Occurrence of Curtobacterium sp. possessing ω-cyclohexyl fatty acids in soil with zinc added

A bacterial strain, Curtobacterium sp., isolated from a soil with zinc added possessed -cyclohexyl fatty acids. -Cyclohexyl undecanoic acid made up 47% of the total fatty acids; it was the most abundant fatty acid in the strain grown in tryptone medium. 12-Methyl tetradecanoic acid (23%) and 14-methyl hexadecanoic acid (22%) were also major fatty acids. The proportion of -cyclohexyl undecanoic acid increased as the pH of the medium decreased and as the culture temperature increased.The bacteria grew almost normally in zinc-enriched medium, and -cyclohexyl undecanoic acid increased with zinc concentration. Zinc added to the medium was not abundant in the cell fraction, and the ratio of increase of zinc in the cells was not so high as in the culture medium. These results suggested that -cyclohexyl fatty acids are related to the zinc tolerance of the isolated strain, and that this tolerance depends on low permeability of the membrane to zinc.     

Omega-cyclohexyl fatty acids in acidophilic thermophilic bacteria. Studies on their presence, structure, and biosynthesis using precursors labeled with stable isotopes and radioisotopes.

Omega-Cyclohexyl undecanoic acid and omega-cyclohexyl tridecanoic acid were found in 10 strains of acido-thermophilic bacteria isolated from different Japanese hot springs. These unusual fatty acids were found in the esterified form in glyceride type complex lipids and constituted 74 to 93% of the total fatty acids in the bacteria. The fatty acids other than omega-cyclohexyl fatty acids found were 14-methyl hexadecanoic acid (3 to 15%) and 15-methyl hexadecanoic acid (1 to 6%), and trace amounts of straight chain and methyl-branched tetra- and penta-decanoic acids. Biosynthesis of omega-cyclohexyl fatty acids increased with increase in the concentration of glucose in the culture medium. The metabolism of omega-cyclohexyl fatty acids was studied using deuterium-labeled precursors by mass fragmentation analysis. The deuterium of [2-D]glucose was specifically incorporated into position 2 of the cyclohexyl ring of the fatty acids, indicating that the ring was synthesized from the glucose molecule. Radioactivity was efficiently incorporated into the omega-cyclohexyl fatty acids from labeled glucose, shikimate, and cyclohexyl carboxylate. These findings indicate that omega-cyclohexyl fatty acids are synthesized with glucose through shikimic acid and probably cyclohexyl carboxylyl-CoA derivative as the intermediates.     

Zinc uptake of Curtobacterium possessing ω-cyclohexyl fatty acids and zinc-binding activity of its membrane

Abstract The immobilization of zinc taken up by Curtobacterium pusillum strain Z-96 possessing ω-cyclohexyl fatty acids and the zinc-binding activity of the membrane were investigated. The zinc taken up was immobilized in the membrane fraction to a great extent; little zinc was found in the cytoplasmic fraction. Zinc-binding activity of membranes was comparable to the amount of zinc immobilized by the intact cells. The level of ω-cyclohexyl fatty acids and the zinc-binding activity of the membrane were increased by the addition of zinc to the culture medium. The amount of bound zinc was approximately proportional to the level of ω-cyclohexyl fatty acids. In addition, the zinc-binding activity was not appreciably influenced by acidic or high-temperature treatment of membranes.     

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.Abbreviations ABA abscisic acid - RWC relative water content - SCFA short-chain fatty acids Deceased May 1977     

Phospholipid and lipopolysaccharide normal and hydroxy fatty acids as potential signatures for methane-oxidizing bacteria

Abstract The extractable ester-linked and the lipopolysaccharide (LPS) normal and hydroxy fatty acids of the methylotrophic bacteria Methylosinus trichosporium 0B3B, Methylobacterium organophilum XX, grown on methane and methanol, Mb. organophilum RG and Methylomonas sp. were analysed by capillary gas chromotography-mass spectrometry (GC-MS). Precise monounsaturated double bond position and geometry was determined by GC-MS analysis of the derivatized fatty acids. The three species were readily distinguished based on the extractable fatty acid and LPS hydroxy acid profiles. Type I and Type II methylotrophs can be separated based on the presence of 16-carbon and 18-carbon monoenoic fatty acids in the two groups of organisms, respectively. Relatively novel components, 18: 1ω8c, 18: 1ω8t, 18: 1ω7t and 18: 1ω6c were present in Ms. trichosporium , and 16: 1ω8c, 16: 1ω8t, 16: 1ω7t, 16: 1ω5c and 16: 1ω5t were detected in Methylomonas sp. These specific lipids may be used, together with other components, as signatures for these methylotrophic bacteria in manipulated laboratory and environmental samples.     

Properties of Bacillus acidocaldarius mutants deficient in ω-cyclohexyl fatty acid biosynthesis

Mutants of the thermoacidophilic Bacillus acidocaldarius, auxotrophic for shikimate or cyclohyxyl-carboxylate, were isolated and characterized. The cyclohexylcarboxylate auxotrophs could be divided by crossfeeding experiments into two groups according to their genetic block. The cyclohexylcarboxylate auxotrophs were deficient in -cyclohexyl fatty acid biosynthesis. If the mutants were fed with branched-chain amino acids or short branched-chain fatty acids instead of cyclohexylcarboxylate they form a fatty acid pattern consisting of branched-chain fatty acids. In the high temperature/low pH range the growth yield of cells with this fatty acid pattern is lower as compared to wild type cells or mutants fed with cyclohexylcarboxylate. The same cells are also more sensitive to heat shocks and ethanol. The transport systems for lysine, glutamate and glucose are severely altered by the fatty acid pattern. It was also shown that the density of the lipids containing -cyclohexyl fatty acids is higher compared to cells with branched-chain fatty acids. Thus it could be supposed that this alteration influences transport systmes in a direct manner or via energization of the cytoplasmic membrane.     

Fatty acid composition of four microsporidian species compared to that of their host fishes

ABSTRACT. The fatty acid composition of four microsporidian species (Glugea atherinae, Spraguea lophii, Glugea americanus , and Pleistophora mirandellae) and their host fishes has been determined using gas chromatography. Twenty-four fatty acids were identified with differences in relative abundance of fatty acids among the four parasites. Certain even-saturated fatty acids were found in a very high proportion: palmitic acid (16:0) represented one-third of total fatty acids in Pleistophora mirandellae. The level of docosahexaenoic acid (22:6ω3) attained 26–28% in Glugea atherinae, Spraguea lophii , and Glugea americanus , but only 8–9% in P. mirandellae. With respect to fatty acid compositions of host organs, some significant differences were evident between marine and freshwater fishes. Palmitic acid was prevalent in the marine fishes, Atherinae boyeri and Lophius piscatorius , and oleic acid (18:1ω9) in the freshwater fish Leuciscus cephalus. The proportion of docosahexaenoic acid in marine fishes was two or three times as great as in freshwater fish Leuciscus. The high polyunsaturated fatty acid content in both parasites and host fishes may be related to the scavenging of these fatty acids by the parasites rather than a microsporidia-specific fatty acid biosynthesis pathway.     

Cellular fatty acids as chemical markers for differentiation of Yersinia pestis and Yersinia pseudotuberculosis

Aims:  Gas chromatography (GC) was utilized to investigate the cellular fatty acids (CFAs) composition of 141 Yersinia pestis isolates from different plague foci of China, and 20 Yersinia pseudotuberculosis strains as well.
Methods and Results:  The whole cell fatty acid methyl esters (FAMEs) were obtained by saponification, methylation and extraction followed with analysis using a standardized Microbial Identification System (MIS). Y. pestis and Y. pseudotuberculosis strains are quite similar in major CFA profiles, which include 16:0, 17:0 cyclo, 3-OH-14:0, 16:1ω7c and 18:1ω7c, accounting for more than 80% of the total CFAs.
Conclusions:  Yersinia pestis could be easily differentiated from Y. pseudotuberculosis by plotting the ratios of some CFA pairs, i.e.,14:0/18:0 vs 18:1ω7c/18:0, 3-OH-14:0/18:0 vs 18:1ω7c/18:0, 16:1ω7c/18:0 vs 18:1ω7c/18:0, 12:0/18:0 vs 18:1ω7c/18:0 and 12:0 ALDE/18:0 vs 16:1ω7c/18:0 fatty acids.
Significance and Impact of the Study:  In the present study, the normalized Sherlock MIS and Sherlock standard libraries were used to analyse the fatty acid composition of different strains of Y. pestis and Y. pseudotuberculosis . Meanwhile, ratios of certain CFA components were found to serve as chemical markers for differentiating the two closely related bacteria that are difficult to be differentiated by simply comparing CFA profiles based on other researches.     

Toxic fatty acid resistant mutant of Trichophyton rubrum.

