Biomedical subjects

H Schlenk

Publications and source records attributed to H Schlenk.

At least 19 recordsLinked to original sources

PubMed1984

Inhibition of blood platelet aggregation by dioxo-ene compounds.

Compounds with a conjugated oxo-ene-oxo system were tested for inhibition of blood platelet aggregation. All compounds with this structure in trans configuration were effective inhibitors of aggregation induced by thrombin and by arachidonic acid. While the oxo-trans-ene-oxo system is prerequisite for such activity, other structural features of the compounds may be varied without loss of activity. Inhibition is exemplified by 9,12-dioxo-trans-10- and 10,13-dioxo-trans-11-octadecenoic acids and their methyl esters, by 11,14-dioxo-trans-12- eicosenoic acid, by 4,7-dioxo-trans-5- decene and by trans- dibenzoylethylene . The half-inhibition concentrations are in the order of 2-6 microM, with complete inhibition at 8-20 microM. According to experiments with the inhibiting 9,12-dioxo-trans-10-octadecenoic acid, the normal oxygenation of exogenous arachidonic acid by platelets is not affected but the thrombin-induced internal release of this acid seems to be abolished by the inhibitor. The inhibition of aggregation in the presence of exogenous arachidonic acid and its products suggests that the inhibitor also interferes with other events leading to aggregation. By implication from other properties of the oxo-trans-ene-oxo system, reaction with SH groups may be a mechanism for inhibition.

Arachidonic Acid↗

PubMed1984

Metabolism of furan fatty acids in fish.

In vivo experiments on interconversions of furan fatty acids in fish are described. Administration of 2- or 3-14C-labelled furan fatty acids showed that the heterocycle does not interfere with conversions at the carboxyl group, such as shortening and elongating the chain, or its reduction to alcohol. There was no indication for desaturation of proximal chains, methylation or demethylation of the ring, or changes in the terminal chains. According to these restricted metabolic correlations, the furan fatty acids can be classified in specific structural families of bis-homologs. Distinct parent furan compounds are likely for each of these families. [1-14C]Acetate was incorporated by fish into furan fatty acids. Their chemical oxidation showed that only the resulting dicarboxylic fragments were labelled. They represent the proximal chain including alpha-C of the ring. Label was not found in the monocarboxylic acids which represent terminal chains with alpha'-C, and ring-methyl substituents with beta- and beta'-C. Accordingly, fish do not synthesize from acetate the terminal alkyl chain including the carbons in the cyclic portion of the furan fatty acids.

Animals↗

PubMed1983

Catabolism of fish furan fatty acids to urofuran acids in the rat.

A mixture of long-chain furan fatty acids was prepared as methyl esters from testes lipids of Northern pike (Esox lucius). Upon feeding these esters to rats, dicarboxylic acids, which still contained the furan structure, were found in the urine. The first phase of a rapid but incomplete catabolism is beta-oxidation of the proximal chain of the furan fatty acids. It proceeds to a distance of three carbon atoms from the ring. omega-Oxidation of the terminal alkyl chain, followed by alpha-oxidation gives rise to a second alkylcarboxyl chain with five carbon atoms or less. The ring methyl substituents of the precursor acids seem to be more resistant to oxidation than the alkyl substituent with three or five carbon atoms. The urinary catabolites from furan fatty acids in the rat are similar to furan acids found in human urine, but only one of the structures occurs in both sources.

Animals↗

PubMed1981

Reduction of fatty acids to alcohols in roe of gourami (Trichogaster cosby).

Reduction of fatty acids to alcohols in gourami roe homogenates and fractions thereof was studied. The reducing activity is associated with the microsomal fraction. Activation of the acid and NADPH as reducing cofactor are required. The optimal pH for reduction is between 6.5 and 7.5. Reduction rates were highest for palmitic acid and were about half of that for oleic and linoleic acids. In contrast to the equal reduction rates of the latter acids in vitro, the percentages of oleyl and linoleyl alcohols in wax esters are greatly different in vivo. Very small amounts of aldehyde are found during the reduction and some substrate label is incorporated into the phospholipids. The traces of triacylglycerols in roe lipids are not markedly labelled. In homogenates, newly formed as well as added substrate alcohol is efficiently incorporated into wax esters. Roe homogenate is capable also of oxidizing fatty alcohol to acid. In contrast to reduction, oxidation proceeds with either NADP+ or NAD+ as cofactor. Only a small portion of the newly formed acid is esterified.

