Cyanidin 3-glucoside (BioDeep_00000003546)

 

Secondary id: BioDeep_00000266878, BioDeep_00000402772, BioDeep_00000640887, BioDeep_00000896107, BioDeep_00001868657, BioDeep_00001891595

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

化学式: [C21H21O11]+ (449.10838160000003)
中文名称: 矢车菊素-3-O-葡萄糖苷
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.55%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
InChI: InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17-,18+,19-,21-/m1/s1

描述信息

Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223).
Acquisition and generation of the data is financially supported in part by CREST/JST.
Found in many plants and fruits, e.g. cherries, olives and grapes

同义名列表

46 个代谢物同义名

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium; 2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium; 2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium; 3-(beta-D-Glucopyranosyloxy)-3,4,5,7-tetrahydroxyflavylium chloride; 3-(β-D-Glucopyranosyloxy)-3’,4’,5,7-tetrahydroxyflavylium chloride; 3-(β-D-Glucopyranosyloxy)-3,4,5,7-tetrahydroxyflavylium chloride; 3-O-(beta-D-Glucopyranosyl)cyanidin; Cyanidin 3-O-beta-D-glucopyranoside; Cyanidin 3-O-beta-glucopyranoside; Cyanidin 3-beta-D-glucopyranoside; Cyanidin 3-beta-glucoside cation; 3-O-(β-D-Glucopyranosyl)cyanidin; Cyanidin 3-O-β-D-glucopyranoside; Cyanidin 3-O-glucoside chloride; Cyanidin 3-beta-glucopyranoside; Cyanidin 3-β-D-glucopyranoside; Cyanidin 3-O-β-glucopyranoside; cyanidin 3-O-beta-D-glucoside; Cyanidin 3-β-glucoside cation; Cyanidin 3-beta-D-O-glucoside; Cyanidin-3-glucoside chloride; Cyanidin 3-glucoside chloride; Cyanidin 3-β-glucopyranoside; Cyanidin 3-O-glucopyranoside; Cyanidin 3-beta-O-glucoside; Cyanidin 3-O-beta-glucoside; Cyanidin 3-O-β-D-glucoside; Cyanidin 3-β-D-O-glucoside; Cyanidin 3-O-b-D-glucoside; Cyanidin 3-beta-glucoside; Cyanidin 3-β-O-glucoside; Cyanidin 3-monoglucoside; Cyanidin 3-O-β-glucoside; cyanidin 3-O-glucoside; Cyanidin 3-β-glucoside; cyanidin-3-glucoside; Cyanidin 3-glucoside; Cyanidol 3-glucoside; Glucocyanidin; Chrysanthemin; Chrysanthenin; Chrysontemin; Kuromanine; Kuromamine; Kuromanin; Asterin



