3,5-CQA (BioDeep_00000230380)
Secondary id: BioDeep_00000018770, BioDeep_00000265009, BioDeep_00000399393, BioDeep_00000402922, BioDeep_00000403172, BioDeep_00000616460
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C25H24O12 (516.1267703999999)
中文名称: (-)-3,5-二咖啡酰奎宁酸, 3,5-二咖啡酰奎宁酸, 异绿原酸 A, 异绿原酸A
谱图信息:
最多检出来源 Viridiplantae(plant) 0.52%
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)O)OC(=O)C=CC3=CC(=C(C=C3)O)O
InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
描述信息
3,5-di-O-caffeoyl quinic acid is a carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities. It has a role as a metabolite, a hepatoprotective agent and an antineoplastic agent. It is a cyclitol carboxylic acid and a carboxylic ester. It is functionally related to a (-)-quinic acid and a trans-caffeic acid.
Isochlorogenic acid A is a natural product found in Psiadia viscosa, Dipsacus inermis, and other organisms with data available.
A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.
D004791 - Enzyme Inhibitors > D019429 - Integrase Inhibitors > D019428 - HIV Integrase Inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents
3,5-O-Dicaffeoylquinic acid reverses Trimethyltin-induced learning and memory deficits[1].
3,5-O-Dicaffeoylquinic acid reverses Trimethyltin-induced learning and memory deficits[1].
Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antioxidant and anti-inflammatory activities .
Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antioxidant and anti-inflammatory activities .
同义名列表
44 个代谢物同义名
CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4-DIHYDROXY-, (1R-(1.ALPHA.,3.ALPHA.(E),4.ALPHA.,5.BETA.(E)))-; CYCLOHEXANECARBOXYLIC ACID, 3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-; CYCLOHEXANECARBOXYLIC ACID, 1,4-DIHYDROXY-3,5-BIS(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1.ALPHA.,3R,4.ALPHA.,5R)-; (1.ALPHA.,3R,4.ALPHA.,5R)-3,5-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID; (1R,3R,4S,5R)-3,5-Bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid; (3R,5R)-3,5-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl))-1,4-dihydroxy-cyclohexanecarboxylic acid; (1S,3R,4R,5R)-3,5-Bis[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexanecarboxylic acid; (1S,3R,4S,5R)-3,5-BIS(((E)-3-(3,4-DIHYDROXYPHENYL)ACRYLOYL)OXY)-1,5-DIHYDROXYCYCLOHEXANE-1-CARBOXYLIC ACID; (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid; (1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylic acid; (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic acid; (1S,3R,4S,5R)-3,5-Bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylicacid; (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid; (1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate; 3,5-Di-o-caffeoylquinic acid/Isochlorogenic acid A; 3,5-Di-caffeoylquinic acid, >=95\\% (LC/MS-ELSD); 3,5-H56:H75dicaffeoyl-epi-quinic acid; (E,E)-3,5-Di-O-caffeoylquinic acid; 3,5-DI-O-(E)-CAFFEOYLQUINIC ACID; 3,5-Dicaffeoyl-epi-quinic acid; (-)-3,5-Dicaffeoyl quinic acid; Rel-3,5-Dicaffeoylquinic Acid; 3,5-di-O-caffeoyl quinic acid; Quinic acid 3,5-di-O-caffeate; 3,5-di-O-caffeoylquinic acid; 3,5-di-O-Aaffeoylquinic acid; 3,5-Dicaffeoylquininic acid; 3,5-O-dicaffeoylquinic acid; 3,5-dicaffeoyl quinic acid; 3,5-dicaffeoylquinic acid; Methylhydrogenphthalate; Dicaffeoylquinic acid; Isochlorogenic acid A; Isochlorogenic-acid-A; 3,5-dicaffeoylquinate; 3,5-Dicaffeoylquinic; UNII-ND94C5E75K; ACon1_002290; ND94C5E75K; 3,5-DICQA; CJ 4-16-4; CJ-4-16-4; 3,5-DCQA; 3,5-CQA
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:65751
- PubChem: 6474310
- ChEMBL: CHEMBL4289566
- ChEMBL: CHEMBL4466054
- ChEMBL: CHEMBL249447
- MeSH: 3,5-dicaffeoylquinic acid
- ChemIDplus: 0089919620
- chemspider: 22912767
- CAS: 879305-14-3
- CAS: 89919-62-0
- CAS: 2450-53-5
- medchemexpress: HY-N9895
- medchemexpress: HY-N0459
- medchemexpress: HY-N0056
- MetaboLights: MTBLC65751
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)
3 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
- Taian Yi, Jiesi Luo, Ruixue Liao, Long Wang, Anguo Wu, Yueyue Li, Ling Zhou, Chengyang Ni, Kai Wang, Xiaoqin Tang, Wenjun Zou, Jianming Wu. An Innovative Inducer of Platelet Production, Isochlorogenic Acid A, Is Uncovered through the Application of Deep Neural Networks.
