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PubMed2004

Isolation of flavonoids and a cerebroside from the stem bark of Albizzia julibrissin.

From the EtOAc fraction of the MeOH extract of Albizzia julibrissin (Leguminosae), a rare 5-deoxyflavone (geraldone, 1), isookanin (2), luteolin (3), an isoflavone (daidzein, 4), five prenylated flavonoids [sophoflavescenol (5), kurarinone (6), kurarinol (7), kuraridin (8) and kuraridinol (9)], a cerebroside (soya-cerebroside I, 10), and (-)-syringaresinol-4-O-beta-D-glucopyranoside (11) were isolated and characterized on the basis of spectral data. Compounds 2, 3, and 11, showed 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity.

Albizzia↗
PubMed1987

Simultaneous determination of psychosine and cerebrosides.

A new method was developed for the simultaneous determination of psychosine and cerebrosides in tissues. Total lipids extracted from the tissues were treated with [3H]acetic anhydride in toluene-methanol. Known amounts of nonradioactive N-acetylpsychosine were added to the reaction product and then subjected to mild alkaline methanolysis. After the product was washed, it was fractionated by silica gel column chromatography and the fraction containing glycolipids was benzoylated. The benzoylated product was finally fractionated on TLC. The amounts of benzoylated derivatives of nonhydroxy- and hydroxycerebrosides and N-acetylpsychosine were determined using a scanning densitometer. The amounts of psychosine in tissues were calculated from the radioactivity in the spot of N-acetylpsychosine and the recovery of added carrier N-acetylpsychosine. This method allowed us to determine 5 to 1000 pmol of psychosine and 1 to 20 nmol of cerebrosides in peripheral nerves and other tissues of the twitcher mouse as well as transfected Schwann cells derived from the sciatic nerves.

Animals↗
PubMed1979

Physical studies of cell surface and cell membrane structure. Deuterium nuclear magnetic resonance investigation of deuterium-labelled N-hexadeconoylgalactosylceramides (cerebrosides).

1. Deuterium Fourier transform nuclear magnetic resonance spectra of a series of N-palmitoylgalactosylceramides (cerebrosides) specifically labelled with deuterium at one of positions 2', 6', 10' and 16' of the acyl chain, or in the C-6 hydroxymethyl group of the galactose residue, have been obtained using a spin-echo technique at 34.1 MHz with a homebuilt superconducting magnet spectrometer. 2. The effects of temperature and cholesterol on the deuterium spectra have been investigated. The results indicate, when compared at the same reduced temperature, that the hydrocarbon chain organization in the liquid crystalline phase of palmitoylgalactosylceramide is essentially identical to that seen in similar chain length glycerophospholipids. In particular, two sets of quadrupole splittings are seen for a 2'-labelled N-palmitoylgalactosylceramide, indicating non-equivalent deuterons as noted previously for phospholipids. 3. Two sets of quadrupole splittings are observed for the headgroup C-6-labelled N-palmitoylgalactosylceramide. It is proposed that these signals arise from the enantiomeric R and S lipids, and that motion of the hydroxymethyl group is slow (greater than 10(-5) S). These results suggest the presence of a hydrogen bond network in the polar headgroup region. 4. The effects of cholesterol on the deuterium spectra of N-palmitoylgalactosylceramide-labelled as C2H3 in the terminal methyl group, at 1:1 mol ratios and in excess water below the crystal to liquid-crystal phase transition temperature (Tc) of the pure lipid (82 degrees C), are different to the effects seen with the phosphatidylcholine-cholesterol system. The spectra below Tc are characterised by two overlapping powder patterns, one with a quadrupole splitting of approx. 6 kHz (fluid liquid-crystalline phase) and one with a quadrupole splitting of about 20--25 kHz (crystal or gel-state lipid). Exchange between these two environments is therefore slow, leading to the possibility of characterising the cerebroside-cholesterol phase diagram using deuterium nuclear magnetic resonance spectroscopy.

Cell Membrane↗
PubMed1979

Two gel states of cerebrosides. Calorimetric and Raman spectroscopic evidence.

The enthalpy of the gel-to-liquid crystalline phase transition for kerasin (15.8 kcal/mol) is found to be markedly higher than that for phrenosin and unfractionated bovine brain cerebrosides (about 7 kcal/mol). Evidence for a higher degree of order in the hydrocarbon chains and a different configuration in the polar region of kerasin is supplied by Raman spectroscopic parameters for these gel phases. The high transition enthalpy for kerasin is ascribed to a lesser accommodation of gauche conformers in the hydrocarbon chains just below the transition temperature. The thermodynamic behavior of these cerebroside fractions, including hysteresis in kerasin gels, is compared to that previously reported for sphingomyelins.

Animals↗
PubMed1989

Molecular species of cerebrosides in fruiting bodies of Lentinus edodes and their biological activity.

Cerebroside fraction was obtained from fresh fruiting bodies of Lentinus edodes and separated into ten molecular species by reverse-phase high-performance liquid chromatography. The species were identified by GLC, GC-MS and NMR. Their component glycosides and sphingoids were uniformly glucose and (4E,8E)-9-methyl-4,8-sphingadienine, respectively. The component fatty acids were 2-hydroxy acids with the carbon chain length of 16, 15, 14, 18, 24, 17, 25, 26, 22 and 23 (from major to minor). The cerebrosides with the C14-18 fatty acids showed strong fruiting-inducing activity in Schizophyllum commune. Those with the C22 and C23 ones had one-eighth and one-sixteenth of the activity, respectively, and those with C24-26 had no detectable activity. 22 and 23 must be the carbon chain lengths of the component fatty acid of the sphingolipids critical for expression of biological activity.

Basidiomycota↗
PubMed1978

Characterization of aminoalkylphosphonyl cerebrosides in muscle tissue of Turbo cornutus.

From muscle tissues of the marine snail (Turbo cornutus) aminoalkylphosphonyl cerebrosides, which had been shown to be present in visceral parts were isolated. Their structure was determined by degradative methods and by characterization of components by gas chromatography-mass spectrometry. The aminoalkylphosphonyl cerebroside fraction consisted of a major portion of 1-O-[6'-O-(N-methylaminoethylphosphonyl) galactosyl] ceramide and a minor portion of a novel lipid, 1-O-[6'-O-(aminoethylphosphonyl)galactosyl] ceramide. The fatty acids of the fraction were mainly palmitic (53.3%) and 2-hydroxy palmitic acid (14.6%). The long chain bases were mainly dihydroxy C22: 2(36.6%), C18:1 (14.6%) and trihydroxy bases were also found as minor components.

Animals↗
PubMed1979

Human leucocyte cerebroside sulphate sulphatase.

Some of the properties of the cerebroside sulphate sulphatase of human leucocyte extracts have been studied. The enzyme has an apparent KM of 2.9 mmol/l and is inhibited by the products of the reaction, sulphate and galactocerebroside. A number of divalent metal ions including manganese and magnesium stimulated the reaction only slightly at 5 mmol/l but inhibited strongly at 20 mmol/l. Triton X-100 present in leucocyte extracts also inhibited, increasing both the apparent KM and Vmax. The enzyme activity was dependent on the presence of anionic detergents. At low substrate concentrations a crude taurocholate preparation was the most active of all bile acids examined. Pure taurocholate and sodium cholate were considerably less active. At highter substrate concentrations however, sodium cholate produced the greatest stimulation of enzyme activity. These data suggest that the bile acid/substrate ratio may be a critical factor in determining cerebroside sulphate sulphatase activity at different substrate concentrations.

Cerebroside-Sulfatase↗
PubMed1991

The organization of the gene for the human cerebroside sulfate activator protein.

The organization of 14 exons covering 97% of the cDNA sequence of human cerebroside sulfate activator protein precursor has been determined from two overlapping EMBL-4 human genomic clones extending over 17 kb. All exons and exon/intron splice junctions and five introns were sequenced. Exon 8 consists of only 9 bp and is involved in alternative splicing which generates three different mRNAs of cerebroside sulfate activator precursor.

Amino Acid Sequence↗
PubMed1991

Cellular incorporation and localization of fluorescent derivatives of gangliosides, cerebroside and sphingomyelin.

Fluorescent dansyl derivatives of 3 natural sphingolipids (gangliosides, cerebroside and sphingomyelin) were shown to be readily taken up by culture cells (HeLa-, MDCK- and primary rat brain cells). A part of the incorporated fluorescent sphingolipids remained associated with the cells after incubation in a culture medium containing serum, showing a cellular integration of these lipids. Microscopical studies indicated a localization of incorporated lipids in distinct subcellular regions; whereas dansyl cerebroside densely stained structures suggestive of the cytoskeleton and the actin filament, dansyl sphingomyelin and dansyl gangliosides were primarily associated with the plasma membrane. The findings are consistent with the current views on the arrangement of sphingolipids in animal cells.

Animals↗
PubMedDate not supplied

Cell-mediated cytotoxicity by peripheral blood lymphocytes against basic protein of myelin, encephalitogenic peptide, cerebrosides and gangliosides in multiple sclerosis.

In studies on 50 patients with multiple sclerosis (MS), all cases in an active stage of the disease, regardless of whether the course was relapsing or chronic progressive, and not dependent on the severity of the disease, it was possible to demonstrate a high cytotoxicity of the T-lymphocytes against the basic protein of myelin (MBP), encephalitogenic peptide, cerebrosides and gangliosides. During an inactive stage of the disease the cytotoxicity was much less and values could be reached which also occur in patients with other organic neurological diseases (OND). Similarly, in the individual case a close correlation of the degree of cytotoxicity to the course of MS was recognizable. It seemed that a cytotoxicity above 20% against the encephalitogenic peptide is specific for MS, since it could not be confirmed in 20 healthy persons and 50 patients with OND. A specificity of cytotoxicity against cerebrosides and gangliosides as well as for MBP does not exist in MS. Only the cytotoxicity against the encephalitogenic peptide can be considered as the pathogenic factor for the demyelinization process in MS. Immunosuppressive therapy with corticosteroids and azathioprine had no significant influence on the cytotoxicity.

Adrenal Cortex Hormones↗
PubMed1982

A change in the cerebrosides and sulfatides in a demyelinating nervous system. Development of the methodology and study of multiple sclerosis and Wallerian degeneration.

This report described a new method for the microanalysis of sphingolipids and its application for the characterization of cerebrosides and sulfatides in multiple sclerosis brain and rat sciatic nerves undergoing Wallerian degeneration. Tissue was extracted with isopropanol/hexane (20:78), and the total lipids obtained were subjected to benzoylation-desulfation. A portion of this was directly analyzed by silica-column high performance liquid chromatography for the determination of nonhydroxycerebroside, hydroxycerebroside, nonhydroxysulfatide, and hydroxysulfatide. Another portion was fractionated by thin-layer chromatography, and the spots corresponding to the sphingolipid derivatives were eluted. The material from each spot was analyzed by reverse phase high performance liquid chromatography for its homolog composition. With this new procedure the concentrations and homolog compositions of cerebrosides and sulfatides were measured in plaque, periplaque, and normal-appearing white matter from brains of multiple sclerosis patients and Wallerian degenerated rat sciatic nerves distal to the nerve transection. One piece of plaque studied contained only 1.86, 2.76, 0.60, and 0.45 nmol of nonhydroxycerebroside, hydroxycerebroside, nonhydroxysulfatide and hydroxysulfatide/mg of protein, respectively. These concentrations are less than 1% of those found in normal white matter. Periplaques were found to contain concentrations of these sphingolipids between those of plaque and normal white matter. The levels of these sphingolipids in degenerative nerves were 10-20% below normal the third day after the nerve was severed and about 70% below normal after 10 days. The rate of decrease lessened from ten days to 55 days. The homolog compositions of these sphingolipids in both multiple sclerosis brain and degenerating nerves were similar to those in the control. The implications of these findings and the advantages of this new analytical method are discussed.

