-3-O-glucoside. Antioxidant activities of the anthocyanin extract were investigated by using various in vitro methods. The 100g/ml concentration of the anthocyanin extracted exhibited 88.83% inhibition on the peroxidation of linoleic acid, 55.20% DPPH free radical scavenging activity, 54.96% superoxide anion radical scavenging activity, and 72.67% hydrogen peroxide scavenging activity. And it also showed high ferrous ion reducing capability. These results suggest that the anthocyanin extracted from black rice may be utilized as a possible antioxdiant agent against ROS.

Anthocyanin Profiling and Radical Scavenging Activity of Selected Pigmented Rice Varieties

  • Ali, Hiba A.;Cho, Il-Kyu;Kim, Sun-Ju;Kim, Se-Na;Kim, So-Young;Cho, Young-Sook;Baek, Hyung-Jin;Kim, Jung-Bong
    • Korean Journal of Environmental Agriculture
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    • v.30 no.2
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    • pp.111-117
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    • 2011
  • BACKGROUND: Anthocyanins have been recognized as health-enhancing substances due to their antioxidant activity, anti-inflammatory, anticancer, and hypoglycemic effects. The objective was to identify anthocyanins-rich rice grains for the development of functional foods and/or functional food colorants METHODS AND RESULTS: Rice grains of one black and three red-hulled rice varieties were extracted with acidified 80% aqueous methanol. The antioxidant activity of the methanolic extracts was screened on TLC plates and in an in vitro assay using DPPH (1, 1-diphenyl-2-picrylhydrazyl) as a free radical source. Red-hulled rice varieties exhibited higher antioxidant activity (88%, 1 mg/mL) than black rice (67%, 1 mg/mL). Among the red-hulled varieties tested, rice variety SSALBYEO54 (901452) was the most active (72%, 0.5 mg/mL). Rice extracted anthocyanin compounds were analyzed by HPLC-DAD-FLD and LC-MS/MS. Red-hulled varieties comprised cyanidin-3-glucoside in addition to ferulic acid esters, apigenin and kaempferol glycosides. CONCLUSION(s): Anthocyanins identified in the black rice variety were cyanidin-7-O-galactoside, cyanidin-3-Oglucoside, cyanidin-3'-O-glucoside, cyanidin-5-O-glucoside, cyanidin-3, 7-O-diglucoside, cyanidin-3, 5-O-diglucoside and peonidin-4'-O-glucoside. The results of this study show that the black rice (IT212512) and red-hulled rice variety SSALBYEO54 (901452) contain notable antioxidant activity for potential use in nutraceutical or functional food formulations.

Comparative Proteome Analysis of Cyanidin 3-O-glucoside Treated Helicobacter pylori

  • Kim, Sa-Hyun;Kim, Jong-Bae
    • Biomedical Science Letters
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    • v.21 no.4
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    • pp.233-240
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    • 2015
  • Some virulence proteins of Helicobacter pylori, such as vacuolating cytotoxic protein A (VacA) and cytotoxin-associated gene protein A (CagA) have been reported to be causative agents of various gastric diseases including chronic gastritis, gastric ulcer or gastric adenocarcinoma. The expression level of these virulence proteins can be regulated when H. pylori is exposed to the antibacterial agent, cyanidin 3-O-glucoside (C3G) as previously reported. In this study, we analyzed the quantitative change of various virulence proteins including CagA and VacA by C3G treatment. We used 2-dimensional electrophoresis (2-DE) to analyze the quantitative change of representative ten proteome components of H. pylori 60190 ($VacA^+/CagA^+$; standard strain of Eastern type). After 2-DE analysis, spot intensities were analyzed using ImageMaster$^{TM}$ 2-DE Platinum software then each spot was identified using matrix assisted laser desorption ionization-time of flight mass spectrometry (MALDI-TOF-MS) or peptide sequencing using Finnigan LCQ ion trap mass spectrometer (LC-MS/MS). Next, we selected major virulence proteins of H. pylori among quantitatively meaningful ten spots and confirmed the 2-DE results by Western blot analysis. These results suggest that cyanidin 3-O-glucoside can modulate a variety of H. pylori pathogenic determinants.

Protective Effect of Cyanidin-3-glucoside, the Major Component of Rubus fruticosus L. Mutants by Irradiation, on H2O2-induced Oxidative Damage in HepG2 Cells (방사선 돌연변이 블랙베리 주성분 Cyanidin-3-glucoside의 과산화수소 유발 산화적 손상에 대한 세포 보호 효과)

  • Cho, Byoung Ok;So, Yangkang;Lee, Chang Wook;Jin, Chang Hyun;Yook, Hong Sun;Jeong, Il Yun
    • Journal of Radiation Industry
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    • v.8 no.1
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    • pp.35-42
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    • 2014
  • This study was conducted to analyze the protective capacity of cyanidin-3-glucoside (C3G), which is rich in mulberry and blackberry as an anthocyanin pigment. In this study, we found that treatment with C3G significantly reduced ROS production in hydrogen peroxide $(H_2O_2)-treated$ HepG2 cells in a dose-dependent manner. In addition, treatment with C3G significantly increased the cell viability in a dose-dependent manner in $H_2O_2-treated$ HepG2 cells. Moreover, treatment with C3G dose-dependently decreased the release of LDH and activation of caspase-3 in HepG2 cells treated with $H_2O_2$. Furthermore, the DNA damage in $H_2O_2-treated$ HepG2 cells was decreased by C3G treatment when compared with the control group in a dose-dependent manner. Additionally, treatment with C3G recovered the activity of antioxidant enzymes such as superoxide dismutase and catalase in $H_2O_2-treated$ HepG2 cells. To summarize, these results suggest that C3G protects cells from $H_2O_2-induced$ oxidative damage by activating antioxidant enzymes.

Analysis of Anthocyanin Glycosides in Korean Mulberry Fruit Cultivars (한국산 오디 품종별 안토시아닌 배당체 성분 분석)

  • So Ah Kim;Ryeong Ha Kwon;Ju Hyung Kim;Hyemin Na;Ji Hae Lee;Soo-Muk Cho;Heon-Woong Kim
    • The Korean Journal of Food And Nutrition
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    • v.36 no.6
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    • pp.543-550
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    • 2023
  • Mulberry fruit is a superior source of polyphenols, especially anthocyanin, and has a long history of use as an edible fruit and traditional medicine. The anthocyanin composition of mulberry fruit from 15 Korean cultivars was analyzed by ultra-performance liquid chromatography diode array detector with quadrupole time of flight/mass spectrometry (UPLC-DAD-QToF/MS) based on a cyanin internal standard. The four glycosides were identified by comparison with authentic standards and published reports. The major anthocyanin was cyanidin 3-O-glucoside (71.7%), followed by cyanidin 3-O-rutinoside (26.6%). The minor components (total of 1.7%) were pelargonidin 3-O-glucoside and pelargonidin 3-O-rutinoside. The total anthocyanin content (mg/100 g, dry weight) of mulberry fruit varied by cultivar and ranged from 471.5±4.0 (Su Hong) to 4,700.2±54.0 (Gwa Sang2). Among the 15 cultivars examined, Gwa Sang2 showed the highest level of cyanidin 3-O-glucoside (3,133.4±32.6), which was 9-fold higher than that of Su Hong (351.5±3.4). In conclusion, anthocyanin profiles, including pelargonidin 3-O-glucoside and pelargonidin 3-O-rutinoside, were reported for the first time from 15 Korean mulberry fruit cultivars. The results will contribute valuable information on pharmaceutical properties, breeding superior mulberry cultivars, and food industries.

Cyanidin-3-O-glucoside Ameliorates Postprandial Hyperglycemia in Diabetic Mice (당뇨 마우스에서 cyanidin-3-O-glucoside의 식후 고혈당 완화 효과)

  • Choi, Kyungha;Choi, Sung-In;Park, Mi Hwa;Han, Ji-Sook
    • Journal of Life Science
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    • v.27 no.1
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    • pp.32-37
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    • 2017
  • Cyanidin-3-O-glucoside (C3G) shows anti-inflammatory and antioxidant effects; however, its effect on postprandial blood glucose levels remains unknown. Alpha-glucosidase inhibitors regulate post-prandial hyperglycemia by impeding carbohydrate digestion in the small intestine. Here, the effect of C3G on ${\alpha}-glucosidase$ and ${\alpha}-amylase$ inhibition and its ability to ameliorate postprandial hyperglycemia in streptozotocin (STZ)-induced diabetic mice were evaluated. ICR normal and STZ-induced diabetic mice were orally administered soluble starch alone or with C3G or acarbose. The half-maximal inhibitory concentrations of C3G for ${\alpha}-glucosidase$ and ${\alpha}-amylase$ were 13.72 and $7.5{\mu}M$, respectively, suggesting that C3G was more effective than acarbose. The increase in postprandial blood glucose levels was more significantly reduced in the C3G groups than in the control group for both diabetic and normal mice. The area under the curve for the diabetic mice was significantly reduced following C3G administration. C3G may be a potent ${\alpha}-glucosidase$ inhibitor and may delay dietary carbohydrate absorption.

