Hydroxy fatty acids in Bacteroides species: D-(--)-3-hydroxy-15-methylhexadecanoate and its homologs

Mayberry, W. R.

doi:10.1128/jb.143.2.582-587.1980

Cited by 51 publications

(21 citation statements)

References 13 publications

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“…Bacteroides are known to produce branched-chain fatty acids although from our MS/MS analysis it was not possible to definitively assign whether the glycines were acylated with straight or branched-chain acyl groups (e.g. 16:0 or methyl-15:0) or if they were iso- or anteiso-branched (28). Importantly, we could not detect any acylated glycine in the Δ glsB mutant (see Table 2).…”

Section: Resultsmentioning

confidence: 95%

Characterization of the role of glycine lipids inBacteroides thetaiotaomicron

Lynch

Tammireddy

Doherty

et al. 2018

Preprint

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18Acylated amino acids function as important components of the cellular membrane in some 19 bacteria. Biosynthesis is initiated by the N-acylation of the amino acid and this is followed by 20 subsequent O-acylation of the acylated molecule resulting in the production of the mature 21 diacylated amino acid lipid. In this study we use both genetics and liquid chromatography- 22 mass spectrometry (LC-MS) to characterize the biosynthesis and function of novel diacylated 23 glycine lipid (GL) species in Bacteroides thetaiotaomicron. We, and others, have previously 24 reported the identification of a gene, named glsB in this study, that encodes a N- 25 acyltransferase activity responsible for the production of a monoacylated glycine called N-26 acyl-3-hydroxy-palmitoyl glycine (or commendamide). In all of the Bacteroidales genomes so 27 far sequenced the glsB gene is located immediately downstream from a gene, named glsA, 28 also predicted to encode a protein with acyltransferase activity. We use LC-MS to show that 29 co-expression of glsB and glsA results in the production of GL in Escherichia coli. We 30 constructed a deletion mutant of the glsB gene in B. thetaiotaomicron and we confirm that 31 glsB is required for the production of GL in B. thetaiotaomicron. Moreover, we show that glsB 32 is important for the ability of B. thetaiotaomicron to adapt to stress and colonize the 33 mammalian gut. Therefore, this report is the first to describe the genetic requirements for 34 the biosynthesis of GL, a novel diacylated amino acids species that contributes to fitness in 35 the human gut bacterium, B. thetaiotaomicron. 36 37 38 39 42 healthy human gut microbiota (1). The gut-associated Bacteroidetes are required to digest 43 complex dietary glycans into short-chain fatty acids (such as acetate and propionate) that 44 are accessible to the host (2-4). A longitudinal study in infants has revealed the presence of 45 Bacteroides in the infant gut within 1 week of birth and some species of Bacteroides have 46 been shown to utilize the polysaccharides present in human breast milk (5, 6). Therefore it 47 has been suggested that Bacteroides may have an important role during the early 48 development of the infant gut (6). 49 50Acylated amino acids can be found in the membranes of many bacteria (7, 8). The best-51 characterized, and most widespread, acylated amino acid is ornithine lipid (OL). OL contains 52 a 3'-hydroxy fatty acid group attached by an amide linkage to the a-amino group of 53 ornithine with a second fatty acid group ester linked to the 3'-hydroxy group of the first 54 fatty acid (9). The genetics of OL production was first described in Sinorhizobium meliloti 55 where it was shown that a N-acyltransferase encoded by olsB catalysed the attachment of 56 the first fatty acid group to ornithine, resulting in monoacylated ornithine or lyso-OL (10). 57 The second fatty acid was subsequently attached to lyso-OL through the activity of an O-58 acyltransferase encoded by olsA, resulting in the producti...

