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SML1868

Brusatol

Name: Brusatol
Brand: SIGMA

From Brucia javanica, ≥95% (HPLC), NRF2 inhibitor, powder

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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About This Item

Empirical Formula (Hill Notation):

C₂₆H₃₂O₁₁

CAS Number:

14907-98-3

Molecular Weight:

520.53

NACRES:

NA.77

UNSPSC Code:

12352200

MDL number:

MFCD23726642

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

Brusatol, ≥95% (HPLC)

biological source

(Brucia javanica)

Quality Level

100

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

InChI

1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1

InChI key

ZZZYHIMVKOHVIH-VILODJCFSA-N

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

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

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.

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 (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Application of Mass Spectrometry Profiling to Establish Brusatol as an Inhibitor of Global Protein Synthesis.

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)

Enhancement of porcine in vitro embryonic development through luteolin-mediated activation of the Nrf2/Keap1 signaling pathway.

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)

Upregulation of nuclear factor (erythroid-derived 2)-like 2 protein level in the human colorectal adenocarcinoma cell line DLD-1 by a heterocyclic organobismuth(III) compound: Effect of organobismuth(III) compound on NRF2 signaling.

Katsuya Iuchi et al.

Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 125, 109928-109928 (2020-02-01)

An increasing number of metal-based compounds, including arsenic trioxide, auranofin, and cisplatin, have been reported to have antitumor activity. Their beneficial effects are controlled by a transcription factor, nuclear factor (erythroid-derived 2)-like 2 (NRF2). In response to oxidative stress, NRF2

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Global Trade Item Number

SKU	GTIN
SML1868-5MG	04061833253960
SML1868-25MG	04061833253953

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