Cyanidin and Cyanidin-3-O-β-D-glucoside Suppress the Inflammatory Responses of Obese Adipose Tissue by Inhibiting the Release of Chemokines MCP-1 and MRP-2

  • Choe, Mi-Ran;Kang, Ji-Hye;Yoo, Hoon;Yang, Chae-Ha;Kim, Mi-Ok;Yu, Ri-Na;Choe, Suck-Young
    • Preventive Nutrition and Food Science
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    • v.12 no.3
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    • pp.148-153
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    • 2007
  • Obesity-induced inflammation plays a crucial role in obesity-related pathologies such as type II diabetes and atherosclerosis. Adipose tissue macrophages and the cell-derived proinflammatory chemokines are key components in augmenting inflammatory responses in obesity. Anthocyanins such as cyanidin and $cyanidin-3-O-{\beta}-D-glucoside$ (C3G) are known to elicit anti-inflammatory activities by suppressing the production of proinflammatory mediators such as tumor necrosis factor alpha and nitric oxide in LPS-stimulated macrophages. In the present study, we investigated whether cyanidin and C3G have the potential to suppress the inflammatory responses of adipose cells. Cyanidin and C3G not only suppressed the migration of RAW 264.7 macrophages induced by mesenteric adipose tissue-conditioned medium, but also inhibited the activation of the cells to produce inflammatory chemokines such as monocyte chemoattractant protein-1 (MCP-1) and macrophage inflammatory protein-related protein-2 (MRP-2) in a dose-dependent manner. Cyanidin and C3G also inhibited the release of MCP-1 and MRP-2 from adipocytes and/or macrophages. These findings suggest that cyanidin and C3G may suppress the inflammatory responses of adipose tissue in obesity.

The Anthocyanin Components and Cytotoxic Activity of Syzygium cumini (L.) Fruits Growing in Egypt

  • Nazif, Naglaa M.
    • Natural Product Sciences
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    • v.13 no.2
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    • pp.135-139
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    • 2007
  • Four anthocyanins were isolated from the acidic alcoholic extract of Syzygium cumini fruits growing in Egypt: Pelargonidin-3-O-glucoside, pelargonidin-3,5-O-diglucoside, cyanidin-3-O-malonyl glucoside, and delphenidin-3-O-glucoside. They were identified by the chromatographic, TLC and PC, and spectral analyses, UV, $^1$H-NMR and FAB/MS. The fruits were found to contain 0.03 gm % anthocyanins calculated on fresh weight basis calculated by spectrophotometric assay. Cytotoxic activity of total alcoholic extract of the fruits was performed against several types of tumor cell lines using the SRB assay. The tested extract exhibited significant cytotoxic activity for MCF7 (breast carcinoma cell line) (IC$_{50}$= 5.9 ${\mu}$g/mL), while the IC$_{50}$ was > 10 ${\mu}$g/mL for both Hela (Cervix carcinoma cell line), HEPG2 (liver carcinoma cell line), H460 (Lung carcinoma cell line) and U251 (Brain carcinoma cell line).

Effects of polyphenol and anthocyanin contents of Punica granatum fruit parts on their antioxidant and anticancer activities (석류 과실 부위별 폴리페놀 및 안토시아닌 함량이 항산화 및 항암 활성에 미치는 영향)

  • Park, Jung-Suk;Chon, Sang-Uk;Moon, Eun Woo;Jeong, Cheol-Yun
    • Food Science and Preservation
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    • v.23 no.4
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    • pp.553-559
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    • 2016
  • The purpose of this study was to determine the content of phenolics and various anthocyanin compounds, and antioxidant and anticancer activities of the extracts from pomergranates, which were produced in two different regions including Goheung, Korea and California, USA. These pomergrantes were divided into juice, pericarp, and seed parts and each part was extracted with 95% methanol. Content of total phenolics [mg chlorogenic acid equivalents/kg DW] was highest in pericarp, followed by juice and seeds from pomergrantes in both regions. The anthocyanins identified in pomegranate fruit were cyanidin-3,5-diglucoside chloride (Cy3,5G), cyanidin-3-O-glucoside chloride (Cy3G), delphini din-3,5-di-O-glucoside chloride (Dp3,5G), delphinidin-3-O-glucoside chloride (Dp3G), pelargonidin-3,5-di-glucoside chloride (Pg3,5G), and pelargonidin-3-glucoside chloride (Pg3G). Among these, cyanidin-3,5-diglucoside chloride (Cy3,5G) was the major anthocyanin in California pomegranate fruit juice and Goheung pomegranate fruit pericarp. DPPH (1,1-diphenyl-2-picryl hydrazyl radical) free radical scavenging activity was dose-dependently increased, and was higher in pericarp part than juice or seed parts from pomergrantes in both regions. By MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay, pericarp extracts from pomergrantes in both regions showed the highest anticancer activity, which was higher on Calu-6 for human pulmonary carcinoma than SNU-601 for human gastric carcinoma. Correlation between polyphenols and anticancer activity on Calu-6 was determined to be in the range of $r^2=0.8904$ to 0.9706.