Piceatannol 3'-O-glucoside

CAS: 94356-26-0 货号: P646524 分子式: C20H22O9 分子量: 406.38 EC号: 112-318-8 PubChem CID: 11968990
有货
级别和纯度: ≥99%
别名
白皮杉醇 3'-O-葡萄糖苷
储存条件
避光,-80℃储存
运输条件
特低温运输
★
规格
库存
价格
数量
1mg
P646524-1mg
期货 Stock Image
¥800.90
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为什么选择此级别

提供 ≥99% 纯度,适用于对基线干扰要求严格的色谱和分析工作流程。

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储存与运输

避光,-80℃储存。特低温运输 。请查阅批次 COA 获取详细规格。

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质量文档

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文献证明

在色谱分析、有机合成和交叉偶联反应领域已被 0 篇同行评审文献引用。

概述


Piceatannol 3'-O-glucoside, an active component of Rhubarb, activates endothelial nitric oxide ( NO ) synthase through inhibition of arginase activity with IC 50 s of 11.22 µM and 11.06 µM against arginase I and arginase II , respectively.

In Vitro

Piceatannol 3'-O-glucoside (Piceatannol-3'-O-β-D-glucopyranoside; PG) is a potent component of stilbenes, inhibits the activity of arginase I and II prepared from mouse liver and kidney lysates, respectively, in a dose-dependent manner. In human umbilical vein endothelial cells, incubation of Piceatannol 3'-O-glucoside markedly blocks arginase activity and increases nitrite and nitrate (NOx) production, as measured by Griess assay. In liver lysates, incubation of different concentrations of Piceatannol 3'-O-glucoside significantly decreases arginase I activity (75±5% at 1 µM, 72±7% at 3 µM, 62±1% at 10 µM) compared to untreated control (100±9%). In kidney lysates, the residual arginase activities after incubation of 1, 3 and 10 µM Piceatannol 3'-O-glucoside are 75±6, 74±5, and 53±8%, respectively. Arginase activity is measured in the presence of different concentration of Piceatannol 3'-O-glucoside (from 0 to 120 µM) using liver lysate and kidney lysate. The 50% inhibitory concentrations (IC 50 ) are 11.22 µM for the liver lysate and 11.06 µM for kidney lysate. The values are obtained using the software of Graphpad prizm 4.0. Piceatannol 3'-O-glucoside inhibits arginase activity and increases NO production in HUVECs. Piceatannol 3'-O-glucoside inhibits lipoxygenase activity upto 66% at the concentration of 100 µM and IC 50 value is 69 µM. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

In order to ascertain whether Piceatannol 3'-O-glucoside (PG) ameliorates vascular function in wild-type (WT) and atherogenic model mice [apolipoprotein E- mice (ApoE -/- )] and to investigate the possible underlying mechanism. Preincubation of aortic vessels from WT mice fed a normal diet (ND) with Piceatannol 3'-O-glucoside attenuates vasoconstriction response to U46619 and phenylephrine (PE), while the vasorelaxant response to acetylcholine (Ach) is markedly enhanced in an endothelium-dependent manner. Piceatannol 3'-O-glucoside treatment attenuates the phenylephrine (PE)-dependent contractile response, and significantly improves the acetylcholine (Ach)-dependent vasorelaxation response in aortic rings from ApoE -/- mice fed a high-cholesterol diet (HCD). Piceatannol 3'-O-glucoside administration in the drinking water significantly reduces fatty streak formation in ApoE -/- mice fed an HCD. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal administration

Mice Twenty 10-week-old male wild-type (WT) (C57BL/6J) and ApoE -/- mice are studied. To determine the effect of Piceatannol 3'-O-glucoside on vascular reactivity, aortic rings isolated from 20 male C57BL/6J WT mice fed a normal diet (ND) and 20 male ApoE -/- mice fed an HCD are studied for 6 weeks. Aortic rings are incubated with or without Piceatannol 3'-O-glucoside (50 μM) for 18 h. For the pathological assay, Piceatannol 3'-O-glucoside is administered in the drinking water to ApoE -/- mice for 6 weeks when the mice are started on the HCD. Given that each mouse consumes ~10 mL water/day this represents a daily dose of ~500 μg/mouse/day of Piceatannol 3'-O-glucoside . aladdin has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:NO synthase, IC50: 11.22 μM (Arginase I), 11.06 μM (Arginase II)

