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A5512

Sigma-Aldrich

Aristolochic acid I

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

Synonym(s):

TR 1736

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About This Item

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

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

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General description

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

Biochem/physiol Actions

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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H340,H350

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
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
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
Jie Wei et al.
Journal of chromatography. A, 1246, 129-136 (2012-04-10)
A novel silica-based reversed-phase/strong anion-exchange mixed-mode stationary phase named C18SAX was synthesized based on the polar-copolymerized approach. C18SAX stationary phase showed excellent compatibility with 100% aqueous mobile phase and comparable performance with commercial SunFire™ C18 column in terms of column
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