1,5-Dicaffeoylquinic acid (BioDeep_00000003652)

Main id: BioDeep_00000395820

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

化学式: C25H24O12 (516.1268)
中文名称: 洋蓟素(1,3-二咖啡酰奎宁酸), 洋蓟素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(ccc(cc1O)/C=C/C(=O)O[C@H]1[C@@H](O)[C@@H](C[C@@](C1)(C(=O)O)OC(=O)/C=C/c1cc(c(cc1)O)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)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

描述信息

Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke. Chemically, it is an ester formed from quinic acid and two units of caffeic acid. 1,5-Dicaffeoylquinic acid is found in cardoon, globe artichoke, and fennel.
1,5-Dicaffeoylquinic acid is found in cardoon. Cynarine is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke. Chemically, it is an ester formed from quinic acid and two units of caffeic acid. (Wikipedia
C78276 - Agent Affecting Digestive System or Metabolism > C66913 - Cholagogues or Choleretic Agents
D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics
[Raw Data] CBA70_Cynarin_neg_30eV.txt
[Raw Data] CBA70_Cynarin_neg_20eV.txt
[Raw Data] CBA70_Cynarin_pos_30eV.txt
[Raw Data] CBA70_Cynarin_neg_50eV.txt
[Raw Data] CBA70_Cynarin_pos_20eV.txt
[Raw Data] CBA70_Cynarin_neg_40eV.txt
[Raw Data] CBA70_Cynarin_neg_10eV.txt
[Raw Data] CBA70_Cynarin_pos_10eV.txt
[Raw Data] CBA70_Cynarin_pos_40eV.txt
[Raw Data] CBA70_Cynarin_pos_50eV.txt
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

20 个代谢物同义名

(1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid; 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate); cynarin, (1alpha,3alpha,4alpha,5beta)-isomer; 1,5-di-O-Caffeoylquinic acid; 1,5-dicaffeoylquinic acid; 1,3-Dicaffeoylquinic acid; 1,3-Dicaffeoylquinate; 1,5-Dicaffeoylquinate; nivellipid; listricol; listrocol; phemocil; cinarine; cinarina; Cynarine; Cynarex; cynarix; cinarin; cynarin; 1,3-Dicaffeoylquinic acid



数据库引用编号

30 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)

