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Merck
CN

SML1868

Sigma-Aldrich

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
CAS Number:
14907-98-3
分子量:
520.53
MDL编号:
MFCD23726642
UNSPSC代码:
12352200
NACRES:
NA.77

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Product Name

鸦胆子苦醇, ≥95% (HPLC)

生物来源

(Brucia javanica)

质量水平

100

方案

≥95% (HPLC)

表单

powder

旋光性

[α]/D +35 to +44°, c = 0.5 in acetone

储存条件

desiccated

颜色

white to beige

溶解性

DMSO: 5 mg/mL, clear (warmed)

储存温度

−20°C

SMILES字符串

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

相关类别

应用

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。

生化/生理作用

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。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°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
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)
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
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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