cinaroside (BioDeep_00000859295)

Main id: BioDeep_00000000277

 

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone

化学式: C21H20O11 (448.100557)
中文名称: 木犀草苷, 木犀草素葡萄糖甙
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
InChI: InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1

描述信息

Cynaroside (Luteolin 7-glucoside) is a flavonoid compound that exhibits anti-oxidative capabilities. Cynaroside is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 32 nM. Cynaroside also is a promising inhibitor for H2O2-induced apoptosis, has cytoprotection against oxidative stress-induced cardiovascular diseases. Cynaroside also has antibacterial, antifungal and anticancer activities, antioxidant and anti-inflammatory activities[1][3][4][5].

同义名列表

40 个代谢物同义名

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-chromone; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, mono-beta-D-glucopyranoside; 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one mono-beta-D-glucopyranoside; 4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-; 2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one; 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside; Flavone, 3,4,5,7-tetrahydroxy-, mono-beta-D-glucopyranoside; 7-O-beta-D-Glucosyl-5,7,3,4-tetrahydroxyflavone; Flavon, 3,4,5,7-tetrahydroxy-, glucoside; Luteolin 7-O-beta-D-glucoside; Luteolin 7-O-glucopyranoside; Luteolin 7-O-D-glucoside; Luteolin 7-monoglucoside; Luteolin 7-O-glucoside; luteolin-7-O-glucoside; Luteolin monoglucoside; luteolin-7-glucoside; Luteolin 7-glucoside; Luteolin, glucoside; 7-Glucosylluteolin; EINECS 226-365-8; NCGC00163589-01; 7-Glucoluteolin; Glucoluteolin; MEGxp0_000619; STOCK1N-08497; CHEBI:27994; luteoloside; AIDS-070478; AIDS070478; cinaroside; Cynaroside; 26811-41-6; C03951; Luteolin 7-O-β-D-glucoside



数据库引用编号

12 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)

