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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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About This Item

Empirical Formula (Hill Notation):
C26H32O11
CAS Number:
14907-98-3
Molecular Weight:
520.53
MDL number:
MFCD23726642
UNSPSC Code:
12352200
NACRES:
NA.77

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

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 (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. Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
Brusatol enhances the efficacy of chemotherapy by inhibiting the Nrf2-mediated defense mechanism.
Ren V, et al.
Proceedings of the National Academy of Sciences of the USA, 108(4), 201014275-201014275 (2011)
W Willingham et al.
Biochimica et biophysica acta, 654(2), 169-174 (1981-07-27)
The mechanism by which brusatol inhibits protein synthesis in rabbit reticulocytes has been investigated. When added to reticulocyte lysates, brusatol inhibits endogenous protein synthesis only after a lag of 2-4 min at 30 degrees C. During this period 80 S
Guangqin Zhu et al.
Hereditas, 159(1), 21-21 (2022-05-14)
Ferroptosis, a novel manner of cell death depended on iron ion, contributed to goat mammary epithelial cell dysfunction. Interleukin-6 (IL-6) is a major pro-inflammatory factor during many inflammation-related diseases including mastitis, and a quite recently identified ferroptosis inducer. This study
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)
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