Aristolochic acid A

Names

[ CAS No. ]:
313-67-7

[ Name ]:
Aristolochic acid A

[Synonym ]:
Aristolohic Acid A
Descresept
8-methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid
Aristolochic acid
birthwort
Phenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid, 8-methoxy-6-nitro-
AristolochicacidI
EINECS 206-238-3
Aristolochia
tardolyt
Aristolochic Acid A
Aristolochia A
aristolochin
8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
TR 1736
Aristolochic
MFCD00004996
aristolochine
8-Methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid

Biological Activity

[Description]:

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

[Related Catalog]:

Research Areas >> Cancer

[In Vitro]

Aristolochic acid A (150, 200 μM, 24 hours) inhibits the cell viabilities of kidney cells HEK293 and HK-2[1]. Aristolochic acid A (100, 200 μM, 24 hours) causes a concentration-dependent decrease in bladder cancer-associated protein (BLCAP) mRNA levels in kidney cells (HEK 293 and HK-2) , and bladder cancer cell line (HT-1376)[1]. Aristolochic acid A (100, 200 μM, 24 hours) weakens the BLCAP protein signals in a dose-dependent manner in both HEK293 and HT-1376 cells[1]. Cell Viability Assay[1] Cell Line: Kidney cells (HEK 293 and HK-2) Concentration: 50, 100, 150, 200 μM Incubation Time: 24 hours Result: The cell viabilities of HEK293 and HK-2 were lower than that of vehicle-treated cultures until 150 μM and 200 μM. RT-PCR[1] Cell Line: Kidney cells (HEK 293 and HK-2), and bladder cancer cell line (HT-1376) Concentration: 100, 200 μM Incubation Time: 24 hours Result: Down regulated the levels of BLCAP mRNA. Western Blot Analysis[1] Cell Line: HEK293 and HT-1376 cells Concentration: 100, 200 μM Incubation Time: 24 hours Result: Reduced the BLCAP protein expression in a dose-dependent manner.

[References]

[1]. Huang YT, et al. Aristolochic acid I interferes with the expression of BLCAP tumor suppressor gene in human cells. Toxicol Lett. 2018 Jul;291:129-137.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
615.5±55.0 °C at 760 mmHg

[ Melting Point ]:
260 °C

[ Molecular Formula ]:
C₁₇H₁₁NO₇

[ Molecular Weight ]:
341.27

[ Flash Point ]:
326.0±31.5 °C

[ Exact Mass ]:
341.053558

[ PSA ]:
110.81000

[ LogP ]:
3.41

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.747

[ Water Solubility ]:
DMSO: soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CF3325000

CHEMICAL NAME :: Aristolochine

CAS REGISTRY NUMBER :: 313-67-7

BEILSTEIN REFERENCE NO. :: 0345159

LAST UPDATED :: 199612

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C17-H11-N-O7

MOLECULAR WEIGHT :: 341.29

WISWESSER LINE NOTATION :: T C5 B666 DO FO EHJ IVQ KNW NO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3 mg/kg/2D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 184 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 74 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 55900 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 14320 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 38400 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1500 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 22 mg/kg/11D-I

TOXIC EFFECTS :: Blood - changes in other cell count (unspecified) Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 105 mg/kg/3W-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Gastrointestinal - tumors

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: DNA adduct

TYPE OF TEST :: Mutation in mammalian somatic cells

TYPE OF TEST :: Mutation in mammalian somatic cells

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 50 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 206,447,1988

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S7-S35-S45

[ RIDADR ]:
UN 1544 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
CF3325000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Precursor & DownStream

Precursor

DownStream

Articles

Bardoxolone methyl (BARD) ameliorates aristolochic acid (AA)-induced acute kidney injury through Nrf2 pathway.

Toxicology 318 , 22-31, (2014)

Bardoxolone methyl (BARD) is an antioxidant modulator that acts through induction of the nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathway. This study aimed to investigate the role ...

Baicalin Protects Mice from Aristolochic Acid I-Induced Kidney Injury by Induction of CYP1A through the Aromatic Hydrocarbon Receptor.

Int. J. Mol. Sci. 16 , 16454-68, (2015)

Exposure to aristolochic acid I (AAI) can lead to aristolochic acid nephropathy (AAN), Balkan endemic nephropathy (BEN) and urothelial cancer. The induction of hepatic CYP1A, especially CYP1A2, was co...

Association of blood lead and mercury with estimated GFR in herbalists after the ban of herbs containing aristolochic acids in Taiwan.

Occup. Environ. Med. 70(8) , 545-51, (2013)

This study was undertaken to explore the association of estimated glomerular filtration rate (GFR) with exposure to aristolochic acids (ALAs) and nephrotoxic metals in herbalists after the ban of herb...