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At least 235 records · Page 13Linked to original sources
PubMed1995

Assembly of Alzheimer-like, insoluble filaments from brain cerebrosides.

Amphiphiles are molecules which contain a polar head and a hydrophobic tail. When the head contains a chiral center, amphiphiles, incubated in the presence of some di- and trivalent metal ions, have been shown to form large fibrous molecular aggregates. In this study, naturally occurring brain cerebroside was tested to determine if it had sufficient amphiphilic properties to form similar supramolecular structures. When galactocerebroside was heated in the presence of magnesium, it was able to form tubules, vesicles and filaments. The filaments included long fibrils that aggregated into dense bundles and short fibrils that were associated to form smaller bundles. These fibrils were shown to be resistant to solubilization in boiling SDS in the presence of reducing agents. This is the first report of a naturally occurring glycolipid being able to form filaments. Since their structural and physical properties are similar to the paired helical filaments of Alzheimer's disease, they may serve as an experimental model for their assembly.

Alzheimer Disease↗
PubMed2003

New cerebrosides from Euphorbia peplis L.: antimicrobial activity evaluation.

The less polar fraction of the methanolic extract from the plant Euphorbia peplis L. exhibited interesting antifungal and antitubercular activity. A complex mixture of four glucocerebrosides was responsible for this activity. Two new cerebrosides were isolated for the first time from Euphorbiaceae, 4 was assigned as 1-O-(beta-D-glucopyranosyl)-(2S,3S,4E,8E)-2N-[(2'R)-2'-hydroxy-hexadecanoyl]-4 (E), 8 (E)-octadecadiene-1,3-diol and 3 as the 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R,8Z)-2N-[(2'R)-2'-hydroxytetracosanoyl]-8 (Z)-octadecene-1,3,4-triol. The structures were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.

Anti-Bacterial Agents↗
PubMed2006

A new cerebroside from Polygala japonica.

The isolation of a new cerebroside, 1-O-beta-d-glucopyranosyl-(2S,3S,4R,11E)-2-[(2'R)-2'-hydroxypalmitoylamino]-11-octadecene-1,3,4-triol (polygalacerebroside) (1), from the aerial part of Polygala japonica is reported.

Cerebrosides↗
PubMed2006

Immunosuppressive diacetylenes, ceramides and cerebrosides from Hydrocotyle leucocephala.

Three C-17 diacetylenic compounds (1-3), one monoterpenoid (4), seven ceramides (leucoceramides A-G, 5a-g), six cerebrosides (leucocerebrosides A-F, 6a-f) and nine known compounds were isolated from the methanolic extract of Hydrocotyle leucocephala. Their structures were established by spectroscopic methods. The isolated compounds 1-3, 5a-g, 6a-f and 7 were shown to be active in the lipopolysaccharide (LPS) induced cytokine production assay for IL-10, IL-12, and TNF-alpha.

Acetylene↗
PubMed1997

Cerebrosides alter the lyotropic and thermotropic phase transitions of DOPE:DOPC and DOPE:DOPC:sterol mixtures.

Freezing injury in rye and oat is a consequence of the formation of the inverted hexagonal (H(II)) phase in regions where the plasma membrane is brought into close proximity with cytoplasmic membranes during freeze-induced dehydration. Susceptibility to plasma membrane destabilization and H(II) phase formation during freezing is associated with alterations in plasma membrane lipid composition. This paper examines the influence of lipid composition and hydration on the propensity of lipid mixtures of DOPE:DOPC and DOPE:DOPC:sterols with added cerebrosides (CER) to form the H(II) phase during dehydration. The addition of CER to DOPE:DOPC:beta-sitosterol mixtures decreased the water content of the dispersions in a manner suggesting that most or all of the water in the dehydrated mixtures was associated with the phospholipids. The addition of CER significantly decreased the osmotic pressure at which the L(alpha) --> H(II) phase transition occurred from an osmotic pressure of 76.1 MPa for DOPE:DOPC (50:50) to 20 MPa in DOPE:DOPC:beta-sitosterol:CER (22.5:22.5:50:5) and 8 MPa in DOPE:DOPC:beta-sitosterol:CER (15:15:50:20). Experiments examining the effects of CER on the thermally-induced formation of the H(II) phase in fully hydrated mixtures and examining the influence of CER on the formation of the H(II) phase in DOPE:DOPC mixtures lacking beta-sitosterol suggested that CER facilitated the L(alpha) --> H(II) phase transition by effecting a decrease in bilayer hydration and by increased lateral packing pressures within the acyl domain of the bilayer. Taken in sum, these data indicate that the differential propensity of the rye and oat plasma membranes to undergo freeze-induced formation of the L(alpha) --> H(II) phase cannot be attributed to one lipid species. Rather, the propensity towards freeze-induced membrane destabilization is a consequence of the summation of physical characteristics of the membrane lipid components that included bilayer hydration, packing pressures within the hydrophobic domain of the membrane, the propensity of the lipid components to demix, and the relative proportions of the various lipid components.

