Malvidin 3-glucoside (BioDeep_00000003547)

 

Secondary id: BioDeep_00000394606, BioDeep_00001874778, BioDeep_00001892190

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite PANOMIX-Anthocyanidin


代谢物信息卡片


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

化学式: [C23H25O12]+ (493.134595)
中文名称: 氯化锦葵色素-3-Β-葡糖苷, 锦葵素3-葡萄糖苷, 锦葵素3-O-β-D-吡喃葡萄糖苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 8.17%

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)OC)O)OC)O)O
InChI: InChI=1/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1/fC23H25O12/h25-27H/q+1

描述信息

Malvidin 3-glucoside is found in alcoholic beverages. Malvidin 3-glucoside is a pigment of skins of black grapes, also in other plants. Malvidin 3-glucoside is found in red wine
Pigment of skins of black grapes, also in other plants. Found in red wine. Malvidin glycoside is a biomarker for the consumption of blueberries.
Acquisition and generation of the data is financially supported in part by CREST/JST.

同义名列表

13 个代谢物同义名

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium; (3-O-methyl-(3)H)malvidin-3-glucoside; Malvidin 3-O-beta-D-glucopyranoside; Malvidin-3-O-glucoside chloride; Malvidin 3-O-β-D-glucoside; Malvidin 3-O-b-D-glucoside; Malvidin 3-O-glucoside; malvidin-3-glucoside; Malvidin 3-Glucoside; Ligulin; Enoside; Oenin; Enin



数据库引用编号

25 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)