Biomolecules.
2024 Feb; 14(3):. doi:
10.3390/biom14030267
. [PMID: 38540688] - Khlood Jamal, Areej Al-Taweel, Sarah I Bukhari, Raha Orfali, Nadine M S Moubayed, Jawaher Al-Qahtani, Hanan Aati, Orazio Taglialatela-Scafati, Jiangnan Peng, Shagufta Perveen. Isochlorogenic Acid Glucosides from the Arabian Medicinal Plant Artemisia sieberi and Their Antimicrobial Activities.
Molecules (Basel, Switzerland).
2023 Nov; 28(22):. doi:
10.3390/molecules28227460
. [PMID: 38005182] - Ya-Jun Yang, Lu-Jiao Lu, Jia-Jia Wang, Shao-Yong Ma, Bi-Lian Xu, Rui Lin, Qiu-Sheng Chen, Zhi-Guo Ma, Yu-Lin Mo, Dong-Tao Wang. Tubson-2 decoction ameliorates rheumatoid arthritis complicated with osteoporosis in CIA rats involving isochlorogenic acid A regulating IL-17/MAPK pathway.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2023 May; 116(?):154875. doi:
10.1016/j.phymed.2023.154875
. [PMID: 37263000] - Pengfei Su, Shuangshuang Ding, Dacheng Wang, Wenjie Kan, Meng Yuan, Xue Chen, Caiguo Tang, Jinyan Hou, Lifang Wu. Plant morphology, secondary metabolites and chlorophyll fluorescence of Artemisia argyi under different LED environments.
Photosynthesis research.
2023 May; ?(?):. doi:
10.1007/s11120-023-01026-w
. [PMID: 37204684] - 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] - Lixian Zhang, Yue Wei, Wei Wang, Yi Fan, Feifei Li, Zhining Li, Aiqin Lin, Haike Gu, Meifang Song, Tao Wang, Guijun Liu, Xiao Li. Quantitative fingerprint and antioxidative properties of Artemisia argyi leaves combined with chemometrics.
Journal of separation science.
2023 Mar; 46(5):e2200624. doi:
10.1002/jssc.202200624
. [PMID: 36579954] - 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] - Helena Mannochio-Russo, Wilhan D G Nunes, Rafael F Almeida, Lorena C Albernaz, Laila S Espindola, Vanderlan S Bolzani. Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata.
Journal of natural products.
2023 Feb; ?(?):. doi:
10.1021/acs.jnatprod.2c00788
. [PMID: 36848642] - Le Chen, Jinxin Li, Yunyun Zhu, Tingting Zhao, Lujuan Guo, Liping Kang, Jinqian Yu, Hongzhi Du, Dahui Liu. Weed Suppression and Molecular Mechanisms of Isochlorogenic Acid A Isolated from Artemisia argyi Extract via an Activity-Guided Method.
Journal of agricultural and food chemistry.