A mutant of Trichophyton rubrum which could tolerate high concentration (110 microgram/ml) of undecanoic acid was isolated from undecanoic (27.5 microgram/ml) sensitive parent. The mutant showed cross resistance towards other fatty acids like propionic acid, caprylic acid and undecenoic acid which were toxic for the parent strain. Development of fatty acid resistance in the mutant strain was associated with increased pigment production. There was no difference in colony or cell morphology between fatty acid resistant mutant and fatty acid sensitive parent.     

Seasonal variations in fat content and fatty acid composition of male and female coregonid' bondella' from Lake Maggiore and landlocked shad from Lake Como (Northern Italy)

The Lake Maggiore bondella Coregonus macrophthalmus use perivisceral adipose tissue for gonadal development (with particular evidence in females), and muscle fat as an energy source. Females use mainly saturated fatty acids (SFA) for energy purposes, while males use monounsaturates (MUFA) also. During vitellogenesis, females can also mobilize fatty acid precursors of gonadal highly unsaturated fatty acids of the ω3 family from muscle tissue, but in both sexes specific retention of docosahexaenoic acid (DHA=22: 6ω3) in muscle is evident. Landlocked shad, unlike several freshwater fishes, can utilize the liver as well as body cavity and muscle as a fat reserve depot. The perivisceral fat stored during the feeding period appears to be utilized mainly for winter energy maintenance requirements. Lipid reserves from liver and muscle are also mobilized to meet the requirements resulting from gonadal development. In particular, females seem to use liver reserves, especially 18: 1ω9, more than males, to meet the demands of ovogenesis. In the muscle, SFA are used mainly for energy purposes. During gonadal development, specific muscular and hepatic ω3 highly unsaturated fatty acids (ω3 HUFA=20: 5 + 22: 5 + 22: 6) and ω6 HUFA (20: 4+22: 4+22: 5) retention is evident in both sexes, while fatty acid precursors of ω3 and ω6 HUFA are mobilized, especially from muscle tissue.     

Degradation and modification of fats, oils and grease by commercial microbial supplements

Fats, oils and greases (FOGs) in wastewater create problems including the production of foul odours, the blockage of sewer lines and may interfere with the proper operation of sewage treatment works. Removal of FOG from wastewater is thus critically important to ensure that wastewater is disposed of efficiently and economically. In this study, the ability of commercial microbial supplements to degrade fat/oil under laboratory conditions was investigated. One of the multi-species supplements examined was capable of significantly enhancing the degradation of several fats and oils by 37–62%, in contrast to all of the single-species supplements which had no significant effect. The multi-species supplement showed no preferential cleavage or degradation of fatty acids in a range of FOGs, whilst wastewater-associated bacteria preferentially degraded octadecatrienoic acid (18:3ω3) and octadecadienoic acid (18:2ω6). A semi-solid, sticky material, likely to cause blockages in pipework and sewer lines formed when the oil was incubated in the presence of wastewater bacteria. The sticky material was enriched in saturated and mono-unsaturated fatty acids and depleted in polyunsaturated fatty acids relative to the original oil, most likely reflecting preferential fatty acid usage by the bacteria. The production of this semi-solid material by the wastewater bacteria was significantly reduced by the presence of the multi-species product, indicating that commercial supplements have the potential to minimize FOG accumulation and blockages in grease traps and sewer lines as well as enhancing FOG degradation.     

Effect of frozen storage on fatty acid composition and changes in lipid content of Scomberomorus commersoni and Carcharhinus dussumieri

Investigated were the changes in fatty acid composition, oxidation and enzymatic deterioration of lipids in frozen (−30°C) fish fillets from the Persian Gulf. The narrow barred Spanish mackerel ( Scomberomorus commersoni ) and white cheek shark ( Carcharhinus dussumieri ) were tested with storage times of 0, 1, 2, 3, 4, 5 and 6 months at −18°C. Statistical results showed that the major fatty acids among the saturated and monounsaturated fatty acids of each fish species were palmitic (C16:0) and oleic (C18:1n-9) acids, respectively. Both linoleic acid (C18:2n-6) and arachidonic acid (AA) (C20:4n-6) were predominant in total n-6 polyunsaturated fatty acids in both mackerel and shark. The EPA (eicosapentaenoic acid; C20:5 n-3) and DHA (docosahexaenoic acid; C22:6 n-3) acids were the major fatty acids among total n-3 acids in both fishes. During frozen storage, the PUFA (40.1 and 23.94%), n-3 (48 and 42.83%), ω 3/ ω 6 (41.36 and 50%), PUFA/SFA (56 and 42.23%) and EPA + DHA/C16 (55.55 and 46.66%) contents decreased in S. commersoni and C. dussumieri , respectively. Also peroxide, thiobarbituric acid (TBA) and free fatty acid (FFA) values significantly increased (P < 0.01) with the time of storage.     

