Raman spectroscopy as a tool for tracking cyclopropane fatty acids in genetically engineeredSaccharomyces cerevisiae

The Analyst ◽  
2019 ◽  
Vol 144 (3) ◽  
pp. 901-912 ◽  
Author(s):  
Kamila Kochan ◽  
Huadong Peng ◽  
Eunice S. H. Gwee ◽  
Ekaterina Izgorodina ◽  
Victoria Haritos ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Raman Spectroscopy ◽  
Fatty Acid ◽  
Cyclopropane Fatty Acid ◽  
Cyclopropane Fatty Acids

We demonstrate the first spectrum of cyclopropane fatty acid and track its presence in yeast using Raman spectroscopy and PLS-DA.

The biosynthesis of cyclopropane fatty acids. II. Mechanistic studies using methionine labelled with one, two, and three deuterium atoms in the methyl group

1982 ◽  
Vol 60 (4) ◽  
pp. 371-378 ◽  
Author(s):  
Peter H. Buist ◽  
David B. MacLean
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Cyclopropane Ring ◽  
Isotope Effects ◽  
Slow Step ◽  
Cyclopropane Fatty Acid ◽  
Methyl Group ◽  
Feeding Experiments ◽  
Cyclopropane Fatty Acids ◽  
Methyl Group Transfer

The mechanism of formation of monodeuterated cyclopropane fatty acids on administration of L-methione-methyl-d3 to L. plantarum has been investigated. It has been found that the extent of exchange is not affected by the presence of oxygen in the medium, that neither formate-d0 nor formaldehyde-d2 is significantly incorporated into the fatty acid, and that methionine reisolated from the intracellular pool does not contain any exchanged species. These experiments militate against any mechanism involving exchange prior to methyl group transfer. Parallel feeding experiments using methionine labelled in the methyl group with one, two, or three deuterium atoms were carried out and in this way that extent of exchange was quantitated. It was found that at least one-third of the cyclopropane fatty acid from methionine methyl-d3 experiments is derived from an exchanged methyl group. The intramolecular and intermolecular primary deuterium isotope effects for biological cyclopropane ring formation were measured and found to be 3.2 ± 0.5, and 1.01 ± 0.04, respectively. These results are consistent with a mechanism in which a methyl group is transferred in a slow step which is followed by a fast, partially reversible, protonation-deprotonation step.

The effect of temperature and other growth conditions on the fatty acid composition of Escherichia coli

1981 ◽  
Vol 27 (8) ◽  
pp. 835-840 ◽  
Author(s):  
James T. McGarrity ◽  
John B. Armstrong
Keyword(s):  
Escherichia Coli ◽  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Acid Composition ◽  
Exponential Growth ◽  
Growth Conditions ◽  
Cyclopropane Fatty Acid ◽  
Cyclopropane Fatty Acids ◽  
K 12

During exponential growth, strain AW405 of Escherichia coli K-12 did not regulate the fatty acid composition of its lipids in response either to temperature or to the addition of NaCl, KCl, or MgCl2 to the medium. Growth was severely restricted at temperatures below 21 °C. Differential scanning calorimetry (DSC) of the isolated lipids from a culture with a typical exponential-phase composition yielded a broad transition, extending from approximately 0 to 33 °C, with a midpoint at 19 °C.During late stages of growth, the fatty acid composition changed. The percentage of palmitic acid increased and cyclopropane fatty acids replaced some of the equivalent unsaturated fatty acids. The increase in palmitate seemed largely independent of growth conditions, whereas the increase in the cyclopropane fatty acids was stimulated by the addition of salts or sucrose. Cultures grown in the presence of sucrose also had higher cyclopropane fatty acid levels during exponential growth. DSC of lipids from a sucrose culture, in which the compositional changes were most pronounced, yielded a much narrower transition with a midpoint at 27 °C.

scholarly journals Occurrence of Cis-11,12-Methylene-Hexadecanoic Acid in the Red Alga Solieria pacifica (Yamada) Yoshida

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2286
Author(s):  
Gwang-Woo Kim ◽  
Jae-Man Sim ◽  
Yutaka Itabashi ◽  
Min-Jeong Jung ◽  
Joon-Young Jun
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Red Alga ◽  
Proton Nuclear Magnetic Resonance ◽  
Animal Origin ◽  
Monoenoic Acid ◽  
Resonance Spectroscopy ◽  
Hexadecenoic Acid ◽  
Cyclopropane Fatty Acid ◽  
Hexadecanoic Acid

