1,5-Dicaffeoylquinic acid (BioDeep_00000230379)

Main id: BioDeep_00000395820

Secondary id: BioDeep_00000003652, BioDeep_00000018734, BioDeep_00000402752, BioDeep_00000403165

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


1,3-Dicaffeoylquinic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)

化学式: C25H24O12 (516.1267703999999)
中文名称: 1,3-二咖啡酰奎宁酸, 1,5-二咖啡酰奎宁酸, 菜蓟素, 洋蓟素, 洋蓟酸, 朝鲜蓟, 1,3-二咖啡酰奎宁酸, 洋蓟素(1,3-二咖啡酰奎宁酸)
谱图信息: 最多检出来源 Viridiplantae(plant) 8.89%

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+

描述信息

1,3-dicaffeoylquinic acid is an alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid. It has a role as a plant metabolite. It is a quinic acid and an alkyl caffeate ester. It is functionally related to a trans-caffeic acid and a (-)-quinic acid. It is a conjugate acid of a 1,3-dicaffeoylquinate.
Cynarine is a natural product found in Saussurea involucrata, Helichrysum italicum, and other organisms with data available.
See also: Cynara scolymus leaf (part of).
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
An alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid.
C78276 - Agent Affecting Digestive System or Metabolism > C66913 - Cholagogues or Choleretic Agents
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

59 个代谢物同义名

1,3-Dicaffeoylquinic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts); (1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-1,3-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-4,5-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID; (1R-(1alpha,3alpha,4alpha,5beta))-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid; Cyclohexanecarboxylic acid, 1,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxy-, (1R,3R,4S,5R)-; (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid; Cyclohexanecarboxylic acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1R,3R,4S,5R)-; (1R,3R,4S,5R)-1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid; (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid; Cyclohexanecarboxylic acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-; 3,4-Dihydroxycinnamic acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; 3,4-Dihydroxycinnamic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate); Cynarine;1,3-Dicaffeoylquinic acid;1,5-DQA;1,5-Dicaffeoylquinic acid; Caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester; 1-O,3-O-Bis(3,4-dihydroxycinnamoyl)chinasaeure; cynarin, (1alpha,3alpha,4alpha,5beta)-isomer; 1,3-Dicaffeoylquinic acid, >=98\\% (HPLC); Chinasaeure-1,3-dikaffeesaeureester; Quinic acid 1,5-dicaffeic ester; 1_5_dihydrocaffeoylquinic_acid; 1,5-di-O-Caffeoylquinic acid; Cynarin, analytical standard; 1,5-Dicaffeoyl quinic acid; 1,5-dicaffeoylquinic acid; 1,3-Dicaffeoylquinic acid; 1,5-Dicaffeoylqunic acid; 1,3-Dicaffeoylquinate; Cynarine [INN:WHO-DD]; 1,5-Dicaffeoylquinate; 1,3-Dicaffeoylquinic; Cynarine [WHO-DD]; Cynarine (MART.); Cynarine [MART.]; UNII-85D81U9JAV; Cynarine [INN]; Tox21_111176_1; Cynarine [MI]; Tox21_111176; 85D81U9JAV; nivellipid; Cynaricine; 1,3-Dicqa; listricol; listrocol; cynarinum; Plemocil; phemocil; cinarine; cinarina; Cynarine; Cynarex; cynarix; cinarin; cynarin; 1,3-O-Dicaffeoylquinic acid



数据库引用编号

26 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)

