Novel sulfated phosphoglycolipids from Natronomonas moolapensis

Hoffmann, A.; Kovermann, Michael; Oberwinkler, Tanja; Siedler, Frank; Cortina, Niña Socorro; Balbach, Jochen; Oesterhelt, Dieter

doi:10.1016/j.chemphyslip.2015.06.004

Cited by 3 publications

(3 citation statements)

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“…This headgroup combined with a diacyl core lipid has been described in halophilic gammaproteobacterium of the genus Halomonas (Giordano et al, 2007), while a very similar diether phosphoglycolipid attached to a sulfated sugar moiety was identified in the alkaliphilic haloarchaeon Natrononomonas ( N .) moolapensis (Hoffmann et al, 2015). The position of the sugar of both the bacterial and archaeal glycosylated-PG described in the literature were determined by NMR to be at the 2-glycero position (Giordano et al, 2007; Hoffmann et al, 2015).…”

Section: Resultsmentioning

confidence: 99%

“…moolapensis (Hoffmann et al, 2015). The position of the sugar of both the bacterial and archaeal glycosylated-PG described in the literature were determined by NMR to be at the 2-glycero position (Giordano et al, 2007; Hoffmann et al, 2015). In our study the MS 2 fragmentation pattern could not confirm whether the hexose was at the 1- or 2- glycerol position, but the similarity of the PG-Gly spectra with those of 1-(6-sulfo-D-glcp/galf-β1,2-glycero)-phospho-2,3-diphytanylglycerol found in N. moolapensis (Hoffmann et al, 2015) provides an indication that they both have same structural arrangement.…”

Section: Resultsmentioning

confidence: 99%

“…The PG-Gly headgroup with a diacyl core has been described in halophilic gammaproteobacteria of the genus Halomonas (Giordano et al, 2007), where it was postulated that the bulky headgroup would enhance steric protection through hydrogen bonding via glycosyl headgroups to ensure the osmotic stability of the cellular membrane under high-salt conditions. Furthermore, a very similar phosphoglycolipid with a sulfated sugar moiety was identified in alkaliphilic haloarchaeon N. moolapensis from the Halobacteriales order (Hoffmann et al, 2015). The presence of this headgroup in both extremely halophilic archaea and moderately halophilic bacteria further supports the hypothesis that this headgroup provides additional osmotic stability.…”

Section: Discussionmentioning

confidence: 96%

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New Insights Into the Polar Lipid Composition of Extremely Halo(alkali)philic Euryarchaea From Hypersaline Lakes

et al. 2019

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We analyzed the polar membrane lipids of 13 strains of halo(alkali)philic euryarchaea from hypersaline lakes. Nine belong to the class Halobacteria, representing two functional groups: aerobic polysaccharide utilizers and sulfur-respiring anaerobes. The other four strains represent halo(alkali)philic methanogens from the class Methanomicrobia and a recently discovered class Methanonatronarchaeia. A wide range of polar lipids were detected across the 13 strains including dialkyl glycerol diethers (archaeols), membrane-spanning glycerol tetraethers and diether-based cardiolipins. The archaeols contained a range of core lipid structures, including combinations of C20 and C25 isoprenoidal alkyl chains, unsaturations, and hydroxy moieties. Several diether lipids were novel, including: (a) a phosphatidylglycerolhexose (PG-Gly) headgroup, (b) a N,N,N-trimethyl aminopentanetetrol (APT)-like lipid with a methoxy group in place of a hydroxy group on the pentanetetrol, (c) a series of polar lipids with a headgroup with elemental composition of either C12H25NO13S or C12H25NO16S2, and (d) novel cardiolipins containing a putative phosphatidylglycerolphosphate glycerophosphate (PGPGP) polar moiety. We found that the lipid distribution of the 13 strains could be generally separated into two groups, the methanogens (group) and the Halobacteria (class) based on the presence of specific core lipids. Within the methanogens, adaption to a high or more moderate salt concentration resulted in different ratios of glycerol dialkyl glycerol tetraethers (GDGTs) to archaeol. The methanogen Methanosalsum natronophilum AME2T had the most complex diether lipid composition of any of the 13 strains, including hydroxy archaeol and macrocyclic archaeol which we surmise is an order-specific membrane adaption. The zwitterionic headgroups APT and APT-Me were detected only in the Methanomicrobiales member Methanocalculus alkaliphilus AMF2T which also contained the highest level of unsaturated lipids. Only alkaliphilic members of the Natrialbales order contained PGPGP cardiolipins and the PG-Gly headgroup. The four analyzed neutrophilic members of the Halobacteria were characterized by the presence of sulfur-containing headgroups and glycolipids. The presence of cardiolipins with one or more i-C25 alkyl chains, generally termed extended archaeol (EXT-AR), in one of the Methanonatronarchaeia strains was unexpected as only one other order of methanogenic archaea has been reported to produce EXT-AR. We examined this further by looking into the genomic potential of various archaea to produce EXT-AR.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 96%

