Identification of sulfoquinovosyldiacyglycerides from <i>Phaeodactylum tricornutum</i> by matrix‐assisted laser desorption/ionization QTrap time‐of‐flight hybrid mass spectrometry

Naumann, Ivonne; Klein, Barbara C.; Bartel, Sebastian; Darsow, Kai; Buchholz, Rainer; Lange, Harald A.

doi:10.1002/rcm.5137

Cited by 17 publications

(17 citation statements)

References 24 publications

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“…The profile is dominated by MGDG, SQDG, and PC, which together represent more than 75% of the total content. We also confirmed the presence of 20:5 acyl-SQDG, as reported previously (Naumann et al, 2011;Supplemental . Photosynthetic activity and lipid accumulation in the Pt1 ecotype of P. tricornutum cultivated in replete or N-or P-depleted conditions.…”

supporting

confidence: 92%

“…Besides the major lipids conserved in photosynthetic membranes (i.e. MGDG, DGDG, SQDG, and PG), we confirmed the presence of 29-O-acylsulfoquinovosyldiacylglycerides (20:5-acyl-SQDG [ASQ]), largely dominated by the molecular species sn-1:20:5/sn-2:16:0/29:20:5 (Naumann et al, 2011). The presence of ASQ has also been reported for C. reinhardtii, although 18:3 or 18:4 acyl groups were the FAs involved in the 29-acylation of the sulfoquinovose moiety (Riekhof et al, 2003).…”

Section: Discussionsupporting

confidence: 58%

“…Given the current state of membrane fractionation techniques, only global analyses can be performed. By contrast with other omics data, and although previous targeted studies have allowed the structural determination of some isolated glycerolipid classes (Arao et al, 1987;Yongmanitchai and Ward, 1993;Naumann et al, 2011), the complete membrane glycerolipidome of P. tricornutum has not been fully characterized. The analyses of membrane glycerolipid remodeling in diatoms should also consider the accumulation of TAG triggered by nutrient shortage, which has been scrutinized in much more detail due to the potential applications for biofuels and green chemistry (Alonso et al, 2000;Rezanka et al, 2011;Zendejas et al, 2012;Levitan et al, 2014).…”

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confidence: 99%

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Membrane Glycerolipid Remodeling Triggered by Nitrogen and Phosphorus Starvation inPhaeodactylum tricornutum

et al. 2014

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Diatoms constitute a major phylum of phytoplankton biodiversity in ocean water and freshwater ecosystems. They are known to respond to some chemical variations of the environment by the accumulation of triacylglycerol, but the relative changes occurring in membrane glycerolipids have not yet been studied. Our goal was first to define a reference for the glycerolipidome of the marine model diatom Phaeodactylum tricornutum, a necessary prerequisite to characterize and dissect the lipid metabolic routes that are orchestrated and regulated to build up each subcellular membrane compartment. By combining multiple analytical techniques, we determined the glycerolipid profile of P. tricornutum grown with various levels of nitrogen or phosphorus supplies. In different P. tricornutum accessions collected worldwide, a deprivation of either nutrient triggered an accumulation of triacylglycerol, but with different time scales and magnitudes. We investigated in depth the effect of nutrient starvation on the Pt1 strain (Culture Collection of Algae and Protozoa no. 1055/3). Nitrogen deprivation was the more severe stress, triggering thylakoid senescence and growth arrest. By contrast, phosphorus deprivation induced a stepwise adaptive response. The time scale of the glycerolipidome changes and the comparison with large-scale transcriptome studies were consistent with an exhaustion of unknown primary phosphorusstorage molecules (possibly polyphosphate) and a transcriptional control of some genes coding for specific lipid synthesis enzymes. We propose that phospholipids are secondary phosphorus-storage molecules broken down upon phosphorus deprivation, while nonphosphorus lipids are synthesized consistently with a phosphatidylglycerol-to-sulfolipid and a phosphatidycholine-to-betaine lipid replacement followed by a late accumulation of triacylglycerol.

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supporting

confidence: 92%

Section: Discussionsupporting

confidence: 58%

mentioning

confidence: 99%

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Membrane Glycerolipid Remodeling Triggered by Nitrogen and Phosphorus Starvation inPhaeodactylum tricornutum

et al. 2014

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“…Taking this into account [34], possibly the higher peak intensity of fragment ion [b] at m/z 537.2 in comparison to fragment ion [a] suggests the position of the palmitic acid to be at the sn-2-postion. Based on this and other references the positions postulated in the literature are assumed also here [29,35,36,37]. Thus for compound 1 at sn-1-position linolenic acid (C18:3) and at sn-2-position palmitic acid (C16:0), for compound 2 at sn-1-position linoleic acid (C18:2) and at sn-2-position palmitic acid (C16:0) and for compound 3 at sn-1-position and sn-2-position palmitic acid (C16:0) are proposed.…”

Section: Resultsmentioning

confidence: 99%

“…The applied method allowed the identification and characterization directly from complex crude extracts without further purification steps. It is strongly suggested, that the identified QC inhibitors are sulfolipids, which are already identified from various microalgae (mainly Rhodophyta) like Porphyridium purpureum [35], Heterosigma carterae , Phaeodactylum tricorntum [37], Heterosigma caterae [38], and Pavlova lutheri [39], as well as from the macroalgae Gigartina tenella [40] and Caulerpa racemosa [41]. Furthermore, the occurrence of sulfolipids is known from cyanobacteria e.g., Lyngbya lagerheimii [42], Oscillatoria raoi [43], Arthrospira platensis , Nostoc punctiforme , Scytonema hofmanni [36], and from spinach ( Spinacia oleeracea) [44].…”

Section: Discussionmentioning

confidence: 99%

Natural Products from Microalgae with Potential against Alzheimer’s Disease: Sulfolipids Are Potent Glutaminyl Cyclase Inhibitors

et al. 2016

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In recent years, many new enzymes, like glutaminyl cyclase (QC), could be associated with pathophysiological processes and represent targets for many diseases, so that enzyme-inhibiting properties of natural substances are becoming increasingly important. In different studies, the pathophysiology connection of QC to various diseases including Alzheimer’s disease (AD) was described. Algae are known for the ability to synthesize complex and highly-diverse compounds with specific enzyme inhibition properties. Therefore, we screened different algae species for the presence of QC inhibiting metabolites using a new “Reverse Metabolomics” technique including an Activity-correlation Analysis (AcorA), which is based on the correlation of bioactivities to mass spectral data with the aid of mathematic informatics deconvolution. Thus, three QC inhibiting compounds from microalgae belonging to the family of sulfolipids were identified. The compounds showed a QC inhibition of 81% and 76% at concentrations of 0.25 mg/mL and 0.025 mg/mL, respectively. Thus, for the first time, sulfolipids are identified as QC inhibiting compounds and possess substructures with the required pharmacophore qualities. They represent a new lead structure for QC inhibitors.

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Fatty acid neutral losses observed in tandem mass spectrometry with collision‐induced dissociation allows regiochemical assignment of sulfoquinovosyl‐diacylglycerols

et al. 2013

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A full characterization of sulfoquinovosyldiacylglycerols (SQDGs) in the lipid extract of spinach leaves has been achieved using liquid chromatography/electrospray ionization-linear quadrupole ion trap mass spectrometry (MS). Low-energy collision-induced dissociation tandem MS (MS/MS) of the deprotonated species [M - H](-) was exploited for a detailed study of sulfolipid fragmentation. Losses of neutral fatty acids from the acyl side chains (i.e. [M - H - RCOOH](-)) were found to prevail over ketene losses ([M - H - R'CHCO](-)) or carboxylates of long-chain fatty acids ([RCOO](-)), as expected for gas-phase acidity of SQDG ions. A new concerted mechanism for RCOOH elimination, based on a charge-remote fragmentation, is proposed. The preferential loss of a fatty acids molecule from the sn-1 position (i.e. [M - H - R(1)COOH](-)) of the glycerol backbone, most likely due to kinetic control of the gas-phase fragmentation process, was exploited for the regiochemical assignment of the investigated sulfolipids. As a result, 24 SQDGs were detected and identified in the lipid extract of spinach leaves, their number and variety being unprecedented in the field of plant sulfolipids. Moreover, the prevailing presence of a palmitic acyl chain (16:0) on the glycerol sn-2 position of spinach SQDGs suggests a prokaryotic or chloroplastic path as the main route for their biosynthesis.

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Identification of sulfoquinovosyldiacyglycerides from Phaeodactylum tricornutum by matrix‐assisted laser desorption/ionization QTrap time‐of‐flight hybrid mass spectrometry

Cited by 17 publications

References 24 publications

Membrane Glycerolipid Remodeling Triggered by Nitrogen and Phosphorus Starvation inPhaeodactylum tricornutum

Membrane Glycerolipid Remodeling Triggered by Nitrogen and Phosphorus Starvation inPhaeodactylum tricornutum

Natural Products from Microalgae with Potential against Alzheimer’s Disease: Sulfolipids Are Potent Glutaminyl Cyclase Inhibitors

Fatty acid neutral losses observed in tandem mass spectrometry with collision‐induced dissociation allows regiochemical assignment of sulfoquinovosyl‐diacylglycerols

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