2022 Feb; 70(5):1494-1506. doi:
10.1021/acs.jafc.1c06417
. [PMID: 35089021] - Minru Liao, Qiang Xie, Yuqian Zhao, Chengcan Yang, Congcong Lin, Guan Wang, Bo Liu, Lingjuan Zhu. Main active components of Si-Miao-Yong-An decoction (SMYAD) attenuate autophagy and apoptosis via the PDE5A-AKT and TLR4-NOX4 pathways in isoproterenol (ISO)-induced heart failure models.
Pharmacological research.
2022 02; 176(?):106077. doi:
10.1016/j.phrs.2022.106077
. [PMID: 35026404] - Rong Yang, Huili Yang, Dansheng Jiang, Linyi Xu, Lian Feng, Yufeng Xing. Investigation of the potential mechanism of the Shugan Xiaozhi decoction for the treatment of nonalcoholic fatty liver disease based on network pharmacology, molecular docking and molecular dynamics simulation.
PeerJ.
2022; 10(?):e14171. doi:
10.7717/peerj.14171
. [PMID: 36389420] - 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] - Guangli Liu, Yan Liang, Min Xu, Ming Sun, Weijun Sun, You Zhou, Xiaojuan Huang, Wenjie Song, Yuan Liang, Zhang Wang. Protective mechanism of Erigeron breviscapus injection on blood-brain barrier injury induced by cerebral ischemia in rats.
Scientific reports.
2021 09; 11(1):18451. doi:
10.1038/s41598-021-97908-x
. [PMID: 34531475] - Alice Raineri, Rachele Campagnari, Roberto Dal Toso, Stefano Copetti, Macarena Gomez-Lira, Marta Menegazzi. 3,5-Dicaffeoylquinic Acid Lowers 3T3-L1 Mitotic Clonal Expansion and Adipocyte Differentiation by Enhancing Heme Oxygenase-1 Expression.
Molecules (Basel, Switzerland).
2021 Aug; 26(16):. doi:
10.3390/molecules26165027
. [PMID: 34443613] - Xue Jintao, Yang Quanwei, Li Chunyan, Liu Xiaolong, Niu Bingxuan. Rapid and simultaneous quality analysis of the three active components in Lonicerae Japonicae Flos by near-infrared spectroscopy.
Food chemistry.
2021 Apr; 342(?):128386. doi:
10.1016/j.foodchem.2020.128386
. [PMID: 33268162] - Fabiana Maia Santos, Camila Adão Malafaia, Daniel Luiz Reis Simas, Aline Barreto Paulino, Michelle F Muzitano, Naomi K Simas, Elaine A Cruz Da-Rocha, Ana Claudia F Amaral, Ivana C R Leal. Phenolic compounds from Tocoyena bullata mart (Rubiaceae) with inhibitory activity in mast cells degranulation.
Natural product research.
2020 Nov; 34(22):3295-3298. doi:
10.1080/14786419.2018.1560281
. [PMID: 30663374] - Young Hye Seo, Tuy An Trinh, Seung Mok Ryu, Hyo Seon Kim, Goya Choi, Byeong Cheol Moon, Sang Hee Shim, Dae Sik Jang, Dongho Lee, Ki Sung Kang, Jun Lee. Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death.
Journal of natural products.
2020 10; 83(10):3149-3155. doi:
10.1021/acs.jnatprod.0c00756
. [PMID: 32991171] - Fatih Karadeniz, Jung Hwan Oh, Jung Im Lee, Youngwan Seo, Chang-Suk Kong. 3,5-dicaffeoyl‑epi-quinic acid from Atriplex gmelinii enhances the osteoblast differentiation of bone marrow-derived human mesenchymal stromal cells via WnT/BMP signaling and suppresses adipocyte differentiation via AMPK activation.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2020 Jun; 71(?):153225. doi:
10.1016/j.phymed.2020.153225
. [PMID: 32464299] - Jing Hu, Yun Shi, Bing Yang, Zibo Dong, Xinxin Si, Kunming Qin. Changes in chemical components and antitumor activity during the heating process of Fructus Arctii.
Pharmaceutical biology.
2019 Dec; 57(1):363-368. doi:
10.1080/13880209.2019.1616778
. [PMID: 31295042] - Chien-Chang Shen, Wen-Chi Wei, Lie-Chwen Lin. Diterpenoids and Bisnorditerpenoids from Blumea aromatica.