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New Insights Into the Polar Lipid Composition of Extremely Halo(alkali)philic Euryarchaea From Hypersaline Lakes

et al. 2019

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N atronomonas

Minegishi¹,

Kamekura²

2018

Bergey's Manual of Systematics of Archaea and Bacteria

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Na.tro.no.mo'nas. N.L. n. natron (arbitrarily derived from the Arabic n. natrun or natron ) soda, sodium carbonate; N.L. pref. natrono ‐, pertaining to soda; L. fem. n. monas , monad, unit; N.L. fem. n. Natronomonas , the soda unit. Euryarchaeota / Halobacteria / Halobacteriales / Haloarculaceae / Natronomonas Natronomonas species are rods or pleomorphic shaped (including short rods, flat shapes, tetragons, and cocci), which stain Gram‐negative. Colonies are pigmented red. Chemoorganotrophic, aerobic, and halophilic, requiring at least 2.0 M NaCl. Alkaliphilic or neutrophilic. Alkaliphilic species ( Natronomonas pharaonis ) grow between pH 8.0 and 11.0, with optimum growth at pH 8.5–9.0, while neutrophilic species ( Natronomonas moolapensis and Natronomonas gomsonensis ) grow at pH 5.5–8.5, with optimum growth at pH 7.0–7.5. Membrane polar lipids are glycerol diether analogs of phosphatidylglycerol, phosphatidylglycerophosphate methyl ester, and phosphatidic acid. Phytanyl‐sesterterpanyl moieties (C 20 C 25 ) are present. Unknown phospholipids or glycolipid may exist. Nmn. pharaonis possesses no membrane glycolipids, while Nnm. moolapensis and Nmn. gomsonensis possess an unidentified glycolipid. The structure of the glycolipid observed in Nmn. moolapensis was determined as 1‐(6‐sulfo‐ d ‐glcp/galf‐β1,2‐glycero)‐phospho‐2,3‐diphytanylglycerol. DNA G + C content (mol%) : 61.8–64.3. Type species : Natronomonas pharaonis (Soliman and Trüper 1982) Kamekura, Dyall‐Smith, Upasani, Ventosa and Kates 1997, 856 VP ( Halobacterium pharaonis Soliman and Trüper 1982, 327; Natronobacterium pharaonis Tindall, Ross and Grant 1984, 355), emend. Burns, Janssen, Itoh, Minegishi, Usami, Kamekura and Dyall‐Smith 2010, 1175.

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Phosphate‐Containing Glycolipids: A Review on Synthesis and Bioactivity

Pinheiro,

Freitas,

Branco

2024

ChemMedChem

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Phosphate‐containing glycolipids (PcGL) are scarcer than the better understood glycolipids. They are composed of arrangements of phosphate, carbohydrates and glycerol units and are always found associated with lipids. PcGL are often found associated with cell membranes, meaning their roles concern cell interactions. This article aims to provide an up‐to‐date overview of the existing knowledge and research on PcGL, emphasizing their synthesis and wide range of biological activities. When it comes to the synthesis of PcGL compounds, the strategies for glycosylation mainly rely on the thioglycoside donor, the trichloroacetmaidate donor and halide donor strategies, while phosphorylation is stapled and falls on either phosphite chemistry or phosphoryl chloride chemistry. Certain bacteria utilize PcGLs in their pathogenicity, triggering an inflammatory response within the host's defense mechanisms. The best‐known examples of these structures are teichoic acids, lipopolysaccharide and the capsular polysaccharide found in bacteria, all of which are frequently implicated in bacterial infections. Given the degree of variability within PcGL structures, they were found to display a wide range of bioactivities. PcGL compounds were found to: (1) have anti‐metastatic properties, (2) behave as agonists or antagonists of platelet aggregation, (3) be mostly pro‐inflammatory, (4) display antifungal and antibiotic activity and (5) have neurogenic activity.

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Novel sulfated phosphoglycolipids from Natronomonas moolapensis

Cited by 3 publications

References 51 publications

New Insights Into the Polar Lipid Composition of Extremely Halo(alkali)philic Euryarchaea From Hypersaline Lakes

New Insights Into the Polar Lipid Composition of Extremely Halo(alkali)philic Euryarchaea From Hypersaline Lakes

N atronomonas

Phosphate‐Containing Glycolipids: A Review on Synthesis and Bioactivity

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