Adult↗
PubMed1975

Cerebroside sulfatase activity in cultivated human skin fibroblasts and amniotic fluid cells;.

In an effort to improve the precision in prenatal monitoring for metachromatic leukodystrophy, levels of cerebroside sulfatase were determined in fibroblasts and amniotic fluid cells. Cells from MLD patients demonstrated no significant sulfatide hydrolysis, whereas cultures from heterozygous subjects hydrolyzed diminished but definite amounts of sulfatide. Cells from a fetus with low arylsulfatase A activity were able to cleave considerable amounts of sulfatide; enzyme assays performed postnatally suggest that the infant is heterozygous for MLD. This report documents the value of cerebroside sulfatase assays in the in utero monitoring for MLD.

Amniotic Fluid↗
PubMed1993

Thermotropic phase behavior of mixtures of long chain fatty acid species of cerebroside sulfate with different fatty acid chain length species of phospholipid.

The thermotropic phase behavior of asymmetric, long fatty acid chain species of cerebroside sulfate, C24-CBS and C26-CBS, with symmetric species of phosphatidylcholine (PC) containing fatty acid chains of 14-18 carbons in length (diC14-PC, diC16-PC, diC18-PC) and dimyristoylphosphatidylethanolamine (diC14-PE) in 0.1 M KCl was studied by differential scanning calorimetry. Novel cerebroside sulfate (CBS) spin labels containing long chain C24 and C26 fatty acid spin labels with the nitroxide group on the twenty-second carbon were used to study the lipid organization of the gel phases of these mixtures. The phase diagrams of all the mixtures indicated the presence of two immiscible gel phases at low CBS concentrations. All except the C26-CBS/diC14-PC mixture had eutectic phase behavior at low CBS concentrations suggesting that the long fatty acid chain of the CBS species had a destabilizing effect on the gel phase of most of the phospholipids. The C26-CBS/diC14-PC mixture had peritectic phase behavior at low CBS concentrations indicating a stabilizing effect of the CBS C26 acyl chain on diC14-PC. These results are consistent with the relative compatibility of the CBS acyl chain length with the bilayer thickness of the PC; only in the case of the C26-CBS/diC14-PC mixture is the acyl chain of CBS long enough to span the PC bilayer. At intermediate to high CBS concentrations, the CBS and phospholipid (PL) were miscible with the exception of the C24-CBS/diC18-PC combination, which had eutectic phase behavior over a wide concentration range. Thus when the PL acyl chain length was similar to the sphingosine chain length of CBS, CBS bilayers could accommodate symmetric phospholipid molecules better than phospholipid bilayers could accommodate asymmetric molecules of CBS. Use of the spin labels indicated that, at low temperatures and at intermediate to high CBS concentrations, all of the mixtures were in a triple chain mixed interdigitated gel phase which immobilized the spin label. This gel phase slowly transformed over a wide temperature range to a double chain partially interdigitated gel phase in which the spin labels had much more motion. This transformation could be detected as a broad low enthalpy transition by differential scanning calorimetry. In all cases the presence of phospholipid destabilized the mixed interdigitated phase. Stabilization of the partially interdigitated bilayer by intermolecular hydrogen bonding interactions must outweigh the destabilizing forces caused by disruptions in packing and van der Waals interactions between CBS molecules resulting from insertion of molecules of phospholipid into this type of bilayer.(ABSTRACT TRUNCATED AT 400 WORDS)

Calorimetry, Differential Scanning↗
PubMed1982

Physical studies of cell surface and cell membrane structure. Deuterium nuclear magnetic resonance studies of N-palmitoylglucosylceramide (cerebroside) head group structure.

