In vitro esterification of plant sterols by the esterifying enzyme of the small intestine of rat

Summary The in vitro esterification of plant sterols,-sitosterol, campesterol and stigmasterol, by the esterifying enzyme of the small intestine of rat was studied in the presence of saturated and unsaturated fatty acids. Campesterol esterification was highest, followed by sitosterol and stigmasterol irrespective of the type of fatty acid. Both campesterol and sitosterol esterification was greater with unsaturated fatty acids than with saturated fatty acids.Acknowledgments. Financed by the Emery Goff Research Award from the American Heart Association, Louisiana, Inc. and the USPHS research grant HL-08974 from the National Institutes of Health, Bethesda, Md.     

Cholesterol esterification activities in the intestines and pancreas of the albino rat

Summary Cholesterol esterification activities in intestines and pancreas are much greater with unsaturated fatty acids than with the saturated ones; the maximum activity is with arachidonic acid in intestines and with oleic acid in pancreas. The pancreatic cholesterol esterification activity is higher than the intestinal one.     

Effects of plant sterols on cholesterol concentration in the rat small intestine

Summary The effects of feeding single doses of -sitosterol, campesterol and stigmasterol on cholesterol concentration in the rat small intestine was studied to clarify their roles in cholesterol absorption. The different plant sterols affected free and ester cholesterol concentrations differently in the different intestinal segments suggesting that they have different effects on such intestinal processes as uptake, esterification and possibly synthesis of cholesterol and transport of cholesterol esters out of the mucosal cells into the lymphatics.Acknowledgments. Financed by the Emergy Goff Research Award from the American Heart Association-Louisiana, Inc. and the NHLBI research grant HL-08974 from the National Institutes of Health, Bethesda, Maryland.     

Biochemical markers in the taxonomy of the Actinomycetales.

Useful biochemical markers for the classification of Actinomycetales are: 1. DL- or LL-diaminopimelic acid in the peptidoglycan, 2. sugar composition of polysaccharides, 3. fatty acid spectrum of cell lipids. The occurrence of various kinds of branched fatty acids and of unsaturated fatty acids is of special value.     

Interaction of chlorpromazine with organic solvents and fatty acids as studied by UV-spectrophotometry

Summary The magnitude of the UV-spectral change of chlorpromazine increases in the presence of increasing concentrations of alcohols or fatty acids and with increasing chain length. A maximum is reached with 14.0- or 16.0-fatty acids. The difference spectrum is still larger with unsaturated fatty acids, a maximum effect being obtained with one cis-double bond. The spectral change is abolished by chaotropic and enhanced by antichaotropic agents.Supported by a grant of the Swiss National Science Foundation.     

New highly irritant euphorbia factors from latex of Euphorbia tirucalli L.

Summary From the latex of Euphorbia tirucalli L. growing in Madagascar, 5 new euphorbia factors were isolated. They were characterized as 13-O-acetyl-12-O-acylphorbol-and 12-O-acetyl-13-O-acylphorbol derivatives carrying homologous conjugated unsaturated fatty acids as acyl groups. Furthermore, 2 mixtures of homologous 3-O-acylingenol derivatives are obtained carrying the same type of unsaturated fatty acids. Due to their highly unsaturated acyl groups all Euphorbia factors or factor groups isolated are highly sensitive to autoxidation.Acknowledgments. We wish to thank Miss B. Pieruschka for excellent technical assistance. The supply of latex by Mr M. Schomerus, Ampanihy-ouest, Madagascar, and Prof. Dr W. Rauth, Botanical Institute of the University of Heidelberg, is gratefully acknowledged.     

Biochemical markers in the taxonomy of theActinomycetales

Summary Useful biochemical markers for the classification ofActinomycetales are: 1.dl-orll-diaminopimelic acid in the peptidoglycan, 2. sugar composition of polysaccharides, 3. fatty acid spectrum of cell lipids. The occurrence of various kinds of branched fatty acids and of unsaturated fatty acids is of special value.We should like to thank the Bundesministerium für Forschung und Technologie, Bonn, German Federal Republic, for the financial support of this project No. BCT 85.     

Sterol composition of three species of sawflies (Hymenoptera: Symphyta) and their dietary plant material

Three species of sawflies, along with their particular host plants, were examined for neutral sterols. Cholesterol was the predominant sterol in the sawfliesDolerus nitens (56.6%) andAneugmenus flavipes (73.0%), with lesser amounts of sitosterol, campesterol and desmosterol.Xiphydria maculata, however, contained unusually high levels (74.9%) of 7-dehydrocholesterol. Based on the sterol composition of their individual host plants, which contained primarily 28- and 29-carbon sterols, it is likely that all three sawfly species are capable of dealkylation of phytosterols.     