数据库引用编号

32 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

961 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Paula Henarejos-Escudero, Berenice Guadarrama-Flores, Francisco García-Carmona, Fernando Gandía-Herrero. Digestive glands extraction and precise pigment analysis support the exclusion of the carnivorous plant Dionaea muscipula Ellis from the Caryophyllales order. Plant science : an international journal of experimental plant biology. 2018 Sep; 274(?):342-348. doi: 10.1016/j.plantsci.2018.06.013. [PMID: 30080622]
  • Aimee N Winter, Erika K Ross, Sonia Khatter, Keith Miller, Daniel A Linseman. Chemical basis for the disparate neuroprotective effects of the anthocyanins, callistephin and kuromanin, against nitrosative stress. Free radical biology & medicine. 2017 02; 103(?):23-34. doi: 10.1016/j.freeradbiomed.2016.12.012. [PMID: 27986528]
  • Nan Song, Ling Zhang, Wei Chen, Hua Zhu, Wei Deng, Yunlin Han, Jianguo Guo, Chuan Qin. Cyanidin 3-O-β-glucopyranoside activates peroxisome proliferator-activated receptor-γ and alleviates cognitive impairment in the APP(swe)/PS1(ΔE9) mouse model. Biochimica et biophysica acta. 2016 09; 1862(9):1786-800. doi: 10.1016/j.bbadis.2016.05.016. [PMID: 27240542]
  • Andreja Vanzo, Urska Vrhovsek, Federica Tramer, Fulvio Mattivi, Sabina Passamonti. Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver. Journal of natural products. 2011 May; 74(5):1049-54. doi: 10.1021/np100948a. [PMID: 21510696]
  • Ryoji Takahashi, Joseph G Dubouzet, Hisakazu Matsumura, Kentaro Yasuda, Tsukasa Iwashina. A new allele of flower color gene W1 encoding flavonoid 3'5'-hydroxylase is responsible for light purple flowers in wild soybean Glycine soja. BMC plant biology. 2010 Jul; 10(?):155. doi: 10.1186/1471-2229-10-155. [PMID: 20663233]
  • Andrea Tarozzi, Fabiana Morroni, Adriana Merlicco, Cecilia Bolondi, Gabriella Teti, Mirella Falconi, Giorgio Cantelli-Forti, Patrizia Hrelia. Neuroprotective effects of cyanidin 3-O-glucopyranoside on amyloid beta (25-35) oligomer-induced toxicity. Neuroscience letters. 2010 Apr; 473(2):72-6. doi: 10.1016/j.neulet.2010.02.006. [PMID: 20152881]
  • Juliana Barrios, Claudia Patricia Cordero, Fabio Aristizabal, Francisco José Heredia, Alicia Lucía Morales, Coralia Osorio. Chemical analysis and screening as anticancer agent of anthocyanin-rich extract from Uva Caimarona ( Pourouma cecropiifolia Mart.) fruit. Journal of agricultural and food chemistry. 2010 Feb; 58(4):2100-10. doi: 10.1021/jf9041497. [PMID: 20121190]
  • Eun-Kyung Kwon, Dae-Young Lee, Hyungjae Lee, Dae-Ok Kim, Nam-In Baek, Young-Eon Kim, Hae-Yeong Kim. Flavonoids from the buds of Rosa damascena inhibit the activity of 3-hydroxy-3-methylglutaryl-coenzyme a reductase and angiotensin I-converting enzyme. Journal of agricultural and food chemistry. 2010 Jan; 58(2):882-6. doi: 10.1021/jf903515f. [PMID: 20038104]
  • Wei Song, Han-Jing Wang, Peter Bucheli, Pei-Fang Zhang, Dong-Zhi Wei, Yan-Hua Lu. Phytochemical profiles of different mulberry (Morus sp.) species from China. Journal of agricultural and food chemistry. 2009 Oct; 57(19):9133-40. doi: 10.1021/jf9022228. [PMID: 19761189]
  • W Ray Edwards, Judy A Hall, Alan R Rowlan, Tama Schneider-Barfield, Tzeli Julia Sun, Mohini A Patil, Margaret L Pierce, R Gary Fulcher, Alois A Bell, Margaret Essenberg. Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity. Phytochemistry. 2008 Sep; 69(12):2320-8. doi: 10.1016/j.phytochem.2008.05.021. [PMID: 18617197]