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Section: Resultsmentioning

confidence: 95%

Characterization of the role of glycine lipids inBacteroides thetaiotaomicron

Lynch

Tammireddy

Doherty

et al. 2018

Preprint

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“…Compared to Bacteroides spp., P. cerevisiophilus LPS are different in that they contain dOclA, which is absent from Bacteroides LPS [ 19 21], and in that their fatty acid compositions are fundamentally different [28,29]. According to Wollenweber et al [28], lipopolysaccharides of Bacteroides spp.…”

Section: Discussionmentioning

confidence: 99%

Characterization of lipopolysaccharides of Pectinatus cerevisiophilus

Helander

1983

FEMS Microbiology Letters

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“…GC/MS fatty acid analysis of the lipid A revealed mainly the presence of four hydroxy fatty acids: OH‐C12:0; OH‐C13:0; OH‐C20:0, which showed a based peak at m/z 103 characteristic of 3‐OH methyl esters,19, 28 and 27‐OH‐C28:0 which showed a diagnostic ion of m/z 410 (M‐44, loss of acetaldehyde) 29. In addition, as main saturated fatty acids, C16:0, C17:0, C18:0 and C 20:0 were observed (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…To carry out fatty acid analysis, the organic phase obtained after acid hydrolysis of the lipid A described above was further dried and methylated with 1 N HCl/MeOH for 2 h at 65°C 19. The solution was evaporated under N 2 and analyzed.…”

Section: Methodsmentioning

confidence: 99%

A matrix‐assisted laser desorption/ionization mass spectrometry approach to the lipid A from Mesorhizobium loti

Casabuono

D'antuono

Sato

et al. 2006

Rapid Comm Mass Spectrometry

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The isolation, purification and analysis of the lipid A obtained from Mesorhizobium loti Ayac 1 BII strain is presented. Analysis of the carbohydrate moiety after acid hydrolysis by high-pH anion-exchange chromatography with pulse amperometric detection (HPAEC-PAD) showed the presence of glucosamine and galacturonic acid as the only sugar components. Gas chromatographic (GC) and GC/mass spectrometric (MS) analysis of the fatty acids revealed the presence of 3-OH-C12:0; 3-OH-C13:0; 3-OH-C20:0 and 27-OH-C28:0 among the major hydroxylated species. In addition, C16:0, C17:0, C18:0 and C 20:0 were shown as main saturated fatty acids. Different polyacylated species were evidenced by thin layer chromatography of lipid A, allowing the purification of two fractions. Ultraviolet matrix-assisted laser desorption/ionization time-of-flight (UV-MALDI-TOF) MS analysis with different matrices, in the positive- and negative-ion mode, was performed. The fast moving component revealed the presence of hexa-acylated species, varying in the fatty acid composition. Species containing three 3-OH fatty acids and a 27-OH-C28:0 fatty acid were observed. Individual ions within this family differ by +/-14 mass units. The slow moving component was enriched mainly in penta-acylated species. Among them, three subgroups were detected: the major one compatible with the sugar core bearing two 3-OH 20:0 fatty acids, a 3-OH 13:0 or a 3-OH 12:0 fatty acid, a 27-OH 28:0 fatty acid and one saturated fatty acid. Each signal differs in a C18:0 acyl unit from the corresponding hexa-acylated family. On the other hand, a subgroup bearing one 3-OH 20:0 fatty acid, one 27-OH 28:0 fatty acid and two non-polar fatty acids was shown. A minor subgroup compatible with structures containing two hydroxylated and three non-polar fatty acids was also detected. The results obtained showed that nor-harmane was an excellent matrix for charged lipid A structural studies in both, positive and negative ion modes.

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Hydroxy fatty acids in Bacteroides species: D-(--)-3-hydroxy-15-methylhexadecanoate and its homologs

Cited by 51 publications

References 13 publications

Characterization of the role of glycine lipids inBacteroides thetaiotaomicron

Characterization of the role of glycine lipids inBacteroides thetaiotaomicron

Characterization of lipopolysaccharides of Pectinatus cerevisiophilus

A matrix‐assisted laser desorption/ionization mass spectrometry approach to the lipid A from Mesorhizobium loti

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