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SML1868

Sigma-Aldrich

Brusatol

≥95% (HPLC)

Synonym(s):

(+)-Brusatol, (11β,12α,15β)-13,20-Epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-picras-3-en-21-oic acid methyl ester, Brutasol, NSC 172924, Yatansin

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1 G
CLP 679,000

CLP 679,000


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Estimated to ship on27 February 2025


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1 G
CLP 679,000

About This Item

Empirical Formula (Hill Notation):
C26H32O11
CAS Number:
Molecular Weight:
520.53
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

CLP 679,000


Availability

Estimated to ship on27 February 2025


To order products, please contact your local dealer.

biological source

(Brucia javanica)

Quality Level

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +35 to +44°, c = 0.5 in acetone

storage condition

desiccated

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CC1=C(O)C(C[C@@]2(C)[C@@]1([H])C[C@]3([H])[C@]45[C@]2([H])[C@@H](O)[C@H](O)[C@](OC5)(C(OC)=O)[C@]4([H])[C@@H](OC(C=C(C)C)=O)C(O3)=O)=O

Application

Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.[1]

Biochem/physiol Actions

Brusatol (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity in cancer cultures (IC50 <1 μM against 457 cancer cell lines) by inhibiting de novo synthesis of cellular proteins (Effective conc. <50 nM in A549 cells), including NRF2.
Brusatol promotes Nrf2 (nuclear factor, erythroid 2 like 2 ) ubiquitination and degradation.[2] Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Steffan Vartanian et al.
Molecular & cellular proteomics : MCP, 15(4), 1220-1231 (2015-12-30)
The KEAP1/Nrf2 pathway senses and responds to changes in intracellular oxidative stress. Mutations that result in constitutive activation of Nrf2 are present in several human tumors, especially non-small cell lung cancer. Therefore, compounds that inhibit Nrf2 activity might be beneficial
Transcription factors Nrf2 and NF-κB contribute to inflammation and apoptosis induced by intestinal ischemia-reperfusion in mice.
Meng Q T, et al.
International Journal of Molecular Medicine, 40(6), 1731-1740 (2017)
Se-Been Jeon et al.
Journal of animal science and biotechnology, 14(1), 148-148 (2023-12-01)
Oxidative stress, caused by an imbalance in the production and elimination of intracellular reactive oxygen species (ROS), has been recognized for its detrimental effects on mammalian embryonic development. Luteolin (Lut) has been documented for its protective effects against oxidative stress
Application of mass spectrometry profiling to establish brusatol as an inhibitor of global protein synthesis.
Vartanian S, et al.
Molecular and Cellular Proteomics, 15(4), 1220-1231 (2016)
Shakeel Mir et al.
Breast cancer research : BCR, 24(1), 48-48 (2022-07-15)
A pro-oxidant enzyme, NADPH oxidase 4 (Nox4) has been reported to be a critical downstream effector of TGFβ-induced myofibroblast transformation during fibrosis. While there are a small number of studies suggesting an oncogenic role of Nox4 derived from activated fibroblasts

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