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D-(-)-水杨苷; D-(-)-水杨甙

D-(-)-水杨苷; D-(-)-水杨甙用途

【用途一】
用于解热、镇痛、抗风湿
【用途二】
测定β-糖苷酶的底物。硝酸试剂。

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D-(-)-水杨苷; D-(-)-水杨甙名称

[ CAS 号 ]:
138-52-3

[ 中文名 ]:
水杨甙

[ 英文名 ]:
D-(-)-Salicin

[中文别名 ]:

[英文别名 ]:

EINECS 205-331-6
Saligenin-β-δ-glucopyranoside
SALICOSIDE
2-(Hydroxymethyl)phenyl β-D-glucopyranoside
Salicyl alcohol-b-glucoside
2-(Hydroxymethyl)phenyl-β-D-glucopyranoside
2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
Saligenin-β-D-glucopyranoside
Saligenin-b-D-glucopyranoside
o-(Hydroxymethyl)phenyl β-D-glucopyranoside

D-(-)-水杨苷; D-(-)-水杨甙生物活性

[ 描述 ]:

Salicin 是一个天然的 COX 抑制剂。

[ 相关类别 ]:

天然产物 >> 酚类

研究领域 >> 癌症

研究领域 >> 炎症/免疫

[ 靶点 ]

COX

[体外研究]

与COLO对照相比,在COLO细胞中用Salicin10μM处理观察到COX2的酶产物PGE2显着下调至裂解物中的76％和上清液中的70％。这伴随着对基因水平的91％的CCD对照的最小COX1抑制。用1μM水杨苷治疗可使结肠癌细胞增殖率在24小时时从144％降至113％,在48小时时降低187％至130％,10μM在24小时时增殖率降低至108％,在48小时时降低119％[1] 。与LPS组相比,用0.07,0.14和0.28μM水杨苷预处理的LPS诱导的细胞中TNF-α,IL-1β和IL-6的浓度显着降低[2]。

[体内研究]

Salicin(D(-)- Salicin)(35,70,140μM)显着抑制LPS诱导的病理变化。与对照组相比,LPS诱导的肺组织中的MPO活性显着增加。然而,Salicin(35,70,140μM)显着抑制了这种变化。用Salicin预处理可以剂量依赖的方式抑制LPS诱导的JNK,ERK,p38/MAPK和p65的激活[2]。

[细胞实验]

在该研究中使用RAW264.7小鼠巨噬细胞系。将RAW264.7细胞机械刮擦并以4×10 5个细胞/ mL的密度接种到96孔板上，在37℃，5％CO 2培养箱中1小时。然后用不同浓度（0至0.28μM）的50μL水杨苷（D（ - ） - 水杨苷）处理细胞1小时，然后用50μL脂多糖（LPS）（4μg/ mL）刺激。 18小时后，向每个孔中加入10μLCCK-8并继续孵育4小时。然后，在酶标仪[2]上测量450nm处的光密度。

[动物实验]

将小鼠随机分为5组，每组3只小鼠：对照组，脂多糖（LPS），LPS +水杨苷（D（ - ） - Salicin）组腹腔注射水杨苷35μM，LPS + Salicin组腹腔注射水杨苷用140μM的水杨苷腹膜内注射70μM，LPS + Salicin组。 1小时后，鼻内滴注溶解在50μLPBS中的10μgLPS以诱导肺损伤。对照小鼠给予50μL不含LPS的PBS。在LPS处理12小时后，通过具有高压灭菌PBS的气管插管收集支气管肺泡灌洗液（BALF）3次。然后，将组织样品在4℃下以3000rpm离心10分钟[2]。

[参考文献]

[1]. Jun Yan He, et al. Salicin as a Multipurpose Therapeutic Approach for Colon Cancer.

[2]. Li Y, et al. D(-)-Salicin inhibits the LPS-induced inflammation in RAW264.7 cells and mouse models. Int Immunopharmacol. 2015 Jun;26(2):286-94.

[相关活性小分子]

D-(-)-水杨苷; D-(-)-水杨甙物理化学性质

[ 密度 ]:
1.5±0.1 g/cm3

[ 沸点 ]:
549.1±50.0 °C at 760 mmHg

[ 熔点 ]:
196-202 °C

[ 分子式 ]:
C₁₃H₁₈O₇

[ 分子量 ]:
286.278

[ 闪点 ]:
285.9±30.1 °C

[ 精确质量 ]:
286.105255

[ PSA ]:
119.61000

[ LogP ]:
-1.85

[ 外观性状 ]:
有吸湿性。水中溶解度: 36 g/L (15°C), 250 g/L (60°C) ，溶于吡啶、碱和冰乙酸，几乎不溶于乙醚和氯仿。水溶液呈中性，而且味苦。有刺激性。密度：1.434熔点：199-202℃

[ 蒸汽压 ]:
0.0±1.6 mmHg at 25°C

[ 折射率 ]:
1.638

[ 储存条件 ]:
Store at RT.

[ 水溶解性 ]:
36 g/L (15 ºC), 250 g/L (60 ºC)

D-(-)-水杨苷; D-(-)-水杨甙MSDS

详细MSDS(安全技术说明书)

D-(-)-水杨苷; D-(-)-水杨甙毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ5901700

CHEMICAL NAME :: beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl-

CAS REGISTRY NUMBER :: 138-52-3

LAST UPDATED :: 199706

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H18-O7

MOLECULAR WEIGHT :: 286.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

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

REFERENCE :: CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 6,63,1954

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D-(-)-水杨苷; D-(-)-水杨甙安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H317

[ 警示性声明 ]:
P280

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R43

[ 安全声明 (欧洲) ]:
S36/37-S37-S24/25

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

[ WGK德国 ]:
3

[ RTECS号 ]:
LZ5901700

[ 海关编码 ]:
2932999099

D-(-)-水杨苷; D-(-)-水杨甙合成路线

详细合成路线

D-(-)-水杨苷; D-(-)-水杨甙上下游产品

D-(-)-水杨苷; D-(-)-水杨甙上游产品

D-(-)-水杨苷; D-(-)-水杨甙下游产品

D-(-)-水杨苷; D-(-)-水杨甙海关

[ 海关编码 ]: 2932999099

[ 中文概述 ]:
2932999099. 其他仅含氧杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

D-(-)-水杨苷; D-(-)-水杨甙文献

Aspen defense chemicals influence midgut bacterial community composition of gypsy moth.

J. Chem. Ecol. 41(1) , 75-84, (2015)

Microbial symbionts are becoming increasingly recognized as mediators of many aspects of plant - herbivore interactions. However, the influence of plant chemical defenses on gut associates of insect h...

Development of a fast extraction method and optimization of liquid chromatography-mass spectrometry for the analysis of phenolic compounds in lentil seed coats.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 969 , 149-61, (2014)

A systematic set of optimization experiments was conducted to design an efficient extraction and analysis protocol for screening six different sub-classes of phenolic compounds in the seed coat of var...

Catechol, a bioactive degradation product of salicortin, reduces TNF-α induced ICAM-1 expression in human endothelial cells.

Planta Med. 77(10) , 1024-6, (2011)

The phenolic glucoside salicortin was isolated from a Willow bark extract, and its ability to reduce the TNF- α induced ICAM-1 expression (10 ng/mL, 30 min pretreatment with salicortin) was tested IN ...

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