Straight-chain Saturated Fatty Acids Research Articles

Relation of Growth Temperature to Fatty Acid Composition of Propionibacterium Strains

The ability of 101 strains of Propionibacterium to grow at 4.5°C in broth culture was measured. Three strains that grew at 4.5°C, Propionibacterium freudenreichii subsp. shermanii strains P8, P22, and P33, and three strains that did not grow at 4.5°C, Propionibacterium jensenii strains P25 and P41 and Propionibacterium acidi-propionici strain P50, were grown individually in batch culture to early stationary phase at 10 and 32°C. Their fatty acids were extracted directly from whole cells by potassium hydroxide digestion and examined as methyl esters by capillary gas-liquid chromatography and mass spectrometry. Percentages of fatty acids were compared at the two growth temperatures. The most abundant acids in both groups were iso- and anteiso-15:0 fatty acids. The fatty acids of the strains that grew at 4.5°C were 38 to 64% anteiso-15:0 and 2 to 10% iso-15:0, whereas the strains that would not grow at 4.5°C contained 25 to 46% of anteiso-15:0 and 14 to 42% of iso-15:0. Both groups tended to increase the proportion of branched chain fatty acids and decrease saturated straight-chain fatty acids at 10°C compared with 32°C. The difference of fatty acid composition between the two groups may be species-related. The change of fatty acid composition with a change of growth temperature frequently was not large, indicating that strains able to grow at low temperature possess a fatty acid composition consistent with this trait rather than possessing the ability to adjust fatty acid composition greatly with a change of growth temperature.

Inhibition of brain prostaglandin d synthetase and prostaglandin D 2 dehydrogenase by some saturated and unsaturated fatty acids

The activities of rat brain prostaglandin D synthetase and swine brain postaglandin D 2 dehydrogenase were inhibited by some saturated and unsaturated fatty acids. Myristic acid was most potent among saturated straight-chain fatty acids so far tested. The IC 50 values of this acid were 80 μM for prostaglandin D synthetase and 7 μM for prostaglandin D 2 dehydrogenase, respectively. Little inhibition was found with methyl myristate and myristyl alcohol. The IC 50 values of these derivatives were more than 200 μM for both enzymes, suggesting that the free carboxyl group was essential for the inhibition. The effects of cis double bond structure of fatty acids on the inhibition potency were examined by the use of the carbon 18 and 20 fatty acids. The inhibition potencies for both enzymes increased with the number of cis double bonds; the IC 50 values of stearic, oleic, linoleic and linolenic acid were, respectively, more than 200, 60, 30 and 30 μM for prostaglndin D synthetase, and 20, 10 8.5 and 7 μM for prostaglandin D 2 dehydrogenase. Arachidonic acid also inhibited the activities of both enzymes with respective IC 50 values of 40 μM for prostaglandin D synthetase and 3.9 μM for prostaglandin D 2 dehydrogenase, while arachidic acid showed little inhibition. The kinetic studies with myristic acid and arachidonic acid demonstrated that the inhibition by these fatty acids was competitive and reversible for both enzymes. Myristic acid and other fatty acids also inhibited the activities of several enzymes in prostaglandin metabolism, although to a lesser extent. The IC 50 values of myristic acid for prostaglandin E isomerase, thromboxane synthetase and NAD-linked prostaglandin dehydrogenase (type I) were 200, 700 and 100 μM, respectively. However, this fatty acid showed little inhibition on fatty acid cyclooxygenase (20% at 800 μM), glutathione-requiring prostaglandin D synthetase from rat spleen (20% at 800 μM), and NADP-linked prostaglandin dehydrogenase (type II) (no inhibition at 200 μM).

