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W D Nes

Publications and source records attributed to W D Nes.

43 records · Page 3Linked to original sources
PubMed1983

Evidence for metabolic and functional discrimination of sterols by Phytophthora cactorum.

When fed 10 ppm of one of the following sterols: cholesterol (cholest-5-en-3beta-ol), wingsterol (21-isopentylcholesterol), desmosterol [cholesta-5,24(25)-dien-3beta-ol], 24-methylenecholesterol [ergosta-5,24(28)-dien-3beta-ol], or fucosterol [stigmasta-5,24(28)-dien-3beta-ol], the pathogenic fungus Phytophthora cactorum, which is naturally unable to epoxidize squalene, accumulated each of the test compounds to similar levels. Fucosterol, the only sterol metabolized, was reduced to yield 24-ethylcholesterol. All the sterols tested induced the formation of sex structures. Fertilization and subsequent maturation of oospores capable of germination occurred only with the naturally occurring sterols. Wingsterol treatments resulted in aborted oospores. None of the sterols tested was inhibitory to growth, measured as changes in the 21-day mycelial dry weight. The results are consistent with the view that the accumulated sterol functions to regulate the life cycle of P. cactorum. However, the metabolism and kinds of recognition of the sterol molecule, in terms of uptake and effects on growth and induction of the various sexual events, contrast sharply with what is known for other oomycetous fungi such as Achlya and Saprolegnia. This implies that the evolutionary histories of the Oomycetes may be different.

Journal Article↗
PubMed1981

Growth characteristics of Saccharomyces cerevisiae and Aspergillus nidulans when biotin is replaced by aspartic and fatty acids.

When either aerobic or anaerobic cultures of Saccharomyces cerevisiae were supplemented with aspartic and fatty acids in place of biotin, stationary phase populations were very small compared with those obtained in the presence of biotin. Similarly, these acids failed to fulfil the role of biotin-requiring strain of Aspergillus nidulans. Furthermore, a requirement for saturated fatty acid was found with anaerobically cultured S. cerevisiae. Cells were fragmented when biotin was replaced by aspartic and oleic acids alone, while cellular integrity was maintained, but with only slight growth, when biotin was replaced by oleic and palmitic acids together with aspartate. The importance of biotin in the growth of A. nidulans was particularly pronounced in the presence of glucose. In a medium containing glucose, growth ceased when biotin was replaced by aspartate and Tween 80 (a source of saturated and unsaturated fatty acids), but such replacement permitted a very small amount of growth to occur in the absence of glucose.

Aspartic Acid↗
PubMed1980

Effect of Steric and Nuclear Changes in Steroids and Triterpenoids on Sexual Reproduction in Phytophthora cactorum.

The comparative biological activity of 21 naturally occurring or synthetically derived steroids, 7 tetracyclic and pentacylic triterpenoids, and antheridiol incubated with cultures of Phytophthora cactorum has been examined. There was greater dependence on precise steric features of the sterol side chain than on the extent of nuclear unsaturation in inducing oospore formation. There was no significant effect on oospore formation by changing nuclear unsaturation in ring B from Delta(5) to Delta(7) or to Delta(5,7). Converting the unsaturated sterol to its corresponding stanol resulted in a significant reduction in the number of oospores produced. The effectiveness of sterols bearing different side chains in inducing oospores was found to be in the following relative order: 24alpha-ethyl = trans-Delta(22)-24alpha-ethyl > trans-Delta(22)-24beta-ethyl = 24alpha-E-ethylidene = 24alpha-methyl > 24beta-methyl = trans-Delta(22)-24beta-methyl = 26-methyl = saturated C(7) side chain and C-20 R (17-alphaH, 20-alphaH, right-handed conformer) = cis-Delta(22)-C(7) side chain and C-20 R > saturated C(7) side chain and C-20 S (17-alphaH, 20-betaH, right-handed conformer) > no sterol = 29-hydroxyporiferasterol = 20alpha-hydroxycholesterol = 24xi-hydroxy-24-vinylcholesterol. Of the sterols examined the most significant stereochemical criterion for the induction of oospore formation was absence of bulk on the front face of C-20. This follows from the observation that 20-isocholesterol and 20alpha-hydroxycholesterol, in which a methyl and hydroxy group, respectively, project to the front in the right handed conformation, were inactive in stimulating production of oospores. None of the triterpenoids studied induced oospore formation to any significant degree. Oospore formation was not induced by antheridiol nor 29-hydroxyporiferasterol in combination or added separately to growing cultures of P. cactorum in the concentration range 0.01 - 10.0 milligrams per liter.