Avena↗
PubMed2000

Trans interactions between galactosylceramide and cerebroside sulfate across apposed bilayers.

The two glycosphingolipids galactosylceramide (GalC) and its sulfated form, cerebroside sulfate (CBS), are present at high concentrations in the multilayered myelin sheath and are involved in carbohydrate-carbohydrate interactions between the lipid headgroups. In order to study the structure of the complex of these two glycolipids by Fourier transform infrared (FTIR) spectroscopy, GalC dispersions were combined with CBS dispersions in the presence and absence of Ca(2+). The FTIR spectra indicated that a strong interaction occurred between these glycolipids even in the absence of Ca(2+). The interaction resulted in dehydration of the sulfate, changes in the intermolecular hydrogen bonding interactions of the sugar and other oxygens, decreased intermolecular hydrogen bonding of the amide C==O of GalC and dehydration of the amide region of one or both of the lipids in the mixture, and disordering of the hydrocarbon chains of both lipids. The spectra also show that Ca(2+) interacts with the sulfate of CBS. Although they do not reveal which other groups of CBS and GalC interact with Ca(2+) or which groups participate in the interaction between the two lipids, they do show that the sulfate is not directly involved in interaction with GalC, since it can still bind to Ca(2+) in the mixture. The interaction between these two lipids could be either a lateral cis interaction in the same bilayer or a trans interaction between apposed bilayers. The type of interaction between the lipids, cis or trans, was investigated using fluorescent and spin-label probes and anti-glycolipid antibodies. The results confirmed a strong interaction between the GalC and the CBS microstructures. They suggested further that this interaction caused the CBS microstructures to be disrupted so that CBS formed a single bilayer around the GalC multilayered microstructures, thus sequestering GalC from the external aqueous phase. Thus the CBS and GalC interacted via a trans interaction across apposed bilayers, which resulted in dehydration of the headgroup and interface region of both lipid bilayers. The strong interaction between these lipids may be involved in stabilization of the myelin sheath.

Animals↗
PubMed2002

Unusual fatty acid composition of cerebrosides from the filamentous soil fungus Mortierella alpina.

The cerebrosides produced by the soil filamentous fungus Mortierella alpina strain KG-1/95 account for about 13% of the total polar lipids extractable from lyophilised cells with chloroform/methanol mixtures. By means of 1H NMR and (13)C NMR spectroscopy, matrix-assisted laser-desorption ionisation mass spectrometry, and chemical degradation experiment, they have been shown to be 1-O-beta-D-glucopyranosyl-2-N-(2'-D-hydroxyalkanoyl)-9-methylsphinga-4(E),8(E)-dienines, the fatty acid composition of which is unusual and consists of 2-hydroxytridecanoic (4%), 2-hydroxytetradecanoic (60%), 2-hydroxypentadecanoic (20%), and 2-hydroxyhexadecanoic (16%) acids.

Cerebrosides↗
PubMed2003

Pinelloside, an antimicrobial cerebroside from Pinellia ternata.

An antimicrobial cerebroside, pinelloside, was isolated from the air-dried tubers of Pinellia ternata (Thunb.) Breit. Its structure was determined as 1-O-beta-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol by chemical transformation and extensive spectroscopic analyses (IR, MS, 1H and 13C NMR, DEPT as well as 2D NMR techniques HMBC, HMQC, 1H-1H COSY and NOESY). The antimicrobial assay showed that this compound was inhibitory to the growth of Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans, with minimum inhibitory concentrations (MICs) of 20, 50, 30 and 10 microg/ml, respectively. The MICs of penicillin G against bacteria B. subtilis, S. aureus, E. coli, P. fluorescens and H. pylori were 0.80, 0.34, 0.56, 1.34 and 0.92, and those of ketoconazole against fungi A. niger, C. albicans and T. rubrum 0.90, 0.65 and 1.0 microg/ml, respectively.

