中文名称:

金合欢素

中文同义词:

金合欢素;刺槐黄素;刺槐素;5,7-二羥-4-甲氧黃酮;阿卡西汀;洋槐素;5,7-二羟基-4-甲氧基黄酮;刺槐黄素,阿卡西汀,洋槐素,金合欢素

英文名称:

Acacetin

英文同义词:

5,7-DIHYDROXY-4-METHOXYFLAVONE;LINARIGENIN;METHYL-4-APIGENIN;ACACETIN;5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone;Abietic;ACACETIN(METHYL-4-APIGENIN)(RG);ACACETIN WITH HPLC

CAS号:

480-44-4

分子式:

C16H12O5

分子量:

284.26

EINECS号:

207-552-3

相关类别:

分析试剂标准品;标准品-对照品;植物提取物;中药对照品;标准品;植提标准品;对照品;Tri-substituted Flavones;Miscellaneous Reagents;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;inhibitor;生物黄酮;化妆品原料;标准品-中药标准品;黄酮;标准品 -中药标准品;标准品，对照品;Aromatics;Heterocycles

Mol文件:

480-44-4.mol

熔点 

260-265 °C(lit.)

沸点 

346.76°C (rough estimate)

密度 

1.2160 (rough estimate)

折射率 

1.6200 (estimate)

储存条件 

2-8°C

酸度系数(pKa)

6.51±0.40(Predicted)

最大波长(λmax)

335nm(EtOH)(lit.)

Merck 

14,13

BRN 

277879

InChIKey

DANYIYRPLHHOCZ-UHFFFAOYSA-N

CAS 数据库

480-44-4(CAS DataBase Reference)

植物来源

金合欢 （Acacia farnesiana (Linn.) Willd.） (Mimosa) 豆科。灌木，高2-4米；枝具刺，刺长可达1-2厘米。二回羽状复叶，羽片4-8对，每羽片具小叶10-20对，小叶片线状长椭圆形。头状花序腋生，直径1.5厘米，常多个簇生。荚果圆柱形，长3-7厘米，直径8-15毫米。种子多数，黑色。 花极香，供提取香精。 刺灌术或小乔木，二回羽状复叶，头状花序簇生于叶腋，盛开时，好像金色的绒球一般。

生物活性

Acacetin (5,7-Dihydroxy-4-methoxyflavone) 是一种口服有效的类黄酮，来自 Tephroseris kirilowii (Turcz.) Holub。Acacetin 停在 PI3Kγ 的 ATP 结合口袋中。Acacetin 导致癌细胞周期停滞，并诱导细胞凋亡和自噬。Acacetin 具有有效的抗癌和抗炎活性，有用于疼痛相关疾病研究的潜力。

体外研究

Acacetin (5,7-Dihydroxy-4-methoxyflavone; 10-200 μM; 24 hours) decreases cell viabilities in a dose-dependent manner. Acacetin has little effect on human normal glial cell line HEB and non-tumorigenic epithelial cell line MCF-10A. Acacetin (50-150 μM; 24 hours) causes G2/M cell cycle arrest and induces apoptosis and autophagy. Acacetin (50-150 μM; 24 hours) leads to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner. Cell Viability Assay Cell Line: Breast cancer MCF-7 cells, hepatocellular carcinoma SMMC-7721 cells, lung adenocarcinoma A549 cells, esophageal carcinoma Eca109 cells Concentration: 10, 20, 40, 60, 80, 100, 150, 200 μM Incubation Time: 24 hours Result: Decreased cancer cell viabilities in a dose-dependent manner. Had IC 50 values of 82.75 μM, 103.9 μM, 157.4 μM, 54.7 μM in MDA-MB-231, MCF-7, A549, Eca109 cells, respectively. Cell Cycle Analysis Cell Line: MDA-MB-231 cells Concentration: 50, 100, 150 μM Incubation Time: 24 hours Result: Resulted in increase in percentage of cells at G2/M phase and decrease in percentage of cells at G1 and S phase in a dose-dependent manner. Apoptosis Analysis Cell Line: MDA-MB-231 cells Concentration: 50, 100, 150 μM Incubation Time: 24 hours Result: Induced apoptosis. Cell Autophagy Assay Cell Line: MDA-MB-231 cells Concentration: 50, 100, 150 μM Incubation Time: 24 hours Result: Induced autophagy. Resulted in marked increases in EGFP-LC3 puncta formation and a dose-dependent accumulation of LC3-II. Western Blot Analysis Cell Line: MDA-MB-231 cells Concentration: 50, 100, 150 μM Incubation Time: 24 hours Result: Resulted in decrease in levels of Bcl-2 and Bcl-xL and increase in levels of p53. Led to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner. Had little or no effect on expression of PI3Kα, PI3Kβ, PI3Kδ, p-ERK, p-p38, and p-JNK.