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]
  • 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]
  • Reham Wagdy, Reham M Abdelkader, Ahmed H El-Khatib, Michael W Linscheid, Nabila Hamdi, Heba Handoussa. Neuromodulatory Activity of Dietary Phenolics Derived from Corchorus olitorius L. Journal of food science. 2019 May; 84(5):1012-1022. doi: 10.1111/1750-3841.14587. [PMID: 31017668]
  • 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]
  • 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]
  • 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]
  • Bui Thi Thuy Luyen, Bui Huu Tai, Nguyen Phuong Thao, Ji Yun Cha, Hoon Yeon Lee, Young Mi Lee, Young Ho Kim. Anti-inflammatory components of Chrysanthemum indicum flowers. Bioorganic & medicinal chemistry letters. 2015 Jan; 25(2):266-9. doi: 10.1016/j.bmcl.2014.11.054. [PMID: 25497988]
  • 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]
  • 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]
  • Y V Vereshchagina, V P Bulgakov, V P Grigorchuk, V G Rybin, G N Veremeichik, G K Tchernoded, T Y Gorpenchenko, O G Koren, N H T Phan, N T Minh, L T Chau, Y N Zhuravlev. The rolC gene increases caffeoylquinic acid production in transformed artichoke cells. Applied microbiology and biotechnology. 2014 Sep; 98(18):7773-80. doi: 10.1007/s00253-014-5869-2. [PMID: 24938208]
  • 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]
  • Giuseppe Colla, Youssef Rouphael, Mariateresa Cardarelli, Eva Svecova, Elvira Rea, Luigi Lucini. Effects of saline stress on mineral composition, phenolic acids and flavonoids in leaves of artichoke and cardoon genotypes grown in floating system. Journal of the science of food and agriculture. 2013 Mar; 93(5):1119-27. doi: 10.1002/jsfa.5861. [PMID: 22936423]
  • Kil Sun Yoo, Eun Jin Lee, Daniel Leskovar, Bhimanagouda S Patil. Development of an automated method for Folin-Ciocalteu total phenolic assay in artichoke extracts. Journal of food science. 2012 Dec; 77(12):C1279-84. doi: 10.1111/j.1750-3841.2012.02973.x. [PMID: 23163965]
  • 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]
  • Donatella Negro, Vincenzo Montesano, Sabrina Grieco, Pasquale Crupi, Giulio Sarli, Antonino De Lisi, Gabriella Sonnante. Polyphenol compounds in artichoke plant tissues and varieties. Journal of food science. 2012 Feb; 77(2):C244-52. doi: 10.1111/j.1750-3841.2011.02531.x. [PMID: 22251096]
  • 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]
  • Paula N Brown, Michael Chan, Lori Paley, Joseph M Betz. Determination of major phenolic compounds in Echinacea spp. raw materials and finished products by high-performance liquid chromatography with ultraviolet detection: single-laboratory validation matrix extension. Journal of AOAC International. 2011 Sep; 94(5):1400-10. doi: 10.5740/jaoacint.11-142. [PMID: 22165004]
  • Shan Qin, Xuesen Wen. [Simultaneous determination of 6 active components in Chrysanthemum morifolium by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jun; 36(11):1474-7. doi: 10.4268/cjcmm20111115. [PMID: 22779181]
  • Katharina Franziska Pirker, Bernard Albert Goodman. Caffeoylquinic acid derived free radicals identified during antioxidant reactions of bitter tea (Ilex latifolia and Ilex kudincha). Food & function. 2010 Dec; 1(3):262-8. doi: 10.1039/c0fo00085j. [PMID: 21776475]
  • 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]
  • A Sannia. [Phytotherapy with a mixture of dry extracts with hepato-protective effects containing artichoke leaves in the management of functional dyspepsia symptoms]. Minerva gastroenterologica e dietologica. 2010 Jun; 56(2):93-9. doi: ". [PMID: 20485248]
  • Rosalia Ferracane, Giulia Graziani, Monica Gallo, Vincenzo Fogliano, Alberto Ritieni. Metabolic profile of the bioactive compounds of burdock (Arctium lappa) seeds, roots and leaves. Journal of pharmaceutical and biomedical analysis. 2010 Jan; 51(2):399-404. doi: 10.1016/j.jpba.2009.03.018. [PMID: 19375261]
