scholarly journals 13,16-Dimethyl Octacosanedioic Acid (iso-Diabolic Acid), a Common Membrane-Spanning Lipid of Acidobacteria Subdivisions 1 and 3

2011 ◽  
Vol 77 (12) ◽  
pp. 4147-4154 ◽  
Author(s):  
Jaap S. Sinninghe Damsté ◽  
W. Irene C. Rijpstra ◽  
Ellen C. Hopmans ◽  
Johan W. H. Weijers ◽  
Bärbel U. Foesel ◽  
...  
Keyword(s):  
Fatty Acids ◽  
High Performance ◽  
Membrane Lipids ◽  
Direct Analysis ◽  
Polar Lipids ◽  
Gas Chromatography Mass Spectrometry ◽  
Content Type ◽  
Alkyl Chains ◽  
Intact Polar Lipids ◽  
Membrane Spanning

ABSTRACTThe distribution of membrane lipids of 17 different strains representing 13 species of subdivisions 1 and 3 of the phylumAcidobacteria, a highly diverse phylum of theBacteria, were examined by hydrolysis and gas chromatography-mass spectrometry (MS) and by high-performance liquid chromatography-MS of intact polar lipids. Upon both acid and base hydrolyses of total cell material, the uncommon membrane-spanning lipid 13,16-dimethyl octacosanedioic acid (iso-diabolic acid) was released in substantial amounts (22 to 43% of the total fatty acids) from all of the acidobacteria studied. This lipid has previously been encountered only in thermophilicThermoanaerobacterspecies but bears a structural resemblance to the alkyl chains of bacterial glycerol dialkyl glycerol tetraethers (GDGTs) that occur ubiquitously in peat and soil and are suspected to be produced by acidobacteria. As reported previously, most species also containediso-C15and C16:1ω7Cas major fatty acids but the presence ofiso-diabolic acid was unnoticed in previous studies, most probably because the complex lipid that contained this moiety was not extractable from the cells; it could only be released by hydrolysis. Direct analysis of intact polar lipids in the Bligh-Dyer extract of three acidobacterial strains, indeed, did not reveal any membrane-spanning lipids containingiso-diabolic acid. In 3 of the 17 strains, ether-boundiso-diabolic acid was detected after hydrolysis of the cells, including one branched GDGT containingiso-diabolic acid-derived alkyl chains. Since the GDGT distribution in soils is much more complex, branched GDGTs in soil likely also originate from other (acido)bacteria capable of biosynthesizing these components.

scholarly journals Ether- and Ester-Boundiso-Diabolic Acid and Other Lipids in Members of Acidobacteria Subdivision 4

2014 ◽  
Vol 80 (17) ◽  
pp. 5207-5218 ◽  
Author(s):  
Jaap S. Sinninghe Damsté ◽  
W. Irene C. Rijpstra ◽  
Ellen C. Hopmans ◽  
Bärbel U. Foesel ◽  
Pia K. Wüst ◽  
...  
Keyword(s):  
High Performance ◽  
Hot Springs ◽  
Membrane Lipids ◽  
Peat Soil ◽  
Major Influence ◽  
Content Type ◽  
Fractional Abundance ◽  
Intact Polar Lipids ◽  
Membrane Spanning ◽  
Hydrolysis Of

ABSTRACTRecently,iso-diabolic acid (13,16-dimethyl octacosanedioic acid) has been identified as a major membrane-spanning lipid of subdivisions 1 and 3 of theAcidobacteria, a highly diverse phylum within theBacteria. This finding pointed to theAcidobacteriaas a potential source for the bacterial glycerol dialkyl glycerol tetraethers that occur ubiquitously in peat, soil, lakes, and hot springs. Here, we examined the lipid composition of seven phylogenetically divergent strains of subdivision 4 of theAcidobacteria, a bacterial group that is commonly encountered in soil. Acid hydrolysis of total cell material releasediso-diabolic acid derivatives in substantial quantities (11 to 48% of all fatty acids). In contrast to subdivisions 1 and 3 of theAcidobacteria, 6 out of the 7 species of subdivision 4 (excepting “CandidatusChloracidobacterium thermophilum”) containediso-diabolic acid ether bound to a glycerol in larger fractional abundance thaniso-diabolic acid itself. This is in agreement with the analysis of intact polar lipids (IPLs) by high-performance liquid chromatography-mass spectrometry (HPLC-MS), which showed the dominance of mixed ether-ester glycerides.iso-Diabolic acid-containing IPLs were not identified, because these IPLs are not released with a Bligh-Dyer extraction, as observed before when studying lipid compositions of subdivisions 1 and 3 of theAcidobacteria. The presence of ether bonds in the membrane lipids does not seem to be an adaptation to temperature, because the five mesophilic isolates contained a larger amount of ether lipids than the thermophile “Ca. Chloracidobacterium thermophilum.” Furthermore, experiments withPyrinomonas methylaliphatogenesdid not reveal a major influence of growth temperature over the 50 to 69°C range.

