Delphinidin 3-glucoside (BioDeep_00000003265)

 

Secondary id: BioDeep_00000270078, BioDeep_00000896134, BioDeep_00001874788, BioDeep_00001891285

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


代谢物信息卡片


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

化学式: [C21H21O12]+ (465.1032966)
中文名称: 飞燕草素-3-O-葡萄糖苷, 飞燕草素葡萄糖苷, 飞燕草苷3-葡萄糖苷
谱图信息: 最多检出来源 Viridiplantae(plant) 1.98%

分子结构信息

SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)c1cc(c(c(c1)O)O)O)O)O
InChI: InChI=1/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1/fC21H21O12/h23-27H/q+1

描述信息

Delphinidin 3-glucoside is found in adzuki bean. Delphinidin 3-glucoside is isolated from grapes and many other plant species Delphinidin 3-glucoside is present in red wine.
Delphinidin 3-glucoside is isolated from grapes and many other plant spp. It is found in red wine, redcurrant, summer grape, strawberry, and green bean.
Acquisition and generation of the data is financially supported in part by CREST/JST.

同义名列表

21 个代谢物同义名

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium; delphinidin 3-O-beta-D-glucopyranoside; Delphinidin-3-O-beta-glucopyranoside; Delphinidin 3-O-beta-D-glucoside; Delphinidin 3-O-glucoside cation; delphinidin 3-O-glucopyranoside; Delfinidin 3-O-beta-D-glucoside; delphinidin 3-O-beta-glucoside; Delphinidin 3-O-β-D-glucoside; Delphinidin 3-O-b-D-glucoside; Delfinidin 3-O-b-D-glucoside; Delfinidin 3-O-β-D-glucoside; Delphinidin 3-monoglucoside; Delphinidin 3-O-glucoside; delphinidin-3-glucoside; Delphinidin 3-glucoside; Delphinidol 3-glucoside; Myrtillin a; myrtillin; Mirtillin; Delphinidin 3-O-glucoside



数据库引用编号

26 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

5 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(4)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

