A5512

Aristolochic acid I

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

• Synonym(s): TR 1736
• Empirical Formula (Hill Notation): C₁₇H₁₁NO₇
• CAS Number: 313-67-7
• Molecular Weight: 341.27
• EC Number: 206-238-3
• MDL number: MFCD00004996
• UNSPSC Code: 41106300
• PubChem Substance ID: 24890982
• NACRES: NA.77

Properties

• Product Name: Aristolochic acid I, powder
• assay: ≥90% (HPLC)
• form: powder
• color: yellow
• mp: 269-270 °C
• solubility: DMSO: soluble; ethanol: soluble
• storage temp.: 2-8°C
• SMILES string: 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)
• InChI key: BBFQZRXNYIEMAW-UHFFFAOYSA-N

Description

General description

Aristolochic acid is a naturally occurring plant metabolite found in Aristolochia sp, Bragantia sp. or Asarum sp. plants.[1] It comprises a mixture of nitrophenanthrene carboxylic acids such as aristolochic acid I and II.[2]

Application

Aristolochic acid I have been used:

• as a standard for the analysis of Aristolochia sprucei crude extract by high-performance liquid chromatography[3]
• to study its effects on histone deacetylase 3 (HDAC3) aberration and renal fibrosis[4]
• to induce acute aristolochic acid nephropathy and to study its impact on miRNA and mRNA expression in mice[5]

Biochem/physiol Actions

Aristolochic acid is a potent inhibitor of phospholipase A2 (PLA2), hyaluronidase, and acetylcholinesterase plasma proteases from snake venoms.[6] Aristolochic acid is considered a herbal medicine and shows therapeutic effects against obstetrics, snake bites, gout, and rheumatism.[2] It exhibits anti-inflammatory and anti-malarial properties.[7] In addition, it is also considered a genotoxic mutagen[2] and causes aristolochic acid nephropathy (AAN), characterized by interstitial fibrosis and urothelial cancer.[2]

Potent phospholipase A₂ inhibitor, including calcium ionophore-induced phospholipase A₂ activity in neutrophils. Kidney tumor initiator in experimental animal model.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H340,H350
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Carc. 1A - Muta. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges