Cyanidin-3,5-diglucoside (BioDeep_00000003545)

 

Secondary id: BioDeep_00000403129, BioDeep_00000640888

natural product human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin Volatile Flavor Compounds


代谢物信息卡片


2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium

化学式: [C27H31O16]+ (611.1612026)
中文名称: 矢车菊素-3,5-二葡萄糖苷
谱图信息: 最多检出来源 Viridiplantae(plant) 11.17%

Reviewed

Last reviewed on 2024-09-27.

Cite this Page

Cyanidin-3,5-diglucoside. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cyanidin-3,5-diglucoside (retrieved 2024-11-25) (BioDeep RN: BioDeep_00000003545). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c(c(c([o+1]2)c(OC(O5)C(C(C(C5CO)O)O)O)cc(c3OC(O4)C(C(C(C4CO)O)O)O)c(cc(c3)O)2)1)c(O)c(O)cc1
InChI: InChI=1S/C27H30O16/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1

描述信息

Cyanidin-3,5-diglucoside is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Cyanidin-3,5-diglucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin-3,5-diglucoside can be found in a number of food items such as winged bean, evening primrose, durian, and peppermint, which makes cyanidin-3,5-diglucoside a potential biomarker for the consumption of these food products.

Cyanidin 3,5-diglucoside. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2611-67-8 (retrieved 2024-09-27) (CAS RN: 2611-67-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

16 个代谢物同义名

2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium; 2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl beta-D-glucopyranoside; 2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl b-D-glucopyranoside; 2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl β-D-glucopyranoside; cyanidin-3,5-di-O-glucoside chloride; Cyanidin 3,5-di-O-beta-D-glucoside; Cyanidin 3,5-di-O-b-D-glucoside; Cyanidin 3,5-di-O-β-D-glucoside; Cyanidin-3, 5-di-O-glucoside; Cyanidin 3,5-di-O-glucoside; Cyanidin-3,5-di-O-glucoside; Cyanidin 3,5-O-diglucoside; cyanidin-3,5-diglucoside; Cyanidin 3,5-diglucoside; Cyanin; Cyanin



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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