170 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

  • Mohamad Fawzi Mahomoodally, Gokhan Zengin, Seebaluck-Sandoram Roumita, Giovanni Caprioli, Ahmed M Mustafa, Diletta Piatti, Evren Yıldıztugay, Gunes Ak, Ayşe Esra Karadağ, Asaad Khalid, Ashraf N Abdalla, Abdullahi Ibrahim Uba, Fatih Demirci. Chemical Characterization and Multidirectional Biological Effects of Different Solvent Extracts of Arum elongatum: in Vitro and in Silico Approaches. Chemistry & biodiversity. 2023 Mar; ?(?):e202201181. doi: 10.1002/cbdv.202201181. [PMID: 36891864]
  • Bo Sun, Fangda Li, Xu Zhang, Wei Wang, Jiang Shao, Yuehong Zheng. Delphinidin-3-O-glucoside, an active compound of Hibiscus sabdariffa calyces, inhibits oxidative stress and inflammation in rabbits with atherosclerosis. Pharmaceutical biology. 2022 Dec; 60(1):247-254. doi: 10.1080/13880209.2021.2017469. [PMID: 35130117]
  • Andrea Del Campo, Catalina Salamanca, Angelo Fajardo, Francisco Díaz-Castro, Catalina Bustos, Camila Calfío, Rodrigo Troncoso, Edgar R Pastene-Navarrete, Claudio Acuna-Castillo, Luis A Milla, Carlos A Villarroel, Francisco A Cubillos, Mario Aranda, Leonel E Rojo. Anthocyanins from Aristotelia chilensis Prevent Olanzapine-Induced Hepatic-Lipid Accumulation but Not Insulin Resistance in Skeletal Muscle Cells. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206149. [PMID: 34684731]
  • 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]
  • Georgiana Horincar, Elena Enachi, Carmen Bolea, Gabriela Râpeanu, Iuliana Aprodu. Value-Added Lager Beer Enriched with Eggplant (Solanum melongena L.) Peel Extract. Molecules (Basel, Switzerland). 2020 Feb; 25(3):. doi: 10.3390/molecules25030731. [PMID: 32046151]
  • Jeewon Koh, Zhimin Xu, Louise Wicker. Blueberry pectin and increased anthocyanins stability under in vitro digestion. Food chemistry. 2020 Jan; 302(?):125343. doi: 10.1016/j.foodchem.2019.125343. [PMID: 31430630]
  • Wei Yang, Maaria Kortesniemi, Xueying Ma, Jie Zheng, Baoru Yang. Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives. Food chemistry. 2019 May; 281(?):189-196. doi: 10.1016/j.foodchem.2018.12.111. [PMID: 30658747]
  • Miey Park, Anshul Sharma, Hae-Jeung Lee. Anti-Adipogenic Effects of Delphinidin-3-O-β-Glucoside in 3T3-L1 Preadipocytes and Primary White Adipocytes. Molecules (Basel, Switzerland). 2019 May; 24(10):. doi: 10.3390/molecules24101848. [PMID: 31091729]
  • Karnell L Grimes, Connor M Stuart, Justin J McCarthy, Baljinder Kaur, Emilio J Cantu, Sarah C Forester. Enhancing the Cancer Cell Growth Inhibitory Effects of Table Grape Anthocyanins. Journal of food science. 2018 Sep; 83(9):2369-2374. doi: 10.1111/1750-3841.14294. [PMID: 30070707]
  • 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]
  • Takaaki Ito, Kin-Ichi Oyama, Kumi Yoshida. Direct Observation of Hydrangea Blue-Complex Composed of 3-O-Glucosyldelphinidin, Al3+ and 5-O-Acylquinic Acid by ESI-Mass Spectrometry. Molecules (Basel, Switzerland). 2018 Jun; 23(6):. doi: 10.3390/molecules23061424. [PMID: 29895788]
  • Ana-Maria Oancea, Cristina Onofrei, Mihaela Turturică, Gabriela Bahrim, Gabriela Râpeanu, Nicoleta Stănciuc. The kinetics of thermal degradation of polyphenolic compounds from elderberry ( Sambucus nigra L.) extract. Food science and technology international = Ciencia y tecnologia de los alimentos internacional. 2018 Jun; 24(4):361-369. doi: 10.1177/1082013218756139. [PMID: 29409346]
  • Candice Mazewski, Katie Liang, Elvira Gonzalez de Mejia. Comparison of the effect of chemical composition of anthocyanin-rich plant extracts on colon cancer cell proliferation and their potential mechanism of action using in vitro, in silico, and biochemical assays. Food chemistry. 2018 Mar; 242(?):378-388. doi: 10.1016/j.foodchem.2017.09.086. [PMID: 29037704]
  • Fuhua Li, Bin Zhang, Gu Chen, Xiong Fu. The novel contributors of anti-diabetic potential in mulberry polyphenols revealed by UHPLC-HR-ESI-TOF-MS/MS. Food research international (Ottawa, Ont.). 2017 10; 100(Pt 1):873-884. doi: 10.1016/j.foodres.2017.06.052. [PMID: 28873762]
