4,5-Di-O-caffeoylquinic acid (BioDeep_00000017258)

Main id: BioDeep_00000230881

Secondary id: BioDeep_00000402884, BioDeep_00000616461

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Cytotoxicity


代谢物信息卡片


Cyclohexanecarboxylic acid, 3,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,5-dihydroxy-, (1R,3R,4S,5R)-

化学式: C25H24O12 (516.1267703999999)
中文名称: 异绿原酸 C, 异绿原酸B, 异绿原酸C
谱图信息: 最多检出来源 Viridiplantae(plant) 1.33%

分子结构信息

SMILES: C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)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(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

描述信息

4,5-di-O-caffeoylquinic acid is a quinic acid.
4,5-Dicaffeoylquinic acid is a natural product found in Centaurea bracteata, Strychnos axillaris, and other organisms with data available.
See also: Lonicera japonica flower (part of); Stevia rebaudiuna Leaf (part of).
Isolated from coffee, Brazilian propolis and maté. 4,5-Di-O-caffeoylquinic acid is found in many foods, some of which are carrot, robusta coffee, coffee, and coffee and coffee products.
4,5-Di-O-caffeoylquinic acid is found in arabica coffee. 4,5-Di-O-caffeoylquinic acid is isolated from coffee and Brazilian propoli
3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3].
3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3].
4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3].
4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3].

同义名列表

35 个代谢物同义名

Cyclohexanecarboxylic acid, 3,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,5-dihydroxy-, (1R,3R,4S,5R)-; (1R,3R,4S,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid; Cyclohexanecarboxylic acid,3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,5-dihydroxy-,(1R,3R,4S,5R)-; (1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-3,4-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylate; (1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid; (4S,1R,3R,5R)-3,4-Bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexanecarboxylic acid; (1R,3R,4S,5R)-3,4-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,5-dihydroxy-cyclohexanecarboxylic acid; (1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylic acid; (1R,3R,4S,5R)-3,4-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,5-dihydroxycyclohexanecarboxylicacid; (1R,3R,4S,5R)-3,4-bis(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,5-dihydroxycyclohexanecarboxylic acid; 3,4-Bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,5-dihydroxycyclohexanecarboxylic acid; 4,5-Di-O-caffeoylquinic acid, >=85\\% (LC/MS-ELSD); 4,5-Bis(3,4-dihydroxycinnamoyl)quinic acid; methyl 3,5-di-O-caffeoyl quinate; methyl-3,5-di-O-caffeoylquinate; 3,4-di-O-caffeoylquinic acid; 4,5-Di-O-caffeoylquinic acid; 3,4-di-O-caffeoylquinicacid; Isochlorogenic acid C(4,5); 4,5-Dicaffeoylquinic acids; 4,5-Dicaffeoylquinic acid; 3,4-dicaffeoylquinic acid; 4,5-Di-O-caffeoylquinate; Isochlorogenic acid C; isochlorogenic-acid-c; isochlorogenic acid B; sochlorogenic acid c; UNII-E57A0DKE0B; Isochlorogenic; ACon1_000313; E57A0DKE0B; 3,4-DICQA; 4,5-DCQA; 3,4-DCQA



数据库引用编号

17 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)

