A5512

Aristolochic acid I

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

• Synonyme(s) : TR 1736
• 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

Propriétés

• Nom du produit: Aristolochic acid I, powder
• Essai: ≥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

Description

Description générale

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]

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H301,H340,H350
• Conseils de prudence: P202 - P264 - P280 - P301 + P310 - P405 - P501
• 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