Fatty acid composition and mycolic acid pattern of some chromogenic mycobacteria

Twenty-nine strains of chromogenic mycobacteria belonging to the species Myco-bacterium aurum (5 strains), M. duvalii (2), M. flavescens (1), M. gordonae (6), M. kansasii (3), M. obuense (1), M. parafortuitum (3), M. phlei (2), M. rhodesiae (1), M. vaccae (2) and Mycobacterium spp. (3) were studied for fatty acid composition and mycolic acid patterns by gas-liquid chromatography and thin-layer chromatog-raphy respectively. Fatty acids found ranged from those with 12–24 carbon atoms and were saturated and monounsaturated straight chain fatty acids, along with 10-methyl branched of 16, 17 and 18 (tuberculostearic acid) carbon atoms. Moreover, 2-methyl tetradecanoic acid was found in M. gordonae, M. kansasii and Mycobacterium spp. (2 strains), and 2,4-dimethyl tetradecanoic acid in M. kansasii and Mycobacterium spp. (2 strains). Nonadecenoic acid was found only in M. flavescens and tuberculostearic acid was not detected in M. gordonae . Three patterns of mycolic acids were obtained: the first, found in M. aurum, M. flavescens, M. phlei, M. rhodesiae and Mycobacterium spp. (1 strain), was characterized by the presence of several spots assigned to α-mycolates, keto-mycolates and wax-ester mycolates (ω-carboxy-rnycolates and 2-eicosanol and related alcohols); the second, found in M. duvalii, M. obuense, M. parafortuitum and M. vaccae was similar to the first, but it contained an additional spot of α-mycolates; the third pattern, found in M. gordonae, M. kansasii and Mycohacterium spp. (2 strains) contained three spots considered to be α-mycoiates, methoxy-mycolates and keto-mycolates. The results obtained confirm previously reported data on the fatty and mycolic acid composition of the species studied.     

Estimation of cell numbers of methanotrophic bacteria in boreal peatlands based on analysis of specific phospholipid fatty acids

Abstract: Concentrations of two phospholipid fatty acids (PLFAs) specific for methane-oxidizing bacteria (16:1 ω8 and 18:1 ω8), were used to estimate the biomass and cell numbers of this group of bacteria in two Sphagnum-dominated boreal peatlands. Concentration ranges of 16:1 ω8 and 18:1 ω8 were 0.0–73 and 1.0–486 pmol g⁻¹ of wet peat, respectively. Concentrations in the peat of each fatty acid were positively correlated with the potential methane oxidation activity ( V _max), which was used as an independent estimate of methanotrophic biomass. This correlation suggests that the two PLFAs are good biomarkers for the population of methanotrophic bacteria in peatlands. Concentrations of the two PLFAs were transformed to cell numbers using conversion factors for the cell content of PLFAs, average cell volume and percentage of cellular dry matter. The total cell number of methanotrophic bacteria in peat samples from a range of sites and depths ranged between 0.3 and 51 × 10⁶ cells g⁻¹ of wet peat, with similar proportions of type I and type II methanotrophic bacteria in most samples. Within particular peat profiles, numbers of methanotrophic bacteria were highest around the level of the water table, implying that the supplies of methane and oxygen largely determine the biomass distribution of methanotrophic bacteria in this type of peatlands.     

Influence of zooplankton and phytoplankton on the fatty acid composition of digesta and tissue lipids of silver carp: mesocosm experiment

Zooplankton appeared to be the major contributor to the diet of 1+ silver carp, whereas 3+ fishes exhibited a more evenly balanced spectrum between zooplankton and phytoplankton. The fatty acids profiles of digesta were influenced by zooplankton, particularly for 1+ silver carp. Together, fatty acid profiles of tank zooplankton and digesta were characterized by high proportion of 20 : 5ω3 and 20 : 6ω3. The fatty acids composition of the phytoplankton reflected the dominance of cyanobacteria and chlorophycea, with high quantities of 18 : 2ω6 and 18 : 3ω3. Although cyanobacteria accounted for >70% of the phytoplankton biomass ingested by the carp, fatty acids profiles of digesta were not influenced by phytoplankton fatty acids composition. The low digestive and conversion efficiency of Microcystis aeruginosa explain this absence of relation. The neutral lipids in silver carp tissues reflected poorly the fatty acids profiles in the diet, the semi-natural conditions and the diet dominated throughout the study by zooplankton, led to little variation in tissues fatty acids. The phospholipids in the muscle, liver and peri-intestinal fat were characterized by a rather low proportion of polyunsaturated fatty acids (PUFA) in both 1+ and 3+ fish. From a qualitative view point, cryptophycea, diatoms, and especially zooplankton are much more valuable food for the silver carp than cyanobacteria and desmid chlorophycea which are poor in long-chain PUFA.     

