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Aristolochic acid A

CAS# 313-67-7

Aristolochic acid A

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Aristolochic acid A: 5mg $12 In Stock
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Chemical structure

Aristolochic acid A

3D structure

Chemical Properties of Aristolochic acid A

Cas No. 313-67-7 SDF Download SDF
PubChem ID 2236 Appearance Yellow powder
Formula C17H11O7N M.Wt 341.27
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms Aristolochic acid; Aristolochic acid A
Solubility DMSO : 25 mg/mL (73.26 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
SMILES COC1=CC=CC2=C3C(=C(C=C21)[N+](=O)[O-])C(=CC4=C3OCO4)C(=O)O
Standard InChIKey BBFQZRXNYIEMAW-UHFFFAOYSA-N
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 Aristolochic acid A

The herb of Aristolochia debilis Sieb. et Zucc.

Biological Activity of Aristolochic acid A

DescriptionAristolochic acid A is a potent nephrotoxin, which strongly induced toxic damage during ovarian maturation by inhibiting Akt phosphorylation-mediated suppression of apoptosis.
TargetsBcl-2/Bax | Caspase | PARP | Akt
In vitro

Aristolochic Acid A induces ovarian toxicity by inhibition of akt phosphorylation.[Pubmed: 25406029]

Chem Res Toxicol. 2014 Dec 15;27(12):2128-35.

Aristolochic acids are natural products found in Chinese herbs of the Aristolochiaceae family. Aristolochic acid I (Aristolochic acid A,AAI) is a potent carcinogen and was found to be toxic in animal and clinical studies. Apoptosis is a rapid, selective process of physiological cell deletion that regulates the balance between cell proliferation and cell death and is induced by various kinds of damage. However, the toxicity of AAI during ovarian maturation in the mouse is unclear and is the subject of the present investigation.
METHODS AND RESULTS:
We used Chinese hamster ovary-K1 (CHO-K1) cells and an AAI injection mouse model: MTT assay was used to assess AA toxicity to cells; ovary size and weight were measured to determine the toxicity of AA to mouse ovary; western blot was used to assess apoptosis; TUNEL assay was used to evaluate apoptotic cell death; and immunohistochemistry was used to examine the local expression of apoptotic proteins in ovary tissue. We found that AAI significantly inhibits the viability of CHO-K1 cells and strongly induces apoptotic cell death in CHO-K1 cells and in mouse ovary. In addition, we observed that AAI markedly increases the expression of pro-apoptotic proteins, including Bax, caspase-3, caspase-9, and poly(ADP) ribose polymerase (PARP). In contrast, anti-apoptotic proteins, such as Bcl-2 and survivin, were decreased by AAI treatment. Furthermore, we observed that ovary size and weight were significantly reduced and that the number of ovulated oocytes was markedly suppressed in AAI-treated mice.
CONCLUSIONS:
These results suggest that AAI strongly induces toxic damage during ovarian maturation by inhibiting Akt phosphorylation-mediated suppression of apoptosis.

In vivo

The determination of aristolochic acid A in different processed Aristolochia manshuriensis and the test of influence about renal function in rats.[Pubmed: 21213532]

Zhong Yao Cai. 2010 Aug;33(8):1228-33.

To study and approach the processing methods and mechanism which can markedly reduce the content of aristolochic acid in Aristolochia manshuriensis and lighten the nephrotoxicity of aristolochic acid.
METHODS AND RESULTS:
A traditional "attenuation" processing method was used and 30 types of samples which contain one crude and 29 types of processed sample were obtained. The contents of Aristolochic acid A in every sample were determined by HPLC. According to the Rat's acute renal injury test, the influence of animal's renal function was investigated for representative samples. The content of aristolochic acid in six types of samples depressed markedly (30% or more depressed) which processing with boiling in the limewater, steaming with limewater, boiling in the juice of liquorice, boiling in the decoction of black soybean, boiling in the soda water and stir-baked with talcum powder, the content of aristolochic acid in other processed samples also depressed with a large discrepancy. The toxicology test results showed that the above-mentioned 6 samples all can relieve renal injury of rats. There could be some associativity between the degree of renal injury relieving and the content of Aristolochic acid A in the samples.
CONCLUSIONS:
The content of aristolochic acid can be reduced and the nephrotoxicity for animals can be lightened with some eligible processing methods for the traditional Chinese medicines containing aristolochic acid with the representative of Aristolochia manshuriensis.