Journal of natural products.
2019 11; 82(11):3181-3185. doi:
10.1021/acs.jnatprod.9b00674
. [PMID: 31646857] - Rumyana Simeonova, Vessela Vitcheva, Dimitrina Zheleva-Dimitrova, Vessela Balabanova, Ionko Savov, Sakina Yagi, Bozhana Dimitrova, Yulian Voynikov, Reneta Gevrenova. Trans-3,5-dicaffeoylquinic acid from Geigeria alata Benth. & Hook.f. ex Oliv. & Hiern with beneficial effects on experimental diabetes in animal model of essential hypertension.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2019 Oct; 132(?):110678. doi:
10.1016/j.fct.2019.110678
. [PMID: 31323233] - Zhengyan Xia, Yiming Sun, Chengyong Cai, Yong He, Pengcheng Nie. Rapid Determination of Chlorogenic Acid, Luteoloside and 3,5-O-dicaffeoylquinic Acid in Chrysanthemum Using Near-Infrared Spectroscopy.
Sensors (Basel, Switzerland).
2019 Apr; 19(9):. doi:
10.3390/s19091981
. [PMID: 31035325] - Peng Wan, Minhao Xie, Guijie Chen, Zhuqing Dai, Bing Hu, Xiaoxiong Zeng, Yi Sun. Anti-inflammatory effects of dicaffeoylquinic acids from Ilex kudingcha on lipopolysaccharide-treated RAW264.7 macrophages and potential mechanisms.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2019 Apr; 126(?):332-342. doi:
10.1016/j.fct.2019.01.011
. [PMID: 30654100] - K J Ryu, M S Yoou, Y Seo, K W Yoon, H M Kim, H J Jeong. Therapeutic effects of Artemisia scoparia Waldst. et Kitaib in a murine model of atopic dermatitis.
Clinical and experimental dermatology.
2018 Oct; 43(7):798-805. doi:
10.1111/ced.13565
. [PMID: 29740850] - Yueran Zhao, Deqiang Dou, Yueqiu Guo, Yue Qi, Jun Li, Dong Jia. Comparison of the Trace Elements and Active Components of Lonicera japonica flos and Lonicera flos Using ICP-MS and HPLC-PDA.
Biological trace element research.
2018 Jun; 183(2):379-388. doi:
10.1007/s12011-017-1138-4
. [PMID: 28864954] - Nuramina Mamat, Jun Dou, Xueying Lu, Aiden Eblimit, Aisa Haji Akber. Isochlorogenic acid A promotes melanin synthesis in B16 cell through the β-catenin signal pathway.
Acta biochimica et biophysica Sinica.
2017 Sep; 49(9):800-807. doi:
10.1093/abbs/gmx072
. [PMID: 28910976] - Antonietta Cerulli, Gianluigi Lauro, Milena Masullo, Vincenza Cantone, Beata Olas, Bogdan Kontek, Filomena Nazzaro, Giuseppe Bifulco, Sonia Piacente. Cyclic Diarylheptanoids from Corylus avellana Green Leafy Covers: Determination of Their Absolute Configurations and Evaluation of Their Antioxidant and Antimicrobial Activities.
Journal of natural products.
2017 06; 80(6):1703-1713. doi:
10.1021/acs.jnatprod.6b00703
. [PMID: 28520428] - Yi Tao, Yingshan Du, Weidong Li, Baochang Cai, Liuqing Di, Liyun Shi, Lihong Hu. Integrating UHPLC-MS/MS quantification and DAS analysis to investigate the effects of wine-processing on the tissue distributions of bioactive constituents of herbs in rats: Exemplarily shown for Dipsacus asper.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2017 Jun; 1055-1056(?):135-143. doi:
10.1016/j.jchromb.2017.04.035
. [PMID: 28467948] - Dimitrina Zheleva-Dimitrova, Reneta Gevrenova, Maya M Zaharieva, Hristo Najdenski, Silviya Ruseva, Valentin Lozanov, Vessela Balabanova, Sakina Yagi, Georgi Momekov, Vanio Mitev. HPLC-UV and LC-MS Analyses of Acylquinic Acids in Geigeria alata (DC) Oliv. & Hiern. and their Contribution to Antioxidant and Antimicrobial Capacity.