Lipid Composition as a Guide to the Classification of Some Coryneform Bacteria-containing an A 4 α Type Peptidoglycan (Schleifer and Kandler)

Fatty acid, menaquinone and polar lipid analyses were performed on Artbrobacter nicotianae, A. citreus, Brevibacterium incertum, B. liquefaciens, B. protopbormiae, "B. sulfureum" and "B. fuscum". The results of the present study indicate A. nicotianae, B. liquefaciens, B. protopbormiae and "B. fuscum" are unrelated to the genus Artbrobacter sensu stricto and possibly warrant a new taxon. Strains labelled A. citreus were heterogeneous on the basis of lipid composition. The type strain of A. citreus (NCIB 8915) is a legitimate Artbrobacter species whereas strain ATCC 15170 was closely related to "B. sulfureum". Brevibacterium incertum differed from all of the other strains examined on the basis of lipid composition. The absence of menaquinones within B. incertum together with the presence of straight-chain saturated and monounsaturated (cis-vaccenic acid series) fatty acids indicates this taxon does not belong to the 'coryneform group of bacteria'.

Capillary gas chromatographic analysis of human skin surface lipids after microsampling on ground-glass platelets

Small amounts of human skin surface lipids, in the 1–20 μg range, sampled on ground-glass platelets are investigated using capillary gas chromatography. A first system allows the separation of the neutral lipids, up to the triglyceride fraction. A second system reveals the distribution of the free fatty acids or of the free + glyceride fatty acids, after a methylation or transesterification step. Examination of samples from nine subjects shows that the unsaturation of the free fatty acids increases during a four-day period of accumulation. Comparison of the free fatty acid fraction and the free + glyceride fatty acid fraction shows that the free fraction is more saturated than the latter. It is concluded that the bacterial lipases which cleave the fatty acids from the ester bond favor the liberation of straight-chain saturated fatty acids from sebum triglycerides. This result is confirmed by comparison of the free fatty acid fraction with the glyceride fatty acid fraction separated from bulk samples of skin surface lipds from hair and scalp.

Acyl chains of phospholipids and their variation with age in Streptomyces griseus.

Total and individual phospholipids ofStreptomyces griseus exhibit a predominance of iso and anteiso fatty acids. The ratio of saturated straight chain fatty acids to branched chain plus unsaturated fatty acids remained unchanged during growth.

Characteristics of a lipolytic and fatty acid-requiring Butyrivibrio sp. isolated from the ovine rumen.

A naturally occurring fatty acid-requiring Butyrivibrio sp. (strain S2), isolated from the ovine rumen, deacylates plant galactolipids, phospholipids and sulpholipids to obtain sufficient fatty acid for growth. Growth in vitro was promoted by adding to the growth medium a single straight-chain saturated fatty acid (C13 to C18) or vaccenic acid. Palmitoleic and oleic acids also supported growth but gave lengthy lag phases probably due to their toxicity. Linolenic and linoleic acids supported good growth but they were completely hydrogenated to trans-11-octadecenoic acid which was incorporated into the bacterial complex lipids. No chain elongation, chain shortening or desaturation of the added fatty acids occurred and all were substantially incorporated into bacterial lipids of the plasmalogen type, partially as a new type of hydrophobic grouping derived from two molecules of fatty acid. The absence of fatty acid unsaturation poses the question of the maintenance of membrane fluidity within this bacterium.

Levels of short-chain fatty acids and of abscisic acid in water-stressed and non-stressed leaves and their effects on stomata in epidermal strips and excised leaves

Straight-chain saturated fatty acids (C6-C11) and abscisic acid (ABA) accumulate in the leaves of Phaseolus vulgaris L. and Hordeum vulgare L. under water stress. ABA and certain of the fatty acids, particularly decanoic and undecanoic acid, can inhibit stomatal opening and cause stomatal closure in epidermal strips of Commelina communis L. depending on the incubating medium used. 10(-4) M (±)-ABA inhibits opening in media containing either high or relatively low concentrations of KCl but causes closure only in the latter medium. The fatty acids (at 10(-4) M) prevent opening in both media while significant closure of open stomata was caused only by undecanoic acid in both media and, additionally, by decanoic acid in the low-KCl medium. 10(-4) M formic acid also caused stomatal closure and prevented opening to significant extents in the low-KCl medium (it was not tested in the high-KCl medium). The efficacy of undecanoic acid in causing 50% inhibition of opening is about three orders of magnitude lower than that of ABA. At a concentration of 10(-3) M, nonanoic, decanoic and particularly undecanoic acid and all-trans-farnesol cause increased cell leakage in Beta vulgaris L. root tissue. Undecanoic acid (10(-4) M) also causes some loss of guard cell integrity in C. communis within 1.5 h of treatment. ABA (10(-4) M) reduces transpiration rates in barley and C. communis leaves when applied via the transpiration stream but decanoic and undecanoic acids did not have this effect. Transpiration was not affected when ABA or the fatty acids were applied to the leaf surfaces.