scholarly journals Lipid composition of the isolated rat intestinal microvillus membrane

1968 ◽  
Vol 109 (1) ◽  
pp. 51-59 ◽  
Author(s):  
G. G. Forstner ◽  
K. Tanaka ◽  
K. J. Isselbacher
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Neutral Lipid ◽  
Lipid Composition ◽  
Plasma Membranes ◽  
Membrane Lipids ◽  
Saturated Fatty Acids ◽  
Polar Lipids ◽  
Published Data ◽  
Microvillus Membrane

1. Rat intestinal microvillus plasma membranes were prepared from previously isolated brush borders and the lipid composition was analysed. 2. The molar ratio of cholesterol to phospholipid was greatest in the membranes and closely resembled that reported for myelin. 3. Unesterified cholesterol was the major neutral lipid. However, 30% of the neutral lipid fraction was accounted for by glycerides and fatty acid. 4. Five phospholipid components were identified and measured, including phosphatidylethanolamine, phosphatidylcholine, phosphatidylserine, sphingomyelin and lysophosphatidylcholine. Though phosphatidylethanolamine was the chief phospholipid, no plasmalogen was detected. 5. In contrast with other plasma membranes in the rat, the polar lipids of the microvillus membrane were rich in glycolipid. The cholesterol:polar lipid (phospholipid+glycolipid) ratio was about 1:3 for the microvillus membrane. Published data suggest that this ratio resembles that of the liver plasma membrane more closely than myelin or the erythrocyte membrane. 6. The fatty acid composition of membrane lipids was altered markedly by a single feeding of safflower oil. Membrane polar lipids did not contain significantly more saturated fatty acids than cellular polar lipids. Differences in the proportion of some fatty acids in membrane and cellular glycerides were noted. These differences may reflect the presence of specific membrane glycerides.

scholarly journals FadD Is Required for Utilization of Endogenous Fatty Acids Released from Membrane Lipids

2011 ◽  
Vol 193 (22) ◽  
pp. 6295-6304 ◽  
Author(s):  
Ángel Pech-Canul ◽  
Joaquina Nogales ◽  
Alfonso Miranda-Molina ◽  
Laura Álvarez ◽  
Otto Geiger ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Stationary Phase ◽  
Free Fatty Acids ◽  
Sinorhizobium Meliloti ◽  
Membrane Lipids ◽  
Membrane Phospholipids ◽  
Content Type ◽  
Fatty Acid Transporter ◽  
In The Wild

FadD is an acyl coenzyme A (CoA) synthetase responsible for the activation of exogenous long-chain fatty acids (LCFA) into acyl-CoAs. Mutation offadDin the symbiotic nitrogen-fixing bacteriumSinorhizobium melilotipromotes swarming motility and leads to defects in nodulation of alfalfa plants. In this study, we found thatS. melilotifadDmutants accumulated a mixture of free fatty acids during the stationary phase of growth. The composition of the free fatty acid pool and the results obtained after specific labeling of esterified fatty acids with a Δ5-desaturase (Δ5-Des) were in agreement with membrane phospholipids being the origin of the released fatty acids.Escherichia colifadDmutants also accumulated free fatty acids released from membrane lipids in the stationary phase. This phenomenon did not occur in a mutant ofE. coliwith a deficient FadL fatty acid transporter, suggesting that the accumulation of fatty acids infadDmutants occurs inside the cell. Our results indicate that, besides the activation of exogenous LCFA, in bacteria FadD plays a major role in the activation of endogenous fatty acids released from membrane lipids. Furthermore, expression analysis performed withS. melilotirevealed that a functional FadD is required for the upregulation of genes involved in fatty acid degradation and suggested that in the wild-type strain, the fatty acids released from membrane lipids are degraded by β-oxidation in the stationary phase of growth.