Phytochemical analysis : PCA.
2017 May; 28(3):176-184. doi:
10.1002/pca.2658
. [PMID: 27910164] - Yi Tao, Yuchao Ren, Weidong Li, Baochang Cai, Liuqing Di, Liyun Shi, Lihong Hu. Comparative pharmacokinetic analysis of extracts of crude and wine-processed Dipsacus asper in rats by a sensitive ultra performance liquid chromatography-tandem mass spectrometry approach.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2016 Nov; 1036-1037(?):33-41. doi:
10.1016/j.jchromb.2016.09.024
. [PMID: 27710888] - Shing-Chung Lam, Sio-Fong Lam, Jing Zhao, Shao-Ping Li. Rapid Identification and Comparison of Compounds with Antioxidant Activity in Coreopsis tinctoria Herbal Tea by High-Performance Thin-Layer Chromatography Coupled with DPPH Bioautography and Densitometry.
Journal of food science.
2016 Sep; 81(9):C2218-23. doi:
10.1111/1750-3841.13402
. [PMID: 27516219] - 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] - Jin Yong Kang, Seon Kyeong Park, Tian Jiao Guo, Jeong Su Ha, Du Sang Lee, Jong Min Kim, Uk Lee, Dae Ok Kim, Ho Jin Heo. Reversal of Trimethyltin-Induced Learning and Memory Deficits by 3,5-Dicaffeoylquinic Acid.
Oxidative medicine and cellular longevity.
2016; 2016(?):6981595. doi:
10.1155/2016/6981595
. [PMID: 28105250] - Wuen Yew Teoh, Hooi Poay Tan, Sui Kiong Ling, Norhanom Abdul Wahab, Kae Shin Sim. Phytochemical investigation of Gynura bicolor leaves and cytotoxicity evaluation of the chemical constituents against HCT 116 cells.
Natural product research.
2016; 30(4):448-51. doi:
10.1080/14786419.2015.1017726
. [PMID: 25738869] - J N Ma, S Bolraa, M Ji, Q Q He, C M Ma. Quantification and antioxidant and anti-HCV activities of the constituents from the inflorescences of Scabiosa comosa and S. tschilliensis.
Natural product research.
2016; 30(5):590-4. doi:
10.1080/14786419.2015.1027701
. [PMID: 25835468] - Jin Qi, You-Hua Chen, Ying Wang, Xi Chen, Lu Wang, Yuan-Jia Hu, Bo-Yang Yu. Screening of peroxynitrite scavengers in Flos Lonicerae by using two new methods, an HPLC-DAD-CL technique and a peroxynitrite spiking test followed by HPLC-DAD analysis.
Phytochemical analysis : PCA.
2016 Jan; 27(1):57-63. doi:
10.1002/pca.2599
. [PMID: 26567775] - Hong Liu, Yan-fang Zheng, Chu-yuan Li, Yu-ying Zheng, De-qin Wang, Zhong Wu, Lin Huang, Yong-gang Wang, Pei-bo Li, Wei Peng, Wei-wei Su. Discovery of Anti-inflammatory Ingredients in Chinese Herbal Formula Kouyanqing Granule based on Relevance Analysis between Chemical Characters and Biological Effects.
Scientific reports.
2015 Dec; 5(?):18080. doi:
10.1038/srep18080
. [PMID: 26657159] - Heino Martin Heyman, François Senejoux, Isabell Seibert, Thomas Klimkait, Vinesh Jaichand Maharaj, Jacobus Johannes Marion Meyer. Identification of anti-HIV active dicaffeoylquinic- and tricaffeoylquinic acids in Helichrysum populifolium by NMR-based metabolomic guided fractionation.
Fitoterapia.
