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A5512

Sigma-Aldrich

Aristolochic acid I

≥90% (HPLC), powder, phospholipase A₂ inhibitor

Synonyme(s) :

TR 1736

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About This Item

Formule empirique (notation de Hill):
C17H11NO7
Numéro CAS:
313-67-7
Poids moléculaire :
341.27
Numéro CE :
206-238-3
Numéro MDL:
MFCD00004996
Code UNSPSC :
41106300
ID de substance PubChem :
24890982
Nomenclature NACRES :
NA.77

product name

Aristolochic acid I, powder

Pureté

≥90% (HPLC)

Forme

powder

Couleur

yellow

Pf

269-270 °C

Solubilité

DMSO: soluble
ethanol: soluble

Température de stockage

2-8°C

Chaîne SMILES 

COc1cccc2c1cc([N+]([O-])=O)c3c(cc4OCOc4c23)C(O)=O

InChI

1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)

Clé InChI

BBFQZRXNYIEMAW-UHFFFAOYSA-N

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Description générale

Aristolochic acid is a naturally occurring plant metabolite found in Aristolochia sp, Bragantia sp. or Asarum sp. plants. It comprises a mixture of nitrophenanthrene carboxylic acids such as aristolochic acid I and II.

Application

Aristolochic acid I have been used:

  • as a standard for the analysis of Aristolochia sprucei crude extract by high-performance liquid chromatography
  • to study its effects on histone deacetylase 3 (HDAC3) aberration and renal fibrosis
  • to induce acute aristolochic acid nephropathy and to study its impact on miRNA and mRNA expression in mice

Actions biochimiques/physiologiques

Aristolochic acid is a potent inhibitor of phospholipase A2 (PLA2), hyaluronidase, and acetylcholinesterase plasma proteases from snake venoms. Aristolochic acid is considered a herbal medicine and shows therapeutic effects against obstetrics, snake bites, gout, and rheumatism. It exhibits anti-inflammatory and anti-malarial properties. In addition, it is also considered a genotoxic mutagen and causes aristolochic acid nephropathy (AAN), characterized by interstitial fibrosis and urothelial cancer.
Potent phospholipase A2 inhibitor, including calcium ionophore-induced phospholipase A2 activity in neutrophils. Kidney tumor initiator in experimental animal model.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H340,H350

Classification des risques

Acute Tox. 3 Oral - Carc. 1A - Muta. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Yongheng Bai et al.
Molecular medicine reports, 16(1), 737-745 (2017-06-01)
Sedum sarmentosum Bunge (SSBE) is a perennial plant widely distributed in Asian countries, and its extract is traditionally used for the treatment of certain inflammatory diseases. Our previous studies demonstrated that SSBE has marked renal anti‑fibrotic effects. However, the underlying molecular
M Refik Gökmen et al.
Annals of internal medicine, 158(6), 469-477 (2013-04-05)
It has been 20 years since the first description of a rapidly progressive renal disease that is associated with the consumption of Chinese herbs containing aristolochic acid (AA) and is now termed aristolochic acid nephropathy (AAN). Recent data have shown
Ziqiang Zhu et al.
Molecular medicine reports, 22(4), 3367-3377 (2020-09-19)
In acute aristolochic acid nephropathy (AAN), aristolochic acid (AA) induces renal injury and tubulointerstitial fibrosis. However, the roles of microRNAs (miRNAs/miRs) and mRNAs involved in AAN are not clearly understood. The aim of the present study was to examine AA‑induced
Volker M Arlt et al.
Mutagenesis, 17(4), 265-277 (2002-07-12)
The old herbal drug aristolochic acid (AA), derived from Aristolochia spp., has been associated with the development of a novel nephropathy, designated aristolochic acid nephropathy (AAN), and urothelial cancer in AAN patients. There is clear evidence that the major components
Ching-Chin Yang et al.
Toxicology, 312, 63-73 (2013-08-14)
Studies have found that ingestion of aristolochic acid (AA) causes nephropathy first by inducing renal tubular cell apoptosis acutely. It is currently unknown whether crosstalk between autophagy and apoptosis orchestrates the fate of tubular cells in acute AA nephropathy. We
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