Anaerobic production of polyunsaturated fatty acids by Shewanella putrefaciens strain ACAM 342

Abstract The fatty acid composition of cultures of Shewanella putrefaciens strain ACAM 342 grown aero-bically and anaerobically at 15°C and 25°C were analysed by capillary gas chromatography. The bacterium was found to produce the polyunsaturated fatty acids (PUFA) 18:2ω3, 18:3ω3 and 20:5ω3 under aerobic and anaerobic conditions at both growth temperatures. This result suggests that the bacterium possesses both the aerobic and anaerobic pathways for unsaturated fatty acid synthesis, where an alternate terminal electron acceptor(s) is utilised in the absence of oxygen.     

In vitro susceptibility to antimycotic drug undecanoic acid,a medium-chain fatty acid,is nutrient-dependent in the dermatophyte Trichophyton rubrum

The antimycotic activity of fatty acids has long been known, and their presence in human skin and sweat appears to protect the host against superficial mycoses. Undecanoic acid is a medium-chain fatty acid that has been used in the treatment of dermatophytoses in humans. In this study, we selected one Trichophyton rubrum undecanoic acid-resistant strain that showed a marked reduction in its capacity to grow on human nail fragments, which correlated with the reduced activity of secreted keratinolytic proteases. Moreover, the susceptibility of T. rubrum to undecanoic acid is also dependent on the carbon source utilized by both control and resistant strains. The growth of the control strain was strongly inhibited by undecanoic acid in Sabouraud medium or in cultures supplemented with low-fat milk, whereas it was ineffective when the cultures were supplemented with Tween 20 or keratin as the carbon source, suggesting that nutrient conditions are crucial in establishing a susceptibility to antifungal drugs, which is helpful for the isolation and characterization of resistant strains, and in the screening for new antifungal drugs.     

Peculiarities of fatty acid composition of the genusCaulobacter

The fatty acid composition of 35 strains of stalked bacteria belonging to 17 of the hitherto described 19 species and 10 unidentified strains of the genusCaulobacter was studied. ll-Methyl-cis-octadec-11-enoic acid presumably synthesized fromcis-vaccenic acid was detected in all the strains in amounts of 0.4 – 34.7 % and was considered as a chemotaxonomic marker of the genus. During growth on a peptone-yeast medium, the caulobacters synthesized, along with the fatty acids which are typical of gram-negative bacteria, some normal and branched fatty acids with 15 and 17 carbon atoms (1–49 %). The synthesis of these acids was inhibited by glucose. The cell shape of stalked bacteria (fusiform, vibrioid or bacteroid) is not obviously associated with the contents of individual fatty acids.     

Carbons from choline present in the phospholipids of Pseudomonas aeruginosa

The phospholipid composition of Pseudomonas aeruginosa grown in a mineral medium with choline as the carbon source was: phosphatidylethanolamine, 71.6±1.4%; phosphatidylglycerol, 11.8±0.4%; diphosphatidylglycerol, 0.8±0.4%; phosphatidic acid, 2.4±0.6%; lysophosphatidylethanolamine, 1.6±0.3%; phosphatidylcholine 7.9±0.3%; lysophosphatidylcholine, 3.9±0.7%. The molar ratio between the acidic and the neutral phospholipids was 0.18. Radiolabeling experiments with [methyl-¹⁴C]choline or [1,2-¹⁴C]choline carried out in cell suspension from bacteria that were grown in the presence of choline as the sole carbon source demonstrated that the carbons of the N-methyl groups of choline contributed to the synthesis of fatty acids while the carbons comprising the backbone of choline were used for the synthesis of glycerol.     

Regulation der fettsäurebildung bei der mikrobiellen alkanoxidation

At the microbial oxidation of long-chain alkanes such monocarbonic acids at a monoterminal oxidation are formed which correspond to the chain length of the alkanes. At diterminal oxidation the corresponding dioic acids are produced. Under the influence of cerulenin a cerulenin a direct incorporation of fatty acids into cell lipids increases. Undecanoic acid cannot be metabolized byMortierella isabellina. It causes an inhibition of alkane oxidation. A main effect of undecanoic acid is an inhibition of the elongation of other fatty acids. The de novo fatty acid biosynthesis has not been inhibited by undecanoic acid.