2015 Jun; 103(?):155-64. doi:
10.1016/j.fitote.2015.03.024
. [PMID: 25841639] - Amel Boudjelal, Laura Siracusa, Cherifa Henchiri, Madani Sarri, Benkhaled Abderrahim, Faiza Baali, Giuseppe Ruberto. Antidiabetic Effects of Aqueous Infusions of Artemisia herba-alba and Ajuga iva in Alloxan-Induced Diabetic Rats.
Planta medica.
2015 Jun; 81(9):696-704. doi:
10.1055/s-0035-1546006
. [PMID: 26018915] - Jianping Zhao, Mei Wang, Bharathi Avula, Lingyun Zhong, Zhonghua Song, Qiongming Xu, Shunxiang Li, Ikhlas A Khan. Effect of Processing on the Traditional Chinese Herbal Medicine Flos Lonicerae: An NMR-based Chemometric Approach.
Planta medica.
2015 Jun; 81(9):754-64. doi:
10.1055/s-0035-1546081
. [PMID: 26039268] - Wen-Zheng Ju, Yang Zhao, Fang Liu, Ting Wu, Jun Zhang, Shi-Jia Liu, Ling Zhou, Guo-Liang Dai, Ning-Ning Xiong, Zhu-Yuan Fang. Clinical tolerability and pharmacokinetics of Erigerontis hydroxybenzene injection: results of a randomized phase I study in healthy Chinese volunteers.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2015 Feb; 22(2):319-25. doi:
10.1016/j.phymed.2014.11.014
. [PMID: 25765839] - Andrea Moglia, Sergio Lanteri, Cinzia Comino, Lionel Hill, Daniel Knevitt, Cecilia Cagliero, Patrizia Rubiolo, Stephen Bornemann, Cathie Martin. Dual catalytic activity of hydroxycinnamoyl-coenzyme A quinate transferase from tomato allows it to moonlight in the synthesis of both mono- and dicaffeoylquinic acids.
Plant physiology.
2014 Dec; 166(4):1777-87. doi:
10.1104/pp.114.251371
. [PMID: 25301886] - Jian Chen, Sven Mangelinckx, Li Ma, Zhengtao Wang, Weilin Li, Norbert De Kimpe. Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity.
Fitoterapia.
2014 Dec; 99(?):1-6. doi:
10.1016/j.fitote.2014.08.015
. [PMID: 25172103] - Hong Ryul Ahn, Hee Ju Lee, Kyung-A Kim, Chul Young Kim, Chu Won Nho, Holim Jang, Cheol-Ho Pan, Chang Yong Lee, Sang Hoon Jung. Hydroxycinnamic acids in Crepidiastrum denticulatum protect oxidative stress-induced retinal damage.
Journal of agricultural and food chemistry.
2014 Feb; 62(6):1310-23. doi:
10.1021/jf4046232
. [PMID: 24428171] - Brigida D'Abrosca, Elisabetta Buommino, Grazia D'Angelo, Lorena Coretti, Monica Scognamiglio, Valeria Severino, Severina Pacifico, Giovanna Donnarumma, Antonio Fiorentino. Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa.
Bioorganic & medicinal chemistry.
2013 Nov; 21(22):7038-46. doi:
10.1016/j.bmc.2013.09.019
. [PMID: 24094434] - Zhen-Yu Li, Hai-Juan Zhi, Fu-Sheng Zhang, Hai-Feng Sun, Li-Zeng Zhang, Jin-Ping Jia, Jie Xing, Xue-Mei Qin. Metabolomic profiling of the antitussive and expectorant plant Tussilago farfara L. by nuclear magnetic resonance spectroscopy and multivariate data analysis.
Journal of pharmaceutical and biomedical analysis.
2013 Mar; 75(?):158-64. doi:
10.1016/j.jpba.2012.11.023
. [PMID: 23261808] - Erdenechimeg Selenge, Toshihiro Murata, Kyoko Kobayashi, Javzan Batkhuu, Fumihiko Yoshizaki. Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana.
Journal of natural products.