Cell Line:

Breast cancer MCF-7 cells, hepatocellular carcinoma SMMC-7721 cells, lung adenocarcinoma A549 cells, esophageal carcinoma Eca109 cells

Concentration:

10, 20, 40, 60, 80, 100, 150, 200 μM

Incubation Time:

24 hours

Result:

Decreased cancer cell viabilities in a dose-dependent manner. Had IC 50 values of 82.75 μM, 103.9 μM, 157.4 μM, 54.7 μM in MDA-MB-231, MCF-7, A549, Eca109 cells, respectively.

Cell Line:

MDA-MB-231 cells

Concentration:

50, 100, 150 μM

Incubation Time:

24 hours

Result:

Resulted in increase in percentage of cells at G2/M phase and decrease in percentage of cells at G1 and S phase in a dose-dependent manner.

Cell Line:

MDA-MB-231 cells

Concentration:

50, 100, 150 μM

Incubation Time:

24 hours

Result:

Induced apoptosis.

Cell Line:

MDA-MB-231 cells

Concentration:

50, 100, 150 μM

Incubation Time:

24 hours

Result:

Induced autophagy. Resulted in marked increases in EGFP-LC3 puncta formation and a dose-dependent accumulation of LC3-II.

Cell Line:

MDA-MB-231 cells

Concentration:

50, 100, 150 μM

Incubation Time:

24 hours

Result:

Resulted in decrease in levels of Bcl-2 and Bcl-xL and increase in levels of p53. Led to decreases in levels of PI3Kγ-p110, p-AKT, p-mTOR, p-p70S6K, and p-ULK in a dose-dependent manner. Had little or no effect on expression of PI3Kα, PI3Kβ, PI3Kδ, p-ERK, p-p38, and p-JNK.

体内研究

Acacetin (5,7-Dihydroxy-4-methoxyflavone; 5, 20 mg/kg/day; orally; for 3 days) significantly suppresses microglial activation in an LPS-induced neuroinflammation mouse model. Acacetin (25 mg/kg/day; orally; for 3 days) reduces neuronal cell death in an animal model of ischemia. Acacetin (1.8-56.2 mg/kg/day; ip; single dose) decreases visceral and inflammatory nociception and prevented the formalin-induced oedema. Animal Model: Male C57BL/6 mice, 7 weeks of age Dosage: 5, 20 mg/kg Administration: Orally; once a day for 3 days Result: Significantly suppressed microglial activation in an LPS-induced (ip; 5mg/kg) neuroinflammation mouse model.

Animal Model:

Male C57BL/6 mice, 7 weeks of age

Dosage:

5, 20 mg/kg

Administration:

Orally; once a day for 3 days

Result:

Significantly suppressed microglial activation in an LPS-induced (ip; 5mg/kg) neuroinflammation mouse model.

化学性质 

黄色针状结晶，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于飞机草，大蓟，金合欢。

用途 

金合欢素具有镇静，抗癌的作用。

用途 

用于含量测定/鉴定/药理实验等。 药理药效:舒郁，理气，安神，活络之功效。

危险品标志 

Xi

危险类别码 

36/37/38

安全说明 

26-36

WGK Germany 

3

RTECS号

DJ3002000

F 

3-8-10

海关编码 

29329990