Sexual dimorphism in the defensive secretion of a carabid beetle

The defensive secretions of male and female Oodes americanus display striking qualitative differences. Altogether 13 carboxylic acids were identified in the secretions of the two sexes. Methacrylic, crotonic, and tiglic acids are produced exclusively by the female; the male lacks these unsaturated components, but produces their saturated analogs. 2-Methylbutyric acid is a major component produced by both sexes. Shared components also include hexanoic, (E)-2-hexenoic, benzoic, and (E)-2-octenoic acid, of which the latter two had not previously been reported from carabid beetles.     

The effect of endotoxin on membrane fatty acid composition in BCG-sensitized mice

The effects of endotoxin on mouse liver phospholipid fatty acid composition have been investigated. Administration of endotoxin from Salmonella abortus equi led to a decrease in the polyunsaturated fatty acid content of livers from mice sensitized with Bacille Calmette Guérin (BCG). The content of arachidonic acid fell significantly in both the phosphatidylcholine and phosphatidylinositol fractions whereas in the phosphatidylethanolamine fraction the linoleic acid content was significantly reduced. The polyunsaturated fatty acids were replaced by increased amounts of oleic acid and palmitic acid, leading to a reduction in the polyunsaturated to saturated fatty acid ratio.     

The effect of endotoxin on membrane fatty acid composition in BCG-sensitized mice

Summary The effects of endotoxin on mouse liver phospholipid fatty acid composition have been investigated. Administration of endotoxin fromSalmonella abortus equi led to a decrease in the polyunsaturated fatty acid content of livers from mice sensitized with Bacille Calmette Guérin (GCG). The content of arachidonic acid fell significantly in both the phosphatidylcholine and phosphatidylinositol fractions whereas in the phosphatidylethanolamine fraction the linoleic acid content was significantly reduced. The polyunsaturated fatty acids were replaced by increased amounts of oleic acid and palmitic acid, leading to a reduction in the polyunsaturated to saturated fatty acid ratio.     

Fatty acid profiles of major food sources of howler monkeys (Alouatta palliata) in the neotropics

Wild howler monkeys (Alouatta palliata) get most of their calories from carbohydrates (65%) and fats (18%) of native tropical plants, but little is known about their intake of individual fatty acids. The fatty acid composition of several natural food sources of howler monkeys collected in Panama was determined by gas-liquid chromatography. The predominant fatty acids were palmitic (30%), linoleic (23%), linoleic (23%), -linolenic (16%) and oleic (15%). Fatty acids with less than 16, and more than 18, carbon chains were uncommon (0–7%). Although total saturated fatty acids were high in some specific food sources (22–54% of total fatty acids and 8 energy %), most of the calories from fat in the animals' diets are derived from mono-and polyunsaturated fatty acids (9.75 energy %) All food sources had significant amounts of the -3 fatty acid, -linolenic acid (2.9 energy %). In terms of human diets, the howler monkey's fat consumption would not be considered atherogenic. Unless these animals show a particular adverse susceptibility to dietary fat, it is unlikely that their fat intake is the primary cause of the low, but significant, incidence of atherosclerosis that develops in these animals in the wild state.     

Sexual dimorphism in the defensive secretion of a carabid beetle

Summary The defensive secretions of male and femaleOodes americanus display striking qualitative differences. Altogether 13 carboxylic acids were identified in the secretions of the two sexes. Methacrylic, crotonic, and tiglic acids are produced exclusively by the female; the male lacks these unsaturated components, but produces their saturated analogs. 2-Methylbutyric acid is a major component produced by both sexes. Shared components also include hexanoic, (E)-2-hexenoic, benzoic, and (E)-2-octenoic acid, of which the latter two had not previously been reported from carabid beetles.Paper no. 98 in the series Defense Mechanisms of Arthropods; no. 97 is by Smedley et al., J. Lepid. Soc., in press.     

Zur Bildung mittelkettiger Fettsäurereste in elektronenbestrahlten Fetten

Summary Investigations of the chemical changes in fats subjected to cathode rays (100 Mrad) indicated the formation of shorter fatty acid chains. Besides splitting off the terminal methyl groups, especially the medial C-C-bonds are readily split and saturated and unsaturated C₆-C₁₁-fragments are formed. The double bond is relatively resistant, but the C-C-bond near the double bond is easily fractured.     