Fatty acids in marine algae have attracted the attention of natural chemists because of their biological activity. The fatty acid compositions of the Solieriaceae families (Rhodophyceae, Gaigartinales) provide interesting information that unusual cyclic fatty acids have been occasionally found. A survey was conducted to profile the characteristic fatty acid composition of the red alga Solieria pacifica (Yamada) Yoshida using gas chromatography-mass spectrometry (GC-MS), infrared spectroscopy (IR), and proton nuclear magnetic resonance spectroscopy (1H-NMR). In S. pacifica, two cyclopentyl fatty acids, 11-cyclopentylundecanoic acid (7.0%), and 13-cyclopentyltridecanoic acid (4.9%), and a cyclopropane fatty acid, cis-11,12-methylene-hexadecanoic acid (7.9%) contributed significantly to the overall fatty acid profile. In particular, this cyclopropane fatty acid has been primarily found in bacteria, rumen microorganisms or foods of animal origin, and has not previously been found in any other algae. In addition, this alga contains a significant amount of the monoenoic acid cis-11-hexadecenoic acid (9.0%). Therefore, cis-11,12-methylene-hexadecanoic acid in S. pacifica was likely produced by methylene addition to cis-11-hexadecenoic acid.

scholarly journals Formation of trans Fatty Acids Is Not Involved in Growth-Linked Membrane Adaptation of Pseudomonas putida

2005 ◽  
Vol 71 (4) ◽  
pp. 1915-1922 ◽  
Author(s):  
Claus Härtig ◽  
Norbert Loffhagen ◽  
Hauke Harms
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Pseudomonas Putida ◽  
De Novo ◽  
Isomerization Reaction ◽  
Cyclopropane Fatty Acid ◽  
Substrate Uptake ◽  
Resting Cells ◽  
Saturation Degree ◽  
Fatty Acid Compositions

ABSTRACT Fatty acid compositions in growing and resting cells of several strains of Pseudomonas putida (P8, NCTC 10936, and KT 2440) were studied, with a focus on alterations of the saturation degree, cis-trans isomerization, and cyclopropane formation. The fatty acid compositions of the strains were very similar under comparable growth conditions, but surprisingly, and contrary to earlier reports, trans fatty acids were not found in either exponentially growing cells or stationary-phase cells. During the transition from growth to the starvation state, cyclopropane fatty acids were preferentially formed, an increase in the saturation degree of fatty acids was observed, and larger amounts of hydroxy fatty acids were detected. A lowered saturation degree and concomitant higher membrane fluidity seemed to be optimal for substrate uptake and growth. The incubation of cells under nongrowth conditions rapidly led to the formation of trans fatty acids. We show that harvesting and sample preparation for analysis could provoke the enzyme-catalyzed formation of trans fatty acids. Freeze-thawing of resting cells and increased temperatures accelerated the formation of trans fatty acids. We demonstrate that cis-trans isomerization only occurred in cells that were subjected to an abrupt disturbance without having the possibility of adapting to the changed conditions by the de novo synthesis of fatty acids. The cis-trans isomerization reaction was in competition with the cis-to-cyclopropane fatty acid conversion. The potential for the formation of trans fatty acids depended on the cyclopropane content that was already present.

Characterization of Pseudomonas aeruginosa fatty acid profiles in biofilms and batch planktonic cultures

2010 ◽  
Vol 56 (12) ◽  
pp. 1028-1039 ◽  
Author(s):  
Jerry Chao ◽  
Gideon M. Wolfaardt ◽  
Michael T. Arts
Keyword(s):  
Fatty Acids ◽  
Pseudomonas Aeruginosa ◽  
Fatty Acid ◽  
Saturated Fatty Acids ◽  
Monounsaturated Fatty Acids ◽  
Bulk Liquid ◽  
Strain Pao1 ◽  
Fatty Acid Chain ◽  
Cyclopropane Fatty Acids ◽  
Gradual Loss