Anti-Infective Agents↗
PubMed1993

A carbohydrate-carbohydrate interaction between galactosylceramide-containing liposomes and cerebroside sulfate-containing liposomes: dependence on the glycolipid ceramide composition.

Galactosylceramide (GalCer) and cerebroside sulfate (CBS) are the major glycolipids found in myelin. They occur in greater concentrations in this membrane than any other. Recently, it was reported that these two glycolipids can participate in a heterotypic carbohydrate-carbohydrate interaction [Hakomori et al. (1991) Glycoconjugate J. 8, 178]. In the present study, the effect of changes in the ceramide composition of both GalCer and CBS on this interaction has been examined. The interaction was monitored by measuring the aggregation of small unilamellar phosphatidylcholine/cholesterol liposomes containing GalCer with similar liposomes containing CBS, through the increase in optical density at 450 nm. Aggregation depends on the addition of a divalent cation and varies inversely with the ionic radius of the cation. Aggregation occurred at millimolar concentrations of divalent cation and was inhibited and reversed by the addition of EDTA. A lesser degree of homotypic self-aggregation of GalCer and of CBS liposomes also occurred in the presence of divalent cations, but the sum of this self-aggregation was significantly less than the heterotypic interaction between the two types of liposomes. Changes in the ceramide composition of GalCer and CBS significantly affected the extent of their interaction with each other. Increasing the fatty acid chain length of either GalCer or CBS resulted in increased aggregation. Hydroxylation of the fatty acid also increased the degree of aggregation of GalCer and CBS liposomes. These findings indicate that a divalent cation-mediated GalCer-CBS interaction could play a role in cell recognition and membrane adhesion phenomena such as the formation of compact multilamellar myelin.(ABSTRACT TRUNCATED AT 250 WORDS)

1,2-Dipalmitoylphosphatidylcholine↗
PubMed1989

Anisotropic 2H NMR spin-lattice relaxation in L alpha-phase cerebroside bilayers.

A series of 2H NMR inversion recovery experiments in the L alpha phase of the cerebroside N-palmitoylgalactosylsphingosine (NPGS) have been performed. In these liquid crystalline lipid bilayers we have observed substantial anisotropy in the spin-lattice relaxation of the CD2 groups in the acyl chains. The form and magnitude of the anisotropy varies with position in the chain, being positive in the upper region, decreasing to zero at the 4-position, and reversing sign at the lower chain positions. It is also shown that addition of cholesterol to the bilayer results in profound changes in the anisotropy. These observations are accounted for by a simple motional model of discrete hops among nine sites, which result from the coupling of two modes of motion--long-axis rotational diffusion and gauche-trans isomerization. This model is employed in quantitative simulations of the spectral line shapes and permits determination of site populations and motional rates. These results, plus preliminary results in sphingomyelin and lecithin bilayers, illustrate the utility of T1 anisotropy measurements as a probe of dynamics in L alpha-phase bilayers.

Cerebrosides↗
PubMed1990

Dependence of the surface expression of the glycolipid cerebroside sulfate on its lipid environment: comparison of sphingomyelin and phosphatidylcholine.

