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Isochlorogenic acid A

CAS# 2450-53-5

Isochlorogenic acid A

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Quality Control of Isochlorogenic acid A

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Chemical structure

Isochlorogenic acid A

3D structure

Chemical Properties of Isochlorogenic acid A

Cas No. 2450-53-5 SDF Download SDF
PubChem ID 6474310 Appearance White-pale yellow powder
Formula C25H24O12 M.Wt 516.45
Type of Compound Phenylpropanoids Storage Desiccate at -20°C
Synonyms 3,5-CQA; Isochlorogenic acid A;89919-62-0;879305-14-3;3,5-Dicaffeoyl-epi-quinic acid
Solubility DMSO : ≥ 50 mg/mL (96.81 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
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
Standard InChIKey KRZBCHWVBQOTNZ-RDJMKVHDSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isochlorogenic acid A

1 Arctium sp. 2 Asarum sp. 3 Bidens sp. 4 Cichorium sp. 5 Coffea sp. 6 Echinacea sp. 7 Hedera sp. 8 Ilex sp. 9 Menyanthes sp. 10 Sorbus sp. 11 Tanacetum sp. 12 Viburnum sp.

Biological Activity of Isochlorogenic acid A

DescriptionIsochlorogenic acid A has antiviral, antioxidant, hepatoprotective and potent anti-hepatitis B activities.
TargetsHBV | HO-1
In vitro

Hepatoprotective and antiviral properties of isochlorogenic acid A from Laggera alata against hepatitis B virus infection.[Pubmed: 22982394]

J Ethnopharmacol. 2012 Oct 31;144(1):190-4.

The aim of this study was to determine the anti-hepatitis B effect of Isochlorogenic acid A isolated from Laggera alata (Asteraceae), a traditional Chinese herbal medicine.
METHODS AND RESULTS:
The anti-hepatitis B activity of Isochlorogenic acid A was evaluated by the D-galactosamine (D-GalN)-induced HL-7702 hepatocyte damage model and the HBV-transfected HepG2.2.15 cells. Isochlorogenic acid A significantly improved HL-7702 hepatocyte viability and markedly inhibited the productions of HBsAg and HBeAg. The inhibitory rates of Isochlorogenic acid A on the HBsAg and HBeAg expressions were 86.9% and 72.9%, respectively. In addition, Isochlorogenic acid A declined markedly the content of hepatitis B virus covalently closed circular DNA (HBV cccDNA) and induced significantly the heme oxygenase-1 (HO-1) expression in HepG2.2.15 cells.
CONCLUSIONS:
Isochlorogenic acid A was verified to possess the potent anti-hepatitis B activity. The anti-HBV target of Isochlorogenic acid A is probably associated with blocking the translation step of the HBV replication. Overexpression of HO-1 may contribute to the anti-HBV activity of Isochlorogenic acid A by reducing the stability of the HBV core protein and thus blocking the refill of nuclear HBV cccDNA. Additionally, the hepatoprotective effect of Isochlorogenic acid A could be achieved by its antioxidative property and induction of HO-1.

Protocol of Isochlorogenic acid A

Structure Identification
PLoS One. 2014 Sep 2;9(9):e106254.

The activity-integrated method for quality assessment of reduning injection by on-line DPPH-CE-DAD.[Pubmed: 25181475]


METHODS AND RESULTS:
A sensitive on-line DPPH-CE-DAD method was developed and validated for both screening and determining the concentration of seven antioxidants of Reduning injection. The pH and concentrations of buffer solution, SDS, β-CD and organic modifier were studied for the detection of DPPH and seven antioxidants. By on-line mixing DPPH and sample solution, a DPPH-CE method for testing the antioxidant activity of the complex matrix was successfully established and used to screen the antioxidant components of Reduning injection. Then, antioxidant components including caffeic acid, Isochlorogenic acid A, isochlorogenic acid B, isochlorogenic acid C, chlorogenic acid, neochlorogenic acid and cryptochlorogenic acid were quantified by the newly established CE-DAD method. Finally, the total antioxidant activity and the multiple active components were selected as markers to evaluate the quality of Reduning injection.
CONCLUSIONS:
The results demonstrated that the on-line DPPH-CE-DAD method was reagent-saving, rapid and feasible for on-line simultaneous determination of total pharmacological activity and contents of multi-components samples. It was also a powerful method for evaluating the quality control and mechanism of action of TCM injection.