2013 Feb; 76(2):186-93. doi:
10.1021/np300609u
. [PMID: 23356964] - Yan-Hong Zhang, Mei-Qin Xue, Yuan-Chao Bai, Hui-Hui Yuan, Hong-Li Zhao, Min-Bo Lan. 3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects.
Fitoterapia.
2012 Oct; 83(7):1281-5. doi:
10.1016/j.fitote.2012.05.016
. [PMID: 22668973] - Zhen-Yu Li, Hai-Juan Zhi, Shui-Yu Xue, Hai-Feng Sun, Fu-Sheng Zhang, Jin-Ping Jia, Jie Xing, Li-Zeng Zhang, Xue-Mei Qin. Metabolomic profiling of the flower bud and rachis of Tussilago farfara with antitussive and expectorant effects on mice.
Journal of ethnopharmacology.
2012 Mar; 140(1):83-90. doi:
10.1016/j.jep.2011.12.027
. [PMID: 22210102] - Jun Lee, Yun Mi Lee, Byong Won Lee, Joo-Hwan Kim, Jin Sook Kim. Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities.
Journal of natural products.
2012 Feb; 75(2):267-70. doi:
10.1021/np200646e
. [PMID: 22264115] - Arpád Könczöl, Zoltán Béni, Márta Meszlényi Sipos, Attila Rill, Viktor Háda, Judit Hohmann, Imre Máthé, Csaba Szántay, György Miklós Keseru, György Tibor Balogh. Antioxidant activity-guided phytochemical investigation of Artemisia gmelinii Webb. ex Stechm.: isolation and spectroscopic challenges of 3,5-O-dicaffeoyl (epi?) quinic acid and its ethyl ester.
Journal of pharmaceutical and biomedical analysis.
2012 Feb; 59(?):83-9. doi:
10.1016/j.jpba.2011.10.012
. [PMID: 22079045] - Kyungsu Kang, Eun Hye Jho, Hee Ju Lee, Sarangerel Oidovsambuu, Ji Ho Yun, Chul Young Kim, Ji-Hye Yoo, Young-Jin Kim, Jong Hwan Kim, Soo Young Ahn, Chu Won Nho. Youngia denticulata protects against oxidative damage induced by tert-butylhydroperoxide in HepG2 cells.
Journal of medicinal food.
2011 Oct; 14(10):1198-207. doi:
10.1089/jmf.2010.1557
. [PMID: 21895413] - 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] - Manuela Jehle, Johanna Bano, Ernst P Ellmerer, Christian Zidorn. Natural products from Scorzonera aristata (Asteraceae).
Natural product communications.
2010 May; 5(5):725-7. doi:
"
. [PMID: 20521536] - Shengqiang Tong, Jizhong Yan, Yi-Xin Guan. Preparative separation of isomeric caffeoylquinic acids from Flos Lonicerae by pH-zone-refining counter-current chromatography.
Journal of chromatography. A.
2008 Nov; 1212(1-2):48-53. doi:
10.1016/j.chroma.2008.09.114
. [PMID: 18952222] - Clémence Queffélec, Fabrice Bailly, Gladys Mbemba, Jean-François Mouscadet, Sean Hayes, Zeger Debyser, Myriam Witvrouw, Philippe Cotelle. Synthesis and antiviral properties of some polyphenols related to Salvia genus.
Bioorganic & medicinal chemistry letters.
2008 Aug; 18(16):4736-40. doi:
10.1016/j.bmcl.2008.06.063
. [PMID: 18674899] - Xiao-jie Tan, Qing Li, Xiao-hui Chen, Zhi-wei Wang, Zheng-yuan Shi, Kai-shun Bi, Ying Jia. Simultaneous determination of 13 bioactive compounds in Herba Artemisiae Scopariae (Yin Chen) from different harvest seasons by HPLC-DAD.
Journal of pharmaceutical and biomedical analysis.
2008 Aug; 47(4-5):847-53. doi:
10.1016/j.jpba.2008.04.010
. [PMID: 18502075] - A Olmos, R M Giner, M C Recio, J L Rios, J M Cerdá-Nicolás, S Máñez. Effects of plant alkylphenols on cytokine production, tyrosine nitration and inflammatory damage in the efferent phase of contact hypersensitivity.
