Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i>
<i>Sphaerostilbella toxica</i> is a mycoparasitic fungus that can be found parasitizing wood-decay basidiomycetes in the southern USA. Organic solvent extracts of fermented strains of <i>S. toxica</i> exhibited potent antimicrobial activity, including potent growth inhibition...
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doaj-1e4c7e09fb364cdb98ff5874ecaff1862020-11-25T03:30:30ZengMDPI AGBiomolecules2218-273X2020-09-01101371137110.3390/biom10101371Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i>Bruno Perlatti0Connie B. Nichols1J. Andrew Alspaugh2James B. Gloer3Gerald F. Bills4Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, TX 77054, USADepartments of Medicine and Molecular Genetics & Microbiology, Duke University Medical Center, Durham, NC 27710, USADepartments of Medicine and Molecular Genetics & Microbiology, Duke University Medical Center, Durham, NC 27710, USADepartment of Chemistry, University of Iowa, Iowa City, IA 52242, USATexas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, TX 77054, USA<i>Sphaerostilbella toxica</i> is a mycoparasitic fungus that can be found parasitizing wood-decay basidiomycetes in the southern USA. Organic solvent extracts of fermented strains of <i>S. toxica</i> exhibited potent antimicrobial activity, including potent growth inhibition of human pathogenic yeasts <i>Candida albicans</i> and <i>Cryptococcus neoformans,</i> the respiratory pathogenic fungus <i>Aspergillus fumigatus</i>, and the Gram-positive bacterium <i>Staphylococcus aureus</i>. Bioassay-guided separations led to the purification and structure elucidation of new peptaibiotics designated as sphaerostilbellins A and B. Their structures were established mainly by analysis of NMR and HRMS data, verification of amino acid composition by Marfey’s method, and by comparison with published data of known compounds. They incorporate intriguing structural features, including an N-terminal 2-methyl-3-oxo-tetradecanoyl (MOTDA) residue and a C-terminal putrescine residue. The minimal inhibitory concentrations for sphaerostilbellins A and B were measured as 2 μM each for <i>C. neoformans</i>, 1 μM each for <i>A. fumigatus</i>, and 4 and 2 μM, respectively, for <i>C. albicans</i>. Murine macrophage cells were unaffected at these concentrations.https://www.mdpi.com/2218-273X/10/10/1371antifungalsHypocreaceaemycoparasitenonribosomal peptideputrescinesecondary metabolite |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Bruno Perlatti Connie B. Nichols J. Andrew Alspaugh James B. Gloer Gerald F. Bills |
spellingShingle |
Bruno Perlatti Connie B. Nichols J. Andrew Alspaugh James B. Gloer Gerald F. Bills Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> Biomolecules antifungals Hypocreaceae mycoparasite nonribosomal peptide putrescine secondary metabolite |
author_facet |
Bruno Perlatti Connie B. Nichols J. Andrew Alspaugh James B. Gloer Gerald F. Bills |
author_sort |
Bruno Perlatti |
title |
Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> |
title_short |
Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> |
title_full |
Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> |
title_fullStr |
Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> |
title_full_unstemmed |
Sphaerostilbellins, New Antimicrobial Aminolipopeptide Peptaibiotics from <i>Sphaerostilbella toxica</i> |
title_sort |
sphaerostilbellins, new antimicrobial aminolipopeptide peptaibiotics from <i>sphaerostilbella toxica</i> |
publisher |
MDPI AG |
series |
Biomolecules |
issn |
2218-273X |
publishDate |
2020-09-01 |
description |
<i>Sphaerostilbella toxica</i> is a mycoparasitic fungus that can be found parasitizing wood-decay basidiomycetes in the southern USA. Organic solvent extracts of fermented strains of <i>S. toxica</i> exhibited potent antimicrobial activity, including potent growth inhibition of human pathogenic yeasts <i>Candida albicans</i> and <i>Cryptococcus neoformans,</i> the respiratory pathogenic fungus <i>Aspergillus fumigatus</i>, and the Gram-positive bacterium <i>Staphylococcus aureus</i>. Bioassay-guided separations led to the purification and structure elucidation of new peptaibiotics designated as sphaerostilbellins A and B. Their structures were established mainly by analysis of NMR and HRMS data, verification of amino acid composition by Marfey’s method, and by comparison with published data of known compounds. They incorporate intriguing structural features, including an N-terminal 2-methyl-3-oxo-tetradecanoyl (MOTDA) residue and a C-terminal putrescine residue. The minimal inhibitory concentrations for sphaerostilbellins A and B were measured as 2 μM each for <i>C. neoformans</i>, 1 μM each for <i>A. fumigatus</i>, and 4 and 2 μM, respectively, for <i>C. albicans</i>. Murine macrophage cells were unaffected at these concentrations. |
topic |
antifungals Hypocreaceae mycoparasite nonribosomal peptide putrescine secondary metabolite |
url |
https://www.mdpi.com/2218-273X/10/10/1371 |
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