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Biomedical subjects

C Djerassi

Publications and source records attributed to C Djerassi.

At least 37 records · Page 2Linked to original sources
PubMed1990

Cholesterol interactions with tetracosenoic acid phospholipids in model cell membranes: role of the double-bond position.

The synthesis and thermotropic properties of 1,2-di-(9Z)-9-tetracosenoylphosphatidylcholine [delta 9-PC(24:1,24:1), 1], 1,2-di-(5Z)-5-tetracosenoylphosphatidylcholine [delta 5-PC(24:1,24:1), 2], and 1,2-di-(15Z)-15- tetracosenoylphosphatidylcholine [delta 15-PC(24:1,24:1), 3] are reported. Liposomes prepared from these phospholipids differ from those of the natural sponge phospholipids, 1,2-di-(5Z,9Z)-5,9-hexacosadienoylphosphatidylcholine (4a) and the corresponding ethanolamine (4b), both of which virtually exclude cholesterol from their bilayers. The behavior of 1 and 2 is similar to that of 1,2-di-(6Z,9Z)-6,9-hexacosadienoylphosphatidylcholine (5), which exhibits a partial molecular interaction with cholesterol. In the case of 3, cholesterol appears to interact with the saturated acyl chain regions of this phospholipid in a manner similar to that of its interaction with DPPC acyl chains. This study delineates the effect of the double-bond location in long fatty acyl chains of phospholipids on their interactions with cholesterol.

Calorimetry, Differential Scanning↗
PubMed1990

Cell separation of Tethya aurantia, an analytical study of embryonic and differentiated sponge cells.

The cells of the sponge Tethya aurantia var. californiana were separated on a Ficoll density gradient and the fractions analyzed for cell types and their lipids. Major cell types were choanocyte, archeocyte, and symbiont. Major differences in archeocyte and choanocyte fatty acid composition were noted for 20:4, 26:1 and 26:2. The fatty acids 26:1, 26:2, and 28:3 were dominant in the phosphatidylcholine fraction. Archeocytes had highest concentrations of 4,7,10,13-20:4 and 5,8,11,14-20:4 (arachidonic) acids which could be derived from symbionts, as odd-chain and methyl-branched fatty acid were also present. Sterol analyses showed cholesterol as a major sterol of the sponge cell fractions and clionasterol (or its 24-isomer) as a major sterol in symbiont cells.

Animals↗
PubMed1989

Unusual pattern of fatty acid biosynthesis. Evidence for C-19 desaturase activity in freshwater sponges.

The two long chain fatty acids common in marine demosponges, (5Z, 9Z)-5,9-hexacosadienoic (delta 5,9-26:2) and (5Z, 9Z, 19Z)-5,9,19-hexacosatrienoic (delta 5,9,19-26:3) acids), were identified also as the major phospholipid components in the freshwater sponge Ephydatia fluviatilis. Whereas the typical marine sponge Microciona prolifera biosynthesizes the delta 5,9,19-26:3 acid solely by homologation of exogenous palmitoleic acid (delta 9-16:1) and subsequent desaturation at positions 5 and 9, it was found that the freshwater sponge could further desaturate the delta 5,9-26:2 acid to the triene, indicating for the first time the existence of delta 19 -desaturase activity in a living organism.

Animals↗
PubMed1989

The bitter pill.

Fundamentally new approaches to birth control--for example, a male pill, a once-a-month menses inducer, and an antifertility vaccine--cannot be realized before the next century, and then only if the virtual withdrawal of the pharmaceutical industry from this field can be reversed. Major changes in product liability would be the most significant incentive.

Animals↗
PubMed1989

The distribution of lipids and sterols in cell types from the marine sponge Pseudaxinyssa sp.

The sponge Pseudaxinyssa sp., unique in sterol and fatty acid composition, was cellularly dissected into fractions enriched in each of the major cell types present in the sponge: microbial symbionts (cyanobacteria), small sponge cells (pinacocytes and choanocytes), and large sponge cells (archeocytes and cyanophytes). Three phototrophic microbial symbionts were also isolated from the cell fractions and grown in culture. An unsymmetrical distribution of fatty acids and sterols was observed for the sponge cells: small cells contained larger quantities of long chain fatty acids (greater than C24) and smaller quantities of sterols than were present in the larger sponge cells. Moreover, the rare sterols 24-isopropylcholesterol predominated in the smaller sponge cells, whereas its 22-dehydro analog predominated in the larger sponge cells. Long chain fatty acids and sterols were not detected in the cultured microbial symbionts. This constitutes the first report of lipid variability according to cell type for this most primitive group of Metazoa.