Isochlorogenic acid A Dilution Calculator

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Isochlorogenic acid A Molarity Calculator

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Preparing Stock Solutions of Isochlorogenic acid A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9363 mL 9.6815 mL 19.363 mL 38.7259 mL 48.4074 mL
5 mM 0.3873 mL 1.9363 mL 3.8726 mL 7.7452 mL 9.6815 mL
10 mM 0.1936 mL 0.9681 mL 1.9363 mL 3.8726 mL 4.8407 mL
50 mM 0.0387 mL 0.1936 mL 0.3873 mL 0.7745 mL 0.9681 mL
100 mM 0.0194 mL 0.0968 mL 0.1936 mL 0.3873 mL 0.4841 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Isochlorogenic acid A

3,5-Dicaffeoylquinic acid is an isolated compound from Artemisia argyi; its ester derivatives exert anti-leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects.

References:
[1]. Zhang YH, et al. 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. [2]. Malarz J, et al. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside. Appl Biochem Biotechnol. 2013 Dec;171(7):1589-601. [3]. Wan C, et al. Isolation and identification of phenolic compounds from Gynura divaricata leaves. Pharmacogn Mag. 2011 Apr;7(26):101-8.

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References on Isochlorogenic acid A

Hepatoprotective and antiviral properties of isochlorogenic acid A from Laggera alata against hepatitis B virus infection.[Pubmed:22982394]

J Ethnopharmacol. 2012 Oct 31;144(1):190-4.

ETHNOPHARMACOLOGICAL RELEVANCE: The aim of this study was to determine the anti-hepatitis B effect of Isochlorogenic acid A isolated from Laggera alata (Asteraceae), a traditional Chinese herbal medicine. MATERIALS AND METHODS: The anti-hepatitis B activity of Isochlorogenic acid A was evaluated by the D-galactosamine (D-GalN)-induced HL-7702 hepatocyte damage model and the HBV-transfected HepG2.2.15 cells. RESULTS: Isochlorogenic acid A significantly improved HL-7702 hepatocyte viability and markedly inhibited the productions of HBsAg and HBeAg. The inhibitory rates of Isochlorogenic acid A on the HBsAg and HBeAg expressions were 86.9% and 72.9%, respectively. In addition, Isochlorogenic acid A declined markedly the content of hepatitis B virus covalently closed circular DNA (HBV cccDNA) and induced significantly the heme oxygenase-1 (HO-1) expression in HepG2.2.15 cells. CONCLUSIONS: Isochlorogenic acid A was verified to possess the potent anti-hepatitis B activity. The anti-HBV target of Isochlorogenic acid A is probably associated with blocking the translation step of the HBV replication. Overexpression of HO-1 may contribute to the anti-HBV activity of Isochlorogenic acid A by reducing the stability of the HBV core protein and thus blocking the refill of nuclear HBV cccDNA. Additionally, the hepatoprotective effect of Isochlorogenic acid A could be achieved by its antioxidative property and induction of HO-1.

The activity-integrated method for quality assessment of reduning injection by on-line DPPH-CE-DAD.[Pubmed:25181475]

PLoS One. 2014 Sep 2;9(9):e106254.

A sensitive on-line DPPH-CE-DAD method was developed and validated for both screening and determining the concentration of seven antioxidants of Reduning injection. The pH and concentrations of buffer solution, SDS, beta-CD and organic modifier were studied for the detection of DPPH and seven antioxidants. By on-line mixing DPPH and sample solution, a DPPH-CE method for testing the antioxidant activity of the complex matrix was successfully established and used to screen the antioxidant components of Reduning injection. Then, antioxidant components including caffeic acid, Isochlorogenic acid A, isochlorogenic acid B, isochlorogenic acid C, chlorogenic acid, neochlorogenic acid and cryptochlorogenic acid were quantified by the newly established CE-DAD method. Finally, the total antioxidant activity and the multiple active components were selected as markers to evaluate the quality of Reduning injection. The results demonstrated that the on-line DPPH-CE-DAD method was reagent-saving, rapid and feasible for on-line simultaneous determination of total pharmacological activity and contents of multi-components samples. It was also a powerful method for evaluating the quality control and mechanism of action of TCM injection.

Description

Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antioxidant and anti-inflammatory activities .

Keywords:

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