The influence of the membrane lipid environment on the reactivity with antibody of the acidic glycolipid cerebroside sulfate (CBS) was examined by using a spin membrane immunoassay. Fewer antibodies in a polyclonal anti-CBS antiserum recognized the antigen in a bovine brain sphingomyelin/cholesterol (SM/CHOL) environment than in dipalmitoylphosphatidylcholine/cholesterol (DPPC/CHOL). Changes in the CBS ceramide group appeared to have less influence on antibody recognition of CBS in SM/CHOL than in DPPC/CHOL [Crook et al. (1986) Biochemistry 25, 7488-7494]. Although the fatty acid chain length of phosphatidylcholine strongly influences CBS recognition, the fatty acid chain length of sphingomyelin had only a moderate effect on CBS recognition and did not account for the decreased recognition in SM compared to in DPPC. Inhibition studies revealed that the antibodies which recognize CBS in SM/CHOL (S antibodies) form a population distinct from those which recognize CBS in DPPC/CHOL (P antibodies). The specificity of the P and S antibodies was examined further by comparing the efficacy of various substances, which share chemical features with the components of CBS in a SM/CHOL or DPPC/CHOL environment, to inhibit lysis of liposomes containing CBS. Intact CBS, cholesterol, and a phosphocholine lipid, at certain antigen densities, were required for optimal recognition of the antigen, especially by the P antibodies, suggesting that a complex of all three lipids in a multivalent array may be recognized by these antibodies. The S antibodies may recognize a smaller complex or monomers of CBS.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1996

Study by infrared spectroscopy of the interdigitation of C26:0 cerebroside sulfate into phosphatidylcholine bilayers.

The insertion mode of the long fatty acid chain of the asymmetric glycosphingolipid C26:0-cerebroside sulfate (C26-CBS) in symmetric matrices of phosphatidylcholines of different acyl chain length has been investigated by transmission and attenuated total reflectance (ATR) infrared spectroscopy. The concentration of C26-CBS in myelin is increased in the demyelinating disease adrenoleukodystrophy. The conformational order and the orientation of the chains of the asymmetric glycosphingolipid have been evaluated for C26-CBS incorporated at 8 mol % in perdeuterated dimyristoylphosphatidylcholine (DMPC-d54) and perdeuterated dipalmitoylphosphatidylcholine (DPPC-d62). The results, for the gel phase, are consistent with interdigitation of the C26-CBS long acyl chain across the bilayer center of an all-trans-DMPC bilayer in which DMPC is less tilted than in the absence of CBS. In contrast, in DPPC the results suggest that although the CBS long chain interdigitates across the center of the bilayer, it does not change the tilt angle of the DPPC molecules in the gel phase. Furthermore, in DPPC, C26-CBS is less well oriented than the host DPPC molecules and it increases the gauche content of the DPPC acyl chains. The observation of the amide spectral region indicates that exposure of the sphingosine amide moiety to buffer is greater in the longer chain length DPPC bilayer than in the shorter chain length DMPC bilayer. The thermotropic behavior of the lipid mixtures of C26-CBS at 8 mol % in DMPC or DPPC shows that the glycosphingolipid stabilizes the gel phase of the short chain length bilayer while it destabilizes the long chain length one. Our results further demonstrate that, at this concentration, C26-CBS is completely miscible in DMPC and DPPC in the gel and the liquid crystalline phases. The difference in behavior of C26-CBS in DMPC and DPPC is a consequence of the greater mismatch between the C26 chain length and the bilayer thickness of DPPC relative to DMPC. They may help to understand the deleterious effects of glycosphingolipids with very long chain fatty acids in adrenoleukodystrophy.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed2006

A ceramide and cerebroside from the starfish asterias amurensis Lütken and their plant-growth promotion activities.

The new phytosphingosine-type ceramide asteriaceramide A (1) and glucocerebroside asteriacerebroside G (2), together with two known cerebrosides, asteriacerebrosides A and B, were isolated from lipophilic fractions of the whole bodies of the Northern Pacific starfish Asterias amurensis Lütken. The water-soluble fraction afforded two known asterosaponins, glycoside B(2) and asterosaponin-1. The structures of 1 and 2 were determined on the basis of chemical and spectroscopic evidence as (2S,3S,4R,13Z)-2-[(2'R)-2-hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3R,4E,13Z)-2-[(2'R)-2-hydroxytetradecanoylamino]-4,13-docosadiene-1,3-diol (2). Compounds 1, 2, and asteriacerebrosides A and B promoted plant growth in sprouts of Brassica campestris.

Animals↗
PubMed1997

New antihepatotoxic cerebroside from Lycium chinense fruits.

