Short chain ladderanes: Oxic biodegradation products of anammox lipids

Rush, Darci; Jaeschke, Andrea; Hopmans, Ellen C.; Geenevasen, Jan A. J.; Schouten, Stefan; Damsté, Jaap S. Sinninghe

doi:10.1016/j.gca.2011.01.013

Cited by 21 publications

(10 citation statements)

References 35 publications

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“…The GC2 retention position of the C 10 authentic acid methyl ester ( Figure S1) and the tentative identification of the C 9 parent acid ( Figure S7) suggested that some of the C 11 + acids present in the OSPW might have this skeleton. Figure 1B; VII), similar in structure to short-chain ladderane fatty acids previously identified as degradation products of ladderane lipids [36]. Ladderane lipids are specific for bacteria capable of anaerobic ammonium oxidation (anammox) and therefore the acids can be used as biomarkers for anammox bacteria [52].…”

Section: Bicyclic Acidssupporting

confidence: 52%

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Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography–mass spectrometry

Wilde

West

Scarlett

et al. 2015

Journal of Chromatography A

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Although bicyclic acids have been reported to be the major naphthenic acids in oil sands process-affected water (OSPW) and a well-accepted screening assay indicated that some bicyclics were the most acutely toxic acids tested, none have yet been identified. Here we show by comprehensive multidimensional gas chromatography-mass spectrometry (GC×GC-MS), that >100 C8-15 bicyclic acids are typically present in OSPW. Synthesis or purchase allowed us to establish the GC×GC retention times of methyl esters of numerous of these and the mass spectra and published spectra of some additional types, allowed us to identify bicyclo[2.2.1]heptane, bicyclo[3.2.1]octane, bicyclo[4.3.0]nonane, bicyclo[3.3.1]nonane and bicyclo[4.4.0]decane acids in OSPW and a bicyclo[2.2.2]octane acid in a commercial acid mixture. The retention positions of authentic bicyclo[3.3.0]octane and bicyclo[4.2.0]octane carboxylic acid methyl esters and published retention indices, showed these were also possibilities, as were bicyclo[3.1.1]heptane acids. Bicyclo[5.3.0]decane and cyclopentylcyclopentane carboxylic acids were ruled out in the samples analysed, on the basis that the corresponding alkanes eluted well after bicyclo[4.4.0]decane (latest eluting acids). Bicyclo[4.2.1]nonane, bicyclo[3.2.2]nonane, bicyclo[3.3.2]decane, bicyclo[4.2.2]decane and spiro[4.5]decane carboxylic acids could not be ruled out or in, as no authentic compounds or literature data were available. Mass spectra of the methyl esters of the higher bicyclic C12-15 acids suggested that many were simply analogues of the acids identified above, with longer alkanoate chains and/or alkyl substituents. Our hypothesis is that these acids represent the biotransformation products of the initially somewhat more bio-resistant bicyclanes of petroleum. Although remediation studies suggest that many bicyclic acids can be relatively quickly removed from suitably treated OSPW, examination by GC×GC-MS may show which isomers are affected most. Knowledge of the structures will allow the toxicity of any residual isomers to be calculated and measured.

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Section: Bicyclic Acidssupporting

confidence: 52%

“…These have cyclopropyl-or cyclobutyl rings; the former are present in carane-and thujane-type compounds and the latter present in bicyclo[3. [36]. For the acids with a C 7 core and the requisite substituents, there are four structural types (examples given in Figure 1B; I-III), for the C 8 core acids, six (e.g.…”

Section: Accepted By J Chromatogr Amentioning

confidence: 99%

Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography–mass spectrometry

Wilde

West

Scarlett

et al. 2015

Journal of Chromatography A

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“…The fatty acid fractions were dissolved in acetone, filtered through a 0.45 μm polytetrafluoroethylene (PTFE) filters (4 mm diameter), and analyzed by high performance liquid chromatography coupled to positive ion atmospheric pressure chemical ionization tandem mass spectrometry (HPLC/APCI-MS/MS) in selective reaction monitoring (SRM) mode following Hopmans et al ( 2006 ) including the recent modifications described by Rush et al ( 2012b ). Ladderane lipids were quantified using external calibration curves of three standards of isolated methylated ladderane fatty acids (C20-[3]-ladderane fatty acid, and C20-[5]-ladderane fatty acid; Hopmans et al, 2006 ; Rush et al, 2011 ).…”