  • Pengbao Shi, Bing Li, Haiju Chen, Changzheng Song, Jiangfei Meng, Zhumei Xi, Zhenwen Zhang. Iron Supply Affects Anthocyanin Content and Related Gene Expression in Berries of Vitis vinifera cv. Cabernet Sauvignon. Molecules (Basel, Switzerland). 2017 Feb; 22(2):. doi: 10.3390/molecules22020283. [PMID: 28216591]
  • Yang-Hsin Hsu, Takayoshi Tagami, Kana Matsunaga, Masayuki Okuyama, Takashi Suzuki, Naonobu Noda, Masahiko Suzuki, Hanako Shimura. Functional characterization of UDP-rhamnose-dependent rhamnosyltransferase involved in anthocyanin modification, a key enzyme determining blue coloration in Lobelia erinus. The Plant journal : for cell and molecular biology. 2017 01; 89(2):325-337. doi: 10.1111/tpj.13387. [PMID: 27696560]
  • Sarmita Jana, Dipak Patel, Shweta Patel, Kapil Upadhyay, Jaymesh Thadani, Rahul Mandal, Santasabuj Das, Ranjitsinh Devkar. Anthocyanin rich extract of Brassica oleracea L. alleviates experimentally induced myocardial infarction. PloS one. 2017; 12(8):e0182137. doi: 10.1371/journal.pone.0182137. [PMID: 28763488]
  • G Aichinger, G Pahlke, L J Nagel, W Berger, D Marko. Bilberry extract, its major polyphenolic compounds, and the soy isoflavone genistein antagonize the cytostatic drug erlotinib in human epithelial cells. Food & function. 2016 Aug; 7(8):3628-36. doi: 10.1039/c6fo00570e. [PMID: 27485636]
  • Bo He, Ling-Li Zhang, Xue-Yang Yue, Jin Liang, Jun Jiang, Xue-Ling Gao, Peng-Xiang Yue. Optimization of Ultrasound-Assisted Extraction of phenolic compounds and anthocyanins from blueberry (Vaccinium ashei) wine pomace. Food chemistry. 2016 Aug; 204(?):70-76. doi: 10.1016/j.foodchem.2016.02.094. [PMID: 26988477]
  • Yong Wang, Di Zhang, YiXiang Liu, Dan Wang, Jia Liu, BaoPing Ji. The protective effects of berry-derived anthocyanins against visible light-induced damage in human retinal pigment epithelial cells. Journal of the science of food and agriculture. 2015 Mar; 95(5):936-44. doi: 10.1002/jsfa.6765. [PMID: 24909670]
  • Maria Paula Junqueira-Gonçalves, Lina Yáñez, Carolina Morales, Muriel Navarro, Rodrigo A Contreras, Gustavo E Zúñiga. Isolation and characterization of phenolic compounds and anthocyanins from Murta (Ugni molinae Turcz.) fruits. Assessment of antioxidant and antibacterial activity. Molecules (Basel, Switzerland). 2015 Mar; 20(4):5698-713. doi: 10.3390/molecules20045698. [PMID: 25838172]
  • Mahmoud Alhosin, Antonio J León-González, Israa Dandache, Agnès Lelay, Sherzad K Rashid, Claire Kevers, Joël Pincemail, Luc-Matthieu Fornecker, Laurent Mauvieux, Raoul Herbrecht, Valérie B Schini-Kerth. Bilberry extract (Antho 50) selectively induces redox-sensitive caspase 3-related apoptosis in chronic lymphocytic leukemia cells by targeting the Bcl-2/Bad pathway. Scientific reports. 2015 Mar; 5(?):8996. doi: 10.1038/srep08996. [PMID: 25757575]
  • Daniel Granato, Alex Koot, Egon Schnitzler, Saskia M van Ruth. Authentication of geographical origin and crop system of grape juices by phenolic compounds and antioxidant activity using chemometrics. Journal of food science. 2015 Mar; 80(3):C584-93. doi: 10.1111/1750-3841.12794. [PMID: 25675840]
  • Huijun Zuo, Lin Tang, Shu Li, Junwei Huang. Combined multispectroscopic and molecular docking investigation on the interaction between delphinidin-3-O-glucoside and bovine serum albumin. Luminescence : the journal of biological and chemical luminescence. 2015 Feb; 30(1):110-7. doi: 10.1002/bio.2704. [PMID: 24891226]
  • Fenglin Song, Yanna Zhu, Zhenyin Shi, Jinju Tian, Xiujuan Deng, Jing Ren, Marc C Andrews, Heyu Ni, Wenhua Ling, Yan Yang. Plant food anthocyanins inhibit platelet granule secretion in hypercholesterolaemia: Involving the signalling pathway of PI3K-Akt. Thrombosis and haemostasis. 2014 Nov; 112(5):981-91. doi: 10.1160/th13-12-1002. [PMID: 25077916]