The fatty acid composition of Pseudomonas aeruginosa PAO1 was compared between biofilm and batch planktonic cultures. Strain PAO1 biofilms were able to maintain a consistent fatty acid profile for up to 6 days, whereas strain PAO1 batch planktonic cultures showed a gradual loss of cis-monounsaturated fatty acids over 4 days. Biofilms exhibited a greater proportion of hydroxy fatty acids but a lower proportion of both cyclopropane fatty acids and saturated fatty acids (SAFAs). SAFAs with ≥16 carbons, in particular, decreased in biofilms when compared with that in batch planktonic cultures. A reduced proportion of SAFAs and a decline in overall fatty acid chain length indicate more fluidic biophysical properties for cell membranes of P. aeruginosa in biofilms. Separating the biofilms into 2 partitions and comparing their fatty acid compositions revealed additional trends that were not observed in the whole biofilm: the shear-nonremovable layer consistently showed greater proportions of hydroxy fatty acid than the bulk liquid + shear-removable portion of the biofilm. The shear-nonremovable portion demonstrated a relatively immediate decline in the proportion of monounsaturated fatty acids between days 2 and 4; which was offset by an increase in the proportion of cyclopropane fatty acids, specifically 19:0cyc(11,12). Simultaneously, the shear-removable portion of the biofilm showed an increase in the proportion of trans-monounsaturated fatty acids and cyclopropane fatty acids.

scholarly journals The reaction of phosphoglycolipids and other lipids with hydrofluoric acid

1974 ◽  
Vol 143 (2) ◽  
pp. 461-464 ◽  
Author(s):  
N. Shaw ◽  
A. Stead
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Free Fatty Acid ◽  
Structure Determination ◽  
Hydrofluoric Acid ◽  
Good Yield ◽  
Glycosidic Linkage ◽  
Cyclopropane Fatty Acids ◽  
Hydrolysis Of

1. The use of HF as a dephosphorylating reagent for phospholipids was examined. 2. Hydrolysis of phosphatidylethanolamine at 0°C for 24h with 60% HF gives a good yield of diglyceride. Under similar conditions phosphatidyldiglucosyl diglyceride gives diglyceride and diglucosyl diglyceride. 3. The glycolipid is also obtained from hydrolysis of glycerylphosphoryldiglucosyl diglyceride. No lyso derivative of the glycolipid could be detected and the glycosidic linkage was also stable. 4. Triglycerides, unsaturated and cyclopropane fatty acids were unaffected by the reagent. 5. 1,2-Diglycerides and 1,3-diglycerides were partially isomerized and also gave small amounts of free fatty acid and monoglyceride. 6. Monoglycerides underwent extensive rearrangement to form 1,2- and 1,3-diglycerides. 7. Lysophosphatidylethanolamine also gave 1,2- and 1,3-diglycerides as well as monoglycerides. 8. The application of this procedure to the structure determination of various phosphoglycolipids is discussed.

scholarly journals Cyclopropane-Containing Fatty Acids from the Marine Bacterium Labrenzia sp. 011 with Antimicrobial and GPR84 Activity

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 369 ◽  
Author(s):  
Jamshid Amiri Moghaddam ◽  
Antonio Dávila-Céspedes ◽  
Stefan Kehraus ◽  
Max Crüsemann ◽  
Meryem Köse ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Marine Bacterium ◽  
Cyclopropane Fatty Acid ◽  
Putative Gene ◽  
Medium Chain ◽  
Bacteria And Fungi ◽  
Roseovarius Oyster Disease ◽  
Family Rhodobacteraceae ◽  
G Protein Coupled

Bacteria of the family Rhodobacteraceae are widespread in marine environments and known to colonize surfaces, such as those of e.g., oysters and shells. The marine bacterium Labrenzia sp. 011 is here investigated and it was found to produce two cyclopropane-containing medium-chain fatty acids (1, 2), which inhibit the growth of a range of bacteria and fungi, most effectively that of a causative agent of Roseovarius oyster disease (ROD), Pseudoroseovarius crassostreae DSM 16950. Additionally, compound 2 acts as a potent partial, β-arrestin-biased agonist at the medium-chain fatty acid-activated orphan G-protein coupled receptor GPR84, which is highly expressed on immune cells. The genome of Labrenzia sp. 011 was sequenced and bioinformatically compared with those of other Labrenzia spp. This analysis revealed several cyclopropane fatty acid synthases (CFAS) conserved in all Labrenzia strains analyzed and a putative gene cluster encoding for two distinct CFASs is proposed as the biosynthetic origin of 1 and 2.

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