cynarin (BioDeep_00000395820)

 

Secondary id: BioDeep_00000003652, BioDeep_00000018734, BioDeep_00000018736, BioDeep_00000230379

natural product PANOMIX_OTCML-2023


代谢物信息卡片


CYCLOHEXANECARBOXYLIC ACID, 1,4-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,5-DIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-

化学式: C25H24O12 (516.1268)
中文名称: 1,4-二咖啡酰奎宁酸, 洋蓟素
谱图信息: 最多检出来源 Viridiplantae(plant) 9.1%

分子结构信息

SMILES: C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)

描述信息

1,4-Di-O-caffeoylquinic acid is a quinic acid.
1,4-Dicaffeoylquinic acid is a natural product found in Urospermum dalechampii, Helminthotheca echioides, and other organisms with data available.
Annotation level-1
1,4-Dicaffeoylquinic acid (1,4-DCQA) is a phenylpropanoid from Xanthii fructus, inhibits LPS-stimulated TNF-α production[1].
1,4-Dicaffeoylquinic acid (1,4-DCQA) is a phenylpropanoid from Xanthii fructus, inhibits LPS-stimulated TNF-α production[1].
Cynarin is an antichoke agent with a variety of biological activities including antioxidant, antihistamic and antiviral activities.
Cynarin is an antichoke agent with a variety of biological activities including antioxidant, antihistamic and antiviral activities.

同义名列表

31 个代谢物同义名

CYCLOHEXANECARBOXYLIC ACID, 1,4-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,5-DIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-; Cyclohexanecarboxylic acid, 1,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-3,5-dihydroxy-, (1alpha,3R,4alpha,5R)-; Cyclohexanecarboxylic acid, 1,4-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,5-dihydroxy-, (1alpha,3alpha,4alpha,5beta)-; rel-(1alpha,3R,4alpha,5R)-1,4-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,5-dihydroxycyclohexanecarboxylic acid; rel-(1alpha,3R,4alpha,5R)-1,4-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,5-dihydroxycyclohexanecarboxylicacid; (1S,2S,3S,4R)-1,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-2,3-dihydroxy-cyclohexanecarboxylic acid; (3R,5R)-1,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-3,5-dihydroxycyclohexane-1-carboxylic acid; (3S,5S)-1,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-3,5-dihydroxycyclohexane-1-carboxylic acid; Cinnamic acid, 3,4-dihydroxy-, 1-carboxy-3,5-dihydroxy-1,4-cyclohexylene ester; 3,4-Dihydroxycinnamic acid 1-carboxy-3,5-dihydroxy-1,4-cyclohexylene ester; 1,4-Bis-(3,4-dihydroxycinnamoyl)quinic acid; Acido, 1,4-dicaffeilchinico [Italian]; 1,4-di-O-caffeoylquinic acid; Acido, 1,4-dicaffeilchinico; 1,4-Dicaffeoylquinic acid; 1,4-Dicaffeylquinic acid; MEGxp0_000656; CIN [Italian]; ACon1_001889; 1,4-Dicqa; cynarin; CIN; (3R,4S,5R)-1,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid; NSC 91529; 1,5-dicaffeoylquinic acid; Dicaffeoylquinic acid; 1,5-Dicaffeoyl quinic acid; 1,3-Dicaffeoylquinic acid; 1,4-DCQA; Cynarine; 1,3-Dicaffeoylquinic acid



数据库引用编号

35 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)