283 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

  • Manisha Thapa, Lei Liu, Bronwyn J Barkla, Tobias Kretzschmar, Suzy Y Rogiers, Terry J Rose. Accumulation patterns of anthocyanin and γ-oryzanol during black rice grain development. PloS one. 2024; 19(5):e0302745. doi: 10.1371/journal.pone.0302745. [PMID: 38776277]
  • Juan Luis Escobar-Ramírez, Jacinto Santiago-Mejía, Maribel Soto-Núñez, Oscar Salvador Barrera-Vázquez, Roberto Vargas-Querea, Gil Alfonso Magos-Guerrero. The Hypotensive and Vasodilatory Effects Observed in Rats Exposed to Chiranthodendron pentadactylon Larreat Flowers Can Be Attributed to Cyanidin 3-O-Glucoside. Molecules (Basel, Switzerland). 2023 Nov; 28(23):. doi: 10.3390/molecules28237698. [PMID: 38067429]
  • Mengyu Yang, Abdullah, Naveed Ahmad, Muhammad Hussain, Xiaoqin Lu, Jie Xu, Hao Zhong, Rongfa Guan. A review of recent advances on cyanidin-3-glucoside: the biotransformation, absorption, bioactivity and applications of nano-encapsulation. Food & function. 2023 Jul; 14(14):6320-6345. doi: 10.1039/d2fo03824b. [PMID: 37403833]
  • Yi-Wei Du, Xiao-Kang Li, Ting-Ting Wang, Lu Zhou, Hui-Rong Li, Lan Feng, Heng Ma, Hong-Bao Liu. Cyanidin-3-glucoside inhibits ferroptosis in renal tubular cells after ischemia/reperfusion injury via the AMPK pathway. Molecular medicine (Cambridge, Mass.). 2023 04; 29(1):42. doi: 10.1186/s10020-023-00642-5. [PMID: 37013504]
  • Arpamas Chariyakornkul, Waristha Juengwiroj, Jetsada Ruangsuriya, Rawiwan Wongpoomchai. Antioxidant Extract from Cleistocalyx nervosum var. paniala Pulp Ameliorates Acetaminophen-Induced Acute Hepatotoxicity in Rats. Molecules (Basel, Switzerland). 2022 Jan; 27(2):. doi: 10.3390/molecules27020553. [PMID: 35056867]
  • Shikai Zhang, Wang Zhan, Anran Sun, Ying Xie, Zhiming Han, Xibin Qu, Jiayi Wang, Laifu Zhang, Mingshun Tian, Xuhong Pang, Jinbao Zhang, Xiyang Zhao. Combined transcriptome and metabolome integrated analysis of Acer mandshuricum to reveal candidate genes involved in anthocyanin accumulation. Scientific reports. 2021 11; 11(1):23148. doi: 10.1038/s41598-021-02607-2. [PMID: 34848790]
  • Rebecca Kowalski, Elvira Gonzalez de Mejia. Phenolic composition, antioxidant capacity and physical characterization of ten blackcurrant (Ribes nigrum) cultivars, their juices, and the inhibition of type 2 diabetes and inflammation biochemical markers. Food chemistry. 2021 Oct; 359(?):129889. doi: 10.1016/j.foodchem.2021.129889. [PMID: 33934030]
  • Ebru Cenk, Cornelia Schmutz, Gudrun Pahlke, Anne Oertel, Jessica Kollarova, Hans-Peter Mock, Andrea Matros, Doris Marko. Immunomodulatory Properties of Blackberry Anthocyanins in THP-1 Derived Macrophages. International journal of molecular sciences. 2021 Sep; 22(19):. doi: 10.3390/ijms221910483. [PMID: 34638824]
  • Nobuhiro Sasaki, Keiichirou Nemoto, Yuzo Nishizaki, Naoki Sugimoto, Keisuke Tasaki, Aiko Watanabe, Fumina Goto, Atsumi Higuchi, Ed Morgan, Takashi Hikage, Masahiro Nishihara. Identification and characterization of xanthone biosynthetic genes contributing to the vivid red coloration of red-flowered gentian. The Plant journal : for cell and molecular biology. 2021 09; 107(6):1711-1723. doi: 10.1111/tpj.15412. [PMID: 34245606]