Deuterium Fourier-transform nuclear magnetic resonance spectra of N-palmitoyl[2,3,4,6,6-2H5]glucosylceramide, N-palmitoyl[1-2H]glucosylceramide, N-palmitoyl-[5,6,6-2H3]glucosylceramide, and N-palmitoyl[6,6-2H2]-glucosylceramide have been obtained at 55.3 MHz (corresponding to a magnetic field strength of 8.5 T) for lipids as multilamellar dispersions in excess water at 90 degrees C, above the gel to liquid-crystal phase transition temperature (Tc = 82 degrees C). Spectra were also obtained for these same lipids dispersed with 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine, and cholesterol, all in excess water at 90 degrees C. The results are analyzed in terms of a model in which the lipid undergoes fast axial diffusion, together with a "wobbling" of the polar head group, by mathematical methods similar to those used previously for the choline and ethanolamine head groups in phosphatidylcholines and phosphatidylethanolamines [Skarjune, R., & Oldfield, E. (1979) Biochemistry 18, 5903--5909]. However, contrary to the results obtained in the previous study, which indicated many possible conformations for the choline and ethanolamine head groups, results with labeled cerebrosides yield at most a few orientations for the glucose head group in each of the systems studied. Furthermore, where multiple solutions do occur, they fall within a narrow orientational subspace so that all solutions exhibit the same general features. We also show that the order parameter describing the head group wobble is fully determined for each system, and it indicates a rather mobile structure for the cerebroside head group, in a variety of environments. In each system studied the polar head group projects essentially straight up from the bilayer surface into the aqueous region, thereby permitting maximum hydration of the four glucose hydroxyl groups by bulk water molecules.

Cell Membrane↗
PubMed1997

Characterization of the interaction of Ca2+ with hydroxy and non-hydroxy fatty acid species of cerebroside sulfate by Fourier transform infrared spectroscopy and molecular modeling.

Ca2+-mediated interactions between the carbohydrate groups of glycolipids, including that of cerebroside sulfate (galactosylceramide I3-sulfate), have recently been implicated as a basis of cell recognition and adhesion. Hydroxylation of the fatty acid of this lipid has an effect on these interactions. Therefore, FT-IR spectroscopy was used to study the interaction of Ca2+ with semisynthetic hydroxy (HFA) and non-hydroxy fatty acid (NFA) species of cerebroside sulfate (CBS). Ca2+ caused partial dehydration of the sulfate group and reduced hydrogen bonding of the sugar hydroxyls of both species. The amide I and II bands of the lipids in the absence of Ca2+ (NH4+ salt forms) suggested that the N-H of the HFA species is involved in a bent intramolecular hydrogen bond, probably with the fatty acid hydroxyl group and the glycosidic oxygen, while that of the NFA species is involved in a linear intermolecular hydrogen bond with the C=O and/or other oxygens. Ca2+ caused a rearrangement of the hydrogen-bonding network in the interfacial region of the HFA species involving the amide group. The results suggested increased hydrogen bonding of the C=O and a shift in hydrogen bonding of the N-H of the Ca2+ salt form of the HFA species from a bent intramolecular hydrogen bond to a linear intermolecular hydrogen bond, probably with the C=O of neighboring molecules, similar to the NFA species. The involvement of the fatty acid alpha-hydroxyl group in the rearranged network was indicated by a reduction in mobility of the alpha-CH group of the HFA species, in contrast to that of the NFA species. Participation of the alpha-OH group in hydrogen-bonding networks in the interfacial region of both the NH4+ and Ca2+ salt forms caused a significant increase in the interchain packing, as evident from correlation field splitting of the HFA-CBS methylene scissoring mode, while this did not occur for the NFA species. The absence of intramolecular hydrogen bonding of the N-H with the glycosidic oxygen for both salt forms of the NFA species and for the Ca2+ salt form of the HFA species may destabilize the "bent shovel", bilayer planar conformation of the sugar and cause it to be in the extended, bilayer perpendicular conformation. Calculations of the three-dimensional interaction energy of Ca2+ with CBS showed strong binding around the sulfate and the surface of galactose facing the bilayer in the bent shovel conformation. Ca2+ binding at this surface would disrupt intra- and intermolecular hydrogen-bonding interactions of the head group, thus accounting for its effect in inducing a transition to the extended conformation.