14 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。

亚细胞结构定位 关联基因列表


文献列表

  • Changgui Wu, Shaohua Chen, Yang Liu, Bo Kong, Wei Yan, Tao Jiang, Hao Tian, Zhaoyi Liu, Qi Shi, Yongjun Wang, Qianqian Liang, Xiaobing Xi, Hao Xu. Cynarin suppresses gouty arthritis induced by monosodium urate crystals. Bioengineered. 2022 05; 13(5):11782-11793. doi: 10.1080/21655979.2022.2072055. [PMID: 35546047]
  • Kateryna Murlanova, Netanela Cohen, Anna Pinkus, Liudmila Vinnikova, Mikhail Pletnikov, Michael Kirby, Jonathan Gorelick, Elyashiv Drori, Albert Pinhasov. Antidepressant-like effects of a chlorogenic acid- and cynarine-enriched fraction from Dittrichia viscosa root extract. Scientific reports. 2022 03; 12(1):3647. doi: 10.1038/s41598-022-04840-9. [PMID: 35256610]
  • Rong Li, Mingfang Tao, Ting Wu, Zhang Zhuo, Tingting Xu, Siyi Pan, Xiaoyun Xu. A promising strategy for investigating the anti-aging effect of natural compounds: a case study of caffeoylquinic acids. Food & function. 2021 Sep; 12(18):8583-8593. doi: 10.1039/d1fo01383a. [PMID: 34338272]
  • Zhe Wang, Shixi Wang, Baoli Qin. An LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and 1-O-acetylbritannilactone in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2017 Mar; 31(3):. doi: 10.1002/bmc.3811. [PMID: 27518585]
  • Maryam Salami, Mehdi Rahimmalek, Mohammad Hossein Ehtemam. Inhibitory effect of different fennel (Foeniculum vulgare) samples and their phenolic compounds on formation of advanced glycation products and comparison of antimicrobial and antioxidant activities. Food chemistry. 2016 Dec; 213(?):196-205. doi: 10.1016/j.foodchem.2016.06.070. [PMID: 27451172]
  • Shah Hussain, Cornelia Pezzei, Yüksel Güzel, Matthias Rainer, Christian W Huck, Günther K Bonn. Zirconium silicate assisted removal of residual proteins after organic solvent deproteinization of human plasma, enhancing the stability of the LC-ESI-MS response for the bioanalysis of small molecules. Analytica chimica acta. 2014 Dec; 852(?):284-92. doi: 10.1016/j.aca.2014.09.014. [PMID: 25441909]
  • A Angelini, R Di Pietro, L Centurione, M L Castellani, P Conti, E Porreca, F Cuccurullo. Inhibition of P-glycoprotein-mediated transport by S-adenosylmethionine and cynarin in multidrug-resistant human uterine sarcoma MES-SA/Dx5 cells. Journal of biological regulators and homeostatic agents. 2012 Jul; 26(3):495-504. doi: . [PMID: 23034269]
  • Maksymilian Kulza, Katarzyna Malinowska, Anna Woźniak, Monika Seńczuk-Przybyłowska, Gerard Nowak, Ewa Florek. [Development and validation of method for the determination of cynarin, luteolin in plasma]. Przeglad lekarski. 2012; 69(10):987-91. doi: . [PMID: 23421076]
  • Jianglin Liu, Guifang Dou, Xiaona Dong, Dan Yuan, Xiwei Ji, Zhuona Wu, ZhiYun Meng. An improved LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma and its application to a pharmacokinetic study in patients. Biomedical chromatography : BMC. 2010 Sep; 24(9):935-40. doi: 10.1002/bmc.1388. [PMID: 20058327]
  • Ruolan Gu, Guifang Dou, Jing Wang, Junxing Dong, Zhiyun Meng. Simultaneous determination of 1,5-dicaffeoylquinic acid and its active metabolites in human plasma by liquid chromatography-tandem mass spectrometry for pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jun; 852(1-2):85-91. doi: 10.1016/j.jchromb.2006.12.055. [PMID: 17267301]
  • Mitja Krizman, Dea Baricevic, Mirko Prosek. Determination of phenolic compounds in fennel by HPLC and HPLC-MS using a monolithic reversed-phase column. Journal of pharmaceutical and biomedical analysis. 2007 Jan; 43(2):481-5. doi: 10.1016/j.jpba.2006.07.029. [PMID: 16930913]
  • Guo-Chung Dong, Ping-Hsien Chuang, Michael D Forrest, Yi-Chen Lin, Hueih Min Chen. Immuno-suppressive effect of blocking the CD28 signaling pathway in T-cells by an active component of Echinacea found by a novel pharmaceutical screening method. Journal of medicinal chemistry. 2006 Mar; 49(6):1845-54. doi: 10.1021/jm0509039. [PMID: 16539370]
  • Ting Han, Hui-Liang Li, Yuan Hu, Qiao-Yan Zhang, Bao-Kang Huang, Han-Chen Zheng, Khalid Rahman, Lu-Ping Qin. Phenolic acids in Fructus Xanthii and determination of contents of total phenolic acids in different species and populations of Xanthium in China. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2006 Mar; 4(2):194-8. doi: 10.3736/jcim20060217. [PMID: 16529699]
  • B Yang, Z Y Meng, L P Yan, J X Dong, L B Zou, Z M Tang, G F Dou. Pharmacokinetics and metabolism of 1,5-dicaffeoylquinic acid in rats following a single intravenous administration. Journal of pharmaceutical and biomedical analysis. 2006 Feb; 40(2):417-22. doi: 10.1016/j.jpba.2005.06.037. [PMID: 16143483]
  • Bo Yang, Zhiyun Meng, Junxing Dong, Liangping Yan, Libo Zou, Zhongming Tang, Guifang Dou. Metabolic profile of 1,5-dicaffeoylquinic acid in rats, an in vivo and in vitro study. Drug metabolism and disposition: the biological fate of chemicals. 2005 Jul; 33(7):930-6. doi: 10.1124/dmd.104.002154. [PMID: 15802385]
  • T Wesołowska, E Szmatłoch, D Wira, J Pieczul-Mróz, J Gregorczyk. [Phospholipid fractions and free fatty acids in the serum of patients with hypertriglyceridemia treated with 1,5-dicaffeequinine acid]. Przeglad lekarski. 1986; 43(7):527-30. doi: NULL. [PMID: 3775065]