  • Xiaojun Chen, Weixia Zhang, Xiuzhen Xu. Cyanidin-3-glucoside suppresses the progression of lung adenocarcinoma by downregulating TP53I3 and inhibiting PI3K/AKT/mTOR pathway. World journal of surgical oncology. 2021 Aug; 19(1):232. doi: 10.1186/s12957-021-02339-7. [PMID: 34362378]
  • Giuseppe Persico, Francesca Casciaro, Alessandra Marinelli, Chiara Tonelli, Katia Petroni, Marco Giorgio. Comparative Analysis of Histone H3K4me3 Distribution in Mouse Liver in Different Diets Reveals the Epigenetic Efficacy of Cyanidin-3-O-glucoside Dietary Intake. International journal of molecular sciences. 2021 Jun; 22(12):. doi: 10.3390/ijms22126503. [PMID: 34204393]
  • Chalermpong Saenjum, Thanawat Pattananandecha, Kouichi Nakagawa. Antioxidative and Anti-Inflammatory Phytochemicals and Related Stable Paramagnetic Species in Different Parts of Dragon Fruit. Molecules (Basel, Switzerland). 2021 Jun; 26(12):. doi: 10.3390/molecules26123565. [PMID: 34200974]
  • Noelia Carballeda-Sangiao, Susana Chamorro, Sonia de Pascual-Teresa. A Red-Berry Mixture as a Nutraceutical: Detailed Composition and Neuronal Protective Effect. Molecules (Basel, Switzerland). 2021 May; 26(11):. doi: 10.3390/molecules26113210. [PMID: 34071973]
  • Miki Hiemori-Kondo, Etsuko Morikawa, Michiko Fujikura, Ayuko Nagayasu, Yuuki Maekawa. Inhibitory effects of cyanidin-3-O-glucoside in black soybean hull extract on RBL-2H3 cells degranulation and passive cutaneous anaphylaxis reaction in mice. International immunopharmacology. 2021 May; 94(?):107394. doi: 10.1016/j.intimp.2021.107394. [PMID: 33582590]
  • Pamela Alves Castilho, Lívia Bracht, Lillian Barros, Bianca R Albuquerque, Maria Inês Dias, Isabel C F R Ferreira, Jurandir Fernando Comar, Tamires Barlati Vieira da Silva, Rosane Marina Peralta, Anacharis Babeto de Sá-Nakanishi, Adelar Bracht. Effects of a Myrciaria jaboticaba peel extract on starch and triglyceride absorption and the role of cyanidin-3-O-glucoside. Food & function. 2021 Mar; 12(6):2644-2659. doi: 10.1039/d0fo02927k. [PMID: 33645616]
  • Enerand Mackon, Guibeline Charlie Jeazet Dongho Epse Mackon, Yafei Ma, Muhammad Haneef Kashif, Niyaz Ali, Babar Usman, Piqing Liu. Recent Insights into Anthocyanin Pigmentation, Synthesis, Trafficking, and Regulatory Mechanisms in Rice (Oryza sativa L.) Caryopsis. Biomolecules. 2021 03; 11(3):. doi: 10.3390/biom11030394. [PMID: 33800105]
  • Linyu Tai, Shiyu Huang, Zhengwu Zhao, Gangliang Huang. Chemical composition analysis and antioxidant activity of black rice pigment. Chemical biology & drug design. 2021 03; 97(3):711-720. doi: 10.1111/cbdd.13806. [PMID: 33179435]
  • Patricia Velásquez, Daniela Bustos, Gloria Montenegro, Ady Giordano. Ultrasound-Assisted Extraction of Anthocyanins Using Natural Deep Eutectic Solvents and Their Incorporation in Edible Films. Molecules (Basel, Switzerland). 2021 Feb; 26(4):. doi: 10.3390/molecules26040984. [PMID: 33673385]
  • Li Li, Jun Li, Hui Xu, Fengmei Zhu, Zhijun Li, Hongzhi Lu, Jinrong Zhang, Zhengsheng Yang, Yongsheng Liu. The Protective Effect of Anthocyanins Extracted from Aronia Melanocarpa Berry in Renal Ischemia-Reperfusion Injury in Mice. Mediators of inflammation. 2021; 2021(?):7372893. doi: 10.1155/2021/7372893. [PMID: 33551679]
  • Monica Barman, Upashana Ghissing, Pritam Kumar Dey, Avinash Agarwal, Bubai Bera, Jhansi Narmada Reddy Kotamreddy, Prakash Karmakar, Adinpunya Mitra. Specialized metabolites contributing to colour and scent volatiles in Uvaria hamiltonii flowers. Natural product research. 2021 Jan; 35(1):140-143. doi: 10.1080/14786419.2019.1610959. [PMID: 31184502]