531 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

  • Yiwei Zhou, Yuhan Huang, Wei Ye, Zijie Chen, Zhengzhong Yuan. Cynaroside improved depressive-like behavior in CUMS mice by suppressing microglial inflammation and ferroptosis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Apr; 173(?):116425. doi: 10.1016/j.biopha.2024.116425. [PMID: 38490155]
  • Sahar Saleh Alghamdi, Sara Abdulaziz Alghashem, Rizwan Ali, Arwa Alsubait, Rasha Saad Suliman, Afrah E Mohammed, Zeyad Alehaideb, Raghad Abdullah Alshafi, Allulu Yousef Alturki, Ishrat Rahman. Exploring the potential of Ziziphus nummularia and luteolin-7-O-glucoside as tubulin inhibitors in cancer therapy and survival. Scientific reports. 2024 03; 14(1):7202. doi: 10.1038/s41598-024-57680-0. [PMID: 38531974]
  • Taghreed A Majrashi, Mahmoud A El Hassab, Sara H Mahmoud, Ahmed Mostafa, Engy A Wahsh, Eslam B Elkaeed, Fatma E Hassan, Wagdy M Eldehna, Shimaa M Abdelgawad. In vitro biological evaluation and in silico insights into the antiviral activity of standardized olive leaves extract against SARS-CoV-2. PloS one. 2024; 19(4):e0301086. doi: 10.1371/journal.pone.0301086. [PMID: 38662719]
  • Lucia Camelia Pirvu, Lucia Pintilie, Adrian Albulescu, Amalia Stefaniu, Georgeta Neagu. Anti-Proliferative Potential of Cynaroside and Orientin-In Silico (DYRK2) and In Vitro (U87 and Caco-2) Studies. International journal of molecular sciences. 2023 Nov; 24(23):. doi: 10.3390/ijms242316555. [PMID: 38068880]
  • Abdelhakim Bouyahya, Douae Taha, Taoufiq Benali, Gokhan Zengin, Nasreddine El Omari, Naoufal El Hachlafi, Asaad Khalid, Ashraf N Abdalla, Chrismawan Ardianto, Ching Siang Tan, Long Chiau Ming, Narjis Sahib. Natural sources, biological effects, and pharmacological properties of cynaroside. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Feb; 161(?):114337. doi: 10.1016/j.biopha.2023.114337. [PMID: 36812715]
  • Sezen Yılmaz Sarıaltın, Özlem Bahadır Acıkara. Assessment of Correlation Analysis, Phytochemical Profile, and Biological Activities of Endemic Scorzonera Species from Turkey. Chemistry & biodiversity. 2022 Oct; 19(10):e202200007. doi: 10.1002/cbdv.202200007. [PMID: 36031843]
  • Gabin Thierry M Bitchagno, Anja Schüffler, Jonathan Gross, Matthias Krumb, Pierre Tane, Till Opatz. Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation. Journal of natural products. 2022 07; 85(7):1681-1690. doi: 10.1021/acs.jnatprod.2c00055. [PMID: 35704432]
  • Shu-Ping Chen, Tian-Hong Hu, Qing Zhou, Tian-Peng Chen, Dong Yin, Huan He, Qing Huang, Ming He. Luteoloside protects the vascular endothelium against iron overload injury via the ROS/ADMA/DDAH II/eNOS/NO pathway. Chinese journal of natural medicines. 2022 Jan; 20(1):22-32. doi: 10.1016/s1875-5364(21)60110-3. [PMID: 35101247]
  • Aboli Girme, Prajkta Bhoj, Ganesh Saste, Sandeep Pawar, Amit Mirgal, Dipak Raut, Machindra Chavan, Lal Hingorani. Development and Validation of RP-HPLC Method for Vicenin-2, Orientin, Cynaroside, Betulinic Acid, Genistein, and Major Eight Bioactive Constituents with LC-ESI-MS/MS Profiling in Ocimum Genus. Journal of AOAC International. 2021 Dec; 104(6):1634-1651. doi: 10.1093/jaoacint/qsab067. [PMID: 33930142]
  • Juanli Ji, Zhongze Wang, Wei Sun, Zekun Li, Huarui Cai, Erhu Zhao, Hongjuan Cui. Effects of Cynaroside on Cell Proliferation, Apoptosis, Migration and Invasion though the MET/AKT/mTOR Axis in Gastric Cancer. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212125. [PMID: 34830011]
  • Bruno César Correa Salles, Krissia Caroline Leme, Marcelo Aparecido da Silva, Cláudia Quintino da Rocha, Marcelo M P Tangerina, Wagner Vilegas, Sônia A Figueiredo, Stella Maris da Silveira Duarte, Maria Rita Rodrigues, Fernanda Borges de Araújo Paula. Protective effect of flavonoids from Passiflora edulis Sims on diabetic complications in rats. The Journal of pharmacy and pharmacology. 2021 Sep; 73(10):1361-1368. doi: 10.1093/jpp/rgab046. [PMID: 33772554]