The Photo-induced Addition of Acetic Acid to Olefins

The photo-induced addition of acetic acid to ethylene gave butyric acid. Small amounts of hexanoic, octanoic, 2-ethylbutyric, and 2-ethylhexanoic acids, and neutral substances were also formed. The presence of a small amount of di-tert. butyl peroxide was effective to form butyric acid. Main neutral substances were dibutyl and di (2-ethylhexyl) phthalates. A straight-chain saturated fatty acid was also obtained in an excellent conversion of a 1-olefin by the photo-induced addition of acetic acid to the 1-olefin [acetic acid : 1-olefin, 200 : 1 (mol)]. It was assumed that a ketone and an ester (s) were present in the by-products.

Lipids in plant tissue cultures II. Unusual fatty acids in lipids of Hydnocarpus anthelminthica cultures

The lipids in callus cultures of Hydnocarpus anthelminthica were studied after 60, 160 and 460 days of growth. In each of the cultures the lipid classes usually found in plant tissue cultures were detected. With increasing age of the cultures the total lipid content as well as the proportions of triglycerides decreased. The major constituent fatty acids of the total lipids were palmitic and linoleic acids. Small amounts of cyclopentenyl fatty acids were also present. The proportions of saturated straight-chain fatty acids increased with the age of the cultures whereas the proportions of monounsaturated straight-chain fatty acids decreased. Only small changes were observed with polyunsaturated fatty acids. The content of cyclopentenyl fatty acids rose with the age of the cultures. The monounsaturated straight-chain fatty acids consisted of mixtures of isomers whose composition changed with the age of the cultures. In contrast, the polyunsaturated straight-chain fatty acids belonged exclusively to the Δ9 series, regardless of the age of the cultures.

On the chemical structure of the apical droplet from eggs of Culex pipiens

The chemical nature of the apical droplet from eggs of Culex pipiens was investigated by chromatographic techniques. Results indicated that the hydrolysate of the apical drop contains C-12, C-14, C-16, and C-18 straightchain aliphatic fatty acids. A C-12β-hydroxy fatty acid was also found, but the largest component of the fatty acid mixture of the apical drop was shown to be a C-14β-OH fatty acid. Two other fractions appear to be unsaturated fatty acids, probably C-12 and C-14. Quantitative estimation of the percentage of each fatty acid in the mixture showed that about 85 per cent of the fatty acid content of the apical drop consisted of hydroxy fatty acids. By thin-layer chromatography, the largest component coincided with β-OH myristic acid. Glycerol was confirmed to be present in the hydrolysate. Feeding studies with radioactive 32PO 4 −3 and 35SO 4 −2 showed no significant incorporation of phosphorus, but a sulphur-containing anionic compound could be detected in the apical drop. Infrared analysis showed the presence of an ester group, double bond, primary and secondary alcohol groups, suggesting the presence of hydroxy-, unsaturated-, saturated straight-chain fatty acids, as well as mono-and diglycerides. The structural evidence explains in part the surfactant properties of the apical drop.

CELLULAR FATTY ACID SPECTRA OF HIOCHI BACTERIA, ALCOHOL-TOLERANT LACTOBACILLI, AND THEIR GROUP SEPARATION

Thirty-eight strains of hiochi bacteria, ethanol-tolerant Sake-spoilage lactobacilli, were analyzed for their cellular fatty acid spectra with special reference to their classification. They were separated, with respect to their fatty acid spectra, into three groups, which corresponded respectively to the homo- fermentor, and mevalonic acid-dependent and -independent hetero-fermentors. Long straight-chain saturated and mono-unsaturated fatty acids with 20-26 carbon atoms were found, in addition to fatty acids ordinarily known in typical lactobacilli, exclusively in the mevalonic acid- dependent hetero- fermentative group (L. heterohiochii), the most predominant Sake-spoilage microorganism. Uniqueness of the synthetic pathways for fatty acids of this alcoholophilic organism producing these long-chain acids was pointed out, and the feasibility of detecting or characterizing rapidly the spoilage bacteria in hiochi-infected Sake through the fatty acid analysis of the sedimented cells was discussed.

