A glycine-containing phosphorus-free lipoaminoacid from the gram-negative marine bacterium Cyclobacterium marinus WH

Batrakov, S. G.; Никитин, Д. И.; Mosezhnyi, Anatolii E.; Ruzhitsky, Alexandr O.

doi:10.1016/s0009-3084(99)00031-6

Cited by 15 publications

(16 citation statements)

References 10 publications

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“…In some bacteria OLs are produced under phosphorus limitation (46,47) or hydroxylated under thermal or acid stress (48)(49)(50). Other amino acid-containing lipids have been identified in various bacteria, including glycine lipids (51,52), a lysine lipid (53), and an ornithine-taurine-linked lipid (54), although they are not nearly as widespread as OLs. While the exact function of OL modifications is not yet fully described, characterization of mutants that are deficient in ornithine lipid biosynthesis and modification genes has further supported a mechanism of bacterial stress response to changing environmental conditions (44,49,50).…”

Section: Discussionmentioning

confidence: 99%

Novel Mono-, Di-, and Trimethylornithine Membrane Lipids in Northern Wetland Planctomycetes

Moore

Hopmans

Rijpstra

et al. 2013

Appl Environ Microbiol

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dNorthern peatlands represent a significant global carbon store and commonly originate from Sphagnum moss-dominated wetlands. These ombrotrophic ecosystems are rain fed, resulting in nutrient-poor, acidic conditions. Members of the bacterial phylum Planctomycetes are highly abundant and appear to play an important role in the decomposition of Sphagnum-derived litter in these ecosystems. High-performance liquid chromatography coupled to high-resolution accurate-mass mass spectrometry (HPLC-HRAM/MS) analysis of lipid extracts of four isolated planctomycetes from wetlands of European north Russia revealed novel ornithine membrane lipids (OLs) that are mono-, di-, and trimethylated at the -nitrogen position of the ornithine head group. Nuclear magnetic resonance (NMR) analysis of the isolated trimethylornithine lipid confirmed the structural identification. Similar fatty acid distributions between mono-, di-, and trimethylornithine lipids suggest that the three lipid classes are biosynthetically linked, as in the sequential methylation of the terminal nitrogen in phosphatidylethanolamine to produce phosphatidylcholine. The mono-, di-, and trimethylornithine lipids described here represent the first report of methylation of the ornithine head groups in biological membranes. Various bacteria are known to produce OLs under phosphorus limitation or fatty-acid-hydroxylated OLs under thermal or acid stress. The sequential methylation of OLs, leading to a charged choline-like moiety in the trimethylornithine lipid head group, may be an adaptation to provide membrane stability under acidic conditions without the use of scarce phosphate in nutrient-poor ombrotrophic wetlands.

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Section: Discussionmentioning

confidence: 99%

Novel Mono-, Di-, and Trimethylornithine Membrane Lipids in Northern Wetland Planctomycetes

Moore

Hopmans

Rijpstra

et al. 2013

Appl Environ Microbiol

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“…Fragmentation of both the m / z 568 and 566 IPLs resulted in fatty acid losses and an m / z 76 fragment ion (Table ). C. marinus is known to produce the glycine‐containing lipid cytolipin . The nominal mass of protonated glycine is 76, which would match with the m / z 76 fragment ion of the m / z 568 and 566 IPLs.…”

Section: Resultsmentioning

confidence: 99%

“…[6,19,22,23] Like OLs, the diagnostic MS fragment ions of other previously described AA-IPLs, typically contain the complete AA head group or smaller AA head group fragment ions. [6,[15][16][17][18][19][20][21]28,29] These fragment ions of AA head groups are an important aid in identification of AA-IPLs.…”

Section: General Ms Fragmentation Characteristic Of Aa-iplsmentioning

confidence: 99%

“…C. marinus is known to produce the glycine-containing lipid cytolipin. [18] The nominal mass of protonated glycine is 76, which would match with the m/z 76 fragment ion of the m/z 568 and 566 IPLs. HRMS analysis confirmed the fatty acid losses of the m/z 568 (C 15:0 , βOH-C 17:0 ) and 566 (C 15:1 , βOH-C 17:0 ) IPLs.…”

Section: Cytolipinmentioning

confidence: 99%

“…1). [15][16][17][18][19] Recently, novel mono-, di-, and trimethylornithine (MMO, DMO, TMO) IPLs and hydroxylysine-containing IPLs (lysine lipids hydroxylated on the fatty acid and/or lysine head group) were characterized from northern wetland planctomycetes and soil bacteria, respectively, and it was suggested that these modifications were related to stress conditions ( Fig. 1).…”

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confidence: 99%

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Elucidation and identification of amino acid containing membrane lipids using liquid chromatography/high‐resolution mass spectrometry

Moore

Hopmans

Rijpstra

et al. 2016

Rapid Comm Mass Spectrometry

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Rationale Intact polar lipids (IPLs) are the building blocks of cell membranes, and amino acid containing IPLs have been observed to be involved in response to changing environmental conditions in various species of bacteria. High‐performance liquid chromatography/mass spectrometry (HPLC/MS) has become the primary method for analysis of IPLs. Many glycerol‐free amino acid containing membrane lipids (AA‐IPLs), which are structurally different than abundant aminophospholipids, have not been characterized using HPLC/MS. This results in many lipids remaining unrecognized in IPL analysis of microbial cultures and environmental samples, hampering the study of their occurrence and functionality. Methods We analyzed the amino acid containing IPLs of a number of bacteria (i.e. Gluconobacter cerinus, Cyclobacterium marinus, Rhodobacter sphaeroides, and Pedobacter heparinus) in order to decipher fragmentation pathways, and explore potential novel lipid structures using HPLC/electrospray ionization ion trap MS (HPLC/ESI‐IT‐MS) and HPLC/high‐resolution MS (HPLC/HRMS). Results We report differentiation between glutamine and lysine lipids with the same nominal masses, novel MS fragmentation pathways of cytolipin, the lipopeptides cerilipin and flavolipin, head group hydroxylated ornithine lipids, and the novel identification of cerilipin with a hydroxylated fatty acid. Conclusions Non‐glycerol AA lipids can be readily recognized as their fragmentation follows a clear pattern with initial dehydration or other loss from the head group, followed by fatty acid losses resulting in a diagnostic fragment ion. Higher level MSn and HRMS are valuable tools in characterizing AA lipid head group structural components. Copyright © 2016 John Wiley & Sons, Ltd.

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Ornithine Lipids and Other Amino Acid-Containing Acyloxyacyl Lipids

Sohlenkamp

2016

Biogenesis of Fatty Acids, Lipids and Membranes

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A glycine-containing phosphorus-free lipoaminoacid from the gram-negative marine bacterium Cyclobacterium marinus WH

Cited by 15 publications

References 10 publications

Novel Mono-, Di-, and Trimethylornithine Membrane Lipids in Northern Wetland Planctomycetes

Novel Mono-, Di-, and Trimethylornithine Membrane Lipids in Northern Wetland Planctomycetes

Elucidation and identification of amino acid containing membrane lipids using liquid chromatography/high‐resolution mass spectrometry

Ornithine Lipids and Other Amino Acid-Containing Acyloxyacyl Lipids

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