  • Zheng Wang, Wen Chen, Yunying Li, Shuying Zhang, He Lou, Xiaoyan Lu, Xiaohui Fan. Reduning injection and its effective constituent luteoloside protect against sepsis partly via inhibition of HMGB1/TLR4/NF-κB/MAPKs signaling pathways. Journal of ethnopharmacology. 2021 Apr; 270(?):113783. doi: 10.1016/j.jep.2021.113783. [PMID: 33421596]
  • Jun Gu Kim, Jin Woo Lee, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang. Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production. Journal of natural products. 2021 03; 84(3):562-569. doi: 10.1021/acs.jnatprod.0c01121. [PMID: 33667099]
  • Alessandro De Stefano, Sabrina Caporali, Nicola Di Daniele, Valentina Rovella, Carmine Cardillo, Francesca Schinzari, Marilena Minieri, Massimo Pieri, Eleonora Candi, Sergio Bernardini, Manfredi Tesauro, Alessandro Terrinoni. Anti-Inflammatory and Proliferative Properties of Luteolin-7-O-Glucoside. International journal of molecular sciences. 2021 Jan; 22(3):. doi: 10.3390/ijms22031321. [PMID: 33525692]
  • Stefania Monari, Maura Ferri, Beatrice Montecchi, Mirko Salinitro, Annalisa Tassoni. Phytochemical characterization of raw and cooked traditionally consumed alimurgic plants. PloS one. 2021; 16(8):e0256703. doi: 10.1371/journal.pone.0256703. [PMID: 34437649]
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  • Faten Emad, Ali K Khalafalah, Magdi A El Sayed, Abou-Elhamd H Mohamed, Marc Stadler, Soleiman E Helaly. Three new polyacetylene glycosides (PAGs) from the aerial part of Launaea capitata (Asteraceae) with anti-biofilm activity against Staphylococcus aureus. Fitoterapia. 2020 Jun; 143(?):104548. doi: 10.1016/j.fitote.2020.104548. [PMID: 32209391]
  • Izabela Szymborska-Sandhu, Jarosław L Przybył, Olga Kosakowska, Katarzyna Bączek, Zenon Węglarz. Chemical Diversity of Bastard Balm (Melittis melisophyllum L.) as Affected by Plant Development. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102421. [PMID: 32455929]
  • Bharath Kumar Velmurugan, Jen-Tsun Lin, B Mahalakshmi, Yi-Ching Chuang, Chia-Chieh Lin, Yu-Sheng Lo, Ming-Ju Hsieh, Mu-Kuan Chen. Luteolin-7-O-Glucoside Inhibits Oral Cancer Cell Migration and Invasion by Regulating Matrix Metalloproteinase-2 Expression and Extracellular Signal-Regulated Kinase Pathway. Biomolecules. 2020 03; 10(4):. doi: 10.3390/biom10040502. [PMID: 32224968]
  • Ewa Witkowska-Banaszczak, Violetta Krajka-Kuźniak, Katarzyna Papierska. The effect of luteolin 7-glucoside, apigenin 7-glucoside and Succisa pratensis extracts on NF-κB activation and α-amylase activity in HepG2 cells. Acta biochimica Polonica. 2020 Mar; 67(1):41-47. doi: 10.18388/abp.2020_2894. [PMID: 32129972]
  • Reham S Ibrahim, Asmaa Khairy, Hala H Zaatout, Hala M Hammoda, Aly M Metwally, Asmaa M Salman. Chemometric evaluation of alfalfa sprouting impact on its metabolic profile using HPTLC fingerprint-efficacy relationship analysis modelled with partial least squares regression. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 179(?):112990. doi: 10.1016/j.jpba.2019.112990. [PMID: 31791836]
  • Jang Hoon Kim, Chang Hyun Jin. Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-O-Glucopyranoside, on Soluble Epoxide Hydrolase from Capsicum chinense. Biomolecules. 2020 01; 10(2):. doi: 10.3390/biom10020180. [PMID: 31991570]
  • Young H Seo, Shin-Young Kang, Ji-Sun Shin, Seung M Ryu, A Y Lee, Goya Choi, Byeong C Moon, Dae-Sik Jang, Sang H Shim, Dongho Lee, Kyung-Tae Lee, Jun Lee. Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages. Journal of natural products. 2019 12; 82(12):3379-3385. doi: 10.1021/acs.jnatprod.9b00697. [PMID: 31747281]
  • Heba Abd El Hady El Gizawy, Mohammed Abdalla Hussein, Essam Abdel-Sattar. Biological activities, isolated compounds and HPLC profile of Verbascum nubicum. Pharmaceutical biology. 2019 Dec; 57(1):485-497. doi: 10.1080/13880209.2019.1643378. [PMID: 31401911]