Adenosine Triphosphate↗

PubMed1979

Oxidation of fatty alcohols to acids in the caecum of a gourami (Trichogaster cosby).

Oxidation of fatty alcohols to acids in gourami caeca was investigated by measuring the reduction of NAD+ and the formation of labeled hexadecanoic acid from [1(-14)C]hexadecanol. Virtually all dehydrogenase activity is in the microsomal fraction. Maximal activity is obtained with NAD+ as cofactor whereas with NADP+ 60% of that activity is obtained. The enzyme is rather specific for long chain alcohols and 2 NADH are formed for each molecule of hexadecanol oxidized to acid. It is stabilized by mercaptoethanol, and completely inhibited by p-chloromercuribenzoate. The activity is optimal at pH 9.5. At higher pH, small amounts of aldehyde are found. The first reaction in the sequence, fatty alcohol leads to aldehyde leads to acid seems to occur under the more physiological condition at a much slower rate than the second reaction so that free aldehyde is not detected. Addition of palmitic acid indicated an uncompetitive product inhibition. The oxidation of alcohol to acid is reversible only to a very minor extent even in the presence of NADPH, CoA, ATP and Mg2+. Location, activity and properties of the enzyme are in agreement with the earlier observation from dietary experiments that in the gourami fatty alcohols of wax esters are oxidized to acids in the course of absorption.

Alcohol Oxidoreductases↗

PubMed1979

Methyl-directed desaturation of arachidonic to eicosapentaenoic acid in the fungus, Saprolegnia parasitica.

The lipids of Saprolegnia parasitica contain 5,8,11,14,17-eicosapentaenoic acid as major constituent. No other acid having (n-3) structure was detected, but 5,8,11,14-eicosatetraenoic (arachidonic) acid and its common precursors of (n-6) structure are present in significant amounts. During rapid growth of the organism, [1-14C]acetate was efficiently incorporated into fatty acids. Arachidonic acid was labeled after 2 h to nearly the same extent as any precursor acid and 14C in eicosapentaenoic acid reached this level within 6 h. Results of incubations with labeled fatty acids indicated that, in S. parasitica, oleic, linoleic, (6,9,12)-linolenic and arachidonic acids are major intermediates in the pathway to eicosapentaenoic acid. Methyl-directed desaturation of (n-6) to (n-3) acids does not occur with C18 acids but is specific for the polyunsaturated C20 chain length. Arachidonic acid is the direct precursor of eicosapentaenoic acid.

Acetates↗

PubMed1977

Synthesis and function of 9,12,15-octadecatrien-6-ynoic acid in the moss ceratodon purpureus.

Biosynthesis of all-cis-9,12,15-octadecatrien-6-ynoic acid in the moss, Ceratodon purpureus, was studied using protonemata cultures with labeled 9,12,15-octadecatrienoic (linolenic) and 6,9,12,15-octadecatetraenoic acids as substrates. Both acids were efficiently converted into the acetylenic and into 5,8,11,14,17-eicosapentaenoic acids. Accordingly, the introduction of a triple bond in position 6 of linolenic acid involves formation of a double bond as a discrete step. Acetylenic acid triglycerides are reserve lipids in the moss. Under suitable growth conditions the acetylenic acids are catabolized and partly reused via acetate for de novo synthesis of fatty acids. They are not used for more direct syntheses of the common polyunsaturated fatty acids.

Fatty Acids↗

PubMed1977

Metabolism of oleic, linoleic and linolenic acids in gourami (Trichogaster cosby) fry and mature females.

1. Female gouramis incorporated pulse-fed [U-14C]oleic, linoleic and linolenic acids more readily into roe than body lipids. Labeling was highest in eggs spawned 20-30 days after feeding. 2. In the fry, linoleic and linolenic were catabolized more slowly than oleic acid, indicating conservation of the polyunsaturated acids in the early stage of life. 3. In the mature female, metabolism of linolenic was distinct from that of the other acids by more extensive conversions and greater use of 14C for de novo synthesis of fatty acids.