  • Erlei Wang, Yongguang Yin, Caina Xu, Jingbo Liu. Isolation of high-purity anthocyanin mixtures and monomers from blueberries using combined chromatographic techniques. Journal of chromatography. A. 2014 Jan; 1327(?):39-48. doi: 10.1016/j.chroma.2013.12.070. [PMID: 24433700]
  • Gad G Yousef, Allan F Brown, Yayoi Funakoshi, Flaubert Mbeunkui, Mary H Grace, James R Ballington, Ann Loraine, Mary A Lila. Efficient quantification of the health-relevant anthocyanin and phenolic acid profiles in commercial cultivars and breeding selections of blueberries ( Vaccinium spp.). Journal of agricultural and food chemistry. 2013 May; 61(20):4806-15. doi: 10.1021/jf400823s. [PMID: 23635035]
  • Iva Fernandes, Victor de Freitas, Celso Reis, Nuno Mateus. A new approach on the gastric absorption of anthocyanins. Food & function. 2012 May; 3(5):508-16. doi: 10.1039/c2fo10295a. [PMID: 22391951]
  • Yan Yang, Zhenyin Shi, Adili Reheman, Joseph W Jin, Conglei Li, Yiming Wang, Marc C Andrews, Pingguo Chen, Guangheng Zhu, Wenhua Ling, Heyu Ni. Plant food delphinidin-3-glucoside significantly inhibits platelet activation and thrombosis: novel protective roles against cardiovascular diseases. PloS one. 2012; 7(5):e37323. doi: 10.1371/journal.pone.0037323. [PMID: 22624015]
  • Guo-Ling Liu, Hong-Hui Guo, Yuan-Ming Sun. Optimization of the extraction of anthocyanins from the fruit skin of Rhodomyrtus tomentosa (Ait.) Hassk and identification of anthocyanins in the extract using High-Performance Liquid Chromatography-Electrospray Ionization-Mass Spectrometry (HPLC-ESI-MS). International journal of molecular sciences. 2012; 13(5):6292-6302. doi: 10.3390/ijms13056292. [PMID: 22754365]
  • 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]
  • Philippe Hugueney, Sofia Provenzano, Clotilde Verriès, Alessandra Ferrandino, Emmanuelle Meudec, Giorgia Batelli, Didier Merdinoglu, Véronique Cheynier, Andrea Schubert, Agnès Ageorges. A novel cation-dependent O-methyltransferase involved in anthocyanin methylation in grapevine. Plant physiology. 2009 Aug; 150(4):2057-70. doi: 10.1104/pp.109.140376. [PMID: 19525322]
  • Mary H Grace, David M Ribnicky, Peter Kuhn, Alexander Poulev, Sithes Logendra, Gad G Yousef, Ilya Raskin, Mary Ann Lila. Hypoglycemic activity of a novel anthocyanin-rich formulation from lowbush blueberry, Vaccinium angustifolium Aiton. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 May; 16(5):406-15. doi: 10.1016/j.phymed.2009.02.018. [PMID: 19303751]
  • Lucia Giordano, Walter Coletta, Paolo Rapisarda, Maria Benedetta Donati, Domenico Rotilio. Development and validation of an LC-MS/MS analysis for simultaneous determination of delphinidin-3-glucoside, cyanidin-3-glucoside and cyanidin-3-(6-malonylglucoside) in human plasma and urine after blood orange juice administration. Journal of separation science. 2007 Dec; 30(18):3127-36. doi: 10.1002/jssc.200700246. [PMID: 18027360]
  • Jason L McCallum, Raymond Yang, J Christopher Young, Judith N Strommer, Rong Tsao. Improved high performance liquid chromatographic separation of anthocyanin compounds from grapes using a novel mixed-mode ion-exchange reversed-phase column. Journal of chromatography. A. 2007 Apr; 1148(1):38-45. doi: 10.1016/j.chroma.2007.02.088. [PMID: 17382950]
  • Takashi Ichiyanagi, M Mamunur Rahman, Yoshiki Kashiwada, Yasumasa Ikeshiro, Yasuo Shida, Yoshihiko Hatano, Hitoshi Matsumoto, Masao Hirayama, Takanori Tsuda, Tetsuya Konishi. Absorption and metabolism of delphinidin 3-O-beta-D-glucopyranoside in rats. Free radical biology & medicine. 2004 Apr; 36(7):930-7. doi: 10.1016/j.freeradbiomed.2004.01.005. [PMID: 15019977]
  • Takashi Ichiyanagi, M Mamunur Rahman, Yoshiki Kashiwada, Yasumasa Ikeshiro, Yasuo Shida, Yoshihiko Hatano, Hitoshi Matsumoto, Masao Hirayama, Tetsuya Konishi. Absorption and metabolism of delphinidin 3-O-beta-D-glucoside in rats. BioFactors (Oxford, England). 2004; 21(1-4):411-3. doi: 10.1002/biof.552210181. [PMID: 15630238]