Animals↗
PubMed1988

Fatty acids as biological markers for bacterial symbionts in sponges.

Analyses of fatty acids with carbon numbers between C12 and C22 are reported for five Great Barrier Reef sponges. These analyses indicate that phototrophic cyanobacterial symbionts (blue-green algae) present in three of the sponges are chemically distinct, whereas the other two sponges do not contain cyanobacterial symbionts. All the sponges contain other, nonphototrophic bacteria. The fatty acid analyses indicate that the non-phototrophic bacterial populations present in the different sponges are distinct in both their chemical compositions and their abundances. Nonphototrophic bacteria are estimated to account for between 60 and 350 micrograms/g (extractable fatty acids:tissue wet weight), whereas cyanobacteria account for between 10 and 910 micrograms/g. One sponge (Pseudaxinyssa sp.) contains a relatively large amount of the isoprenoid acid, 4, 8, 12-trimethyltridecanoic acid; this acid is presumed to be derived from phytol, a degradation product of chlorophyll. This sponge also contains relatively large amounts of the nonmethylene interrupted fatty acid, octadeca-5,9-dienoic acid. Analyses of interior and cyanobacteria-rich surface tissues of this sponge indicate that these two acids are probably not associated with the symbiotic cyanobacteria.

Animals↗
PubMed1988

Localization of long-chain fatty acids and unconventional sterols in spherulous cells of a marine sponge.

The first direct evidence is provided for the presence of unconventional lipids in a particular subcellular membrane system of a sponge. Spherulous cells were isolated from the variety of cell types present in the marine sponge Aplysina fistularis by density gradient centrifugation. Spherulous cell plasma membrane was subsequently isolated by cell rupture followed by differential centrifugation and sucrose, or Percoll, density gradient ultracentrifugation. Plasma membrane isolates were identified and assessed for purity using [3H]concanavalin A plasma membrane marker, sodium dodecyl sulfate polyacrylamide gel electrophoresis and ratios of protein, sterol and phosphate. Plasma membrane isolates could not be assessed for purity by traditional enzymatic means. Spherulous cell plasma membrane was found to contain unusual lipids, including long-chain (C24-C30) fatty acids (16.8-27.2%) and unconventional 26-alkylated sterols (66.4-72.6%), in addition to more conventional fatty acids and sterols. Spherulous cell intracellular membranes were also found to contain long-chain fatty acids and unconventional sterols, although the relative importance of these unusual lipids apparently varies between intracellular membranes, with some containing approximately 50% long-chain acids.

Animals↗
PubMed1988

Cell membrane localization of long chain C24-C30 fatty acids in two marine demosponges.

Subcellular fractionation by differential centrifugation was performed on two previously unstudied marine sponges (Reniera sp. and Pseudaxinyssa sp.) that represent both major subclasses of the Demospongiae. Long chain fatty acids (LCFA) with 24-30 carbon units were found as major constituents of cell membrane isolates of both sponges. Most LCFA were polyunsaturated and were constituents of the phospholipids, which are typical membrane lipids, and in particular the amino-phospholipids. The LCFA composition of phospholipids from whole sponge tissue was shown to provide a reliable indication of the LCFA composition of cell membrane phospholipids in the sponges studied. An unusual triply branched C16 isoprenoid fatty acid, 4,8,12-trimethyltridecanoic acid, also was identified as a cell membrane acid in the sponge Pseudaxinyssa sp.

Animals↗
PubMed1988

Cell membrane localization of sterols with conventional and unusual side chains in two marine demosponges.

Subcellular fractionation by differential centrifugation was performed on two previously unstudied marine sponges that predominantly contain either conventional (Reniera sp.) or unconventional (Pseudaxinyssa sp.) sterols. Direct evidence for the presence of unconventional sterols with C24 alkylated side chains in the cellular membranes of Pseudaxinyssa sp. is provided, but the presence of unconventional sterols in sponge membranes is shown not to be a universal feature of the Porifera. Possible structural and functional roles of unconventional lipid molecules in sponge cell membranes are discussed.