Adipose Tissue↗

PubMed1976

Synthesis of anacardic acids in seeds of Ginkgo biloba.

Anacardic (6-alkylsalicylic) acids and common lipids are efficiently synthesized by immature seeds of Ginkgo biloba. The seeds were incubated with 14C-labeled acetic, malonic and palmitoleic acids, glucose, and other potential precursors. Levels of 14C in common lipids and in anacardic acids, and the distribution of 14C in anacardic acids were determined. The results show that the salicylic moiety is synthesized by a polyketide pathway via malonic acid. The chain moiety for anacardic acid synthesis is in a different state of activation and/or site than chains that are used for synthesis of the common lipids. Labeled shikimic acid did not contribute 14C to anacardic acids, nor to other lipids, and palmitoleic acid was incorporated only into common lipids.

Acetates↗

PubMed1975

Distribution of arachidonic and eicosapentaenoic acids in the lipids of mosses.

Lipid classes from four species of mosses, Mnium cuspidatum, and Mnium medium from Minnesota, and Hylocomium splendens and Pleurozium schreberi from Alaska, were analyzed. The total lipids of all species contained 30-40% arachidonic and eicosapentaenoic acids. However, the lipids from the Alaskan mosses contained about 75% neutral lipids (triacylglycerols, steryl esters and wax esters) whereas the lipids of the other species contained only 20% or less of these neutral lipids. Consistently, monogalactosyldiacylglycerols and phosphatidylethanol-amines were enriched in arachidonic acid and the galactolipids in eicosapentaenoic acid. The distribution of these acids in the phospholipids shows some preference for position 2. Together, the highly unsaturated C20 acids represented 80% of acyl groups in steryl esters. In triacylglycerols they were at average levels, while they were much less in sulfolipids and phosphatidylglycerols. Wax esters contained very little of the highly unsaturated acids but appreciable amounts of phytol and phytenic acid were found as wax constituents.

Arachidonic Acids↗

PubMed1975

Acetylenic acids from mosses.

Two new acetylenic fatty acids, 9, 12-octadecadien-6-ynoic and 11, 14-eicosadien-8-ynoic, were identified from lipids of the moss, Fontinalis antipyretica. They resemble the previously identified 9,12,15-octadecatrien-6-ynoic acid by having a methylene interrupted unsaturated system. The C20 acetylenic acid shows that the capability of mosses to synthesize polyolefinic acids of this chain length applies, in certain species, also to olefinic-acetylenic acids.

Acetylene↗

PubMed1975

Synthesis and analysis of phytyl and phytenoyl wax esters.

An efficient procedure for preparing phytenic acid methyl ester, free of isomers, from phytol is reported. Phytyl phytenate and other isoprenoid wax esters were synthesized. Gas liquid chromatography of these wax esters and other compounds related to phytol and phytenic acid is described. The alkyl constituents of isoprenoid wax esters can be analyzed after alkaline methanolysis and the acyl constituents after acidic methanolysis. The applicability of these methods to natural mixtures was demonstrated with wax esters from mosses which contained both types of isoprenoids and with wax esters from healthy and frost damaged grass which contained phytol, but not phytenic acid.

Chemical Phenomena↗

PubMed1975

Furanoid fatty acids from fish lipids.

Fatty acids, recently reported as constituents of certain fish lipids, were identified to be derivatives of furan (furanoid fish fatty acids). 12,15-Epoxy-13,14-dimethyleicosa-12,14-dienoic acid is predominant among the furan acids and is associated with bis-homologs in regard to chain length. Monomethyl acids, such as 12,15-epoxy-13-methyleicosa-12,14-dienoic, are present in appreciable amounts. The structures were concluded from oxidative degradations, from mass spectrometry of methyl esters of the novel acids and fatty acids derived from them by opening the ring, and from nuclear magnetic resonance, infrared, and Raman spectra. The results from chemical procedures and from spectrometric methods were in agreement with those obtained with authentic methyl 9,12-epoxyoctadeca-9,11-dienoate. The number of substituents at the furan ring greatly influences hydrogenation, hydrogenolysis, and hydrolysis reactions of the ring.

Animals↗

PubMed1974