Unveiling the biodiversity of lipid species in Corynebacteria- characterization of the uncommon lipid families in C. glutamicum and pathogen C. striatum by mass spectrometry

Wang, Hay-Yan J.; Tatituri, Raju V. V.; Goldner, Nicholas K.; Dantas, Gautam; Hsu, Fong‐Fu

doi:10.1016/j.biochi.2020.07.002

Cited by 8 publications

(19 citation statements)

References 28 publications

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“…25 The findings were in accordance with data obtained via GC−MS, FAB-MS, and proton NMR by Wolucka et al 34 on two GlcA-DAG isolated from Mycobacterum smegmatis, both containing a C16:0 and either a C19:0 or a C18:1 acyl chain. The proposed fragmentation rules were confirmed by Hsu and co-workers 26 in both negative and positive polarities. In negative-ion mode, the regiochemistry of a GlcA-DAG can be easily assigned looking at the neutral loss of fatty acyl chains as ketenes (KE), since this fragmentation prevails for the chain linked to the sn-2 position.…”

Section: Resultssupporting

confidence: 58%

“…In negative-ion mode, the regiochemistry of a GlcA-DAG can be easily assigned looking at the neutral loss of fatty acyl chains as ketenes (KE), since this fragmentation prevails for the chain linked to the sn-2 position. 25,26,34 Wang et al 35 reported the synthesis of polyunsaturated fatty acyl chains-containing GlcA-DAG through direct glycosylation; these compounds were characterized via NMR and LC−MS/MS analysis and compared with those found in natural products by Okazaki et al 12 Based on the regiochemical similarity with SQDG, which are sulfurcontaining anionic glycolipids occurring in the thylakoid membranes, the neutral loss of acyl chains as fatty acids, prevailing from the sn-1 position of glycerol, was incorrectly invoked to infer the regiochemistry of GlcA-DAG. As already proved, 36−38 the regiochemistry of SQDG can be easily assessed in negative ion mode, considering that the gas-phase neutral loss of fatty acids (FA) from the sn-1 position is empirically more abundant than that located on the sn-2 one.…”

Section: Resultsmentioning

confidence: 99%

“…A standard nomenclature system for 1,2-diacyl-3-O-glucuronosylglycerols has not been defined so far, as they are abbreviated as DGGA, 9 GlcAD, 1 GlcA-DG, 8 GlcAGroAc 2 , 25 and GlcADG, 12 according to the case. Herein, we use the abbreviation recently proposed by Hsu, 26 i.e., GlcA-DAG, slightly modified to include, when necessary, an indication to the anomeric configuration of GlcA. Acylated species were indicated as acyl-GlcA-DAG and acyl-GlcA-MAG.…”

Section: Methodsmentioning

confidence: 99%

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Characterization of Glucuronosyl-diacyl/monoacylglycerols and Discovery of Their Acylated Derivatives in Tomato Lipid Extracts by Reversed-Phase Liquid Chromatography with Electrospray Ionization and Tandem Mass Spectrometry

Ventura

Calvano

Cinquepalmi

et al. 2021

J. Am. Soc. Mass Spectrom.

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Glucuronic acid containing diacylglycerols (3-(O-α-d-glucuronopyranosyl)-1,2-diacyl-sn-glycerols, GlcA-DAG) are glycolipids of plant membranes especially formed under phosphate-depletion conditions. An analytical approach for the structural characterization of GlcA-DAG in red ripe tomato (Solanum lycopersicum L.) extracts, based on reversed-phase liquid chromatography (RPLC) coupled with electrospray ionization (ESI) and tandem mass spectrometry (MS/MS) using a linear ion trap, is described in this paper. At least 14 GlcA-DAG (R1/R2) species, including four regioisomers, containing three predominant fatty acyl chains C16:0, C18:2, and C18:3, were identified for the first time. Moreover, 29 GlcA-DAG acylated on the glucuronosyl ring (acyl-R3 GlcA-DAG) were discovered, alongside 15 acylated lyso-forms, i.e., acylated 3-(O-α-d-glucuronosyl)monoacylglycerols, abbreviated as acyl-R3 GlcA-MAG (R1/0) or (0/R2). Although many of these acylated lyso-forms were isomeric with GlcA-DAG (i.e., acyl chains with equivalent sum composition), they were successfully separated by reversed-phase liquid chromatography (RPLC) using a solid-core C18 column packed with 2.6 μm particle size. Tandem MS (and eventually MS3) data obtained from sodium adducts ([M + Na]+) and deprotonated molecules ([M – H]−) were fundamental to detect diagnostic product ions related to the glucuronosyl ring and then determine the identity of all investigated glycolipids, especially to recognize the acyl chain linked to the ring. A classification of GlcA-MAG, GlcA-DAG, and acylated GlcA-DAG and GlcA-MAG was generated by an in house-built database. The discovery of acylated derivatives emphasized the already surprising heterogeneity of glucuronic acid-containing mono- and diacylglycerols in tomato plants, stimulating interesting questions on the role played by these glycolipids.

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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Characterization of Glucuronosyl-diacyl/monoacylglycerols and Discovery of Their Acylated Derivatives in Tomato Lipid Extracts by Reversed-Phase Liquid Chromatography with Electrospray Ionization and Tandem Mass Spectrometry

Ventura

Calvano

Cinquepalmi

et al. 2021

J. Am. Soc. Mass Spectrom.

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“…As such, our finding shed new light on current endeavors to use C. glutamicum as lipid production platform ( Takeno et al, 2013 ) and on pathogenicity of relatives ( Burkovski, 2018 ), in that key enzymes of the lipid biosynthesis pathway ( Figure 4 ) differing in abundance between the WT and Δcg2767 / Δcg0049 strain are direct targets or indirectly regulated by rhomboids. This might contribute to the high lipid diversity of corynebacteria ( Klatt et al, 2018 ; Wang et al, 2020 ).…”

Section: Discussionmentioning

confidence: 99%

Functional Genomics Uncovers Pleiotropic Role of Rhomboids in Corynebacterium glutamicum

et al. 2022

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The physiological role of ubiquitous rhomboid proteases, membrane-integral proteins that cleave their substrates inside the lipid bilayer, is still ill-defined in many prokaryotes. The two rhomboid genes cg0049 and cg2767 of Corynebacterium glutamicum were mutated and it was the aim of this study to investigate consequences in respect to growth phenotype, stress resistance, transcriptome, proteome, and lipidome composition. Albeit increased amount of Cg2767 upon heat stress, its absence did not change the growth behavior of C. glutamicum during exponential and stationary phase. Quantitative shotgun mass spectrometry was used to compare the rhomboid mutant with wild type strain and revealed that proteins covering diverse cellular functions were differentially abundant with more proteins affected in the stationary than in the exponential growth phase. An observation common to both growth phases was a decrease in ribosomal subunits and RNA polymerase, differences in iron uptake proteins, and abundance changes in lipid and mycolic acid biosynthesis enzymes that suggested a functional link of rhomboids to cell envelope lipid biosynthesis. The latter was substantiated by shotgun lipidomics in the stationary growth phase, where in a strain-dependent manner phosphatidylglycerol, phosphatidic acid, diacylglycerol and phosphatidylinositol increased irrespective of cultivation temperature.

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“…The MS 2 spectrum of peak b is identical to that of peak a, and peak b thus probably reflects an isomer. Although glucuronic acid is not a very common head group in intact polar lipids, it has been observed in bacteria and fungi (e.g., Burugupalli et al, 2020;Fontaine et al, 2009;Wang et al, 2020). We therefore tentatively identify these compounds as C 14 :0-N-acylglucuronosyl-aminotriols (Fig.…”

Section: Multi-conjugated Composite Aminotriolsmentioning

confidence: 88%

Novel lipid biomarkers for detecting microbial oxidation of methane in the environment

Smit¹

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Demethylated hopanoids in 'Ca. Methylomirabilis oxyfera' as biomarkers for environmental nitritedependent methane oxidation Published in Organic Geochemistry Chapter 3 Anaerobic methanotrophic archaea of the ANME-2d clade feature lipid composition that differs from other ANME archaea Published in FEMS Microbiology Ecology Chapter 4 Lipid biomarker insights into hydrocarbon sources and microbial communities in the terrestrial mud volcanoes of Sicily, Italy Under review at Organic Geochemistry Chapter 5Analysis of non-derivatized bacteriohopanepolyols using UHPLC-HRMS reveals great structural diversity in environmental lipid assemblages Under review at Organic Geochemistry

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Unveiling the biodiversity of lipid species in Corynebacteria- characterization of the uncommon lipid families in C. glutamicum and pathogen C. striatum by mass spectrometry

Cited by 8 publications

References 28 publications

Characterization of Glucuronosyl-diacyl/monoacylglycerols and Discovery of Their Acylated Derivatives in Tomato Lipid Extracts by Reversed-Phase Liquid Chromatography with Electrospray Ionization and Tandem Mass Spectrometry

Characterization of Glucuronosyl-diacyl/monoacylglycerols and Discovery of Their Acylated Derivatives in Tomato Lipid Extracts by Reversed-Phase Liquid Chromatography with Electrospray Ionization and Tandem Mass Spectrometry

Functional Genomics Uncovers Pleiotropic Role of Rhomboids in Corynebacterium glutamicum

Novel lipid biomarkers for detecting microbial oxidation of methane in the environment

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