  • Perihan Koysu, Nusret Genc, Mahfuz Elmastas, Huseyin Aksit, Ramazan Erenler. Isolation, identification of secondary metabolites from Salvia absconditiflora and evaluation of their antioxidative properties. Natural product research. 2019 Dec; 33(24):3592-3595. doi: 10.1080/14786419.2018.1488700. [PMID: 30445824]
  • Aleksandra Maria Juszczak, Marijana Zovko-Končić, Michał Tomczyk. Recent Trends in the Application of Chromatographic Techniques in the Analysis of Luteolin and Its Derivatives. Biomolecules. 2019 11; 9(11):. doi: 10.3390/biom9110731. [PMID: 31726801]
  • Liyue Qin, Ziyu Chen, Liu Yang, Hailian Shi, Hui Wu, Beibei Zhang, Weiqi Zhang, Qi Xu, Fei Huang, Xiaojun Wu. Luteolin-7-O-glucoside protects dopaminergic neurons by activating estrogen-receptor-mediated signaling pathway in MPTP-induced mice. Toxicology. 2019 10; 426(?):152256. doi: 10.1016/j.tox.2019.152256. [PMID: 31381935]
  • Hongyan Liu, Shu Zhu, Qian Liu, Yongqing Zhang. Spectrum-effect relationship study between HPLC fingerprints and antioxidant of honeysuckle extract. Biomedical chromatography : BMC. 2019 Oct; 33(10):e4583. doi: 10.1002/bmc.4583. [PMID: 31087668]
  • Antonio Lama-Muñoz, María Del Mar Contreras, Francisco Espínola, Manuel Moya, Antonia de Torres, Inmaculada Romero, Eulogio Castro. Extraction of oleuropein and luteolin-7-O-glucoside from olive leaves: Optimization of technique and operating conditions. Food chemistry. 2019 Sep; 293(?):161-168. doi: 10.1016/j.foodchem.2019.04.075. [PMID: 31151597]
  • Wenlong Li, Xu Yan, Jianchao Pan, Shaoyong Liu, Dongsheng Xue, Haibin Qu. Rapid analysis of the Tanreqing injection by near-infrared spectroscopy combined with least squares support vector machine and Gaussian process modeling techniques. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2019 Jul; 218(?):271-280. doi: 10.1016/j.saa.2019.03.110. [PMID: 31004970]
  • Bo Zhang, Tie-Gui Nan, Jie Xin, Zhi-Lai Zhan, Li-Ping Kang, Yuan Yuan, Bao-Min Wang, Lu-Qi Huang. Development of a colloidal gold-based lateral flow dipstick immunoassay for rapid detection of chlorogenic acid and luteoloside in Flos Lonicerae Japonicae. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):83-88. doi: 10.1016/j.jpba.2019.03.035. [PMID: 30909057]
  • Seung Hwan Hwang, Hyun-Yong Kim, Yanymee N Guillen Quispe, Zhiqiang Wang, Guanglei Zuo, Soon Sung Lim. Aldose Reductase, Protein Glycation Inhibitory and Antioxidant of Peruvian Medicinal Plants: the Case of Tanacetum parthenium L. and Its Constituents. Molecules (Basel, Switzerland). 2019 May; 24(10):. doi: 10.3390/molecules24102010. [PMID: 31130646]
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  • Zhengyan Xia, Yiming Sun, Chengyong Cai, Yong He, Pengcheng Nie. Rapid Determination of Chlorogenic Acid, Luteoloside and 3,5-O-dicaffeoylquinic Acid in Chrysanthemum Using Near-Infrared Spectroscopy. Sensors (Basel, Switzerland). 2019 Apr; 19(9):. doi: 10.3390/s19091981. [PMID: 31035325]
  • Hee Ju Lee, Basanta Dhodary, Ju Yong Lee, Jin-Pyo An, Young-Kyoung Ryu, Kyoung-Shim Kim, Chul-Ho Lee, Won Keun Oh. Dereplication of Components Coupled with HPLC-qTOF-MS in the Active Fraction of Humulus japonicus and It's Protective Effects against Parkinson's Disease Mouse Model. Molecules (Basel, Switzerland). 2019 Apr; 24(7):. doi: 10.3390/molecules24071435. [PMID: 30979037]
  • Zhicong Wang, Rongjie Fu, Jianguo Ji, Bo Chen. [Simultaneous determination of chlorogenic acid and cynaroside contents in Lonicerae Japonica Flos by high resolution sampling two-dimensional liquid chromatography]. Se pu = Chinese journal of chromatography. 2019 Feb; 37(2):201-206. doi: 10.3724/sp.j.1123.2018.10008. [PMID: 30693729]
  • Angélica Ferraz Gomes, Maiara Prates Almeida, Mateus Freire Leite, Stefan Schwaiger, Hermann Stuppner, Maria Halabalaki, Juliano Geraldo Amaral, Jorge Mauricio David. Seasonal variation in the chemical composition of two chemotypes of Lippia alba. Food chemistry. 2019 Feb; 273(?):186-193. doi: 10.1016/j.foodchem.2017.11.089. [PMID: 30292367]
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