The effect of straight-chain saturated, monoenoic and branched-chain fatty acids on growth and fatty acid composition of mycoplasma strain Y.

Summary: The fatty acid growth requirements of a sterol-requiring Mycoplasma (strain y), unable to synthesize or alter the chain length of either saturated or unsaturated fatty acids, were investigated. In some cases adaptation was required for growth when mycoplasmas were transferred to media of differing fatty acid composition. No straight-chain saturated acid supported growth when tested alone, but good growth was obtained with three branched-chain acids (isopalmitate, isostearate and anteisoheptadecanoate) tested singly and with some straight-chain saturated acids when tested in pairs (e.g. when equal proportions of C12 and C22 acids were supplied together). Of the unsaturated fatty acids tested, cis-12-octadecenoate and two trans-octadecenoates (elaidate and trans-vaccenate) supported good growth alone. Little or no growth was obtained with any cis-monoenoic acid of the oleic acid series unless a straight-chain acid was also supplied and both the chain length of the monoenoic acid and the position of the double bond had a marked effect on the range of saturated acids with which it could be successfully paired. With myrist-oleate, long-chain saturated acids of chain length C20, C22 gave the best growth; with oleate the range extended from C12 to C20 (optimal at C17) and with erucate from C10 to C18 (optimal at C15). When the double bond was near the carboxyl group, as in cis-6-octadecenoate, strain y grew only when paired with C14 to C16 saturated acids; as it became further removed from the carboxyl group as in cis-vaccenate, addition of a single saturated acid from an extended range (C10 to C24) could support growth. Only those fatty acids supplied in the growth medium were present in the lipids of the organism, and in cases where strain y grew well when a single fatty acid was supplied, this was the sole fatty acid found. Marked differences in morphology were observed in mycoplasmas of differing fatty acid composition.

Comparative studies on the hydrolysis of odd-chain and even-chain fatty acid cholesterol esters by rat liver sterol ester hydrolase

The complete series of even- and odd-chain straight chain saturated fatty acid cholesterol esters were synthesized. Their melting points alternated in a fashion resembling that of the corresponding fatty acids. Rat liver cholesterol ester hydrolase (sterol ester hydrolase, EC 3.1.1.13) exhibited rates which were markedly dependent on the chain length of the fatty acid constituent. Most important, they were alternating with each one of the even-chain fatty acid cholesterol ester hydrolyzed at a higher rate than did the odd-chain ester containing either one more or one less carbon atom. Alternations in physical properties and in hydrolyzability are discussed in terms of tilting of the hydrocarbon chain with respect to the carboxyl group. It is suggested, that tilting gives rise to geometric differences which influence hydrocarbon chain interactions. In crystals they are reflected in melting points. In reaction rates they manifest themselves during the formation of the substrate-enzyme complex.

Major occurrence of [formula omitted] fatty acids in three psychrophilic species of [formula omitted

Monounsaturated fatty acids occur in Bacillus insolitus, Bacillus psychrophilus , and Bacillus globisporus in unusually large proportions for this genus. These unsaturated fatty acids have been identified as exclusively the cis -Δ 5 omers. Large proportions of branched-chain and small proportions of straight-chain saturated fatty acids common to this genus have also been found.

Chemical reactions at lipid‐gas interfaces: I. Terminal chain elongation of fatty acids

AbstractReactions of free methyl radicals and monolayers of potassium palmitate and of potassiumn‐heptadecanoate on an aqueous surface yielded straight chain saturated fatty acids containing longer hydrocarbon chains than those of the reactant acids. Similar results were obtained from the reactions of free ethyl radicals and potassium palmitate under similar conditions. The results of this investigation indicate that extension of hydrocarbon chains by free radical addition reactions can be achieved if the growing chains are suitably packed in a monolayer on a surface.

