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26791-73-1

中文名称 苍耳亭
英文名称 xanthatin
CAS 26791-73-1
分子式 C15H18O3
分子量 246.3
MOL 文件 26791-73-1.mol
更新日期 2024/06/03 09:47:42
26791-73-1 结构式 26791-73-1 结构式

基本信息

中文别名
苍耳亭
苍耳亭对照品
苍耳亭(反式)
苍耳亭(标准品)
英文别名
( - ) - xanthatin
(3aR)-3-Methylene-7β-methyl-6-(3-oxo-1-butenyl)-3,3aα,4,7,8,8aβ-hexahydro-2H-cyclohepta[b]furan-2-one
(3aR)-3,3aα,4,7,8,8aβ-Hexahydro-7β-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta[b]furan-2-one
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
2H-Cyclohepta[b]furan-2-one,3,3a,4,7,8,8a-hexahydro-7-Methyl-3-Methylene-6-(3-oxo-1-buten-1-yl)-,(3aR,7S,8aS)-
(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-[(1E)-3-oxo-1-buten-1-yl]-, (3aR,7S,8aS)-
所属类别
天然产物:萜类

物理化学性质

外观性状来源于菊科植物苍耳Xanthium sibiricum干燥成熟带总苞的果实
熔点114.5-115°
比旋光度D30 -20° (ethanol)
储存条件Sealed in dry,2-8°C
沸点444.3±45.0 °C(Predicted)
密度1.10±0.1 g/cm3(Predicted)

安全数据

应用领域

用途1
用于含量测定/鉴定/药理实验等。
药理药效:抗菌、消炎作用。

常见问题列表

用途

苍耳亭(标准品)用于含量测定、鉴别、药理实验、活性筛选等。

药理
抗菌、消炎作用、祛风散热,除湿解毒。
抗肿瘤研究

苍耳子的毒性源于其富含的倍半帖内酯类化合物,这类 成分常含有α,β不饱和y内酯结构,是其生物活性的一个主要基团。研究表明,从苍耳属(Xanthium L.)植物(如苍耳 子)中提取得到的倍半黏内酯化合物苍耳亭( Xanthatin),在 体内外实验中均显示出较强的抗肿瘤活性,其对非小细胞肺 癌的生长存在显著的抑制作用,且对正常肺上皮细胞生长影响较小。

生物活性
Xanthatin 从 Xanthium strumarium 叶子中提取,诱导细胞凋亡 (apoptosis)。Xanthatin 通过抑制 PGE2 的合成和 5-脂氧合酶的活性而显示出抗炎活性。Xanthatin 抑制布鲁氏菌的 IC50 值为 2.63 μg/ mL,对寄生虫特异性锥虫硫磷还原酶具有不可逆的弱抑制作用。
靶点

IC50: apoptosis; 3.8 μM (VEGFR2 kinase); 2.63 µg/mL ( T. b. brucei )

体外研究

Xanthatin is against T. b. brucei with an IC 50 value of 2.63 µg/mL and exhibits weak irreversible inhibition of parasite specific trypanothione reductase.Xanthatin (0-40 μM; 24 hours) has obscure inhibition effect on the proliferation of HUVEC in the absence of VEGF.Xanthatin (5-40 μM; 24 hours) inhibits breast cancer cell proliferation in a dose responsive manner. Xanthatin inhibits HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 with IC 50 values of 81 μM, 31 μM, 38 μM, 30 μM, and 17 μM, respectively.Xanthatin (0-10 μM; 24 hours) dose dependently suppresses the phosphorylation of STAT3 (Ser727), at the same time, it also results in a rapid dephosphorylation of down-stream kinases of STAT3, including PI3K and Akt, including PI3K (p-PI3K p85 tyr458 ) and Akt.

Cell Proliferation Assay

Cell Line: HUVEC cells
Concentration: 0 μM, 5 μM, 10 μM, 15 μM, 20 μM, 30 μM, 40 μM
Incubation Time: 24 hours
Result: Inhibited cell growth from dose 10 μM in the presence of vEGF.

Cell Viability Assay

Cell Line: HCC1937, MDA-MB-415, SK-BR-3, MCF-7 and MDA-MB-231 cells
Concentration: 5, 10, 15, 20, 30, and 40 μM
Incubation Time: 24 hours
Result: Inhibited breast cancer cell growth.

Western Blot Analysis

Cell Line: HUVEC cells
Concentration: 0, 3, and 10 μM
Incubation Time: 24 hours
Result: Inhibited VEGFR2 downstream signaling pathways and blocked VEGF-induced STAT3 activation in HUVEC.
体内研究

Xanthatin (intragastric administration; 20 mg/kg; once daily; 25 days) leads to significant inhibition of tumor volume. And this compound is well-tolerated and exhibits no significant difference in weight compares to the vehicle group.

Animal Model: Transplanted MDA-MB-231 cells into mice and constucted human breast cancer xenograft mouse model
Dosage: 20 mg/kg; once daily; 25 days
Administration: Intragastric administration
Result: Supressed tumor growth and tumor angiogenesis in vivo.
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