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Biomedical subjects

C Djerassi

Publications and source records attributed to C Djerassi.

At least 19 recordsLinked to original sources
PubMed1994

A new look at male contraception.

As a first step towards a new form of male contraception--sperm cryopreservation, vasectomy and eventual artificial insemination--the military services should begin a large-scale sperm cryopreservation programme.

Cell Survival↗
PubMed1993

Biosynthetic studies of marine lipids. 42. Biosynthesis of steroid and triterpenoid metabolites in the sea cucumber Eupentacta fraudatrix.

The saponins, conjugated sterols, and free sterols of the sea cucumber Eupentacta fraudatrix were examined. A total of 85 steroids, twelve of them new, were identified in the free sterol, sulfated sterol, and sterol-xyloside fractions. The free sterol fraction contained 4 alpha,14 alpha-dimethylcholest-9(11)-en-3 beta-ol(6) and 14 alpha-methylcholest-9(11)-en-3 beta-ol(7) together with 18 minor sterols. Examination of the aglycone moieties of the sterol-beta-xyloside fraction afforded 31 different sterols. Cholestan-3 beta-ol (15) and 24-methylcholesta-7,22-dien-3 beta-ol (20) were the major sterols in this group. Cholestanol sulfate (74) and cholesterol sulfate (64) were identified as the major components among the 34 different sterol sulfates present. Finally, cucumariosides G1 (1), C1 (2), C2 (3), H (4), and G2 (5) were isolated from the saponin fraction. Radiolabeling experiments indicated that there are two pathways of sterol biosynthesis in E. fraudratix. The first involves transformation of squalene to produce lanosta-9(11),24-dien-3 beta-ol(parkeol) which is subsequently demethylated to form 4 alpha,14 alpha-dimethylcholest-9(11)-en-3 beta-ol (6) and 14 alpha-methylcholest-9(11)-en-3 beta-ol (7). The second proceeds through squalene to lanosterol which is further metabolized to produce the triterpene saponins, 5 alpha-cholest-7-en-3 beta-ol (19) and its xyloside (49).

Animals↗
PubMed1992

Steroid research at Syntex: "the pill" and cortisone.

The period from late 1949 through 1951 was an extraordinarily productive one in steroid chemistry and especially so at Syntex S.A. in Mexico City. Two of the most important Syntex contributions--the synthesis of 19-nor-17 alpha-ethynyltestosterone (norethindrone) and of cortisone from diosgenin--are described from a historical perspective.

Contraceptives, Oral, Hormonal↗
PubMed1991

Metabolism of unusual membrane phospholipids in the marine sponge Microciona prolifera.

Sponges are unique in regard to membrane phospholipid composition. Features virtually without parallel in other organisms are the predominance of the C26-C30 polyenoic acids (demospongic acids) in the phosphatidylethanolamines (PE) and the attachment of identical acyl groups to the glycerol moiety. The biosynthesis and disposition of these unusual phospholipids were followed in the marine sponge Microciona prolifera where PE ( delta 5,9-26:2, delta 5,9-26:2) is a major molecular species. Incorporation experiments with radiolabeled fatty acids, bases, and intact phospholipids revealed the de novo biosynthesis of the two major phosphatides, phosphatidylethanolamines (PE) and phosphatidylcholines (PC), via the cytidine pathway as in higher animals, with ethanolamine selectively incorporated into PE( delta 5,9-26:2, delta 5,9-26:2). Methylation of PE and random acyl chain migration across different phospholipid classes were marginal, but the exchange of PC for PE, apparently mediated by the action of phospholipase, was indicated after uptake of the unnatural PC( delta 9-27:1, delta 9-26:1). The present study demonstrates in the most primitive multicellular animals a phospholipid metabolic pattern similar to that in higher organisms, with unique acyl and phosphoethanolamine transferases apparently involved in the biosynthesis of the (demospongic) di-C26-acyl-PE molecular species.

Animals↗
PubMed1991

Phospholipid studies of marine organisms: 26. Interactions of some marine sterols with 1-stearoyl-2-oleoyl phosphatidylcholine (SOPC) in model membranes.

The thermotropic behavior of multilamellar vesicles (MLV) composed of different mole fractions of various marine sterols and 1-stearoyl-2-oleoyl phosphatidylcholine (SOPC) was examined by differential scanning calorimetry (DSC), and was compared to pure SOPC as well as their mixtures with cholesterol. The marine sterols investigated were capable of interacting with the phospholipid bilayers. Upon addition of marine sterols, the apparent transition temperature (Tm) of SOPC decreased significantly. Desmosterol (cholesta-5,24-dien-3 beta-ol) had the least interaction with SOPC, as reflected by the larger delta H values of its mixtures with the phospholipid. Fucosterol (24-ethylcholesta-5,24(28)-dien-3 beta-ol) showed a non-linear trend as the mole percent of the sterol increased. Mixtures of sutinasterol (24R-24-ethyl-26,26-dimethylcholesta-7,25(27)-dien-3 beta-ol) with SOPC had similar enthalpy values to cholesterol. The shape of the SOPC/marine sterol endotherm and their delta H values were not identical when liposomes prepared by dialysis were compared to MLV.

Calorimetry, Differential Scanning↗
PubMed1991

Biosynthetic studies of marine lipids. 35. The demonstration of de novo sterol biosynthesis in sponges using radiolabeled isoprenoid precursors.

1. De novo sterol biosynthesis in the sponges Tethya aurantia and Aplysina fistularis was investigated, using sodium [5,5-3H]-mevalonate, [1-3H]-farnesol and [3-3H]-squalene. [3-3H]-Squalene was found to be the best precursor for demonstrating de novo sterol biosynthesis in a wider range of sponges. 2. By feeding [3-3H]-squalene and using cell-free techniques, the de novo sterol biosynthesis was established in 18 sponges belonging to nine orders. Among these sponges were Axinella polypoides and Axinella verrucosa which had previously been thought to be incapable of de novo sterol biosynthesis based on work with radiolabeled lanosterol, cycloartenol, mevalonate, and acetate. 3. In contrast to earlier assumptions, it is likely that all sponges are capable of de novo sterol biosynthesis.

Animals↗
PubMed1990

Inhibition and substrate specificity of yeast delta 22-desaturase.

Using yeast microsomes, 23-hydroxysterols were tested as intermediates in the formation of the sterol side delta 22-double bond. No evidence could be found supporting a two-stage mechanism of desaturation via hydroxylation and dehydration. Sterols with various side chains were tested as substrates. Those with alkyl substituents in the 24-alpha position were poor substrates. A series of sterols, including cyclopropyl sterols, were tested as mechanism-based inhibitors without success. Inhibition was observed with an isocyano-sterol.

Cytochrome P-450 Enzyme System↗
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↗