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A1304

Sigma-Aldrich

β-Amanitin

from Amanita phalloides, ≥85% (HPLC), powder, RNA polymerase inhibitor

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About This Item

Formule empirique (notation de Hill):
C39H53N9O15S
Numéro CAS:
21150-22-1
Poids moléculaire :
919.95
Numéro CE :
244-244-8
Numéro MDL:
MFCD00151212
Code UNSPSC :
12352200
ID de substance PubChem :
24890528
Nomenclature NACRES :
NA.77

product name

β-Amanitin from Amanita phalloides, ≥85% (HPLC)

Niveau de qualité

200

Pureté

≥85% (HPLC)

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2

InChI

1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)

Clé InChI

IEQCUEXVAPAFMQ-UHFFFAOYSA-N

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Description générale

β-Amanitin belongs to the family of amatoxins. Amanitins are made of bicyclic octapeptides. β-Amanitin is composed of a carboxyl group and is acidic in nature.

Application

β-Amanitin from Amanita phalloides has been used:
  • as a calibration standard for the quantification of β-Amanitin using liquid chromatography-high resolution-mass spectrometry/mass spectrometry (LC-HR-MS/MS) method.
  • to determine its concentration in urine samples by capillary zone electrophoresis (CZE).
  • in the analysis of β-amanitin in toxic mushrooms by liquid chromatography coupled to time-of-flight mass spectrometry.

Actions biochimiques/physiologiques

Toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but not RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330

Classification des risques

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Chiemi Nishizawa et al.
Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology, 16(4), 441-445 (2004-01-27)
High-performance liquid chromatographic (HPLC) assay has been developed for the simultaneous determination of alpha-amanitin, beta-amanitin and phalloidin in serum. Three toxins were extracted by reflux in a water bath at 80 degrees C for one hour and purified by Sep-Pak
Peng Li et al.
Gene, 532(1), 63-71 (2013-09-21)
Amanita exitialis is a lethal mushroom that was first discovered in Guangdong Province, China. The high content of amanitin in its basidiocarps makes it lethal to humans. To comprehensively characterize the A. exitialis transcriptome and analyze the Amanita toxins as
V A Robinson-Fuentes et al.
Journal of pharmaceutical and biomedical analysis, 47(4-5), 913-917 (2008-05-27)
Amanitins are toxins found in species of the mushroom genera Amanita, Lepiota and Galerina. Intoxication after ingestion of these mushrooms can be fatal with an estimated 20% of mortality rate. An early diagnosis is necessary in order to avoid invasive
H Faulstich et al.
Toxicon : official journal of the International Society on Toxinology, 26(5), 491-499 (1988-01-01)
A monoclonal antibody, with high affinity against the mushroom toxin alpha-amanitin, was prepared. Administration of the Fab fragment of the monoclonal antibody to mice caused a 50-fold increase in alpha-amanitin toxicity. Electron micrographs showed normal appearance of hepatocytes but typical
F Jehl et al.
Analytical biochemistry, 149(1), 35-42 (1985-08-15)
A high-performance liquid chromatographic assay of alpha-amanitin and beta-amanitin in human serum, urine, or stomach washings is described. Sample preparation involves a chemical step with deproteinization and organic solvent treatment, and a selective cleanup and concentration step on reversed-phase prepacked
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