42 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
Cytoplasm 9 BCL2, CASP3, CAT, MAPK14, MAPK3, PIK3CA, TP53, TYR, XDH
Peripheral membrane protein 2 ACHE, GORASP1
Endoplasmic reticulum membrane 1 BCL2
Nucleus 7 ACHE, BCL2, CASP3, GABPA, MAPK14, MAPK3, TP53
cytosol 9 BCL2, CASP3, CAT, CD28, MAPK14, MAPK3, PIK3CA, TP53, XDH
centrosome 1 TP53
nucleoplasm 5 CASP3, GABPA, MAPK14, MAPK3, TP53
Cell membrane 4 ACHE, CD28, CD80, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 GORASP1
Synapse 1 ACHE
cell surface 4 ACHE, CD28, CD80, TNF
glutamatergic synapse 3 CASP3, MAPK14, MAPK3
Golgi apparatus 3 ACHE, GORASP1, MAPK3
Golgi membrane 1 GORASP1
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
Lysosome 2 GAA, TYR
plasma membrane 8 ACHE, CD28, CD80, GAA, IFNLR1, MAPK3, PIK3CA, TNF
Membrane 7 ACHE, BCL2, CAT, CD80, GAA, IFNLR1, TP53
caveola 1 MAPK3
extracellular exosome 3 CAT, GAA, MMP9
Lysosome membrane 1 GAA
endoplasmic reticulum 2 BCL2, TP53
extracellular space 6 ACHE, CCL2, IL6, MMP9, TNF, XDH
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 3 ACHE, PIK3CA, TYR
intercalated disc 1 PIK3CA
mitochondrion 5 BCL2, CAT, MAPK14, MAPK3, TP53
protein-containing complex 3 BCL2, CAT, TP53
intracellular membrane-bounded organelle 3 CAT, GAA, TYR
postsynaptic density 1 CASP3
Single-pass type I membrane protein 3 CD80, IFNLR1, TYR
Secreted 4 ACHE, CCL2, GAA, IL6
extracellular region 8 ACHE, CAT, CCL2, GAA, IL6, MAPK14, MMP9, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 TP53
mitochondrial matrix 2 CAT, TP53
Extracellular side 1 ACHE
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 CD28, CD80, TNF
Secreted, extracellular space, extracellular matrix 1 MMP9
nucleolus 1 TP53
Melanosome membrane 1 TYR
Early endosome 1 MAPK3
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK3
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 2 CAT, MAPK3
cis-Golgi network 1 GORASP1
Peroxisome 2 CAT, XDH
basement membrane 1 ACHE
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 1 MMP9
nuclear speck 1 MAPK14
Late endosome 1 MAPK3
chromatin 2 GABPA, TP53
phagocytic cup 1 TNF
cytoskeleton 1 MAPK3
spindle pole 1 MAPK14
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 TP53
nuclear envelope 1 MAPK3
Membrane, caveola 1 MAPK3
tertiary granule membrane 1 GAA
Melanosome 1 TYR
side of membrane 1 ACHE
germ cell nucleus 1 TP53
replication fork 1 TP53
myelin sheath 1 BCL2
pseudopodium 1 MAPK3
ficolin-1-rich granule lumen 3 CAT, MAPK14, MMP9
secretory granule lumen 2 CAT, MAPK14
endoplasmic reticulum lumen 2 IL6, MAPK3
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
tertiary granule lumen 1 MMP9
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
immunological synapse 1 CD28
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
[Isoform 1]: Nucleus 1 TP53
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
[Isoform 3]: Cell surface 1 CD28
protein complex involved in cell adhesion 2 CD28, CD80
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Rei Uranishi, Raju Aedla, Doaa H M Alsaadi, Dongxing Wang, Ken Kusakari, Hirotaka Osaki, Koji Sugimura, Takashi Watanabe. Evaluation of Environmental Factor Effects on the Polyphenol and Flavonoid Content in the Leaves of Chrysanthemum indicum L. and Its Habitat Suitability Prediction Mapping. Molecules (Basel, Switzerland). 2024 Feb; 29(5):. doi: 10.3390/molecules29050927. [PMID: 38474439]
  • Pu Zhang, Kewei Rong, Jiadong Guo, Lei Cui, Keyu Kong, Chen Zhao, Huan Yang, Hongtao Xu, An Qin, Peixiang Ma, Xiao Yang, Jie Zhao. Cynarin alleviates intervertebral disc degeneration via protecting nucleus pulposus cells from ferroptosis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Aug; 165(?):115252. doi: 10.1016/j.biopha.2023.115252. [PMID: 37536034]
  • Chang Ho Yoon, Hyun-Jae Jang, Jin Suk Ryu, Jung Hwa Ko, Kyung-Seop Ahn, Sei-Ryang Oh, Jang-Hee Oh, Jin Ho Chung, Joo Youn Oh. 1,5-Dicaffeoylquinic acid from Pseudognaphalium affine ameliorates dry eye disease via suppression of inflammation and protection of the ocular surface. The ocular surface. 2023 Jun; 29(?):469-479. doi: 10.1016/j.jtos.2023.06.016. [PMID: 37390940]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Cheng-Wei Lu, Tzu-Yu Lin, Pei-Wen Hsieh, Kuan-Ming Chiu, Ming-Yi Lee, Su-Jane Wang. Cynarin, a caffeoylquinic acid derivative in artichoke, inhibits exocytotic glutamate release from rat cortical nerve terminals (synaptosomes). Neurochemistry international. 2023 May; 167(?):105537. doi: 10.1016/j.neuint.2023.105537. [PMID: 37164158]
  • Chun-Yong Sun, Le-Le Yang, Pan Zhao, Pei-Zheng Yan, Jia Li, Dong-Sheng Zhao. Mechanisms of Cynarine for treatment of non-alcoholic fatty liver disease based on the integration of network pharmacology, molecular docking and cell experiment. Hereditas. 2022 Dec; 159(1):44. doi: 10.1186/s41065-022-00256-7. [PMID: 36451177]