65 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

  • Hanjiao He, Qing Wei, Jiao Chang, Xu Yi, Xiang Yu, Guoyong Luo, Xinfeng Li, Wude Yang, Yi Long. Exploring the hypoglycemic mechanism of chlorogenic acids from Pyrrosia petiolosa (Christ) Ching on type 2 diabetes mellitus based on network pharmacology and transcriptomics strategy. Journal of ethnopharmacology. 2024 Mar; 322(?):117580. doi: 10.1016/j.jep.2023.117580. [PMID: 38104881]
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  • 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]
  • Fan Wang, Bobby Lim-Ho Kong, Yun-Sang Tang, Hung-Kay Lee, Pang-Chui Shaw. Bioassay guided isolation of caffeoylquinic acids from the leaves of Ilex pubescens Hook. et Arn. and investigation of their anti-influenza mechanism. Journal of ethnopharmacology. 2023 Mar; 309(?):116322. doi: 10.1016/j.jep.2023.116322. [PMID: 36868436]
  • Chung-Fan Hsieh, Yu-Li Chen, Guan-Hua Lin, Yoke Fun Chan, Pei-Wen Hsieh, Jim-Tong Horng. 3,4-Dicaffeoylquinic Acid from the Medicinal Plant Ilex kaushue Disrupts the Interaction Between the Five-Fold Axis of Enterovirus A-71 and the Heparan Sulfate Receptor. Journal of virology. 2022 04; 96(7):e0054221. doi: 10.1128/jvi.00542-21. [PMID: 35319229]
  • Yuanyuan Zhao, Yiran Ren, Zhenqing Liu, Zijian Wang, Ying Liu. The metabolite profiling of 3,4-dicaffeoylquinic acid in Sprague-Dawley rats using ultra-high performance liquid chromatography equipped with linear ion trap-Orbitrap MS. Biomedical chromatography : BMC. 2022 Feb; 36(2):e5276. doi: 10.1002/bmc.5276. [PMID: 34741336]
  • 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]
  • Shi-Wei Sun, Rong-Rong Wang, Xiao-Ying Sun, Jia-He Fan, Hang Qi, Yang Liu, Guo-Qing Qin, Wei Wang. Identification of Transient Receptor Potential Vanilloid 3 Antagonists from Achillea alpina L. and Separation by Liquid-Liquid-Refining Extraction and High-Speed Counter-Current Chromatography. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092025. [PMID: 32357572]
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  • Chunxu Chen, Guijie Chen, Peng Wan, Dan Chen, Tao Zhu, Bing Hu, Yi Sun, Xiaoxiong Zeng. Characterization of Bovine Serum Albumin and (-)-Epigallocatechin Gallate/3,4- O-Dicaffeoylquinic Acid/Tannic Acid Layer by Layer Assembled Microcapsule for Protecting Immunoglobulin G in Stomach Digestion and Release in Small Intestinal Tract. Journal of agricultural and food chemistry. 2018 Oct; 66(42):11141-11150. doi: 10.1021/acs.jafc.8b04381. [PMID: 30277397]
  • Shao-Nan Wang, Yong-Sheng Ding, Xiao-Jie Ma, Cheng-Bowen Zhao, Ming-Xuan Lin, Jing Luo, Yi-Nan Jiang, Shuai He, Jian-You Guo, Jin-Li Shi. Identification of Bioactive Chemical Markers in Zhi zhu xiang Improving Anxiety in Rat by Fingerprint-Efficacy Study. Molecules (Basel, Switzerland). 2018 Sep; 23(9):. doi: 10.3390/molecules23092329. [PMID: 30213112]
  • Benjamin J Knollenberg, Jingjing Liu, Shu Yu, Hong Lin, Li Tian. Cloning and functional characterization of a p-coumaroyl quinate/shikimate 3'-hydroxylase from potato (Solanum tuberosum). Biochemical and biophysical research communications. 2018 02; 496(2):462-467. doi: 10.1016/j.bbrc.2018.01.075. [PMID: 29337064]
  • Lu Wang, Shu Liu, Junpeng Xing, Zhiqiang Liu, Fengrui Song. Characterization of interaction property of multi-components in Gardenia jasminoides with aldose reductase by microdialysis combined with liquid chromatography coupled to mass spectrometry. Rapid communications in mass spectrometry : RCM. 2016 08; 30 Suppl 1(?):87-94. doi: 10.1002/rcm.7620. [PMID: 27539421]
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  • Jin Han, Qing-Yuan Lv, Shi-Ying Jin, Tian-Tian Zhang, Shi-Xiao Jin, Xian-Yi Li, Hai-Long Yuan. Comparison of anti-bacterial activity of three types of di-O-caffeoylquinic acids in Lonicera japonica flowers based on microcalorimetry. Chinese journal of natural medicines. 2014 Feb; 12(2):108-13. doi: 10.1016/s1875-5364(14)60017-0. [PMID: 24636060]
  • Jing Zhou, Hong-yue Ma, Xin-sheng Fan, Wei Xiao, Tuan-jie Wang. [Molecular docking of chlorogenic acid, 3,4-di-O-caffeoylquinic acid and 3,5-di-O-caffeoylquinic acid with human serum albumin]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2012 Oct; 10(10):1149-54. doi: 10.3736/jcim20121012. [PMID: 23073199]
  • Nassira Kacem, Anne-Emmanuelle Hay, Andrew Marston, Amar Zellagui, Salah Rhouati, Kurt Hostettmann. Antioxidant compounds from Algerian Convolvulus tricolor (Convolvulaceae) seed husks. Natural product communications. 2012 Jul; 7(7):873-4. doi: ". [PMID: 22908568]
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  • Weicheng Hu, Ting Shen, Myeong-Hyeon Wang. Cell cycle arrest and apoptosis induced by methyl 3,5-dicaffeoyl quinate in human colon cancer cells: Involvement of the PI3K/Akt and MAP kinase pathways. Chemico-biological interactions. 2011 Oct; 194(1):48-57. doi: 10.1016/j.cbi.2011.08.006. [PMID: 21872580]
  • Sirima Puangpraphant, Mark A Berhow, Karl Vermillion, Greg Potts, Elvira Gonzalez de Mejia. Dicaffeoylquinic acids in Yerba mate (Ilex paraguariensis St. Hilaire) inhibit NF-κB nucleus translocation in macrophages and induce apoptosis by activating caspases-8 and -3 in human colon cancer cells. Molecular nutrition & food research. 2011 Oct; 55(10):1509-22. doi: 10.1002/mnfr.201100128. [PMID: 21656672]
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