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A5512

Sigma-Aldrich

Aristolochic acid I

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

Synonim(y):

TR 1736

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About This Item

Wzór empiryczny (zapis Hilla):
C17H11NO7
Numer CAS:
313-67-7
Masa cząsteczkowa:
341.27
Numer WE:
206-238-3
Numer MDL:
MFCD00004996
Kod UNSPSC:
41106300
Identyfikator substancji w PubChem:
24890982
NACRES:
NA.77

product name

Aristolochic acid I, powder

Próba

≥90% (HPLC)

Postać

powder

kolor

yellow

mp

269-270 °C

rozpuszczalność

DMSO: soluble
ethanol: soluble

temp. przechowywania

2-8°C

ciąg 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)

Klucz InChI

BBFQZRXNYIEMAW-UHFFFAOYSA-N

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Opis ogólny

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.

Zastosowanie

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

Działania biochem./fizjol.

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.

Piktogramy

Skull and crossbonesHealth hazard
GHS06,GHS08

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H301,H340,H350

Zwroty wskazujące środki ostrożności

P202 - P264 - P280 - P301 + P310 - P405 - P501

Klasyfikacja zagrożeń

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

Kod klasy składowania

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

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

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

Certyfikaty analizy (CoA)

Poszukaj Certyfikaty analizy (CoA), wpisując numer partii/serii produktów. Numery serii i partii można znaleźć na etykiecie produktu po słowach „seria” lub „partia”.

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Chung-Hsin Chen et al.
International journal of cancer, 133(1), 14-20 (2013-01-08)
Aristolochic acid (AA), a component of all Aristolochia-based herbal medicines, is a potent nephrotoxin and human carcinogen associated with upper urinary tract urothelial carcinoma (UUC). To investigate the clinical and pathological characteristics of AA-induced UUC, this study included 152 UUC
Isela I González Rodríguez et al.
Toxicon: X, 7, 100049-100049 (2020-07-03)
A bioactive compound isolated from the stem extract of Aristolochia sprucei through High Performance Liquid Chromatography (HPLC) was identified via Nuclear Magnetic Resonance (NMR) as the aristolochic acid (AA). This compound showed an inhibitory effect over the myotoxic activity of
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
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
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
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