Section: Methodsmentioning

confidence: 99%

Abundance and Diversity of Denitrifying and Anammox Bacteria in Seasonally Hypoxic and Sulfidic Sediments of the Saline Lake Grevelingen

et al. 2016

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Denitrifying and anammox bacteria are involved in the nitrogen cycling in marine sediments but the environmental factors that regulate the relative importance of these processes are not well constrained. Here, we evaluated the abundance, diversity, and potential activity of denitrifying, anammox, and sulfide-dependent denitrifying bacteria in the sediments of the seasonally hypoxic saline Lake Grevelingen, known to harbor an active microbial community involved in sulfur oxidation pathways. Depth distributions of 16S rRNA gene, nirS gene of denitrifying and anammox bacteria, aprA gene of sulfur-oxidizing and sulfate-reducing bacteria, and ladderane lipids of anammox bacteria were studied in sediments impacted by seasonally hypoxic bottom waters. Samples were collected down to 5 cm depth (1 cm resolution) at three different locations before (March) and during summer hypoxia (August). The abundance of denitrifying bacteria did not vary despite of differences in oxygen and sulfide availability in the sediments, whereas anammox bacteria were more abundant in the summer hypoxia but in those sediments with lower sulfide concentrations. The potential activity of denitrifying and anammox bacteria as well as of sulfur-oxidizing, including sulfide-dependent denitrifiers and sulfate-reducing bacteria, was potentially inhibited by the competition for nitrate and nitrite with cable and/or Beggiatoa-like bacteria in March and by the accumulation of sulfide in the summer hypoxia. The simultaneous presence and activity of organoheterotrophic denitrifying bacteria, sulfide-dependent denitrifiers, and anammox bacteria suggests a tight network of bacteria coupling carbon-, nitrogen-, and sulfur cycling in Lake Grevelingen sediments.

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“…Unfortunately, it has so far not been possible to assess anammox further back in time using ladderane lipids as they are not resistant to the degradative stresses of sediment burial. Ladderane fatty acids undergo b-oxidation in the presence of even very low oxygen concentrations to form short chain ladderane fatty acids, which have been found in sediments underlying OMZs (Rush et al, 2011;. However, these too appear to undergo further degradation, and these Arabian Sea sediments are currently the oldest known detection of past anammox activity (Jaeschke et al, 2009).…”

Section: Application Of Biomarkers To Interpret Nitrogen Cycling In Tmentioning

confidence: 99%

Lipids as paleomarkers to constrain the marine nitrogen cycle

Rush

Damsté

2017

Environmental Microbiology

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SummaryGlobal climate is, in part, regulated by the effect of microbial processes on biogeochemical cycling. The nitrogen cycle, in particular, is driven by microorganisms responsible for the fixation and loss of nitrogen, and the reduction‐oxidation transformations of bio‐available nitrogen. Within marine systems, nitrogen availability is often the limiting factor in the growth of autotrophic organisms, intrinsically linking the nitrogen and carbon cycles. In order to elucidate the state of these cycles in the past, and help envisage present and future variability, it is essential to understand the specific microbial processes responsible for transforming bio‐available nitrogen species. As most microorganisms are soft‐bodied and seldom leave behind physical fossils in the sedimentary record, recalcitrant lipid biomarkers are used to unravel microbial processes in the geological past. This review emphasises the recent advances in marine nitrogen cycle lipid biomarkers, underlines the missing links still needed to fully elucidate past shifts in this biogeochemically‐important cycle, and provides examples of biomarker applications in the geological past.

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Short chain ladderanes: Oxic biodegradation products of anammox lipids

Cited by 21 publications

References 35 publications

Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography–mass spectrometry

Bicyclic naphthenic acids in oil sands process water: Identification by comprehensive multidimensional gas chromatography–mass spectrometry

Abundance and Diversity of Denitrifying and Anammox Bacteria in Seasonally Hypoxic and Sulfidic Sediments of the Saline Lake Grevelingen

Lipids as paleomarkers to constrain the marine nitrogen cycle

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