21 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

  • Francisco Chamizo-González, Belén Gordillo, Francisco J Heredia. Elucidation of the 3D structure of grape seed 7S globulin and its interaction with malvidin 3-glucoside: A molecular modeling approach. Food chemistry. 2021 Jun; 347(?):129014. doi: 10.1016/j.foodchem.2021.129014. [PMID: 33493840]
  • Sisir Kumar Barik, Budheswar Dehury, Wendy R Russell, Kim M Moar, Morven Cruickshank, Lorraine Scobbie, Nigel Hoggard. Analysis of polyphenolic metabolites from in vitro gastrointestinal digested soft fruit extracts identify malvidin-3-glucoside as an inhibitor of PTP1B. Biochemical pharmacology. 2020 08; 178(?):114109. doi: 10.1016/j.bcp.2020.114109. [PMID: 32569626]
  • 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]
  • Simone Giacosa, Carolina Ossola, Riccardo Botto, Susana Río Segade, Maria Alessandra Paissoni, Matteo Pollon, Vincenzo Gerbi, Luca Rolle. Impact of specific inactive dry yeast application on grape skin mechanical properties, phenolic compounds extractability, and wine composition. Food research international (Ottawa, Ont.). 2019 02; 116(?):1084-1093. doi: 10.1016/j.foodres.2018.09.051. [PMID: 30716892]
  • Patrick C Setford, David W Jeffery, Paul R Grbin, Richard A Muhlack. Modelling the Mass Transfer Process of Malvidin-3-Glucoside during Simulated Extraction from Fresh Grape Solids under Wine-Like Conditions. Molecules (Basel, Switzerland). 2018 Aug; 23(9):. doi: 10.3390/molecules23092159. [PMID: 30150601]
  • H Du, L Lai, F Wang, W Sun, L Zhang, X Li, L Wang, L Jiang, Y Zheng. Characterisation of flower colouration in 30 Rhododendron species via anthocyanin and flavonol identification and quantitative traits. Plant biology (Stuttgart, Germany). 2018 Jan; 20(1):121-129. doi: 10.1111/plb.12649. [PMID: 29054107]
  • Marcelo Queiroz, David Oppolzer, Irene Gouvinhas, Amélia M Silva, Ana I R N A Barros, Raúl Domínguez-Perles. New grape stems' isolated phenolic compounds modulate reactive oxygen species, glutathione, and lipid peroxidation in vitro: Combined formulations with vitamins C and E. Fitoterapia. 2017 Jul; 120(?):146-157. doi: 10.1016/j.fitote.2017.06.010. [PMID: 28625733]
  • Sally M Yacout, Elizabeth R Gaillard. The Anthocyanins, Oenin and Callistephin, Protect RPE Cells Against Oxidative Stress. Photochemistry and photobiology. 2017 03; 93(2):590-599. doi: 10.1111/php.12683. [PMID: 27935050]
  • 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]
  • Zhiyong He, Haidong Zhu, Mingzhu Xu, Maomao Zeng, Fang Qin, Jie Chen. Complexation of bovine β-lactoglobulin with malvidin-3-O-glucoside and its effect on the stability of grape skin anthocyanin extracts. Food chemistry. 2016 Oct; 209(?):234-40. doi: 10.1016/j.foodchem.2016.04.048. [PMID: 27173557]
  • Sibel Karakaya, Sebnem Simsek, Alper Tolga Eker, Carlos Pineda-Vadillo, Didier Dupont, Beatriz Perez, Blanca Viadel, Marisa Sanz-Buenhombre, Alberto Guadarrama Rodriguez, Zsófia Kertész, Adrienn Hegyi, Alessandra Bordoni, Sedef Nehir El. Stability and bioaccessibility of anthocyanins in bakery products enriched with anthocyanins. Food & function. 2016 Aug; 7(8):3488-96. doi: 10.1039/c6fo00567e. [PMID: 27415853]
  • 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]
  • Luis Cruz, Iva Fernandes, Marta Guimarães, Victor de Freitas, Nuno Mateus. Enzymatic synthesis, structural characterization and antioxidant capacity assessment of a new lipophilic malvidin-3-glucoside-oleic acid conjugate. Food & function. 2016 Jun; 7(6):2754-62. doi: 10.1039/c6fo00466k. [PMID: 27220831]
  • Lukáš Kučera, Salvatore Fanali, Zeineb Aturki, Tomáš Pospíšil, Petr Bednář. Comparison of nano and conventional liquid chromatographic methods for the separation of (+)-catechin-ethyl-malvidin-3-glucoside diastereoisomers. Journal of chromatography. A. 2016 Jan; 1428(?):126-33. doi: 10.1016/j.chroma.2015.09.074. [PMID: 26433264]
  • Fei He, Wei-Kai Chen, Ke-Ji Yu, Xiang-Nan Ji, Chang-Qing Duan, Malcolm J Reeves, Jun Wang. Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis. Phytochemistry. 2015 Sep; 117(?):363-372. doi: 10.1016/j.phytochem.2015.06.023. [PMID: 26159788]
  • Zhenzhou Zhu, Nao Wu, Minjie Kuang, Olusola Lamikanra, Gang Liu, Shuyi Li, Jingren He. Preparation and toxicological evaluation of methyl pyranoanthocyanin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Sep; 83(?):125-32. doi: 10.1016/j.fct.2015.05.004. [PMID: 26028581]