  • E J Verspohl, M Ploch, T Windeck, M Klaes, T Schmidt, K Bauer. Effect of two artichoke extracts (36_U and 36_EB) on rat ileum (with respect to bowel syndrome) and the peristaltic threshold. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Nov; 15(11):1002-9. doi: 10.1016/j.phymed.2008.02.011. [PMID: 18424104]
  • 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]
  • B Benedek, N Geisz, W Jäger, T Thalhammer, B Kopp. Choleretic effects of yarrow (Achillea millefolium s.l.) in the isolated perfused rat liver. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Nov; 13(9-10):702-6. doi: 10.1016/j.phymed.2005.10.005. [PMID: 16303291]
  • Susan J Murch, Sriyani E Peiris, Wendy L Shi, S M A Zobayed, Praveen K Saxena. Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition. Plant cell reports. 2006 Jun; 25(6):522-32. doi: 10.1007/s00299-006-0118-5. [PMID: 16477405]
  • 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]
  • 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]
  • E Speroni, R Cervellati, P Govoni, S Guizzardi, C Renzulli, M C Guerra. Efficacy of different Cynara scolymus preparations on liver complaints. Journal of ethnopharmacology. 2003 Jun; 86(2-3):203-11. doi: 10.1016/s0378-8741(03)00076-x. [PMID: 12738088]
  • I Koubaa, M Damak. A new dilignan from Cynara cardunculus. Fitoterapia. 2003 Feb; 74(1-2):18-22. doi: 10.1016/s0367-326x(02)00300-3. [PMID: 12628389]
  • Ari Tolonen, Topi Joutsamo, Sampo Mattlla, Terttu Kämäräinen, Jorma Jalonen. Identification of isomeric dicaffeoylquinic acids from Eleutherococcus senticosus using HPLC-ESI/TOF/MS and 1H-NMR methods. Phytochemical analysis : PCA. 2002 Nov; 13(6):316-28. doi: 10.1002/pca.663. [PMID: 12494749]
  • Shannon E Binns, John F Livesey, John T Arnason, Bernard R Baum. Phytochemical variation in echinacea from roots and flowerheads of wild and cultivated populations. Journal of agricultural and food chemistry. 2002 Jun; 50(13):3673-87. doi: 10.1021/jf011439t. [PMID: 12059142]
  • Magali Laasonen, Tero Wennberg, Tuulikki Harmia-Pulkkinen, Heikki Vuorela. Simultaneous analysis of alkamides and caffeic acid derivatives for the identification of Echinacea purpurea, Echinacea angustifolia, Echinacea pallida and Parthenium integrifolium roots. Planta medica. 2002 Jun; 68(6):572-4. doi: 10.1055/s-2002-32561. [PMID: 12094312]
  • F Pérez-García, T Adzet, S Cañigueral. Activity of artichoke leaf extract on reactive oxygen species in human leukocytes. Free radical research. 2000 Nov; 33(5):661-5. doi: 10.1080/10715760000301171. [PMID: 11200096]
  • A Carnat, A Heitz, D Fraisse, A P Carnat, J L Lamaison. Major dicaffeoylquinic acids from Artemisia vulgaris. Fitoterapia. 2000 Sep; 71(5):587-9. doi: 10.1016/s0367-326x(00)00163-5. [PMID: 11449516]
  • 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]
  • Y Kiso, M Tohkin, H Hikino. Assay method for antihepatotoxic activity using galactosamine-induced cytotoxicity in primary-cultured hepatocytes. Journal of natural products. 1983 Nov; 46(6):841-7. doi: 10.1021/np50030a003. [PMID: 6677713]
  • O Palacz, D Czepita, J Wójcicki. [Electroretinographic investigations in subjects in chronic exposure to carbon disulphide: III. Cynarex effect on ERG related to blood lipid pattern (author's transl)]. Klinika oczna. 1981 Apr; 83(4-5):223-5. doi: ". [PMID: 6895532]
  • M Woyke, H Cwajda, J Wójcicki, K Kośmider. [Platelet aggregation in workers chronically exposed to carbon disulfide and subjected to prophylactic treatment with Cynarex]. Medycyna pracy. 1981; 32(4):261-4. doi: ". [PMID: 6895541]
  • G Vorberg. [Cynarix. Therapeutic experiences with Cynarix in disorders of fat metabolism in general practice]. ZFA. Zeitschrift fur Allgemeinmedizin. 1980 Sep; 56(25):1598-602. doi: ". [PMID: 6893780]
  • W Scheffler, W Schwartzkopff. Frequently used lipid-lowering drugs having no guaranteed effect. Artery. 1980; 8(2):120-7. doi: ". [PMID: 6893927]