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brusatol

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brusatol Basic information

Product Name:
brusatol
Synonyms:
  • 13,20-Epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester
  • 13,20-Epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicrasa-3-ene-21-oic acid methyl ester
  • methyl (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbut-2-enoyl)oxy)-5,10-dioxo-1,4,5,6a,7,7a,10,11,11a,11b-decahydro-2H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3(3aH)-carboxylate
  • Picras-3-en-21-oicacid,13,20-epoxy-3,11,12-trihydroxy-15-[(3-Methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-,Methyl ester, (11b,12a,15b)-
  • NSC 172924
  • Yatansin
  • Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-
  • Brustaol
CAS:
14907-98-3
MF:
C26H32O11
MW:
520.53
Mol File:
14907-98-3.mol
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brusatol Chemical Properties

Boiling point:
724.3±60.0 °C(Predicted)
Density 
1.46±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. 
-20°C
solubility 
DMF: 1 mg/ml; DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
pka
8.81±0.70(Predicted)
form 
powder
color 
white to beige
biological source
(Brucia javanica)
optical activity
[α]/D +35 to +44°, c = 0.5 in acetone
InChIKey
ZZZYHIMVKOHVIH-YHSWLYNENA-N
LogP
0.393 (est)
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brusatol Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Brucea javanica.

Uses

Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.

Definition

ChEBI: Brusatol is a triterpenoid.

Biochem/physiol Actions

Brusatol promotes Nrf2 (nuclear factor, erythroid 2 like 2 ) ubiquitination and degradation. Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.

in vivo

Brusatol is able to reach the tumor tissue and inhibit the Nrf2 pathway. Nude mice are injected with A549 cells to induce tumor growth, followed by a single i.p. injection of 2 mg/kg Brusatol. Nrf2 protein levels are significantly decreased at 24 h or 48 h postinjection[1].
Cisplatin (2 mg/kg) or Brusatol (2 mg/kg) alone does not inhibit tumor growth significantly, whereas in the combination group, tumor size is significantly reduced[1]. "

Animal Model:Athymic nude mice 4-6 wk old bearing A549 xenografts[1]
Dosage:2 mg/kg
Administration:Treated i.p.; Cisplatin (2 mg/kg), Brusatol (2 mg/kg), or in combination every other day for a total of five times
Result:Nrf2 protein levels were significantly decreased at 24 h or 48 h postinjection.
Cisplatin or Brusatol alone did not inhibit tumor growth significantly, whereas in the combination group, tumor size was significantly reduced.?"

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