L-Chicoric Acid
(Synonyms: L-菊苣酸; (-)-Chicoric acid; trans-Caffeoyltartaric acid) 目录号 : GC60978
A dicaffeoyl ester with diverse biological activities
Cas No.:70831-56-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Chicoric acid is a dicaffeoyl ester that has been found in C. intybus with diverse biological activities.1 Chicoric acid (50-200 μg/ml) dose-dependently reduces the viability of Caco-2 and HCT116 human colorectal cancer cells.2 It inhibits HIV integrase activities, including 3'-processing of a DNA oligonucleotide and integration with template DNA (IC50s = 1.1 and 0.8 μM, respectively).3 Chicoric acid (0.5-10 μM) noncompetitively inhibits integration of HIV DNA by HIV integrase and, at concentrations greater than or equal to 5 μM, inhibits HIV entry into H9 cells.4 Oral administration of chicoric acid (10 and 30 mg/kg) reduces hepatic lipid accumulation, lipid peroxidation, and fibrosis, inhibits production of pro-inflammatory cytokines and activation of NF-kB, and activates the AMPK signaling pathway in a mouse model of non-alcoholic steatohepatitis (NASH) induced by a methionine and choline-deficient diet.5 Chicoric acid (2 mg/kg) also reduces blood glucose levels by 54% in mice with streptozotocin-induced diabetes.6
1.Xiao, H., Xie, G., Wang, J., et al.Chicoric acid prevents obesity by attenuating hepatic steatosis, inflammation and oxidative stress in high-fat diet-fed miceFood Res. Int.54(1)345-353(2013) 2.Tsai, Y.-L., Chiu, C.-C., Chen, J.Y.-F., et al.Cytotoxic effects of Echinacea purpurea flower extracts and cichoric acid on human colon cancer cells through induction of apoptosisJ. Ethnaopharmacol.143(3)914-919(2012) 3.Lin, Z., Neamati, N., Zhao, H., et al.Chicoric acid analogues as HIV-1 integrase inhibitorsJ. Med. Chem.42(8)1401-1414(1999) 4.Reinke, R.A., Lee, D.J., McDougall, B.R., et al.L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitroVirology326(2)203-219(2004) 5.Kim, M., Yoo, G., Randy, A., et al.Chicoric acid attenuate a nonalcoholic steatohepatitis by inhibiting key regulators of lipid metabolism, fibrosis, oxidation, and inflammation in mice with methionine and choline deficiencyMol. Nutr. Food Res.61(5)(2017) 6.Casanova, L.M., da Silva, D., Sola-Penna, M., et al.Identification of chicoric acid as a hypoglycemic agent from Ocimum gratissimum leaf extract in a biomonitoring in vivo studyFiloterapia93132-141(2014)
| Cas No. | 70831-56-0 | SDF | |
| 别名 | L-菊苣酸; (-)-Chicoric acid; trans-Caffeoyltartaric acid | ||
| Canonical SMILES | O=C(O[C@@H](C(O)=O)[C@H](C(O)=O)OC(/C=C/C1=CC=C(O)C(O)=C1)=O)/C=C/C2=CC=C(O)C(O)=C2.[Rotation(-)] | ||
| 分子式 | C22H18O12 | 分子量 | 474.37 |
| 溶解度 | DMSO: 100 mg/mL (210.81 mM) | 储存条件 | -20°C, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1081 mL | 10.5403 mL | 21.0806 mL |
| 5 mM | 0.4216 mL | 2.1081 mL | 4.2161 mL |
| 10 mM | 0.2108 mL | 1.054 mL | 2.1081 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Increase in insulin sensitivity by the association of chicoric acid and chlorogenic acid contained in a natural chicoric acid extract (NCRAE) of chicory (Cichorium intybus L.) for an antidiabetic effect
J Ethnopharmacol 2018 Apr 6;215:241-248.PMID:29325917DOI:10.1016/j.jep.2017.12.035.