Aristolochic acid A Dilution Calculator

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Preparing Stock Solutions of Aristolochic acid A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9302 mL 14.6512 mL 29.3023 mL 58.6046 mL 73.2558 mL
5 mM 0.586 mL 2.9302 mL 5.8605 mL 11.7209 mL 14.6512 mL
10 mM 0.293 mL 1.4651 mL 2.9302 mL 5.8605 mL 7.3256 mL
50 mM 0.0586 mL 0.293 mL 0.586 mL 1.1721 mL 1.4651 mL
100 mM 0.0293 mL 0.1465 mL 0.293 mL 0.586 mL 0.7326 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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References on Aristolochic acid A

Aristolochic Acid I induces ovarian toxicity by inhibition of akt phosphorylation.[Pubmed:25406029]

Chem Res Toxicol. 2014 Dec 15;27(12):2128-35.

Aristolochic acids are natural products found in Chinese herbs of the Aristolochiaceae family. Aristolochic acid I (AAI) is a potent carcinogen and was found to be toxic in animal and clinical studies. Apoptosis is a rapid, selective process of physiological cell deletion that regulates the balance between cell proliferation and cell death and is induced by various kinds of damage. However, the toxicity of AAI during ovarian maturation in the mouse is unclear and is the subject of the present investigation. We used Chinese hamster ovary-K1 (CHO-K1) cells and an AAI injection mouse model: MTT assay was used to assess AA toxicity to cells; ovary size and weight were measured to determine the toxicity of AA to mouse ovary; western blot was used to assess apoptosis; TUNEL assay was used to evaluate apoptotic cell death; and immunohistochemistry was used to examine the local expression of apoptotic proteins in ovary tissue. We found that AAI significantly inhibits the viability of CHO-K1 cells and strongly induces apoptotic cell death in CHO-K1 cells and in mouse ovary. In addition, we observed that AAI markedly increases the expression of pro-apoptotic proteins, including Bax, caspase-3, caspase-9, and poly(ADP) ribose polymerase (PARP). In contrast, anti-apoptotic proteins, such as Bcl-2 and survivin, were decreased by AAI treatment. Furthermore, we observed that ovary size and weight were significantly reduced and that the number of ovulated oocytes was markedly suppressed in AAI-treated mice. These results suggest that AAI strongly induces toxic damage during ovarian maturation by inhibiting Akt phosphorylation-mediated suppression of apoptosis.

[The determination of aristolochic acid A in different processed Aristolochia manshuriensis and the test of influence about renal function in rats].[Pubmed:21213532]

Zhong Yao Cai. 2010 Aug;33(8):1228-33.

OBJECTIVE: To study and approach the processing methods and mechanism which can markedly reduce the content of aristolochic acid in Aristolochia manshuriensis and lighten the nephrotoxicity of aristolochic acid. METHODS: A traditional "attenuation" processing method was used and 30 types of samples which contain one crude and 29 types of processed sample were obtained. The contents of Aristolochic acid A in every sample were determined by HPLC. According to the Rat's acute renal injury test, the influence of animal's renal function was investigated for representative samples. RESULTS: The content of aristolochic acid in six types of samples depressed markedly (30% or more depressed) which processing with boiling in the limewater, steaming with limewater, boiling in the juice of liquorice, boiling in the decoction of black soybean, boiling in the soda water and stir-baked with talcum powder, the content of aristolochic acid in other processed samples also depressed with a large discrepancy. The toxicology test results showed that the above-mentioned 6 samples all can relieve renal injury of rats. There could be some associativity between the degree of renal injury relieving and the content of Aristolochic acid A in the samples. CONCLUSION: The content of aristolochic acid can be reduced and the nephrotoxicity for animals can be lightened with some eligible processing methods for the traditional Chinese medicines containing aristolochic acid with the representative of Aristolochia manshuriensis.

Description

Aristolochic acid A (Aristolochic acid I; TR 1736) is the main component of plant extract Aristolochic acids, which are found in various herbal plants of genus Aristolochia and Asarum. Aristolochic acid A significantly reduces both activator protein 1 (AP-1) and NF-κB activities. Aristolochic acid A reduces BLCAP gene expression in human cell lines.

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