  • Hui Feng, Fang Yuan, Patricia A Skinkis, Michael C Qian. Influence of cluster zone leaf removal on Pinot noir grape chemical and volatile composition. Food chemistry. 2015 Apr; 173(?):414-23. doi: 10.1016/j.foodchem.2014.09.149. [PMID: 25466040]
  • 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]
  • 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]
  • 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]
  • Alain Decendit, Maria Mamani-Matsuda, Virginie Aumont, Pierre Waffo-Teguo, Daniel Moynet, Katia Boniface, Emmanuel Richard, Stéphanie Krisa, Jérôme Rambert, Jean-Michel Mérillon, M D Mossalayi. Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats. Biochemical pharmacology. 2013 Nov; 86(10):1461-7. doi: 10.1016/j.bcp.2013.06.010. [PMID: 23796750]
  • Andrea Bunea, Dumitriţa Rugină, Zoriţa Sconţa, Raluca M Pop, Adela Pintea, Carmen Socaciu, Flaviu Tăbăran, Charlotte Grootaert, Karin Struijs, John VanCamp. Anthocyanin determination in blueberry extracts from various cultivars and their antiproliferative and apoptotic properties in B16-F10 metastatic murine melanoma cells. Phytochemistry. 2013 Nov; 95(?):436-44. doi: 10.1016/j.phytochem.2013.06.018. [PMID: 23890760]
  • 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]
  • Denise K Gessner, Anja Fiesel, Erika Most, Jennifer Dinges, Gaiping Wen, Robert Ringseis, Klaus Eder. Supplementation of a grape seed and grape marc meal extract decreases activities of the oxidative stress-responsive transcription factors NF-κB and Nrf2 in the duodenal mucosa of pigs. Acta veterinaria Scandinavica. 2013 Mar; 55(?):18. doi: 10.1186/1751-0147-55-18. [PMID: 23453040]
  • Susana Soares, Susann Kohl, Sophie Thalmann, Nuno Mateus, Wolfgang Meyerhof, Victor De Freitas. Different phenolic compounds activate distinct human bitter taste receptors. Journal of agricultural and food chemistry. 2013 Feb; 61(7):1525-33. doi: 10.1021/jf304198k. [PMID: 23311874]
  • 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]
  • Bahman Nickavar, Gholamreza Amin. Bioassay-guided separation of an alpha-amylase inhibitor anthocyanin from Vaccinium arctostaphylos berries. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2010 Sep; 65(9-10):567-70. doi: 10.1515/znc-2010-9-1006. [PMID: 21138057]
  • Linga R Gutha, Luis F Casassa, James F Harbertson, Rayapati A Naidu. Modulation of flavonoid biosynthetic pathway genes and anthocyanins due to virus infection in grapevine (Vitis vinifera L.) leaves. BMC plant biology. 2010 Aug; 10(?):187. doi: 10.1186/1471-2229-10-187. [PMID: 20731850]
  • Jia Liu, Wei Zhang, Hao Jing, David G Popovich. Bog bilberry (Vaccinium uliginosum L.) extract reduces cultured Hep-G2, Caco-2, and 3T3-L1 cell viability, affects cell cycle progression, and has variable effects on membrane permeability. Journal of food science. 2010 Apr; 75(3):H103-7. doi: 10.1111/j.1750-3841.2010.01546.x. [PMID: 20492295]
  • Hiroyuki Sakakibara, Takeshi Ogawa, Akiharu Koyanagi, Saori Kobayashi, Toshinao Goda, Shigenori Kumazawa, Hirokazu Kobayashi, Kayoko Shimoi. Distribution and excretion of bilberry anthocyanins [corrected] in mice. Journal of agricultural and food chemistry. 2009 Sep; 57(17):7681-6. doi: 10.1021/jf901341b. [PMID: 19663426]
  • Pascale Goupy, Ana-Belen Bautista-Ortin, Helene Fulcrand, Olivier Dangles. Antioxidant activity of wine pigments derived from anthocyanins: hydrogen transfer reactions to the dpph radical and inhibition of the heme-induced peroxidation of linoleic acid. Journal of agricultural and food chemistry. 2009 Jul; 57(13):5762-70. doi: 10.1021/jf900841b. [PMID: 19566083]
  • 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]
  • Monica Rossetto, Paola Vanzani, Fulvio Mattivi, Michele Lunelli, Marina Scarpa, Adelio Rigo. Synergistic antioxidant effect of catechin and malvidin 3-glucoside on free radical-initiated peroxidation of linoleic acid in micelles. Archives of biochemistry and biophysics. 2002 Dec; 408(2):239-45. doi: 10.1016/s0003-9861(02)00561-1. [PMID: 12464277]
  • J Wang, G Mazza. Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages. Journal of agricultural and food chemistry. 2002 Feb; 50(4):850-7. doi: 10.1021/jf010976a. [PMID: 11829656]
  • T Lapidot, S Harel, B Akiri, R Granit, J Kanner. PH-dependent forms of red wine anthocyanins as antioxidants. Journal of agricultural and food chemistry. 1999 Jan; 47(1):67-70. doi: 10.1021/jf980704g. [PMID: 10563851]