Lipid metabolism in the parasitic and free-living spirochetes Treponema pallidum (Reiter) and Treponema zuelzerae

The parasitic Treponema pallidum (Reiter) can neither synthesize nor desaturate fatty acids and depends on an outside source for these compounds. In contrast, the free-living Treponema zuelzerae synthesizes all of its fatty acids, primarily isoacids and straight-chain saturated fatty acids plus smaller amounts of monoenoic acids and free fatty aldehydes. Both organisms synthesize all of their complex lipids. Glycolipids account for one-fourth to one-third of the total lipids, principally monogalactosyl diglyceride ( T. pallidum) and monoglucosyl diglyceride ( T. zuelzerae). The major phospholipids of T. zuelzerae are phosphatidyl glycerol (31%) and cardiolipin (21%). T. pallidum contains phosphatidyl choline (33%), choline plasmalogen (8%), phosphatidyl glycerol (7%) and cardiolipin (6%). T. pallidum has substantial amounts of cholesterol which originate from the medium. T. zuelzerae has no sterols.

The structure of viscosin, a peptide antibiotic. I. Syntheses of D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin.

Sixteen D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin have been synthesized. Condensation of DL-3-hydroxy fatty acids with L-leucine methyl ester by the azide method or the active ester method gave DL-3-hydroxyacyl-L-leucine methyl esters, which were then converted to their hydrazides. Each of the racemic hydrazides could readily be resolved into the respective optically active diastereoisomers by means of fractional crystallization using alcohols.All of the D- and L-3-hydroxyacyl-L-leucine hydrazides prepared showed antimicrobial activity against four kinds of microorganisms only comparable to or less than that of the saturated straight chain fatty acids of corresponding carbon numbers.

Preparation of extracts of culture liquids for gas-chromatographic determination of acidic fermentation products

An extraction method coupled with gas-chromatographic analysis has been devised for the determination of small amounts of C1-C7 branched and straight-chain saturated fatty acids as well as 18 mono-, di- and tricarboxylic acids and related compounds, the latter being analyzed either as their methylesters or as their trimethylsilyl-derivatives. Methods for extracting non-volatile acids or both volatile and non-volatile acids are described for large and small volumes of culture media. The proposed methods have been successfully applied to the determination of non-acidic fermentation products, known amounts of alcohols, and to volatile and non-volatile acids in bacterial fermentation solutions, namely a batch culture ofLactobacillus casei subsp.rhamnosus ATCC 7469. A carbon balance sheet of this organism's metabolic behaviour throughout growth is proposed.

Fatty acid biosynthesis in the silkmoth, Hyalophora cecropia

Gas chromatographic and mass spectrographic analysis established that the six major fatty acids of Hyalophora cecropia are palmitic, palmitoleic, stearic, oleic, linoleic, and linolenic acids. Radiotracer studies at several developmental stages reveal that H. cecropia can synthesize only straight-chain saturated and mono-unsaturated fatty acids from acetate. This insect does have the capacity to lengthen palmitic acid to stearic acid and can dehydrogenate both to the corresponding monoenes. The data demonstrate that the rates of lipid synthesis from acetate, distribution of label among various fatty acids, chain lengthening, and desaturation are functions of developmental stage. An analysis of our data and that in the literature suggests that no insect has been shown to synthesize polyenoic acids or can synthesize monoenoic acids other than by direct desaturation of existing or newly synthesized saturated fatty acids.

Gas chromatographic separation and determination of micro quantitative of C 1—C 7 Branched and straight-chain saturated fatty acids

A survey of thirteen different columns was carried out to find a suitable combination for the separation and determination of micro quantities of formic, acetic, propionic, isobutyric, n-butyric, isovaleric, n-valeric, isocaproic, n-caproic and heptanoic acid. A 4 ft. x 1 4 in. O.D. stainless steel column with 3.125% PEGA on acid-washed Chromosorb W ( 60 80 mesh) gave the best results in separation and sensitivity under isothermal and temperature-programming conditions. Using the dual hydrogen flame ionization detector on a Beckman GC-M, a helium flow rate of 100 ml/min and temperature programming between 100–150° at a rate of 5°/min, all acids could be separated and 0.5 μg of acid could be estimated. Isothermally with the thermoconductivity cell, 10 μg was the lowest amount detectable, for all investigated acids.