  • Jin Jeon, Seung-A Baek, Nam Su Kim, Ramaraj Sathasivam, Jong Seok Park, Jae Kwang Kim, Sang Un Park. Elevated Ozone Levels Affect Metabolites and Related Biosynthetic Genes in Tartary Buckwheat. Journal of agricultural and food chemistry. 2020 Dec; 68(50):14758-14767. doi: 10.1021/acs.jafc.0c04716. [PMID: 33264023]
  • Geum-Hwa Lee, The-Hiep Hoang, Eun-Soo Jung, Su-Jin Jung, Seong-Kyu Han, Myoung-Ja Chung, Soo-Wan Chae, Han-Jung Chae. Anthocyanins attenuate endothelial dysfunction through regulation of uncoupling of nitric oxide synthase in aged rats. Aging cell. 2020 12; 19(12):e13279. doi: 10.1111/acel.13279. [PMID: 33274583]
  • Maria Sofia Molonia, Cristina Occhiuto, Claudia Muscarà, Antonio Speciale, Romina Bashllari, Francesc Villarroya, Antonella Saija, Francesco Cimino, Mariateresa Cristani. Cyanidin-3-O-glucoside restores insulin signaling and reduces inflammation in hypertrophic adipocytes. Archives of biochemistry and biophysics. 2020 09; 691(?):108488. doi: 10.1016/j.abb.2020.108488. [PMID: 32692982]
  • Yaoyao Jia, Chunyan Wu, Young-Suk Kim, Seung Ok Yang, Yeonji Kim, Ji-Sun Kim, Mi-Young Jeong, Ji Hae Lee, Bobae Kim, Soyoung Lee, Hyun-Seok Oh, Jia Kim, Min-Young So, Ye Eun Yoon, Trung Thanh Thach, Tai Hyun Park, Sung-Joon Lee. A dietary anthocyanin cyanidin-3-O-glucoside binds to PPARs to regulate glucose metabolism and insulin sensitivity in mice. Communications biology. 2020 09; 3(1):514. doi: 10.1038/s42003-020-01231-6. [PMID: 32948821]
  • Zhihong Wang, Min Zhang, Zhong Wang, Zongjun Guo, Zongqiu Wang, Qun Chen. Cyanidin-3-O-glucoside attenuates endothelial cell dysfunction by modulating miR-204-5p/SIRT1-mediated inflammation and apoptosis. BioFactors (Oxford, England). 2020 Sep; 46(5):803-812. doi: 10.1002/biof.1660. [PMID: 32593198]
  • Wei Hu, Tianhao Zhou, Zhongmin Han, Cong Tan, Yongzhong Xing. Dominant complementary interaction between OsC1 and two tightly linked genes, Rb1 and Rb2, controls the purple leaf sheath in rice. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2020 Sep; 133(9):2555-2566. doi: 10.1007/s00122-020-03617-w. [PMID: 32458058]
  • Madumani Amararathna, David W Hoskin, H P Vasantha Rupasinghe. Cyanidin-3-O-Glucoside-Rich Haskap Berry Administration Suppresses Carcinogen-Induced Lung Tumorigenesis in A/JCr Mice. Molecules (Basel, Switzerland). 2020 Aug; 25(17):. doi: 10.3390/molecules25173823. [PMID: 32842605]
  • Nadia Lombardi, Anna Maria Salzano, Antonio Dario Troise, Andrea Scaloni, Paola Vitaglione, Francesco Vinale, Roberta Marra, Simonetta Caira, Matteo Lorito, Giada d'Errico, Stefania Lanzuise, Sheridan Lois Woo. Effect of Trichoderma Bioactive Metabolite Treatments on the Production, Quality, and Protein Profile of Strawberry Fruits. Journal of agricultural and food chemistry. 2020 Jul; 68(27):7246-7258. doi: 10.1021/acs.jafc.0c01438. [PMID: 32426974]
  • Yongzhong Ouyang, Lei Chen, Liu Qian, Xiujun Lin, Xiaoyun Fan, Hui Teng, Hui Cao. Fabrication of caseins nanoparticles to improve the stability of cyanidin 3-O-glucoside. Food chemistry. 2020 Jul; 317(?):126418. doi: 10.1016/j.foodchem.2020.126418. [PMID: 32087512]
