Structural analysis of glucosylceramides (GlcCer) from species of the Pseudallescheria/Scedosporium complex

Calixto, Renata O.R.; Rollin-Pinheiro, Rodrigo; Silva, Mariana I.D. da; Liporagi-Lopes, Livia Cristina; Vieira, Jardel M.; Sassaki, Guilherme L.; Barreto‐Bergter, Eliana

doi:10.1016/j.funbio.2015.05.007

Cited by 12 publications

(27 citation statements)

References 24 publications

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“…GlcCer structures similar to those previously described for S. apiospermum , S. aurantiacum and P. minutispora have been isolated in several fungi from the Pseudallescheria / Scedosporium complex (Calixto et al, 2016). Thus, elucidation of the primary structure of fungal GlcCer that function as virulence determinant is important for understanding the mechanism of fungal pathogenicity.…”

Section: Introductionmentioning

confidence: 60%

“…Crude lipid extraction and GlcCer species purification were carried out as previously described (Rollin-Pinheiro et al, 2014; Calixto et al, 2016). After extraction with mixtures of chloroform and methanol followed by different steps of chromatographic separation, orcinol-reactive bands were detected by HPTLC.…”

Section: Resultsmentioning

confidence: 99%

“…Mass spectrometry was carried out by electrospray ionization (ESI-MS) in positive mode according to Calixto et al (2016).…”

Section: Methodsmentioning

confidence: 99%

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Glucosylceramides From Lomentospora prolificans Induce a Differential Production of Cytokines and Increases the Microbicidal Activity of Macrophages

et al. 2019

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Lomentospora prolificans is an emerging opportunistic fungus with a high resistance to antifungal agents and it can cause localized infections in immunocompetent patients and disseminated infections with a high mortality rate in immunosuppressed patients. Glucosylceramides (GlcCer) are synthetized in the majority of known fungal pathogens. They are bioactive molecules presenting different functions, such as involvement in fungal growth and morphological transitions in several fungi. The elucidation of the primary structure of the fungal surface glycoconjugates could contribute for the understanding of the mechanisms of pathogenicity. In this work, GlcCer species were isolated from mycelium and conidia forms of L. prolificans and their chemical structures were elucidated by mass spectrometry (ESI-MS). GlcCer purified from both forms presented a major species at m/z 750 that corresponds to N -2-hydroxyhexadecanoyl-1-β- D -glucopyranosyl-9-methyl-4,8-sphingadienine. Monoclonal antibodies against GlcCer could recognize L. prolificans GlcCer species from mycelium and conidia, suggesting a conserved epitope in fungal GlcCer. In addition, in vivo assays showed that purified GlcCer species from both forms was able to induce a high secretion of pro-inflammatory cytokines by splenocytes. GlcCer species also promote the recruitment of polymorphonuclear, eosinophils, small peritoneal macrophage (SPM) and mononuclear cells to the peritoneal cavity. GlcCer species were also able to induce the oxidative burst by peritoneal macrophages with NO and superoxide radicals production, and to increase the killing of L. prolificans conidia by peritoneal macrophages. These results indicate that GlcCer species from L. prolificans are a potent immune response activator.

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Section: Introductionmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 99%

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Glucosylceramides From Lomentospora prolificans Induce a Differential Production of Cytokines and Increases the Microbicidal Activity of Macrophages

et al. 2019

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“…CMHs were analyzed by electrospray ionization (ESI-MS) in positive (ESI+) ion mode, using an ESI-ion Trap instrument (Model Amazon SL, Bruker, Germany). CMHs were diluted in chloroform/methanol/water (5:4:1 v / v ), containing 1 mM lithium chloride and analyzed via direct injection using a microsyringe pump (Hamilton) [ 42 ]. Nitrogen was used as nebulizer and carrier gas.…”

Section: Methodsmentioning

confidence: 99%

Monohexosylceramides from Rhizopus Species Isolated from Brazilian Caatinga: Chemical Characterization and Evaluation of Their Anti-Biofilm and Antibacterial Activities

et al. 2018

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Monohexosylceramides (CMHs) are highly conserved fungal glycosphingolipids playing a role in several cellular processes such as growth, differentiation and morphological transition. In this study, we report the isolation, purification and chemical characterization of CMHs from Rhizopus stolonifer and R. microspores. Using positive ion mode ESI-MS, two major ion species were observed at m/z 750 and m/z 766, respectively. Both ion species consisted of a glucose/galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to a hydroxylated C16:0 fatty acid. The antimicrobial activity of CMH was evaluated against Gram positive and Gram negative bacteria using the agar diffusion assay. CMH from both Rhizopus species inhibited the growth of Bacillus terrae, Micrococcus luteus (M. luteus) and Pseudomonas stutzeri (P. stutzeri) with a MIC50 of 6.25, 6.25 and 3.13 mg/mL, respectively. The bactericidal effect was detected only for M. luteus and P. stutzeri, with MBC values of 25 and 6.25 mg/mL, respectively. Furthermore, the action of CMH on the biofilm produced by methicillin-resistant Staphylococcus aureus (MRSA) was analyzed using 12.5 and 25 mg/mL of CMH from R. microsporus. Total biofilm biomass, biofilm matrix and viability of the cells that form the biofilm structure were evaluated. CMH from R. microsporus was able to inhibit the MRSA biofilm formation in all parameters tested.

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“…In contrast with mammalian glycosphingolipids, fungal GlcCer shows some differences in the ceramide portion such as the presence of C-8 unsaturation and a methyl group in the C-9 of the sphingosine (Figure 3). [11] and Calixto et al [24].…”

Section: Structural Characterization Of Glccermentioning

confidence: 95%

Fungal Hyphal Growth – Spitzenkörper versus Apical Vesicle Crescent

Rollin-Pinheiro¹,

Jv²,

Mc³

et al. 2017

Fungal Genom Biol

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Pseudallescheria/Scedosporium species are filamentous fungi widely distributed in nature. Some are considered emerging pathogen due to its clinical importance, especially in immunocompromised patients. During the last few years, many virulence factors have been described, some of them being molecules localized on the fungal cell wall, such as glycoproteins, polysaccharides and glycolipids. In this context, one glycosphingolipid specifically, glucosylceramide (GlcCer), has been chemically identified and its biological roles have been described. GlcCer is a conserved structure in the Pseudallescheria/Scedosporium complex and also in other fungal species. In addition, it plays important roles in fungal growth and differentiation, host-pathogen interaction, immune response modulation and it has been considering a potential target for new antifungal drugs. The use of monoclonal antibodies has shown a possible synergism with current antifungal drugs use in the clinical settings. Therefore, the study of this class of lipids is promising in order to clarify the Pseudallescheria/Scedosporium growth, pathogenesis and fungal treatment.

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Structural analysis of glucosylceramides (GlcCer) from species of the Pseudallescheria/Scedosporium complex

Cited by 12 publications

References 24 publications

Glucosylceramides From Lomentospora prolificans Induce a Differential Production of Cytokines and Increases the Microbicidal Activity of Macrophages

Glucosylceramides From Lomentospora prolificans Induce a Differential Production of Cytokines and Increases the Microbicidal Activity of Macrophages

Monohexosylceramides from Rhizopus Species Isolated from Brazilian Caatinga: Chemical Characterization and Evaluation of Their Anti-Biofilm and Antibacterial Activities

Fungal Hyphal Growth – Spitzenkörper versus Apical Vesicle Crescent

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