Structural elucidation of two types of novel glycosphingolipids in three strains of <i>Skeletonema</i> by liquid chromatography coupled with mass spectrometry

Zhao, Fang; Xu, Jilin; Chen, Juanjuan; Yan, Xiaojun; Zhou, Chengxu; Li, Shuang; Xu, Xiaoyan; Ye, Fangting

doi:10.1002/rcm.6602

Cited by 14 publications

(9 citation statements)

References 43 publications

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“…This putative precursor did not differ in cellular abundance subject to P stress. Chemically identical and related lipids have been reported previously in another marine diatom, Skeletonema costatum ( 43 ), and genes encoding sphingolipid biochemistry are also annotated in the genome of T. pseudonana ( 24 ). This lends further credence to our identification and highlights these molecules as an area of interest for future research into diatom lipid biochemistry.…”

Section: Discussionsupporting

confidence: 65%

“…These data could yield additional insight into the level of P stress experienced by the phytoplankton directly, which would be information complementary to the more-routine measurement of dissolved or particulate P concentrations in the medium. Targeted quantification of these lipids would be readily achievable using commercially available lactosylceramide standards (as in reference 43 ). Such a lipid biomarker could be useful for monitoring P-related biogeochemical processes in the environment, pending further validation.…”

Section: Discussionmentioning

confidence: 99%

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Lipidomics of Thalassiosira pseudonana under Phosphorus Stress Reveal Underlying Phospholipid Substitution Dynamics and Novel Diglycosylceramide Substitutes

Hunter

Brandsma

Dymond

et al. 2018

Appl Environ Microbiol

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Phytoplankton replace phosphorus-containing lipids (P-lipids) with non-P analogues, boosting growth in P-limited oceans. In the model diatom Thalassiosira pseudonana, the substitution dynamics of lipid headgroups are well described, but those of the individual lipids, differing in fatty acid composition, are unknown. Moreover, the behavior of lipids outside the common headgroup classes and the relationship between lipid substitution and cellular particulate organic P (POP) have yet to be reported. We investigated these through the mass spectrometric lipidomics of P-replete (P+) and P-depleted (P−) T. pseudonana cultures. Nonlipidic POP was depleted rapidly by the initiation of P stress, followed by the cessation of P-lipid biosynthesis and per-cell reductions in the P-lipid levels of successive generations. Minor P-lipid degradative breakdown was observed, releasing P for other processes, but most P-lipids remained intact. This may confer an advantage on efficient heterotrophic lipid consumers in P-limited oceans. Glycerophosphatidylcholine (PC), the predominant P-lipid, was similar in composition to its betaine substitute lipid. During substitution, PC was less abundant per cell and was more highly unsaturated in composition. This may reflect underlying biosynthetic processes or the regulation of membrane biophysical properties subject to lipid substitution. Finally, levels of several diglycosylceramide lipids increased as much as 10-fold under P stress. These represent novel substitute lipids and potential biomarkers for the study of P limitation in situ, contributing to growing evidence highlighting the importance of sphingolipids in phycology. These findings contribute much to our understanding of P-lipid substitution, a powerful and widespread adaptation to P limitation in the oligotrophic ocean.IMPORTANCE Unicellular organisms replace phosphorus (P)-containing membrane lipids with non-P substitutes when P is scarce, allowing greater growth of populations. Previous research with the model diatom species Thalassiosira pseudonana grouped lipids by polar headgroups in their chemical structures. The significance of the research reported here is threefold. (i) We described the individual lipids within the headgroups during P-lipid substitution, revealing the relationships between lipid headgroups and hinting at the underlying biochemical processes. (ii) We measured total cellular P, placing P-lipid substitution in the context of the broader response to P stress and yielding insight into the implications of substitution in the marine environment. (iii) We identified lipids previously unknown in this system, revealing a new type of non-P substitute lipid, which is potentially useful as a biomarker for the investigation of P limitation in the ocean.

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Section: Discussionsupporting

confidence: 65%

Section: Discussionmentioning

confidence: 99%

Lipidomics of Thalassiosira pseudonana under Phosphorus Stress Reveal Underlying Phospholipid Substitution Dynamics and Novel Diglycosylceramide Substitutes

Hunter

Brandsma

Dymond

et al. 2018

Appl Environ Microbiol

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“…In comparison with the conventional HPLC method, ultraperformance liquid chromatography (UPLC) has the advantages of shorter retention time, higher analytical sensitivity and excellent peak capacity (Liu et al, 2010;Yan et al, 2013). In addition, a quadrupole time-of-flight (Q/TOF) mass analyzer operating in MS E mode allows the selection and isolation of precursor ions with high efficiency, sensitivity and mass accuracy (Fu et al, 2014;Zhao et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Rapid screening and identification of lycodine‐type alkaloids in Lycopodiaceae and Huperziaceae plants by ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight mass spectrometry

Shan

Luo

Pan

et al. 2016

Biomedical Chromatography

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Lycodine-type alkaloids have gained significant interest owing to their unique skeletal characteristics and acetylcholinesterase activity. This study established a rapid and reliable method using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q/TOF-MS/MS) for comprehensive characterization of lycodine-type alkaloids for the first time. The lycodine-type alkaloids were detected successfully from Lycopodiastrum casuarinoides, Huperzia serrata and Phlegmarirus carinatus in seven plants of the Lycopodiaceae and Huperziaceae families, based on the established characteristic MS fragmentation of five known alkaloids. Furthermore, a total of 13 lycodine-type alkaloids were identified, of which three pairs of isomers were structurally characterized and differentiated. This study further improves mass analysis of lycodine-type alkaloids and demonstrates the superiority of UPLC with a high-resolution mass spectrometer for the rapid and sensitive structural elucidation of other trace active compounds. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Zhao et al . used [M + Li] + precursor ions for the characterization of two types of novel glycosphingolipids . Roche and Leblond adopted [M + Na] + precursor ions for the structural illustration of DGTS and DGTA .…”

Section: Resultsmentioning

confidence: 99%

Simultaneous structural identification of diacylglyceryl‐N‐trimethylhomoserine (DGTS) and diacylglycerylhydroxymethyl‐N,N,N‐trimethyl‐β‐alanine (DGTA) in microalgae using dual Li⁺/H⁺ adduct ion mode by ultra‐performance liquid chromatography/quadrupole time‐of‐flight mass spectrometry

Lou

Mu³

et al. 2017

Rapid Comm Mass Spectrometry

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Structural elucidation of two types of novel glycosphingolipids in three strains of Skeletonema by liquid chromatography coupled with mass spectrometry

Abstract: A qualitative method was developed for the identification of GSLs in microalgae. Two types of novel GSLs were identified from three strains of Skeletonema, which might have important biological functions. It could also provide a reliable tool for chemotaxonomy of microalgae.

Cited by 14 publications

References 43 publications

Lipidomics of Thalassiosira pseudonana under Phosphorus Stress Reveal Underlying Phospholipid Substitution Dynamics and Novel Diglycosylceramide Substitutes

Lipidomics of Thalassiosira pseudonana under Phosphorus Stress Reveal Underlying Phospholipid Substitution Dynamics and Novel Diglycosylceramide Substitutes

Rapid screening and identification of lycodine‐type alkaloids in Lycopodiaceae and Huperziaceae plants by ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight mass spectrometry

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