Journal Article↗
PubMed1978

The functional importance of structural features of ergosterol in yeast.

As an approach to the study of the relationship between the structure of sterols and their capacity to function in the lipid leaflet of membranes, various sterols were examined for their ability to support the growth of anaerobic Saccharomyces cerevisiae. A marked dependence on precise structural features was observed in growth-response and morphology. Of the chemical groups which distinguish ergosterol, the main sterol of S. cerevisiae, the hydroxyl group at C-3 was obligatory, and the other groups were found to be of the following relative importance: 24beta-methyl-delta22-grouping greater than 24beta-methyl group greater than delta5,7-diene system = delta5-bond approximately or equal to no double bond. Methyl groups at C-4 and C-14 were inconsistent with activity. Consequently, the data strongly suggest that the normal biosynthetic processes removal of methyl groups from the nucleus and introduction of one in the side chain are of functional significance. A double bond between C-17 and C-20 joining the steroidal side chain to the nucleus had no deleterious effect on the growth process but only if C-22 was trans-oriented to C-13. In the cis-case no growth at all proceeded. This means the natural sterol probably acts functionally in the form of its preferred conformer in which C-22 is to the right ("right-handed") in the usual view. Since the placing of a substituent (OH or CH3) in the molecule at C-20 in such a way that it appears on the front side in the right-handed conformer completely destroyed activity, the sterol apparently presents its front face to protein or phospholipid when complexing occurs.

Anaerobiosis↗
PubMedDate not supplied

Concerning the role of 24,25-dihydrolanosterol and lanostanol in sterol biosynthesis by cultured cells.

Rat hepatoma cells (H4-II-E-C3) efficiently converted a dietary supplement of [2-3H]24,25-dihydrolanosterol (1) to [3H]cholesterol while [2-3H]lanostanol (4,4,14 alpha-trimethylcholestanol (2) was recovered from the cells without apparent transformation, although it was esterified and induced an accumulation of lanosterol. A comparison of the chromatographic (TLC, GLC and HPLC), spectral (MS and 1H-NMR) and physical properties of 1 and 2 is given for the first time. The inability to detect 2 in nature coupled with our findings that 1 but not 2 is metabolized to cholesterol by H4 cells is interpreted to imply that the biosynthetic inclusion of the delta 8(9)-bond during the cyclization process of squalene-oxide to a tetracyclic product is an evolutionary adaptation selected for because the olefinic linkage is structually important in the subsequent conversion of lanosterol and its stereoisomers, e.g., cycloartenol, to delta 5-sterols.

Animals↗
PubMedDate not supplied

Evidence for similarities and differences in the biosynthesis of fungal sterols.

The sterol composition of two ascomycetous fungi, Saccharomyces cerevisiae and Gibberella fujikuroi, was examined by chromatographic (TLC, GLC, and HPLC) and spectral (MS and 1H-NMR) methods. Of notable importance was that both fungi produced cholesterol and a homologous series of long chain fatty alcohols (C22 to C30). In addition to ergosterol two novel sterols, ergosta-5,7, 9(11), 22-tetraenol and ergosterol endoperoxide, were isolated as minor compounds in growth-arrested cultures of yeast and in mycelia of G. fujikuroi. 24-Ethylidenelanosterol was also detected in mycelia of G. fujikuroi. A shift in sterol biosynthesis was observed by treatment with 24 (RS), 25-epiminolanosterol (an inhibitor of the S-adenosylmethionine C-24 transferase) and by monitoring the sterol composition at various stages of development. The results are interpreted to imply that the genes for 24-desalkyl, e.g., cholesterol, and 24-alkyl sterols, e.g., 24 beta- methyl cholesterol and 24-ethyl cholesterol, are distributed (but not always expressed) generally throughout the fungi but the occurrence of one or another compounds is influenced by the fitness (structure and amount) for specific sterols to act functionally during fungal ontogeny; sterol fitness is coordinated with Darwinian selection pressures.

Cell Division↗