scholarly journals Nonmarine Crenarchaeol in Nevada Hot Springs

2004 ◽  
Vol 70 (9) ◽  
pp. 5229-5237 ◽  
Author(s):  
A. Pearson ◽  
Z. Huang ◽  
A. E. Ingalls ◽  
C. S. Romanek ◽  
J. Wiegel ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Performance ◽  
Hot Springs ◽  
Denaturing Gradient Gel Electrophoresis ◽  
Membrane Lipids ◽  
Marine Species ◽  
Gas Chromatography Mass Spectrometry ◽  
Rrna Gene ◽  
Chromatography Mass Spectrometry ◽  
Group I

ABSTRACT Glycerol dialkyl glycerol tetraethers (GDGTs) are core membrane lipids of the Crenarchaeota. The structurally unusual GDGT crenarchaeol has been proposed as a taxonomically specific biomarker for the marine planktonic group I archaea. It is found ubiquitously in the marine water column and in sediments. In this work, samples of microbial community biomass were obtained from several alkaline and neutral-pH hot springs in Nevada, United States. Lipid extracts of these samples were analyzed by high-performance liquid chromatography-mass spectrometry and by gas chromatography-mass spectrometry. Each sample contained GDGTs, and among these compounds was crenarchaeol. The distribution of archaeal lipids in Nevada hot springs did not appear to correlate with temperature, as has been observed in the marine environment. Instead, a significant correlation with the concentration of bicarbonate was observed. Archaeal DNA was analyzed by denaturing gradient gel electrophoresis. All samples contained 16S rRNA gene sequences which were more strongly related to thermophilic crenarchaeota than to Cenarchaeum symbiosum, a marine nonthermophilic crenarchaeon. The occurrence of crenarchaeol in environments containing sequences affiliated with thermophilic crenarchaeota suggests a wide phenotypic distribution of this compound. The results also indicate that crenarchaeol can no longer be considered an exclusive biomarker for marine species.

scholarly journals Cryobacterium ruanii sp. nov. and Cryobacterium breve sp. nov., isolated from glaciers

2020 ◽  
Vol 70 (3) ◽  
pp. 1918-1923 ◽  
Author(s):  
Qing Liu ◽  
Ji-Hui Tian ◽  
Hong-Can Liu ◽  
Yu-Guang Zhou ◽  
Yu-Hua Xin
Keyword(s):  
Fatty Acids ◽  
Type Strain ◽  
Type Species ◽  
Gansu Province ◽  
Polar Lipids ◽  
Close Relative ◽  
Unidentified Phospholipid ◽  
Content Type ◽  
Link Type ◽  
Unidentified Glycolipid

Strains Sr36T and TMT4-23T were isolated from No. 1 glacier in Xinjiang Uygur Autonomous Region and Toumingmengke glacier in Gansu Province, PR China, respectively. They were Gram-stain-positive and rod-shaped micro-organisms. The optimum growth temperature of the two strains was 10–14 °C. Phylogenetic analysis showed that the two strains were related to members of the genus Cryobacterium . The average nucleotide identity (ANI) and digital DNA–DNA hybridization (dDDH) values between strain Sr36T and its close relatives Cryobacterium luteum Hh15T, Cryobacterium aureum Hh31T, Cryobacterium levicorallinum Hh34T and Cryobacterium flavum Hh8T were 81.16–87.24 and 28.0–32.5 %, respectively. The ANI and dDDH values between strain TMT4-23T and its close relative Cryobacterium psychrotolerans 0549T were 81.16 and 22.3 %. The polar lipids of strain Sr36T were diphosphatidylglycerol, phosphatidylglycerol, one unidentified glycolipid and three unidentified lipids. The polar lipids of strain TMT4-23T were diphosphatidylglycerol, phosphatidylglycerol, one unidentified glycolipid, one unidentified phospholipid and six unidentified lipids. The major fatty acids of strain Sr36T were anteiso-C15 : 0, iso-C16 : 0, anteiso-C17 : 0 and anteiso-C15 : 1. The major fatty acids of strain TMT4-23T were anteiso-C15 : 0, anteiso-C17 : 0, iso-C16 : 0, anteiso-C15 : 1 and iso-C15 : 1. Both strains contained 2,4-diaminobutyric acid and their predominant menaquinone was MK-10. On the basis of the phenotypic, phylogenetic and genotypic data, two novel species Cryobacterium ruanii sp. nov. (type strain = Sr36T=CGMCC 1.9275T=NBRC 113797T) and Cryobacterium breve sp. nov. (type strain =TMT4-23T=CGMCC 1.9556T=NBRC 113800T) are proposed.

