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异甘草素； 4,2',4'-三羟基查耳酮

异甘草素； 4,2',4'-三羟基查耳酮用途

Isoliquiritigenin 是从光果甘草根中分到的黄酮类化合物,具有抗肿瘤的活性,能够抑制 aldose reductase 的活性,IC50 值为 320 nM。

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异甘草素； 4,2',4'-三羟基查耳酮名称

[ CAS 号 ]:
961-29-5

[ 中文名 ]:
异甘草素

[ 英文名 ]:
Isoliquiritigenin

[中文别名 ]:

[英文别名 ]:

iso-Liquiritigenin
Isoliquiritigenin
QR CQ DV1U1R DQ &&E Form
ISL
gu17
MFCD00075907
ISOLIQUIRTIGENIN
4,2',4'-TRIHYDROXYCHALCONE
Isqliquiritigenin
2',4',4-TRIHYDROXYCHALCONE

异甘草素； 4,2',4'-三羟基查耳酮生物活性

[ 描述 ]:

Isoliquiritigenin 是从光果甘草根中分到的黄酮类化合物,具有抗肿瘤的活性,能够抑制 aldose reductase 的活性,IC50 值为 320 nM。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 醛糖还原酶

信号通路 >> 自噬 >> 自噬

研究领域 >> 癌症

天然产物 >> 黄酮类化合物

[ 靶点 ]

IC50: 320 nM (Aldose reductase)

[体外研究]

异甘草素可通过抑制大鼠晶状体醛糖还原酶预防糖尿病并发症,IC50为320 nM,山梨醇在人红细胞中积聚,IC50为2.0μM[1]。异甘草素(100μM)显着抑制缺氧诱导的心肌细胞TPS和TR90延长。与载体组相比,异甘草素显着触发AMPK Thr172磷酸化。异甘草素处理还诱导心肌细胞中的细胞外信号调节激酶(ERK)信号传导途径。异甘草素处理显着降低缺氧/复氧期间分离的心肌细胞的细胞内ROS水平[3]。异甘草素不仅可以下调IL-6的表达,还可以显着降低磷酸化ERK和STAT3的水平,并且可以抑制重组人IL-6诱导的ERK和STAT3的磷酸化水平,重组人IL-6是IL-6信号调节网络中的关键信号蛋白[4]。。

[体内研究]

异甘草素显示由各种类型的兴奋剂如CCh(1 mM),KCl(60 mM)和BaCl 2(0.3 mM)诱导的小鼠空肠强直收缩的浓度依赖性抑制,IC50值为4.96±1.97 mM,4.03±1.34分别为mM和3.70±0.58 mM [2]。异甘草素在MM异种移植模型中显示出显着的抗肿瘤活性,并协同增强阿霉素的抗骨髓瘤活性[4]。

[参考文献]

[1]. Aida K, et al. Isoliquiritigenin: a new aldose reductase inhibitor from glycyrrhizae radix. Planta Med. 1990 Jun;56(3):254-8.

[2]. Sato Y, et al. Isoliquiritigenin, one of the antispasmodic principles of Glycyrrhiza ularensis roots, acts in the lower part of intestine. Biol Pharm Bull. 2007 Jan;30(1):145-9.

[3]. Zhang X. Natural antioxidant-isoliquiritigenin ameliorates contractile dysfunction of hypoxic cardiomyocytes via AMPK signaling pathway. Mediators Inflamm. 2013;2013:390890.

[4]. Chen X, et al. Isoliquiritigenin inhibits the growth of multiple myeloma via blocking IL-6 signaling. J Mol Med (Berl). 2012 Nov;90(11):1311-9.

[相关活性小分子]

异甘草素； 4,2',4'-三羟基查耳酮物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
504.0±42.0 °C at 760 mmHg

[ 熔点 ]:
206-210°C

[ 分子式 ]:
C₁₅H₁₂O₄

[ 分子量 ]:
256.253

[ 闪点 ]:
272.7±24.4 °C

[ 精确质量 ]:
256.073547

[ PSA ]:
77.76000

[ LogP ]:
3.11

[ 外观性状 ]:
粉末

[ 蒸汽压 ]:
0.0±1.3 mmHg at 25°C

[ 折射率 ]:
1.715

[ 储存条件 ]:
2-8°C

[ 水溶解性 ]:
H2O: <0.1 mg/mL

异甘草素； 4,2',4'-三羟基查耳酮MSDS

详细MSDS(安全技术说明书)

异甘草素； 4,2',4'-三羟基查耳酮毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FL7080000

CHEMICAL NAME :: Chalcone, 2',4,4'-trihydroxy-

CAS REGISTRY NUMBER :: 961-29-5

LAST UPDATED :: 199606

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H12-O4

MOLECULAR WEIGHT :: 256.27

WISWESSER LINE NOTATION :: QR CQ DV1U1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 100 ug/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 3,401,1981

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异甘草素； 4,2',4'-三羟基查耳酮安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xi

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
3

[ RTECS号 ]:
FL7080000

[ 海关编码 ]:
2914501900

异甘草素； 4,2',4'-三羟基查耳酮合成路线

详细合成路线

异甘草素； 4,2',4'-三羟基查耳酮上下游产品

异甘草素； 4,2',4'-三羟基查耳酮上游产品

异甘草素； 4,2',4'-三羟基查耳酮下游产品

异甘草素； 4,2',4'-三羟基查耳酮海关

[ 海关编码 ]: 2914501900

[ 中文概述 ]:
2914501900 其他酮酚。监管条件:无。增值税率:17.0%。退税率:9.0%。最惠国关税:5.5%。普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 丙酮报明包装

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

异甘草素； 4,2',4'-三羟基查耳酮文献

Isoliquiritigenin attenuates oxidative hepatic damage induced by carbon tetrachloride with or without buthionine sulfoximine.

Chem. Biol. Interact. 225 , 13-20, (2015)

Glycyrrhizae radix (G. radix) has been demonstrated to have hepatoprotective properties. This study determined the therapeutic effects of isoliquiritigenin (isoLQ) in G. radix, against liver injury in...

Effects of phytochemicals on in vitro anti-inflammatory activity of Bifidobacterium adolescentis.

Biosci. Biotechnol. Biochem. 79 , 799-807, (2015)

Probiotics have been shown to improve the condition of not only the human gastrointestinal tract but also the entire body. We found that quercetin enhances the anti-inflammatory activity of Bifidobact...

Flavonoids and Auxin Transport Inhibitors Rescue Symbiotic Nodulation in the Medicago truncatula Cytokinin Perception Mutant cre1.

Plant Cell 27 , 2210-26, (2015)

Initiation of symbiotic nodules in legumes requires cytokinin signaling, but its mechanism of action is largely unknown. Here, we tested whether the failure to initiate nodules in the Medicago truncat...

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