  • Bianca R Albuquerque, José Pinela, Lillian Barros, M Beatriz P P Oliveira, Isabel C F R Ferreira. Anthocyanin-rich extract of jabuticaba epicarp as a natural colorant: Optimization of heat- and ultrasound-assisted extractions and application in a bakery product. Food chemistry. 2020 Jun; 316(?):126364. doi: 10.1016/j.foodchem.2020.126364. [PMID: 32058190]
  • Gustavo Heinrich Lang, Igor da Silva Lindemann, Jorge Tiago Goebel, Cristiano Dietrich Ferreira, Tanize Dos Santos Acunha, Maurício de Oliveira. Fluidized-bed drying of black rice grains: Impact on cooking properties, in vitro starch digestibility, and bioaccessibility of phenolic compounds. Journal of food science. 2020 Jun; 85(6):1717-1724. doi: 10.1111/1750-3841.15145. [PMID: 32406950]
  • Na-Hyun Kim, Jonghwan Jegal, Yun Na Kim, Jeong-Doo Heo, Jung-Rae Rho, Min Hye Yang, Eun Ju Jeong. The Effects of Aronia melanocarpa Extract on Testosterone-Induced Benign Prostatic Hyperplasia in Rats, and Quantitative Analysis of Major Constituents Depending on Extract Conditions. Nutrients. 2020 May; 12(6):. doi: 10.3390/nu12061575. [PMID: 32481550]
  • Vaida Kitrytė, Aistė Narkevičiūtė, Laura Tamkutė, Michail Syrpas, Milda Pukalskienė, Petras Rimantas Venskutonis. Consecutive high-pressure and enzyme assisted fractionation of blackberry (Rubus fruticosus L.) pomace into functional ingredients: Process optimization and product characterization. Food chemistry. 2020 May; 312(?):126072. doi: 10.1016/j.foodchem.2019.126072. [PMID: 31893552]
  • Hong Xing Zheng, Shan Shan Qi, Jia He, Ching Yuan Hu, Hao Han, Hai Jiang, Xin Shen Li. Cyanidin-3-glucoside from Black Rice Ameliorates Diabetic Nephropathy via Reducing Blood Glucose, Suppressing Oxidative Stress and Inflammation, and Regulating Transforming Growth Factor β1/Smad Expression. Journal of agricultural and food chemistry. 2020 Apr; 68(15):4399-4410. doi: 10.1021/acs.jafc.0c00680. [PMID: 32192334]
  • Loredana Dumitrascu, Nicoleta Stănciuc, Leontina Grigore-Gurgu, Iuliana Aprodu. Investigation on the interaction of heated soy proteins with anthocyanins from cornelian cherry fruits. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Apr; 231(?):118114. doi: 10.1016/j.saa.2020.118114. [PMID: 32014659]
  • Monruedee Sukprasansap, Pithi Chanvorachote, Tewin Tencomnao. Cyanidin-3-glucoside activates Nrf2-antioxidant response element and protects against glutamate-induced oxidative and endoplasmic reticulum stress in HT22 hippocampal neuronal cells. BMC complementary medicine and therapies. 2020 Feb; 20(1):46. doi: 10.1186/s12906-020-2819-7. [PMID: 32046712]
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  • Jin-Long Tian, Xiao-Jun Liao, Yue-Hua Wang, Xu Si, Chi Shu, Er-Sheng Gong, Xu Xie, Xu-Long Ran, Bin Li. Identification of Cyanidin-3-arabinoside Extracted from Blueberry as a Selective Protein Tyrosine Phosphatase 1B Inhibitor. Journal of agricultural and food chemistry. 2019 Dec; 67(49):13624-13634. doi: 10.1021/acs.jafc.9b06155. [PMID: 31743023]
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  • Yong Wang, Wentao Qi, Yazhen Huo, Ge Song, Hui Sun, Xiaoxuan Guo, Chengtao Wang. Cyanidin-3-glucoside attenuates 4-hydroxynonenal- and visible light-induced retinal damage in vitro and in vivo. Food & function. 2019 May; 10(5):2871-2880. doi: 10.1039/c9fo00273a. [PMID: 31070214]
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