Animals↗
PubMed1988

Analogs of unusual sponge phospholipids. Synthesis and thermotropic properties of 1,2-di-(6Z,9Z)-6,9-hexacosadienoyl phosphatidylcholine and phosphatidylethanolamine.

The major marine sponge phospholipids 1,2-di-(5Z,9Z)-5,9-hexacosadienoyl phosphatidylcholine (PC) and phosphatidyl-ethanolamine (PE) hardly incorporate cholesterol into their liposomal bilayers, as reported earlier. Our previous studies indicated that their synthetic short chain (C18-C24) analogs with the same double bond pattern readily incorporated cholesterol, thus demonstrating the importance of the chain length. In order to investigate the possible role of the unusual delta 5,9 diunsaturation 1,2-di-(6Z,9Z)-6,9-hexacosadienoyl phosphatidylcholine and phosphatidylethanolamine were synthesized and their thermotropic behavior studied. Both analogs shows a transition endoterm at 45 degrees C, while the natural 1,2-di-(5Z,9Z)-5,9-hexacosadienoyl PC and its PE counterpart exhibited it at 42 degrees C. A partial incorporation of cholesterol into liposomal bilayers of 1,2-di-(6Z,9Z)-6,9-hexacosadienoyl PC was observed. Our results suggest that while the chain length is the predominant factor in the interactions of these phospholipids with sterols, the double bond location may also play a contributing role.

Animals↗
PubMed1987

Phospholipid studies of marine organisms: 14. Ether lipids of the sponge Tethya aurantia.

The novel unesterified alkyl glycerol monoethers, (2S)-1-(hexadecyloxy)-2,3-propanediol (1), (2S)-1-(16-methylheptadecyloxy)-2,3-propanediol (2) and (2S)-1-(15-methylheptadecyloxy)-2,3-propanediol (3) were isolated from the marine sponge Tethya aurantia and were characterized by spectroscopic methods. These three saturated ethers as well as a series of alk-1'-enyl glycerol monoethers were also encountered in the phospholipids of the same sponge after reduction with LiAlH4. Incorporation experiments with dissociated cells of T. aurantia indicated that [1-14C]-hexadecanol was incorporated into the unesterified alkyl glycerol monoethers.

Animals↗
PubMed1987

High performance liquid chromatography and fast atom bombardment mass spectrometry of unusual branched and unsaturated phospholipid molecular species.

The unusual symmetrical molecular species 1,2-di-3,7,11,15-tetramethylhexadecanoyl-sn-glycero-3-phosphoglyce rol, 1,2-di-5,8,11,14-docosatetraenoyl-sn-glycero-3-phosphocholine, 1,2-di-5,9,19-octacosatrienoyl-sn-glycero-3-phosphoethanolamine, and 1,2-di-5,9,23-triacontatrienoyl-sn-glycero-3-phosphoethanolamine were isolated from the marine sponges Axinella verrucosa, Higginsia tethyoides, Tethya aurantia and Aplysina fistularis by HPLC and studied by fast atom bombardment (FAB) mass spectrometry. In addition to molecular weights, branching and double bonds were located in the fatty acyl chains of the intact phospholipid molecules, using FAB either in a positive or negative mode. Some mass spectral results were obtained on enriched phospholipid fractions rather than pure molecular species using MS/MS.

Animals↗
PubMed1986

Biophysical properties of unusual phospholipids and sterols from marine invertebrates.

Liposomes composed of 1,2-di-(5Z,9Z)-5-9-hexacosadienoyl-sn-glycero-3-pho sph ocholine underwent an endothermic phase transition at 42 degrees C. Cholesterol or the marine sterols studied did not affect this transition to an appreciable extent, but rather were excluded from the phospholipid bilayers. Membranes composed of 1,2-di-(5Z,9Z)-5,9-hexacosadienoyl-sn-glycero-3-pho sph ocholine displayed very similar phase properties. Effects of the marine sterols on dipalmitoylphosphatidylcholine bilayers were also investigated.

Animals↗
PubMed1985

New natural 2-acetoxy fatty acids using chemical ionization and electron impact mass spectrometry.

The phospholipids of the sponge Polymastia gleneni contain saturated long chain (C22-30)-acetoxy fatty acids. Their structures were assigned based on chromatographic and spectrometric data as well as comparison with a synthetic sample. The use of capillary gas chromatography combined with chemical ionization and electron impact mass spectrometry was instrumental in the eludication of structures, since only a very small amount of crude lipids was available.

Acetates↗