  • Marcella Renis, Laura Calandra, Christian Scifo, Barbara Tomasello, Venera Cardile, Luca Vanella, Roberto Bei, Luca La Fauci, Fabio Galvano. Response of cell cycle/stress-related protein expression and DNA damage upon treatment of CaCo2 cells with anthocyanins. The British journal of nutrition. 2008 Jul; 100(1):27-35. doi: 10.1017/s0007114507876239. [PMID: 18053307]
  • Tong Ho Kang, Jin Young Hur, Hyun Bok Kim, Jong Hoon Ryu, Sun Yeou Kim. Neuroprotective effects of the cyanidin-3-O-beta-d-glucopyranoside isolated from mulberry fruit against cerebral ischemia. Neuroscience letters. 2006 Jan; 391(3):122-6. doi: 10.1016/j.neulet.2005.08.053. [PMID: 16181734]
  • Min Xia, Mengjun Hou, Huilian Zhu, Jing Ma, Zhihong Tang, Qing Wang, Yan Li, Dongsheng Chi, Xiaoping Yu, Ting Zhao, Pinghua Han, Xiaodong Xia, Wenhua Ling. Anthocyanins induce cholesterol efflux from mouse peritoneal macrophages: the role of the peroxisome proliferator-activated receptor {gamma}-liver X receptor {alpha}-ABCA1 pathway. The Journal of biological chemistry. 2005 Nov; 280(44):36792-801. doi: 10.1074/jbc.m505047200. [PMID: 16107338]
  • José Cheel, Cristina Theoduloz, Jaime Rodríguez, Guillermo Saud, Peter D S Caligari, Guillermo Schmeda-Hirschmann. E-cinnamic acid derivatives and phenolics from Chilean strawberry fruits, Fragaria chiloensis ssp. chiloensis. Journal of agricultural and food chemistry. 2005 Nov; 53(22):8512-8. doi: 10.1021/jf051294g. [PMID: 16248546]
  • Takashi Ichiyanagi, Yasuo Shida, M Mamunur Rahman, Yoshihiko Hatano, Tetsuya Konishi. Extended glucuronidation is another major path of cyanidin 3-O-beta-D-glucopyranoside metabolism in rats. Journal of agricultural and food chemistry. 2005 Sep; 53(18):7312-9. doi: 10.1021/jf051002b. [PMID: 16131148]
  • Takashi Ichiyanagi, Yasuo Shida, M Mamunur Rahman, Yoshihiko Hatano, Hitoshi Matsumoto, Masao Hirayama, Tetsuya Konishi. Metabolic pathway of cyanidin 3-O-beta-D-glucopyranoside in rats. Journal of agricultural and food chemistry. 2005 Jan; 53(1):145-50. doi: 10.1021/jf0485943. [PMID: 15631521]
  • Annalucia Serafino, Paola Sinibaldi-Vallebona, Giuseppe Lazzarino, Barbara Tavazzi, Guido Rasi, Pasquale Pierimarchi, Federica Andreola, Gabriella Moroni, Giacomo Galvano, Fabio Galvano, Enrico Garaci. Differentiation of human melanoma cells induced by cyanidin-3-O-beta-glucopyranoside. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2004 Dec; 18(15):1940-2. doi: 10.1096/fj.04-1925fje. [PMID: 15451888]
  • Mi-Yeon Kim, Kunihisa Iwai, Akio Onodera, Hajime Matsue. Identification and antiradical properties of anthocyanins in fruits of Viburnum dilatatum thunb. Journal of agricultural and food chemistry. 2003 Oct; 51(21):6173-7. doi: 10.1021/jf034647p. [PMID: 14518940]
  • Angela Maria Amorini, Giuseppe Lazzarino, Fabio Galvano, Giovanna Fazzina, Barbara Tavazzi, Giacomo Galvano. Cyanidin-3-O-beta-glucopyranoside protects myocardium and erythrocytes from oxygen radical-mediated damages. Free radical research. 2003 Apr; 37(4):453-60. doi: 10.1080/1071576021000055253. [PMID: 12747740]
  • A M Amorini, G Fazzina, G Lazzarino, B Tavazzi, D Di Pierro, R Santucci, F Sinibaldi, F Galvano, G Galvano. Activity and mechanism of the antioxidant properties of cyanidin-3-O-beta-glucopyranoside. Free radical research. 2001 Dec; 35(6):953-66. doi: 10.1080/10715760100301451. [PMID: 11811546]
  • Y M Knox, K Hayashi, T Suzutani, M Ogasawara, I Yoshida, R Shiina, A Tsukui, N Terahara, M Azuma. Activity of anthocyanins from fruit extract of Ribes nigrum L. against influenza A and B viruses. Acta virologica. 2001; 45(4):209-15. doi: ". [PMID: 11885927]