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(Synonyms: 鞘磷脂(鸡蛋)) 目录号 : GC18328 复制 一键复制产品信息

Sphingomyelins是哺乳动物细胞膜中主要的鞘脂类物质,特异性地富集于质膜中。

Sphingomyelins Chemical Structure

Cas No.:383907-87-7

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Description

Sphingomyelins are a dominant sphingolipid in membranes of mammalian cells, and this lipid class is specifically enriched in the plasma membrane [1]. Sphingomyelins have a favorable interaction with cholesterol (and other sterols), regulating the distribution of cholesterol within the cell membrane and maintaining the cholesterol homeostasis [2]. Sphingomyelins have been widely used to regulate the lipid mobility of high-density lipoproteins (HDL) and the extracellular flow of cholesterol[3].

In vitro, Sphingomyelins treatment (50µM) for 1 hour significantly promoted the vacuolation in HeLa cells mediated by 10nM vacuolating cytotoxin (VacA)[4].

In vivo, Sphingomyelins treatment via oral administration at a dose of 8mg daily for 7 days aggravated the intestinal mucosal inflammation in a mouse model of colitis induced by dextran sulfate sodium (DSS), and impaired the intestinal mucosal function[5]. Oral administration of 0.05% Sphingomyelins in AIN76A diet for 45 weeks significantly inhibited the progression of colon tumors induced by 1,2-dimethylhydrazine (DMH) in mice[6].

References:
[1] Slotte J P. Biological functions of sphingomyelins[J]. Progress in lipid research, 2013, 52(4): 424-437.
[2] Slotte J P, Ramstedt B. The functional role of sphingomyelin in cell membranes[J]. European journal of lipid science and technology, 2007, 109(10): 977-981.
[3] Martínez-Beamonte R, Lou-Bonafonte J M, Martínez-Gracia M V, et al. Sphingomyelin in high-density lipoproteins: structural role and biological function[J]. International journal of molecular sciences, 2013, 14(4): 7716-7741.
[4] Gupta V R, Patel H K, Kostolansky S S, et al. Sphingomyelin functions as a novel receptor for Helicobacter pylori VacA[J]. PLoS pathogens, 2008, 4(5): e1000073.
[5] Fischbeck A, Leucht K, Frey-Wagner I, et al. Sphingomyelin induces cathepsin D-mediated apoptosis in intestinal epithelial cells and increases inflammation in DSS colitis[J]. Gut, 2011, 60(1): 55-65.
[6] Lemonnier L A, Dillehay D L, Vespremi M J, et al. Sphingomyelin in the suppression of colon tumors: prevention versus intervention[J]. Archives of biochemistry and biophysics, 2003, 419(2): 129-138.

Sphingomyelins是哺乳动物细胞膜中主要的鞘脂类物质,特异性地富集于质膜中[1]。Sphingomyelins与胆固醇(及其他甾醇)具有良好的相互作用,可调节胆固醇在细胞膜内的分布并维持胆固醇稳态[2]。Sphingomyelins已被广泛用于调节高密度脂蛋白的脂质流动性以及胆固醇的细胞外流动[3]

在体外,50µM的Sphingomyelins处理HeLa细胞1小时,显著促进了10nM空泡毒素介导的细胞空泡化[4]

在体内,每日口服8mg剂量的Sphingomyelins,连续7天,加剧了葡聚糖硫酸钠(DSS)诱导的结肠炎小鼠模型的肠道黏膜炎症,并损害了肠道黏膜功能[5]。在AIN76A饲料中添加0.05%的Sphingomyelins并每日喂养45周,显著抑制了1,2-dimethylhydrazine (DMH)诱导的小鼠结肠肿瘤的进展[6]

实验参考方法

Cell experiment [1]:

Cell lines

HeLa cells

Preparation Method

HeLa cells were grown in minimum essential medium (MEM) with 10% (v/v) fetal bovine serum (FBS), 100μg/ml streptomycin, and 100U/ml penicillin at 37°C in 5% CO2/atmosphere. HeLa cells were pretreated for 1h with different concentrations of Sphingomyelins (0,1 5, 10, 25, and 50µM) and were then further incubated at 37°C with 10nM VacA. After 24h, cells were evaluated by DIC microscopy or neutral red uptake assays. DIC images of cells stained with neutral red.

Reaction Conditions

0,1 5, 10, 25, and 50µM; 1h

Applications

Sphingomyelins treatment significantly promoted VacA-mediated vacuolation in HeLa cells in a dose-dependent manner.
Animal experiment [2]:

Animal models

Female C57-BL/6J-Fue mice

Preparation Method

Female C57-BL/6J-Fue mice were housed singly in a standard environment with food and water ad libitum. Acute colitis was induced in C57-BL/6 mice with 2.0% DSS over 7 days. 8mg of Sphingomyelins (calculated as 0.2% of the total daily food intake) was resuspended in drinking water and applied by oral gavage for 7 days. Assessment of colonoscopy and histological score in mice.

Dosage form

8mg/day for 7 days; p.o.

Applications

Sphingomyelins treatment significantly aggravated the intestinal mucosal inflammation in mice with DSS-mediated colitis.

References:
[1] Gupta V R, Patel H K, Kostolansky S S, et al. Sphingomyelin functions as a novel receptor for Helicobacter pylori VacA[J]. PLoS pathogens, 2008, 4(5): e1000073.
[2] Fischbeck A, Leucht K, Frey-Wagner I, et al. Sphingomyelin induces cathepsin D-mediated apoptosis in intestinal epithelial cells and increases inflammation in DSS colitis[J]. Gut, 2011, 60(1): 55-65.

化学性质

Cas No. 383907-87-7 SDF
别名 鞘磷脂(鸡蛋)
Canonical SMILES [R]C(N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC)=O
分子式 C39H79N2O6P (for palmitoyl) 分子量 703
溶解度 Chloroform: Soluble,Ethanol: Warmed,Methanol: Soluble 储存条件 Store at -20°C
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1 mM 1.4225 mL 7.1124 mL 14.2248 mL
5 mM 284.5 μL 1.4225 mL 2.845 mL
10 mM 142.2 μL 711.2 μL 1.4225 mL
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