  • 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]
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  • Nuramina Mamat, Xue Ying Lu, Maidina Kabas, Haji Akber Aisa. Potential anti-vitiligo properties of cynarine extracted from Vernonia anthelmintica (L.) Willd. International journal of molecular medicine. 2018 Nov; 42(5):2665-2675. doi: 10.3892/ijmm.2018.3861. [PMID: 30226537]
  • Yankun Chen, Xi Chen, Ganggang Luo, Xu Zhang, Fang Lu, Liansheng Qiao, Wenjing He, Gongyu Li, Yanling Zhang. Discovery of Potential Inhibitors of Squalene Synthase from Traditional Chinese Medicine Based on Virtual Screening and In Vitro Evaluation of Lipid-Lowering Effect. Molecules (Basel, Switzerland). 2018 Apr; 23(5):. doi: 10.3390/molecules23051040. [PMID: 29710800]
  • Zineb Hakkou, Alexandre Maciuk, Veronique Leblais, Nour Elhouda Bouanani, Hassane Mekhfi, Mohammed Bnouham, Mohammed Aziz, Abderrahime Ziyyat, Abdur Rauf, Taibi Ben Hadda, Usama Shaheen, Seema Patel, Rodolphe Fischmeister, Abdelkhaleq Legssyer. Antihypertensive and vasodilator effects of methanolic extract of Inula viscosa: Biological evaluation and POM analysis of cynarin, chlorogenic acid as potential hypertensive. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Sep; 93(?):62-69. doi: 10.1016/j.biopha.2017.06.015. [PMID: 28623784]
  • Peng-Fei Yang, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, Pei-Cheng Zhang. Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium. Journal of natural products. 2017 04; 80(4):1028-1033. doi: 10.1021/acs.jnatprod.6b01026. [PMID: 28248102]
  • 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]
  • Jing Tong, Qi-Gui Mo, Bing-Xin Ma, Lan-Lan Ge, Gao Zhou, You-Wei Wang. The protective effects of Cichorium glandulosum seed and cynarin against cyclophosphamide and its metabolite acrolein-induced hepatotoxicity in vivo and in vitro. Food & function. 2017 Jan; 8(1):209-219. doi: 10.1039/c6fo01531j. [PMID: 27966724]
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  • Meryem Topal, Hulya Gocer, Fevzi Topal, Pınar Kalin, Leyla Polat Köse, İlhami Gülçin, Kader C Çakmak, Murat Küçük, Lokman Durmaz, Ahmet C Gören, Saleh H Alwasel. Antioxidant, antiradical, and anticholinergic properties of cynarin purified from the Illyrian thistle (Onopordum illyricum L.). Journal of enzyme inhibition and medicinal chemistry. 2016; 31(2):266-75. doi: 10.3109/14756366.2015.1018244. [PMID: 25792498]
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  • Veronika Petruľová, Zuzana Dučaiová, Miroslav Repčák. Short-term UV-B dose stimulates production of protective metabolites in Matricaria chamomilla leaves. Photochemistry and photobiology. 2014 Sep; 90(5):1061-8. doi: 10.1111/php.12300. [PMID: 24913599]
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  • Hosakatte Niranjana Murthy, Yun-Soo Kim, So-Young Park, Kee-Yoeup Paek. Biotechnological production of caffeic acid derivatives from cell and organ cultures of Echinacea species. Applied microbiology and biotechnology. 2014 Sep; 98(18):7707-17. doi: 10.1007/s00253-014-5962-6. [PMID: 25077780]
  • Ning Xia, Andrea Pautz, Ursula Wollscheid, Gisela Reifenberg, Ulrich Förstermann, Huige Li. Artichoke, cynarin and cyanidin downregulate the expression of inducible nitric oxide synthase in human coronary smooth muscle cells. Molecules (Basel, Switzerland). 2014 Mar; 19(3):3654-68. doi: 10.3390/molecules19033654. [PMID: 24662080]
  • Zhi-Yu Zhang, Duan-Yun Si, Xiu-Lin Yi, Chang-Xiao Liu. Inhibitory effect of medicinal plant-derived carboxylic acids on the human transporters hOAT1, hOAT3, hOATP1B1, and hOATP2B1. Chinese journal of natural medicines. 2014 Feb; 12(2):131-8. doi: 10.1016/s1875-5364(14)60021-2. [PMID: 24636064]
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  • Maha Ahmed Aboul-Ela, Abdalla Mohamed El-Lakany, Safa Mohamed Shams Eldin, Hala Mostafa Hammoda. A new validated HPTLC method for quantitative determination of 1, 5-dicaffeoylquinic acid in Inula crithmoides roots. Pakistan journal of pharmaceutical sciences. 2012 Oct; 25(4):721-5. doi: ". [PMID: 23009986]
  • 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]
  • Zheng Sun, Jingnan Chen, Jinyu Ma, Yue Jiang, Mingfu Wang, Guixing Ren, Feng Chen. Cynarin-rich sunflower (Helianthus annuus) sprouts possess both antiglycative and antioxidant activities. Journal of agricultural and food chemistry. 2012 Mar; 60(12):3260-5. doi: 10.1021/jf300737y. [PMID: 22394088]
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  • 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]
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  • 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]
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