规格

别名
白皮杉醇 3'-O-葡萄糖苷
规格或纯度
≥99%
英文名称
Piceatannol 3'-O-glucoside
生化机理
大黄的活性成分皮夏单宁 3'-O- 葡萄糖苷通过抑制精氨酸酶的活性激活内皮一氧化氮(NO)合成酶,对精氨酸酶 I 和精氨酸酶 II 的 IC 50 s 分别为 11.22 µM 和 11.06 µM。
储存条件
避光,-80℃储存
运输条件
特低温运输
作用类型
抑制剂
纯度
≥99%
名称和识别符
分子类型
小分子
IUPAC Name
(2S,3R,4S,5S,6R)-2-[5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
INCHI
1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-7-10(3-4-14(15)24)1-2-11-5-12(22)8-13(23)6-11/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
InChi Key
UMGCIIXWEFTPOC-CUYWLFDKSA-N
Smiles
C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)OC3C(C(C(C(O3)CO)O)O)O)O
Isomeric SMILES
C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
PubChem CID
分子量
406.38

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高级数据

系统学分类

分类树(Taxonomy Tree)

界(kingdom) 有机化合物
超类(Superclass) 苯丙素类和聚酮类
类(Class) 芪类
亚类(Subclass) 二苯乙烯苷
中间层级节点(Intermediate Tree Nodes) 暂无
直接上位类(Direct Parent) 二苯乙烯苷
其他上位类(Alternative Parents) 酚苷类  己糖  O-糖基化合物  苯乙烯  间苯二酚  苯氧基化合物  酚醚  1-羟基-2-未取代苯类化合物  1-羟基-4-未取代苯类化合物  氧烷  仲醇  多元醇  氧环化合物  缩醛  碳氢化合物衍生物  伯醇  
分子骨架(Molecular Framework) 芳香族杂单环化合物
取代基(Substituents) 1-羟基-2-未取代苯环化合物 - 1-羟基-4-未取代苯环化合物 - 乙醛酸 - 羟基苯甲酸酯 - 芳香族杂单环化合物 - 苯基化合物 - 糖基化合物 - 己糖单糖 - 烃衍生物 - 单环苯基基团 - 单糖 - O-羧基化合物 - 有机氧化合物 - 有机杂环化合物 - 有机氧化合物 - 氧杂环 - 氧杂环丁烷 - 苯酚 - 苯酚醚 - 苯酚糖苷 - 苯氧基化合物 - 多醇 - 初级醇 - 间苯二酚 - 醛基 - 苯乙烯糖苷 - 苯乙烯
描述(Description) 该化合物属于苯乙烯糖苷类有机化合物。这类化合物结构特征在于含有通过糖苷键与苯乙烯骨架连接的糖类基团。
外部描述符(External Descriptors) 暂无
三维结构
交互式化学结构模型





关联靶点(其它种属)
Mus musculus (284745 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
作用机制
作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献
化学和物理性质
溶解性
DMSO : 50 mg/mL (123.04 mM; Need ultrasonic) H2O : <0.1 mg/mL (ultrasonic;warming;heat to 60°C) (insoluble)
分子量
406.400 g/mol
XLogP3
0.700
氢键供体数Hydrogen Bond Donor Count
7
氢键受体数Hydrogen Bond Acceptor Count
9
可旋转键计数Rotatable Bond Count
5
精确质量Exact Mass
406.126 Da
单同位素质量Monoisotopic Mass
406.126 Da
拓扑极表面积Topological Polar Surface Area
160.000 Ų
重原子数Heavy Atom Count
29
形式电荷Formal Charge
0
复杂度Complexity
534.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
5
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
1
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
1
共价键合单元计数Covalently-Bonded Unit Count
1
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