Ethnopharmacological relevance: Chicory (Cichorium intybus L.) is an indigenous vegetable widely cultivated in Europe, America and Asia. In ancient times, the leaves, flowers, seeds, and roots have been used as a wealth of health benefits including its tonic effects, the ability to ease digestive problems and to detoxify liver. In Indian traditional therapy, chicory was known to possess antidiabetic effect. In the traditional medicine of Bulgaria and Italy, chicory was used as hypoglycemic decoctions. Aims of the studies: We wanted to obtain the complete chemical composition of the natural chicoric acid extract (NCRAE), a chicory root extract rich in chicoric acid, which previously showed its glucose tolerance effect in normal rats. To investigate if the whole NCRAE is required to be effective, we performed a comparative in vivo experiment on STZ diabetic rats treated either with NCRAE or a mixture composed of the two major compounds of NCRAE. Materials and methods: LC-MS method has been used to analyze the exhaustive composition of NCRAE: we have determined that chicoric acid and chlorogenic acid represented 83.8% of NCRAE. So, we have prepared a solution mixture of chicoric acid and chlorogenic acid named SCCAM, in order to compare in vivo the antidiabetic effects of this last and NCRAE in streptozotocin diabetic rats. In vitro experiments were performed on L6 cell line both for glucose uptake and for the protective effect against H2O2 oxidative stress. Also, we have evaluated DPPH and ORAC (Oxygen Radical Absorbance Capacity) antioxidative capacities of the two compositions. Results: The LC-MS analysis confirmed the high abundance of chicoric acid (64.2%) in NCRAE and a second part of NCRAE is composed of caffeoylquinic acids (CQAs) at 19.6% with among them the chlorogenic acid. This result has permitted us to prepare a mixture of synthetic L-Chicoric Acid (70%) and synthetic chlorogenic acid (30%): the solution is designated SCCAM. Our results showed that both NCRAE and SCCAM are able to improve a glucose tolerance in STZ diabetic rats after a subchronic administration of seven days. Alone NCRAE allows to significantly decrease the basal hyperglycemia after six days of treatment. To explain these difference of effects between NCRAE and SCCAM, we have compared their in vitro effects on the L6 muscle cell line both for the insulin sensitizing effect and for their protective action in pretreatment against H2O2. We have also compared their antioxidant capacities. In conclusion, we demonstrated that NCRAE, a natural extract of chicory (Cichorium intybus) rich in CRA and CQAs improves glucose tolerance and reduces the basal hyperglycemia in STZ diabetic rats.
Catechol-substituted L-Chicoric Acid analogues as HIV integrase inhibitors
Bioorg Med Chem Lett 2003 Dec 15;13(24):4331-4.PMID:14643320DOI:10.1016/j.bmcl.2003.09.046.
HIV integrase catalyzes the integration of HIV DNA copy into the host cell DNA, which is essential for the production of progeny viruses. L-Chicoric Acid and dicaffeoylquinic acids, isolated from plants, are well known potent inhibitors of HIV integrase. The common structural features of these inhibitors are caffeic acid derivatives connected to tartaric acid or quinic acid through ester bonds. In the present study, we have synthesized and tested the inhibitory activities of a new type of HIV IN inhibitors, which has catechol groups in place of caffeoyl groups in the structure of L-Chicoric Acid. Upon substitution of catechol groups at succinic acid, pyrrole-dicarboxylic acid, maleimide or maleic anhydride, the inhibitory activities (IC(50)=3.8-23.6 microM) were retained or remarkably increased when compared to parent compound L-Chicoric Acid (IC(50)=13.7 microM).
L-Chicoric Acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro
Virology 2004 Sep 1;326(2):203-19.PMID:15302207DOI:10.1016/j.virol.2004.06.005.
The human immunodeficiency virus (HIV) integrase (IN) must covalently join the viral cDNA into a host chromosome for productive HIV infection. L-Chicoric Acid (l-CA) enters cells poorly but is a potent inhibitor of IN in vitro. Using quantitative real-time polymerase chain reaction (PCR), l-CA inhibits integration at concentrations from 500 nM to 10 microM but also inhibits entry at concentrations above 1 microM. Using recombinant HIV IN, steady-state kinetic analyses with l-CA were consistent with a noncompetitive or irreversible mechanism of inhibition. IN, in the presence or absence of l-CA, was successively washed. Inhibition of IN diminished, demonstrating that l-CA was reversibly bound to the protein. These data demonstrate that l-CA is a noncompetitive but reversible inhibitor of IN in vitro and of HIV integration in vivo. Thus, l-CA likely interacts with amino acids other than those which bind substrate.
A docking study of L-Chicoric Acid with HIV-1 integrase
J Mol Graph Model 2009 Jan;27(5):584-9.PMID:19004651DOI:10.1016/j.jmgm.2008.09.011.
Human immunodeficiency virus 1 integrase (HIV-1 IN) is the enzyme responsible for integrating the viral DNA into the host genome, and is essential to the replication of the virus. L-Chicoric Acid (L-CA) is a bidentate catechol that has been identified as a potent inhibitor of HIV-1 IN. Using the new Autodock 4.0 free-energy function we have obtained a L-CA binding mode that explains its observed potency and is consistent with available experimental data. Because of the alpha,beta-unsaturated ester functionality of the side arms of L-CA we first performed an extensive conformational analysis of L-CA using semiempirical and ab initio calculations. As a result we have identified two distinct L-CA binding modes, one for the s-cis/s-cis and another for the s-cis/s-trans isomers. The most stable conformer was found to be the structure with the alpha,beta-unsaturated ester in the s-cis conformation for both arms of L-CA. This conformer also gave the top-ranked docking solution. Analysis of the interactions with key IN residues, combined with results using a L-CA tetraacetylated derivative and a Q148A IN mutant, correlate well with the experimental data.
Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-Chicoric Acid, as new HIV-1 integrase inhibitors
Eur J Med Chem 2007 Oct;42(10):1309-15.PMID:17434650DOI:10.1016/j.ejmech.2007.02.016.
Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric Acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures of L-Chicoric Acid 2 were synthesized for the purpose of simplifying the structure of L-Chicoric Acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC(50) values of 10.5 and 12.0 microM, respectively, comparable to that of parent compound L-Chicoric Acid (IC(50)=15.7 microM).