Biosynthesis of 1-0-(1′-Alkenyl)glycerolipids (Plasmalogens)

Paltauf, Fritz

doi:10.1016/b978-0-12-468780-6.50010-x

Cited by 20 publications

(10 citation statements)

References 80 publications

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“…Plasmalogens are also widespread in anaerobes (e.g., 6, 51, 53), but the pathway and mechanism for anaerobic plasmalogen biosynthesis, which differ from that in higher (aerobic) organisms, remain incompletely understood (12,13). Aside from the absence of oxygen, isotopic experiments have suggested G3P instead of DHAP as an intermediate in the anaerobic pathway to plasmalogen (51,54,55) (Fig. 5b).…”

Section: Dialkylglycerols In Mesophilic Bacteria the Membrane Lipidsmentioning

confidence: 99%

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T

Grossi

Mollex

Vinçon‐Laugier

et al. 2015

Appl Environ Microbiol

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bBacterial glycerol ether lipids (alkylglycerols) have received increasing attention during the last decades, notably due to their potential role in cell resistance or adaptation to adverse environmental conditions. Major uncertainties remain, however, regarding the origin, biosynthesis, and modes of formation of these uncommon bacterial lipids. We report here the preponderance of monoalkyl-and dialkylglycerols (1-O-alkyl-, 2-O-alkyl-, and 1,2-O-dialkylglycerols) among the hydrolyzed lipids of the marine mesophilic sulfate-reducing proteobacterium Desulfatibacillum alkenivorans PF2803 T grown on n-alkenes (pentadec-1-ene or hexadec-1-ene) as the sole carbon and energy source. Alkylglycerols account for one-third to two-thirds of the total cellular lipids (alkylglycerols plus acylglycerols), depending on the growth substrate, with dialkylglycerols contributing to one-fifth to two-fifths of the total ether lipids. The carbon chain distribution of the lipids of D. alkenivorans also depends on that of the substrate, but the chain length and methyl-branching patterns of fatty acids and monoalkyl-and dialkylglycerols are systematically congruent, supporting the idea of a biosynthetic link between the three classes of compounds. Vinyl ethers (1-alken-1=-yl-glycerols, known as plasmalogens) are not detected among the lipids of strain PF2803 T . Cultures grown on different (per)deuterated n-alkene, n-alkanol, and n-fatty acid substrates further demonstrate that saturated alkylglycerols are not formed via the reduction of hypothetic alken-1=-yl intermediates. Our results support an unprecedented biosynthetic pathway to monoalkyl/monoacyl-and dialkylglycerols in anaerobic bacteria and suggest that n-alkyl compounds present in the environment can serve as the substrates for supplying the building blocks of ether phospholipids of heterotrophic bacteria.

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Section: Dialkylglycerols In Mesophilic Bacteria the Membrane Lipidsmentioning

confidence: 99%

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T

Grossi

Mollex

Vinçon‐Laugier

et al. 2015

Appl Environ Microbiol

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“…This sebaceous gland is known to be very lipid-rich and particularly active in ether lipid synthesis (25). Since the formation of vinylether lipids is also dependent on the action of a desaturase complex, called ∆1-alkyl desaturase (26), one could argue that this desaturase contributes to the dihydroceramide desaturation. However, both complexes differ with regard to stereochemistry and cofactor requirement, ∆1-alkyl desaturase introducing cis-bonds and being NADH dependent (see also Ref.…”

Section: Resultsmentioning

confidence: 99%

Further characterization of rat dihydroceramide desaturase: Tissue distribution, subcellular localization, and substrate specificity

Causeret

Geeraert

Hoeven

et al. 2000

Lipids

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The introduction of the double bond in the sphingoid backbone of sphingolipids occurs at the level of dihydroceramide via an NADPH-dependent desaturase, as discovered in permeabilized rat hepatocytes. In the rat, the enzyme activity, which has now been further characterized, appeared to be mostly enriched in liver and Harderian gland. By means of subcellular fractionation of rat liver homogenates and density gradient separation of microsomal fractions, the desaturase was localized to the endoplasmic reticulum. Various detergents were inhibitory to the enzyme, and maximal activities were obtained in the presence of NADPH and when the substrate was complexed to albumin. In the presence of albumin, the chain length of the fatty acid of the truncated dihydroceramides hardly affected the activity. Finally, in view of a likely evolutionary relationship between desaturases and hydroxylases, the formation of hydroxylated intermediates was analyzed. No evidence for their presence was found under our assay conditions.

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“…1-O-(Alk-1 -enyl)-2,3-diacyl-snglycerol (neutral plasmalogens) are believed to be generated from their polar analogue plasmenyl-ethanolamine by removal of the polar head, achieved either by phospholipase or by the reverse reaction of ethanolamine-PT. The resulting 1-O-(alk-1 -enyl)-2-acyl-sn-glycerol is then esterified with acyl-CoA, yielding the diacyl derivative (Paltauf, 1983a).…”

Section: Biosynthesis and 1-o-alkyl Chain Compositionmentioning

confidence: 99%

Ether lipids

Magnusson

Haraldsson

2011

Chemistry and Physics of Lipids

124

119

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The naturally occurring 1-O-alkyl-sn-glycerols and their methoxylated congeners, 1-O-(2'-methoxyalkyl)-sn-glycerols, are biologically active compounds, ubiquitously found in nature as diacyl glyceryl ether lipids and phosphoether lipids. The chief objective of this article is to provide a comprehensive and up to date review on such ether lipids. The occurrence and distribution of these compounds in nature are extensively reviewed, their chemical structure and molecular variety, their biosynthesis and chemical synthesis and, finally, their various biological effects are described and discussed. An unprecedented biosynthesis of the 2'-methoxylated alkylglycerols is proposed. The first synthesis of enantiopure (Z)-(2'R)-1-O-(2'-methoxyhexadec-4'-enyl)-sn-glycerol, the most prevalent 2'-methoxylated type alkylglycerol present in cartilaginous fish, is described. It was accomplished by a highly convergent five step process.

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Biosynthesis of 1-0-(1′-Alkenyl)glycerolipids (Plasmalogens)

Cited by 20 publications

References 80 publications

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T

Further characterization of rat dihydroceramide desaturase: Tissue distribution, subcellular localization, and substrate specificity

Ether lipids

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Biosynthesis of 1-0-(1′-Alkenyl)glycerolipids (Plasmalogens)

Cited by 20 publications

References 80 publications

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 T

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 T

Further characterization of rat dihydroceramide desaturase: Tissue distribution, subcellular localization, and substrate specificity

Ether lipids

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Product

Resources

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Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T

Mono- and Dialkyl Glycerol Ether Lipids in Anaerobic Bacteria: Biosynthetic Insights from the Mesophilic Sulfate Reducer Desulfatibacillum alkenivorans PF2803 ^T