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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:
分子量:
520.53
NACRES:
NA.77
UNSPSC Code:
12352200
MDL number:
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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

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

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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
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)
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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