Fatty acid modulation of antiestrogen action and antiestrogen-binding protein in cultured lymphoid cells

Nonsteroidal antiestrogens reversibly and specifically inhibited the proliferation of two estrogen receptor-negative lymphoid cell lines (EL4 and Raji) in a dose-dependent manner. [3H]Thymidine incorporation of concanavalin A-stimulated primary splenocytes was also inhibited by 10(-6) M clomiphene (1-[4-(2-diethylaminoethoxy)phenyl]-1,2-diphenyl-2-chloroethylene). The antiproliferative effect could be prevented by the simultaneous presence in the growth medium of 10(-5) M linoleic acid or 10(-5) M arachidonic acid but not by 10(-6) M estradiol. Both lymphoid cell lines had high affinity antiestrogen-binding sites whose affinity could be altered by conditions of growth. Growth of EL4 cells in RPMI 1640 medium supplemented with charcoal-pretreated 5% fetal calf serum (charcoal-stripped medium) resulted in significantly higher affinity (Kd 0.54 nM +/- 0.11 nM; n = 6) than growth in medium supplemented with untreated serum (complete medium) (Kd = 1.68 nM +/- 0.48 nM; n = 6) (p less than 0.001). This change in affinity was partly due to removal of fatty acids from the growth medium by charcoal pretreatment, since addition of 10(-5) M linoleic acid or 10(-5) M gamma-linolenic to charcoal-stripped medium decreased the affinity of the antiestrogen-binding protein. In contrast, growth in 10(-5) M stearic acid or 10(-5) M oleic acid did not significantly alter the affinity of the antiestrogen-binding protein, whereas 10(-5) M palmitic acid significantly increased its affinity. The same fatty acids were also tested for their intrinsic effects on EL4 cell proliferation. Oleic, linoleic and gamma-linolenic acids were growth stimulatory while stearic and palmitic acids were not. Thus linoleic and gamma-linolenic acids whose presence in the growth medium was associated with decreased affinity of [3H]tamoxifen (1-[4-(2-dimethylaminoethoxy)phenyl]-1,2-diphenylbut-1(Z)-ene) binding to the intracellular antiestrogen-binding protein were also growth stimulatory. Unsaturated fatty acids have previously been shown to inhibit binding of [3H]tamoxifen to the antiestrogen-binding protein in a cell-free system. The present observations demonstrate that unsaturated fatty acids also modify the affinity of the antiestrogen-binding protein in intact cells.     

Über die Oxydation ungesättigter Fettsäuren durch Pflanzensäfte

Summary Extracts from various parts, including root nodules, of different leguminous plants, and extracts from leaves of several other plants (belonging toSolanaceae andLabiatae) are able to accelerate efficiently the oxidation of unsaturated fatty acids.     

Organtypische und phasenspezifische Verteilung ungesättigter Lipoide im Schwanz der Larve vonXenopus laevis

Summary Barrollier's method for unsaturated fatty acids (u. f. a.) in paper chromatograms has been adapted for cytochemical detection of u. f. a. in the tails ofXenopus-larvae. A specific pattern in the different organs was found. It was further shown that the content in u. f. a. changes quickly, apparently indicating rapid changes in physiological conditions during growth and regeneration.     

Polyunsaturated fatty acids and cardiovascular disease

Replacing saturated with polyunsaturated (PUFAs) rather than monounsaturated fatty acids or carbohydrates results in cardiovascular prevention over a wide range of intakes. The mechanisms by which PUFAs reduce cardiovascular risk are manifold, and the extent and precise nature of their activities is the subject of several investigations, spanning from in vitro mechanistic studies to human intervention trials. This article reviews the most up-to-date evidence of the association between PUFA consumption and reduced cardiovascular mortality.     

Pulmonary di-and-triacylglycerols during the perinatal development of the rat

Summary Diacylglycerol (DG) and triacylglycerol (TG) levels in rat lung tissue were determined from day 17 of gestation to day 10 post partum and studied in parallel with ultrastructural differentiation. The DG level, although rather low at all measured stages, rose significantly between days 17 and 19 and at birth. TG level increased steadily during the whole studied period and especially between days 17 and 19 and at birth. In DG as well as in TG, saturated fatty acids were predominant. The rising of TG levels paralleled the appearance and accumulation of lipid vacuoles in mesodermal cells lying in contact with type II cells. The possible role of these cells is discussed.     

Biosynthesis of 1-alkenes in the defensive secretions ofTribolium confusum (Tenebrionidae); stereochemical implications

Summary The terminally unsaturated hydrocarbons of the defensive secretion ofTribolium confusum are biosynthesized from fatty acids by oxidative decarboxylation. The process involves an enantiospecific cleavage of the C–H bond of thepro-(S) C(3)–H atom and simultaneous decarboxylation of the acid into an 1-alkene and carbon dioxide via ananti-periplanar transition state geometry (anti-elimination). The stereochemistry of this biotranformation is identical in all respects with the same reaction in higher plants. The mechanism seems to be of general importance for the biosynthesis of many vinylic substructures of natural products from oxygen-containing precursors.