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Merck
CN

SML1868

鸦胆子苦醇

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

别名:

(+)-鸦胆子苦醇, (11β,12α,15β)-13,20-环氧-3,11,12-三羟基-15-[（3-甲基-1-氧代-2-丁烯-1-基）氧]-2,16-二氧代-picras-3-烯-21-酸甲酯, NSC 172924, 鸦胆子苦醇

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关于此项目

经验公式（希尔记法）:
C26H32O11
化学文摘社编号:
14907-98-3
分子量:
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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产品名称

鸦胆子苦醇, ≥95% (HPLC)

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

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 key

ZZZYHIMVKOHVIH-VILODJCFSA-N

biological source

(Brucia javanica)

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

Quality Level

100

相关类别

Application

鸦胆子苦醇已被用于研究 Nrf2（核因子，红系 2 样 2）在肠缺血/再灌注诱导损伤中的保护作用。

Biochem/physiol Actions

鸦胆子苦醇促进 Nrf2（核因子，红系 2 样 2）泛素化和降解。鸦胆子苦醇上调多种核糖体成分的表达，控制大分子复合物功能。
鸦胆子苦醇是一种植物来源的天然苦木苦味素，在癌症培养物中表现出广泛的细胞毒性（IC 50 <1 μM， 457 个癌细胞系），通过抑制细胞蛋白的从头合成（在 A549 细胞中有效浓度 <50 nM），包括 NRF2
鸦胆子苦醇是一种植物来源的天然苦木苦味素，表现出广泛的细胞毒性。

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000443692
0000443691
0000443691
0000443692
0000277797

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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)
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)
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
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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