1,3-Dicaffeoylquinic acid (BioDeep_00000018734)

Main id: BioDeep_00000395820

 

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


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

化学式: C25H24O12 (516.1267703999999)
中文名称: 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: C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)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

1,3-Dicaffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313)
D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics
1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative that exhibits antioxidant activity and radical scavenging activity.
1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative that exhibits antioxidant activity and radical scavenging activity.
1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative that exhibits antioxidant activity and radical scavenging activity.
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

23 个代谢物同义名

(1S,3R,4R,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-1,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylate; 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate); cynarin, (1alpha,3alpha,4alpha,5beta)-isomer; 15-O-trans-Dicaffeoylquinic acid; 15-O-trans-Dicaffeoylquinate; 1,3-Di-O-caffeoylquinic acid; 1,5-Dicaffeoylquinic acid?; 1,5-dicaffeoylquinic acid; 1,3-Dicaffeoylquinic acid; 1,3-Dicaffeoylquinate; nivellipid; listricol; listrocol; phemocil; cinarine; cinarina; Cynarine; Cynarex; cynarix; cinarin; cynarin; 1,3-O-Dicaffeoylquinic acid



数据库引用编号

18 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)

17 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

  • 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]
  • 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]
  • Shiv Bharadwaj, Sherif Aly El-Kafrawy, Thamir A Alandijany, Leena Hussein Bajrai, Altaf Ahmad Shah, Amit Dubey, Amaresh Kumar Sahoo, Umesh Yadava, Mohammad Amjad Kamal, Esam Ibraheem Azhar, Sang Gu Kang, Vivek Dhar Dwivedi. Structure-Based Identification of Natural Products as SARS-CoV-2 Mpro Antagonist from Echinacea angustifolia Using Computational Approaches. Viruses. 2021 02; 13(2):. doi: 10.3390/v13020305. [PMID: 33672054]
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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]
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  • 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]
  • Przemysław Sitarek, Ewa Skała, Monika Toma, Marzena Wielanek, Janusz Szemraj, Tomasz Skorski, Adam J Białas, Tomasz Sakowicz, Tomasz Kowalczyk, Maciej Radek, Halina Wysokińska, Tomasz Śliwiński. Transformed Root Extract of Leonurus sibiricus Induces Apoptosis through Intrinsic and Extrinsic Pathways in Various Grades of Human Glioma Cells. Pathology oncology research : POR. 2017 Jul; 23(3):679-687. doi: 10.1007/s12253-016-0170-6. [PMID: 28032310]
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  • 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]
  • 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]
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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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