Identification of the unknown transformation products derived from lincomycin using LC‐HRMS technique

Calza, Paola; Medana, Claudio; Padovano, Elisa; Bello, Federica Dal; Baiocchi, Claudio

doi:10.1002/jms.3012

Cited by 30 publications

(14 citation statements)

References 24 publications

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“… Retention time, RT; Accuracy, Δmmu * ; OH, hydroxy group attached to fatty acids; Gln, glutamine; I, proposed lysine lipid (LL); I', proposed lysine lipid with hydroxylated fatty acid (LL HFA ); I, proposed hydroxylysine lipid (HLL); II', proposed hydroxylysine lipid with hydroxylated fatty acid (HLL HFA ) . *In general the 0.5 Δmmu (milli mass unit) range represented very high confidence molecular formula assignments and the 1.0 Δmmu range represented good confidence molecular formula assignments (Kostiainen et al, 1997 ; Sakayanagi et al, 2006 ; Calza et al, 2012 ) . …”

Section: Resultsmentioning

confidence: 99%

Lysine and novel hydroxylysine lipids in soil bacteria: amino acid membrane lipid response to temperature and pH in Pseudopedobacter saltans

et al. 2015

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Microbial decomposition of organic matter is an essential process in the global carbon cycle. The soil bacteria Pseudopedobacter saltans and Flavobacterium johnsoniae are both able to degrade complex organic molecules, but it is not fully known how their membrane structures are adapted to their environmental niche. The membrane lipids of these species were extracted and analyzed using high performance liquid chromatography-electrospray ionization/ion trap/mass spectrometry (HPLC-ESI/IT/MS) and high resolution accurate mass/mass spectrometry (HRAM/MS). Abundant unknown intact polar lipids (IPLs) from P. saltans were isolated and further characterized using amino acid analysis and two dimensional nuclear magnetic resonance (NMR) spectroscopy. Ornithine IPLs (OLs) with variable (hydroxy) fatty acid composition were observed in both bacterial species. Lysine-containing IPLs (LLs) were also detected in both species and were characterized here for the first time using HPLC-MS. Novel LLs containing hydroxy fatty acids and novel hydroxylysine lipids with variable (hydroxy) fatty acid composition were identified in P. saltans. The confirmation of OL and LL formation in F. johnsoniae and P. saltans and the presence of OlsF putative homologs in P. saltans suggest the OlsF gene coding protein is possibly involved in OL and LL biosynthesis in both species, however, potential pathways of OL and LL hydroxylation in P. saltans are still undetermined. Triplicate cultures of P. saltans were grown at three temperature/pH combinations: 30°C/pH 7, 15°C/pH 7, and 15°C/pH 9. The fractional abundance of total amino acid containing IPLs containing hydroxylated fatty acids was significantly higher at higher temperature, and the fractional abundance of lysine-containing IPLs was significantly higher at lower temperature and higher pH. These results suggest that these amino acid-containing IPLs, including the novel hydroxylysine lipids, could be involved in temperature and pH stress response of soil bacteria.

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Section: Resultsmentioning

confidence: 99%

Lysine and novel hydroxylysine lipids in soil bacteria: amino acid membrane lipid response to temperature and pH in Pseudopedobacter saltans

et al. 2015

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“…The filtrates in the 180-d samples were examined using the precursor ion scan mode by liquid chromatography/tandem mass spectrometry. Based on Calza et al (2012), no degradation candidates of lincomycin were detected (Supplemental Fig. S2), suggesting that the disappearance of lincomycin from the aqueous phase was caused by sorption onto biochars instead of degradation.…”

Section: Sorption Kineticsmentioning

confidence: 99%

Sorption of Lincomycin by Manure-Derived Biochars from Water

Liu

Chuang

et al. 2016

J. Environ. Qual.

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The presence of antibiotics in agroecosystems raises concerns about the proliferation of antibiotic-resistant bacteria and adverse effects to human health. Soil amendment with biochars pyrolized from manures may be a win-win strategy for novel manure management and antibiotics abatement. In this study, lincomycin sorption by manure-derived biochars was examined using batch sorption experiments. Lincomycin sorption was characterized by two-stage kinetics with fast sorption reaching quasi-equilibrium in the first 2 d, followed by slow sorption over 180 d. The fast sorption was primarily attributed to surface adsorption, whereas the long-term slow sorption was controlled by slow diffusion of lincomycin into biochar pore structures. Two-day sorption experiments were performed to explore effects of biochar particle size, solid/water ratio, solution pH, and ionic strength. Lincomycin sorption to biochars was greater at solution pH 6.0 to 7.5 below the dissociation constant of lincomycin (7.6) than at pH 9.9 to 10.4 above its dissociation constant. The enhanced lincomycin sorption at lower pH likely resulted from electrostatic attraction between the positively charged lincomycin and the negatively charged biochar surfaces. This was corroborated by the observation that lincomycin sorption decreased with increasing ionic strength at lower pH (6.7) but remained constant at higher pH (10). The long-term lincomycin sequestration by biochars was largely due to pore diffusion plausibly independent of solution pH and ionic composition. Therefore, manure-derived biochars had lasting lincomycin sequestration capacity, implying that biochar soil amendment could significantly affect the distribution, transport, and bioavailability of lincomycin in agroecosystems.

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“…abun., relative abundance, i.e., the peak area percentage of each lipid within its respective group. d In general the 0.5-⌬ mmu (milli-mass unit) range was used as a measure of very high-confidence molecular formula assignments, and the 1.0-⌬ mmu range was used as a measure of good-confidence molecular formula assignments (63)(64)(65). chemical shift as well compared to the head group ␦-position signal in the ornithine lipid spectra.…”

Section: Unknown Ipls Detected By Hplc-esi/it/msmentioning

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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Identification of the unknown transformation products derived from lincomycin using LC‐HRMS technique

Cited by 30 publications

References 24 publications

Lysine and novel hydroxylysine lipids in soil bacteria: amino acid membrane lipid response to temperature and pH in Pseudopedobacter saltans

Lysine and novel hydroxylysine lipids in soil bacteria: amino acid membrane lipid response to temperature and pH in Pseudopedobacter saltans

Sorption of Lincomycin by Manure-Derived Biochars from Water

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

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