A5512

Aristolochiasäure I

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

• Synonym(e): TR 1736
• Empirische Formel (Hill-System): C₁₇H₁₁NO₇
• CAS-Nummer: 313-67-7
• Molekulargewicht: 341.27
• EG-Nummer: 206-238-3
• MDL-Nummer: MFCD00004996
• UNSPSC-Code: 41106300
• PubChem Substanz-ID: 24890982
• NACRES: NA.77

Eigenschaften

• Produktbezeichnung: Aristolochiasäure I, powder
• Assay: ≥90% (HPLC)
• Form: powder
• Farbe: yellow
• mp (Schmelzpunkt): 269-270 °C
• Löslichkeit: DMSO: soluble; ethanol: soluble
• Lagertemp.: 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)
• InChIKey: BBFQZRXNYIEMAW-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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

Biochem./physiol. Wirkung

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.

Sicherheitshinweise

• Piktogramme: GHS06,GHS08
• Signalwort: Danger
• H-Sätze: H301,H340,H350
• P-Sätze: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Gefahreneinstufungen: Acute Tox. 3 Oral - Carc. 1A - Muta. 1B
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges