Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
 
NCBI PubMed ID: 31103599
Publication DOI: 10.1016/j.fgb.2019.05.003
Journal NLM ID: 9607601
Publisher: Orlando, FL : Academic Press / Elsevier
Correspondence: sandrockstaff.uni-marburg.de
Institutions: Department of Biology, Philipps-Universität Marburg, Marburg, Germany, Department of Chemistry, Philipps-Universität Marburg, Marburg, Germany

Mannosylerythritol lipids (MELs) are surface active molecules produced by many basidiomycetous fungi. MELs consist of a mannosylerythritol disaccharide, which is acylated with short and medium chain fatty acids at the mannosyl moiety. A gene cluster composed of five genes is required for MEL biosynthesis. Here we show that the plant pathogenic fungus Ustilago hordei secretes these glycolipids under nitrogen starvation conditions. In contrast to MELs produced by the closely related fungus Ustilago maydis those secreted by U. hordei are mostly mono-acetylated and contain a different mixture of acyl groups. Cross-species complementation between these fungi revealed that these differences result from different catalytic activities of the acetyltransferase Mat1 and the acyltransferases Mac1 and Mac2. U. maydis mat1 mutants expressing the homologous mat1 gene from U. hordei produced mostly mono-acetylated variants and lack di-acetylated MELs normally produced by U. maydis. Furthermore, we determined that the acyltransferase Mac1 acylates the mannosylerythritol moiety at position C2 while Mac2 acylates C3. The identification of decorating enzymes with different substrate specificities will allow the tailor-made production of novel subsets of MELs.

acetyltransferase, acyltransferase, mannosylerythritol lipids, smut fungi, heterologous expression

Structure type: oligomer
Location inside paper: Fig. 1, a, MEL-A
Trivial name: MEL-A (mannosylerythritol lipid), mannosylerythritol-A, MEL-A, mannosylerythritol, mannosylerythritol-A, MEL-A
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
 
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, TLC, HPLC, Southern blotting, extraction, ESI-ICR-MS/MS, cloning, cell growth, ESI-FTICR-MS
 
Related record ID(s): 41839, 41840, 42095, 43338, 44224, 44226, 44229, 44232, 45939, 48588, 48740, 49744, 49762, 49763, 49764
NCBI Taxonomy refs (TaxIDs): 5270, 1128400
Show glycosyltransferases
 

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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
 
NCBI PubMed ID: 31103599
Publication DOI: 10.1016/j.fgb.2019.05.003
Journal NLM ID: 9607601
Publisher: Orlando, FL : Academic Press / Elsevier
Correspondence: sandrockstaff.uni-marburg.de
Institutions: Department of Biology, Philipps-Universität Marburg, Marburg, Germany, Department of Chemistry, Philipps-Universität Marburg, Marburg, Germany

Mannosylerythritol lipids (MELs) are surface active molecules produced by many basidiomycetous fungi. MELs consist of a mannosylerythritol disaccharide, which is acylated with short and medium chain fatty acids at the mannosyl moiety. A gene cluster composed of five genes is required for MEL biosynthesis. Here we show that the plant pathogenic fungus Ustilago hordei secretes these glycolipids under nitrogen starvation conditions. In contrast to MELs produced by the closely related fungus Ustilago maydis those secreted by U. hordei are mostly mono-acetylated and contain a different mixture of acyl groups. Cross-species complementation between these fungi revealed that these differences result from different catalytic activities of the acetyltransferase Mat1 and the acyltransferases Mac1 and Mac2. U. maydis mat1 mutants expressing the homologous mat1 gene from U. hordei produced mostly mono-acetylated variants and lack di-acetylated MELs normally produced by U. maydis. Furthermore, we determined that the acyltransferase Mac1 acylates the mannosylerythritol moiety at position C2 while Mac2 acylates C3. The identification of decorating enzymes with different substrate specificities will allow the tailor-made production of novel subsets of MELs.

acetyltransferase, acyltransferase, mannosylerythritol lipids, smut fungi, heterologous expression

Structure type: oligomer
Location inside paper: Fig. 1, a, MEL-B
Trivial name: MEL-B
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
 
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, TLC, HPLC, Southern blotting, extraction, ESI-ICR-MS/MS, cloning, cell growth, ESI-FTICR-MS
 
Related record ID(s): 42098, 42103, 42284, 43339, 44225, 44227, 44230, 44233, 44237, 47169, 48589, 49745, 49761, 49763, 49764
NCBI Taxonomy refs (TaxIDs): 5270, 1128400
Show glycosyltransferases
 

Convert structure to SMILES & 3D GlycoCT β-test WURCS 2.0 GLYCAM GlycoCT (external) GlycoCT XML (ext) GlydeII XML LinUCS Fragmentize Mol. weight

Simulate NMR spectra (GODDESS)

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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
 
NCBI PubMed ID: 31103599
Publication DOI: 10.1016/j.fgb.2019.05.003
Journal NLM ID: 9607601
Publisher: Orlando, FL : Academic Press / Elsevier
Correspondence: sandrockstaff.uni-marburg.de
Institutions: Department of Biology, Philipps-Universität Marburg, Marburg, Germany, Department of Chemistry, Philipps-Universität Marburg, Marburg, Germany

Mannosylerythritol lipids (MELs) are surface active molecules produced by many basidiomycetous fungi. MELs consist of a mannosylerythritol disaccharide, which is acylated with short and medium chain fatty acids at the mannosyl moiety. A gene cluster composed of five genes is required for MEL biosynthesis. Here we show that the plant pathogenic fungus Ustilago hordei secretes these glycolipids under nitrogen starvation conditions. In contrast to MELs produced by the closely related fungus Ustilago maydis those secreted by U. hordei are mostly mono-acetylated and contain a different mixture of acyl groups. Cross-species complementation between these fungi revealed that these differences result from different catalytic activities of the acetyltransferase Mat1 and the acyltransferases Mac1 and Mac2. U. maydis mat1 mutants expressing the homologous mat1 gene from U. hordei produced mostly mono-acetylated variants and lack di-acetylated MELs normally produced by U. maydis. Furthermore, we determined that the acyltransferase Mac1 acylates the mannosylerythritol moiety at position C2 while Mac2 acylates C3. The identification of decorating enzymes with different substrate specificities will allow the tailor-made production of novel subsets of MELs.

acetyltransferase, acyltransferase, mannosylerythritol lipids, smut fungi, heterologous expression

Structure type: oligomer
Location inside paper: Fig. 1, a, MEL-C
Trivial name: MEL-C (mannosylerythritol lipid), mannosylerythritol-C, MEL-C, mannosylerythritol, mannosylerythritol-C, MEL-C
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
 
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, TLC, HPLC, Southern blotting, extraction, ESI-ICR-MS/MS, cloning, cell growth, ESI-FTICR-MS
 
Related record ID(s): 42097, 42099, 42104, 43340, 44228, 44231, 44234, 45941, 48590, 49746, 49761, 49762, 49764
NCBI Taxonomy refs (TaxIDs): 5270, 1128400
Show glycosyltransferases
 

Convert structure to SMILES & 3D GlycoCT β-test WURCS 2.0 GLYCAM GlycoCT (external) GlycoCT XML (ext) GlydeII XML LinUCS Fragmentize Mol. weight

Simulate NMR spectra (GODDESS)

Show Sweet-II 3D model Generate 3D coords by GLYCAM

Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
 
NCBI PubMed ID: 31103599
Publication DOI: 10.1016/j.fgb.2019.05.003
Journal NLM ID: 9607601
Publisher: Orlando, FL : Academic Press / Elsevier
Correspondence: sandrockstaff.uni-marburg.de
Institutions: Department of Biology, Philipps-Universität Marburg, Marburg, Germany, Department of Chemistry, Philipps-Universität Marburg, Marburg, Germany

Mannosylerythritol lipids (MELs) are surface active molecules produced by many basidiomycetous fungi. MELs consist of a mannosylerythritol disaccharide, which is acylated with short and medium chain fatty acids at the mannosyl moiety. A gene cluster composed of five genes is required for MEL biosynthesis. Here we show that the plant pathogenic fungus Ustilago hordei secretes these glycolipids under nitrogen starvation conditions. In contrast to MELs produced by the closely related fungus Ustilago maydis those secreted by U. hordei are mostly mono-acetylated and contain a different mixture of acyl groups. Cross-species complementation between these fungi revealed that these differences result from different catalytic activities of the acetyltransferase Mat1 and the acyltransferases Mac1 and Mac2. U. maydis mat1 mutants expressing the homologous mat1 gene from U. hordei produced mostly mono-acetylated variants and lack di-acetylated MELs normally produced by U. maydis. Furthermore, we determined that the acyltransferase Mac1 acylates the mannosylerythritol moiety at position C2 while Mac2 acylates C3. The identification of decorating enzymes with different substrate specificities will allow the tailor-made production of novel subsets of MELs.

acetyltransferase, acyltransferase, mannosylerythritol lipids, smut fungi, heterologous expression

Structure type: oligomer
Location inside paper: Fig. 1, a, MEL-D
Trivial name: mannosylerythritol, MEL-D
Compound class: glycolipid
Contained glycoepitopes: IEDB_114707,IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
 
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, TLC, HPLC, Southern blotting, extraction, ESI-ICR-MS/MS, cloning, cell growth, ESI-FTICR-MS
 
Related record ID(s): 44239, 48235, 48744, 49747, 49761, 49762, 49763
NCBI Taxonomy refs (TaxIDs): 5270, 1128400
Show glycosyltransferases
 

Convert structure to SMILES & 3D GlycoCT β-test WURCS 2.0 GLYCAM GlycoCT (external) GlycoCT XML (ext) GlydeII XML LinUCS Fragmentize Mol. weight

Simulate NMR spectra (GODDESS)

Show Sweet-II 3D model Generate 3D coords by GLYCAM