Structure Versus Activity of Substituted Pyridazinones as Related to Mechanism of Action

Weed Science ◽  
1976 ◽  
Vol 24 (6) ◽  
pp. 579-582 ◽  
Author(s):  
J. B. St. John ◽  
J. L. Hilton
Keyword(s):  
Fatty Acids ◽  
Phenyl Ring ◽  
Membrane Lipids ◽  
Carotenoid Biosynthesis ◽  
Polar Lipids ◽  
Maximum Effect ◽  
Hill Reaction ◽  
Methyl Substitution ◽  
Chloroplast Membrane ◽  
The Hill

In at least three metabolic processes in wheat (Triticum aestivumL. var. ‘Arthur’) shoots inhibitory activity can be related to the chemical structure of substituted pyridazinones. Inhibitory activities include: inhibition of the Hill reaction and photosynthetic CO2fixation; inhibition of carotenoid biosynthesis accompanied by photodestruction of chlorophyll; and interference with the formation of chloroplast membrane polar lipids. The parent compound, pyrazon [5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone], inhibits the Hill reaction and photosynthetic CO2fixation. Trifluoromethyl substitution of the phenyl ring of pyrazon, mono-methyl substitution of the amine, or substitutions at both positions result in inhibition of carotenoid biosynthesis. However, both substitutions are required for maximum effect. Substitutions onto the molecular structure of pyrazon are also related to alterations in the formation of membrane polar lipids. Dimethyl substitution of the amine of pyrazon is related to a decrease in linolenic acid accompanied by an increase in linoleic acid without a shift in the relative proportion of saturated to unsaturated fatty acids of the membrane lipids. The trifluoromethyl substitution of the phenyl ring and mono-methyl substitution of the amine are related to a shift toward a higher proportion of saturated fatty acids of chloroplast membrane lipids. Results obtained with diuron [3-(3,4-dichlorophenyl)-1,1-dimethylurea] and with dark-grown wheat tissue indicated that activity of the pyridazinones on the formation of membrane lipids was probably not related to inhibition of the Hill reaction.

scholarly journals Carotenoids, Fatty Acids, and Volatile Compounds in Apricot Cultivars from Romania—A Chemometric Approach

Antioxidants ◽  
2020 ◽  
Vol 9 (7) ◽  
pp. 562
Author(s):  
Adela Pintea ◽  
Francisc Vasile Dulf ◽  
Andrea Bunea ◽  
Sonia Ancuța Socaci ◽  
Elena Andreea Pop ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acids ◽  
High Performance ◽  
Atmospheric Pressure Chemical Ionization ◽  
Principal Component ◽  
Gas Chromatography Mass Spectrometry ◽  
Carotenoid Content ◽  
Array Detector ◽  
Fatty Acids Profile ◽  
Pressure Chemical Ionization

Lipophilic constituents are important for the color and aroma of apricots, but also for their health benefits. In the present study, carotenoids, fatty acids, and volatiles were analyzed in 11 apricot cultivars, from which nine were obtained in Romania. High performance liquid chromatography coupled to a diode array detector with atmospheric pressure chemical ionization and mass spectrometry (HPLC-DAD-APCI-MS methodology applied on unsaponified carotenoid extracts allowed the identification and quantification of 19 compounds. The predominant carotenoids in all cultivars were all-trans-β-carotene and its cis isomers. Lutein was present exclusively in non-esterified form, while β-cryptoxanthin was predominantly esterified, mainly with oleic, palmitic, lauric, and stearic acid. Moreover, β-cryptoxanthin linoleate, linolenate, and stearate were detected for the first time in Harogem cultivar. Variation in carotenoid content and composition was observed, with the highest carotenoid content being recorded in Tudor, Harogem, and Mamaia cultivars. The predominant fatty acids determined by gas chromatography–mass spectrometry (GC-MS) were linoleic (up to 47%), palmitic (up to 32.7%), and linolenic (up to 17.16%), with small variations among cultivars. In-tube extraction technique (ITEX)/GC-MS was applied for profiling the volatiles in apricot fruits and 120 compounds were identified, with terpenoids and esters as the most abundant classes. Principal component analysis (PCA) revealed that the carotenoids and the fatty acids profile can be used for variety authentication and discrimination in apricots.

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