British journal of pharmacology.
2007 Oct; 152(3):366-73. doi:
10.1038/sj.bjp.0707402
. [PMID: 17660848] - Ruo-peng Zha, Wei Xu, Wen-yi Wang, Li Dong, Yi-ping Wang. Prevention of lipopolysaccharide-induced injury by 3,5-dicaffeoylquinic acid in endothelial cells.
Acta pharmacologica Sinica.
2007 Aug; 28(8):1143-8. doi:
10.1111/j.1745-7254.2007.00595.x
. [PMID: 17640475] - Xiao Yao, Gongyu Gongyu, Gang Chen. Determination of active constituents in Lonicera confusa DC. by capillary electrophoresis with amperometric detection.
Biomedical chromatography : BMC.
2006 Nov; 20(11):1192-9. doi:
10.1002/bmc.684
. [PMID: 16799927] - Hyoung Ja Kim, Eun Jung Kim, Seon Hee Seo, Cha-Gyun Shin, Changbae Jin, Yong Sup Lee. Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.
Journal of natural products.
2006 Apr; 69(4):600-3. doi:
10.1021/np050447r
. [PMID: 16643034] - Fumihiro Teramachi, Takashi Koyano, Thaworn Kowithayakorn, Masahiko Hayashi, Kanki Komiyama, Masami Ishibashi. Collagenase inhibitory quinic acid esters from Ipomoea pes-caprae.
Journal of natural products.
2005 May; 68(5):794-6. doi:
10.1021/np0500631
. [PMID: 15921434] - Sung-Soo Kim, Ran-Young Park, Hyun-Jung Jeon, Yong-Soo Kwon, Wanjoo Chun. Neuroprotective effects of 3,5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells.
Phytotherapy research : PTR.
2005 Mar; 19(3):243-5. doi:
10.1002/ptr.1652
. [PMID: 15934031] - Paul Cos, Louis Maes, Dirk Vanden Berghe, Nina Hermans, Luc Pieters, Arnold Vlietinck. Plant substances as anti-HIV agents selected according to their putative mechanism of action.
Journal of natural products.
2004 Feb; 67(2):284-93. doi:
10.1021/np034016p
. [PMID: 14987070] - Jin Young Hur, Pyeongjae Lee, Hocheol Kim, Insug Kang, Kang Ro Lee, Sun Yeou Kim. (-)-3,5-Dicaffeoyl-muco-quinic acid isolated from Aster scaber contributes to the differentiation of PC12 cells: through tyrosine kinase cascade signaling.
Biochemical and biophysical research communications.
2004 Jan; 313(4):948-53. doi:
10.1016/j.bbrc.2003.11.178
. [PMID: 14706634] - Makiko Takenaka, Xiaojun Yan, Hiroshi Ono, Mitsuru Yoshida, Tadahiro Nagata, Tateo Nakanishi. Caffeic acid derivatives in the roots of yacon (Smallanthus sonchifolius).
Journal of agricultural and food chemistry.
2003 Jan; 51(3):793-6. doi:
10.1021/jf020735i
. [PMID: 12537459] - 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] - M Takenaka, T Nagata, M Yoshida. Stability and bioavailability of antioxidants in garland (Chrysanthemum coronarium L.).
Bioscience, biotechnology, and biochemistry.
2000 Dec; 64(12):2689-91. doi:
10.1271/bbb.64.2689
. [PMID: 11210137] - H C Kwon, C M Jung, C G Shin, J K Lee, S U Choi, S Y Kim, K R Lee. A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.
Chemical & pharmaceutical bulletin.
2000 Nov; 48(11):1796-8. doi:
10.1248/cpb.48.1796
. [PMID: 11086919] - L C Lin, Y C Kuo, C J Chou. Immunomodulatory principles of Dichrocephala bicolor.
Journal of natural products.
1999 Mar; 62(3):405-8. doi:
10.1021/np980153o
. [PMID: 10096846]