Binding Sites↗
PubMed1977

Micelles of cerebroside sulphate.

The critical micelle concentration of cerebroside sulphate in water is 0-01 mM: it increases with increasing concentrations of buffer to 0-07 mM in 0-1 M sodium acetate and formate buffers, pH 5-6 and 4-5 respectively. The partial specific volume of the micelles is about 0-94. The behaviour of the micelles in the ultracentrifuge and on Sephadex G-200 shows them to be grossly heterogeneous with respect to size. In 0-1 M buffer s20,w is about 26 S; in water or 0-01 M buffer smaller micelles with an s20,w of about 6 S are also present. In 0-01 M formate, pH 4-5, the smallest species detectable by equilibrium ultracentrifugation had a micellar weight of about 180,000 corresponding to an aggregation number of about 180. Much larger aggregates were also present. It is suggested that the smallest micelles are the substrate for sulphatase A when this is acting as a cerebroside sulphatase in buffers of low ionic strength.

Animals↗
PubMed2004

Cerebroside analogues from marine-derived fungus Aspergillus flavipes.

From the mycelium of the marine-derived fungus Aspergillus flavipes, isolated from the sea anemone Anthopleura xanthogrammica, two new cerebroside analogues, namely flavicerebrosides A (1): [(2S,2'R,3R,4E,8E)-N-2'-hydroxyoctadecanoyl-1-O-beta--galactopyranosyl-9-methyl-4,8-sphingadienine], and B (2): [(2S,2'R,3R,3'E,4E,8E)-N-2'-hydroxy-3'-octadecenoyl-1-O-beta--galactopyranosyl-9-methyl-4,8-sphingadienine], together with two known glycosphingolipids cerebrosides D (3) and C (4), were isolated. Their structures were identified by means of extensive spectroscopic analysis (IR, UV, 2D NMR, MS, CD) and chemical degradation. All four compounds showed cytotoxic activity against the KB cell line.

Antineoplastic Agents↗
PubMed2006

Longifoside-A and -B: two new cerebrosides from Mentha longifolia (Lamiaceae).

Two new N-acyl-glycosphingosines (cerebrosides) named longifoside-A {6'-tetracosenamide, N-[3,4-dihydroxy-1-(hydroxymethyl)-2-(beta-D-glucopyranosyl) heptadecyl]-(6'E)} and B {6'-tetracosenamide, N-[3-hydroxy-1-(hydroxymethyl)-2-(beta-D-glucopyranosyl)-4Z-heptadecenyl]-(6'E)} have been obtained from the methanolic extract of Mentha longifolia belonging to the family Lamiaceae. Both the cerebrosides were purified as their acetate-derivatives: 6'-tetracosenamide, N-[3,4-diacetoxy-1-(acetoxymethyl)-2-(tetraacetoxy-beta-D-glucopyranosyl) heptadecyl]-(6'E) and 6'-tetracosenamide, N-[3-acetoxy-1-(acetoxymethyl)-2-(tetraacetoxy-beta-D-glucopyranosyl)-4Z-heptadecenyl]-(6'E). They were characterized with the aid of 1D and sophisticated 2D-NMR spectroscopic techniques.

Cerebrosides↗