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  • Catalog #:2211

  • Scientific Name:N-Hexanoyl-biotin-phytosphingosine

  • Common Name:N-C6:0-biotin-Phytoceramide

  • Empirical Formula:C34H64N4O6S

  • SDS:View Safety Data Sheet

  • Data Sheet:View Data Sheet

  • Formula Weight:657

  • Unit:5 mg

  • Solvent:none

  • Source:semisynthetic, yeast (Pichia ciferri)

  • Purity:98+%

  • Analytical Methods:TLC, HPLC, identity confirmed by MS

  • Solubility:chloroform/methanol 2:1, DMF

  • Physical Appearance:solid

  • Storage:-20℃

  • Dry Ice:No

  • Hazardous:No


Application Notes:

N-乙酰基-生物素-植物鞘氨醇这种植物神经酰胺类似物包含一个生物素单元,该生物素单元通过己酸连接子连接到植物鞘苷部分的胺上,非常适合用于鞘脂研究。 生物素结构允许神经酰胺附着在链霉亲和素上,亲和素使其对结合底物和毒素检测非常有用1。 植物鞘氨醇是一种长链鞘氨醇碱基,具有信号转导、细胞骨架结构、细胞周期和热应激反应等重要的细胞功能。 它主要存在于哺乳动物、植物和酵母中。 植物鞘氨醇由于其对皮肤的作用,如通过抑制过敏细胞因子IL-4和TNF-α的表达来减轻炎症,以及在组胺刺激的皮肤组织中激活转录因子NF-jB和c-jun,因此在化妆品中得到了广泛的应用 植物鞘氨醇可通过两种不同的途径导致细胞凋亡,并已被研究作为一种可能的癌症治疗方法。 植物神经酰胺(脂肪酸酰化为植物鞘氨酸)分布在小肠上皮细胞的微绒毛膜上。 隐窝细胞和邻近的上皮细胞产生植物鞘糖脂的数量远多于分化的上皮细胞 肾脏和皮肤也含有植物鞘糖脂,尽管浓度比小肠低得多。 植物神经酰胺是皮肤水屏障脂质的一部分。 2-羟基四氧基植物神经酰胺最近被证实对人类有免疫刺激作用 植物神经酰胺在中枢神经系统中的作用已被发现具有重要的神经保护功能 。 

This phytoceramide analogue contains a biotin unit attached to the amine of the phytosphingosine moiety via a hexanoic acid linker and is ideal for use in sphingolipid studies. The biotin structure allows for attachment of the ceramide to streptavidin and avidin making it extremely useful for binding to substrates and for toxin detection1. Phytosphingosine is a long-chain sphingoid base having important cellular functions such as signaling, cytoskeletal structure, cellular cycle, and heat stress response.  It is found largely in mammals, plants, and yeast.  Phytosphingosine has seen much use in cosmetics due to its effects on the skin such as reducing inflammation by inhibiting the expression of the allergic cytokines IL-4 and TNF-α and the activation of the transcription factors NF-jB and c-jun in histamine-stimulated skin tissues.2  Phytosphingosine can lead to apoptosis via two distinct pathways and has been investigated as a possible cancer therapeutic treatment.  Phytoceramides (fatty acid acylated to Phytosphingosine) are distributed at the microvillous membrane of the epithelial cells of the small intestine.  Crypt cells and the adjacent epithelial cells produce phytosphingoglycolipids in much greater quantities than more differentiated epithelial cells.3  The kidney and skin also contain phytosphingoglycolipids although in much lower concentrations than in the small intestine.  Phytoceramides form part of the water barrier lipids of the skin.  2-hydroxytetracosanoyl-phytoceramide has recently been shown to have immunostimulating effects in humans.4  Phytoceramides have lately been studied in regards to their role in the central nervous system and have been found to have important functions in neuroprotection.5

1. A. Mukhopadhyay et al. “Direct interaction between the inhibitor 2 and ceramide via sphingolipid-protein binding is involved in the regulation of protein phosphatase 2A activity and signaling” FASEB, Vol. 23(3) pp. 751-763, 2009
2. K. Ryu et al. “Anti-scratching Behavioral Effects of N-Stearoylphytosphingosine and 4-Hydroxysphinganine in Mice” Lipids, Vol. 45 pp. 615-618, 2010
3. F. Omae et al. “DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine” Journal of Biochemistry, vol. 379 pp. 687-695, 2004
4. M. Sekiya et al. “A phytoceramide analog stimulates the production of chemokines through CREB activation in human endothelial cells” Int Immunopharmacol., vol. 11 pp. 1497-503, 2011
5. J-C. Jung et al. “Phytoceramide Shows Neuroprotection and Ameliorates Scopolamine-Induced Memory Impairment” Molecules, vol. 16 pp. 9090-9100, 2011