Ceramide 1-sulfates

Two ceramide 1-sulfates (9-10) have been obtained from the Japanese bryozoan Watersipora cucullata. These compounds are potent deoxyribonucleic acid (DNA) topoisomerase I inhibitors [37],... 

Ojika, M., Yoshino, G., and Sakagami, Y. (1997) Novel ceramide 1-sulfates, potent DNA topo-isomerase I inhibitors isolated from the bryozoa Watersipora cucullata. Tetrahedron Lett., 38, 4235-4238. 

The galactose bears a 3-sulfate group in cerebroside sulfatides, e.g., in lactosyl ceramide sulfate ... 

An important group of glycolipids are acidic glycosphingolipids, which contain either bound sialic acid or sulfuric acid. They were previously called mucolipids. The sugar moiety is sulfated in sulfoglycosphingolipids for example, in glycosyl-ceramide sulfates (Figure 5.5.1). 

Three sulfated ceramides, calyceramides A-C (626-628) were isolated as inhibitors of neuraminidase from the marine sponge Discodermia calyx. Their structures were determined by spectroscopic and chemical methods [497],... 

Glycolipids are important constituents of the plasma membranes, of the endoplasmic reticulum, and of chloroplasts. The cerebrosides and their sulfate esters, the sulfatides, are especially abundant in myelin. In plant membranes, the predominant lipids are the galactosyl diglycerides.29 74 The previously described ether phospholipids (archaebacteria), ceramide arnino-ethylphosphonate (invertebrates), and sulfolipid (chloroplasts) are also important membrane components. 

A partial synthesis of cerebroside sulfate [ sulfatide, the glycoside of ceramide with galactose 3-sulfate, (90)] was achieved [90] by acylating the sphingosine galactosyl 3-sulfate (89) (obtained by basic hydrolysis of natural sulfatide) with palmitoyl chloride or D-2-acetoxypalmitoyl chloride (and subsequent basic hydrolysis of the... 

In recessive X-linked ichthyosis, the amount of cholesterol sulfate in the stratum corneum is increased due to a deficiency in cholesterol sulfatase deficiency [69,70], Lipid analysis of scales reveals a nearly 10-fold increase in the cholesterol sulfate to free cholesterol ratio as compared to healthy stratum corneum [71]. Previous x-ray diffraction studies on isolated ceramide mixtures revealed that increased cholesterol sulfate levels induce the formation of a fluid phase, which is likely to reduce the skin barrier function [72]. 

Figure 17-3. Important glycolipids affected in I-cell disease. The dotted lines represent the respective P-linked glycosides. Ceramide, 2-N-acylsphingosine NANA, A -acetyl n c u ram i n i c acid. GL-lbs is shown sulfated in the 3 position of galactose (SOjH — 3).

The major lipids found in the stratum comeum are ceramides, fatty acids, and cholesterol. Free fatty acids make up 10-15% of the lipid mass of the stratum corneum and predominantly consist of straight-chain saturated species ranging from 14 to 28 carbons in length. Cholesterol, a major lipid found in the stratum corneum, represents approximately 25% of the total stratum comeum lipid while cholesterol sulfate accounts for another 5%. 

Mammalian stratum comeum (SC) consists of highly comified cells embedded in a matrix of lipid bilayers (Matoltsy, 1976). These extracellular lipids are arranged in the form of multiple lamellae that are believed to constitute the major barrier to percutaneous penetration (Michaels et al., 1975 Elias, 1983). As discussed, the SC lipid membranes are made up predominantly of ceramides, cholesterol, free fatty acids, cholesteryl sulfate, and small amounts of some less well-defined nonpolar components (Gray et al., 1982 Yardley and Summerly, 1981). Six groups of ceramides have been characterized in porcine SC, as shown in Fig. 4 (Wertz et al., 1983). This classification was based on the polarity of the ceramides, with ceramide 1 being the least polar. 

Ceramides Cholesterol Palmitic acid Cholesteryl sulfate ... 

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