Two cerebrosides isolated from Lycium chinense fruits have been characterized as 1-O-beta-D-glucopyranosyl-(2S, 3R,4E,8Z)-2-N-palmitoyloctadecasphinga-4,8-dienine+ ++ (1) and 1-O-beta-D-glucopyranosyl -(2S,3R,4E,8Z)-2-N-(2'-hydroxypalmitoyl)octadecasph inga-4,8-dienine (2). While 2 is already known, the structure of 1 was determined by spectral and chemical studies. Incubation of CCl4-intoxicated hepatocytes with 1 and 2, respectively, significantly reduced the levels of glutamic pyruvic transaminase (GPT) and sorbitol dehydrogenase (SDH) released by injured cells.

Animals↗
PubMed2003

The cerebrosides.

This review covers distribution, structural determination, syntheses and biological activities of the cerebrosides reported so far. Those with absolute stereochemistry assigned are marked herein with '*'. The literature from 1969 to mid-2003 is reviewed and 189 references cited.

Animals↗
PubMed1983

Juvenile and adult metachromatic leukodystrophy: partial restoration of arylsulfatase A (cerebroside sulfatase) activity by inhibitors of thiol proteinases.

Arylsulfatase A polypeptides were examined in cultured fibroblasts from a patient with juvenile metachromatic leukodystrophy and three patients with the adult form of the disease, with the aid of metabolic labeling and immunoprecipitation. The mutant cells were severely deficient in the arylsulfatase polypeptides. The apparent rate of synthesis, however, as estimated from the secretion of polypeptides or activity by cells incubated in the presence of 10 mM NH4Cl was 20-50% of control. In the absence of NH4Cl, the mutant enzyme was rapidly degraded upon transport into lysosomes. In the presence of inhibitors of thiol proteinases arylsulfatase A polypeptides were partially protected from degradation, and the catalytic activity of arylsulfatase A was increased. In addition, the treatment partially corrected the capacity of the cells to degrade cerebroside sulfates. Inhibitors of thiol proteinases may be of therapeutic value in variants of metachromatic leukodystrophy, in which an unstable arylsulfatase A is synthesized.

Adult↗
PubMed2001

Effect of the structure of natural sterols and sphingolipids on the formation of ordered sphingolipid/sterol domains (rafts). Comparison of cholesterol to plant, fungal, and disease-associated sterols and comparison of sphingomyelin, cerebrosides, and ceramide.

Ordered lipid domains enriched in sphingolipids and cholesterol (lipid rafts) have been implicated in numerous functions in biological membranes. We recently found that lipid domain/raft formation is dependent on the sterol component having a structure that allows tight packing with lipids having saturated acyl chains (Xu, X., and London, E. (2000) Biochemistry 39, 844-849). In this study, the domain-promoting activities of various natural sterols were compared with that of cholesterol using both fluorescence quenching and detergent insolubility methods. Using model membranes, it was shown that, like cholesterol, both plant and fungal sterols promote the formation of tightly packed, ordered lipid domains by lipids with saturated acyl chains. Surprisingly ergosterol, a fungal sterol, and 7-dehydrocholesterol, a sterol present in elevated levels in Smith-Lemli-Opitz syndrome, were both significantly more strongly domain-promoting than cholesterol. Domain formation was also affected by the structure of the sphingolipid (or that of an equivalent "saturated" phospholipid) component. Sterols had pronounced effects on domain formation by sphingomyelin and dipalmitoylphosphatidylcholine but only a weak influence on the ability of cerebrosides to form domains. Strikingly it was found that a small amount of ceramide (3 mol %) significantly stabilized domain/raft formation. The molecular basis for, and the implications of, the effects of different sterols and sphingolipids (especially ceramide) on the behavior and biological function of rafts are discussed.

1,2-Dipalmitoylphosphatidylcholine↗
PubMed2005

A new cerebroside from Uvaria tonkinensis var. subglabra.

A new cerebroside, subglain A (1), together with five known compounds (2-6) have been isolated from the stems of Uvaria tonkinensis var. subglabra. The structure of 1 has been determined to be 1-O-beta-D-glucopyranosyl-(2S,3S,4R,8Z,2'R)-2-[N-(2'-hydroxytetracosanyl)-N-(1'',2''-dihydroxyethyl)-amide]-8-tetradecene-1,3,4-triol by spectroscopic evidence. The known compounds were identified as schisandriside (2), erythritol (3), beta-D-glucopyranose (4), kaempferol-3,7-O-alpha-L-dirhamnoside (5), and (+)-lyoniresinol (6).

Cerebrosides↗