Skyllamycins D and E, Non-Ribosomal Cyclic Depsipeptides from Lichen-Sourced Streptomyces anulatus
- Joe BracegirdleJoe BracegirdleSchool of Chemical and Physical Sciences, School of Biological Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by Joe Bracegirdle
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- Peng HouPeng HouSchool of Biological Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by Peng Hou
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- Vincent V. NowakVincent V. NowakSchool of Biological Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by Vincent V. Nowak
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- David F. AckerleyDavid F. AckerleySchool of Biological Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by David F. Ackerley
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- Robert A. Keyzers*Robert A. Keyzers*Email: [email protected]School of Chemical and Physical Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by Robert A. Keyzers
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- Jeremy G. Owen*Jeremy G. Owen*Email: [email protected]School of Biological Sciences and Centre for Biodiscovery, Victoria University of Wellington, Wellington 6012, New ZealandMore by Jeremy G. Owen
Abstract
The skyllamycins are a class of heavily modified, non-ribosomal peptides, first isolated from Streptomyces sp. KY11784. A Streptomyces strain with potent antibiotic activity against Bacillus subtilis was isolated from a sample of the New Zealand lichen Pseudocyphellaria dissimilis. Whole genome sequencing and biosynthetic gene cluster genetic analysis coupled with GNPS LCMS/MS molecular networking revealed that this strain had the capacity to produce skyllamycins, including previously undescribed congeners, and that these were likely the source of the observed biological activity. Guided by the results of the molecular networking, we isolated the previously reported skyllamycins A–C (1–3), along with two new congeners, skyllamycins D (4) and E (5). The structures of these compounds were elucidated using comprehensive 1D and 2D NMR analyses, along with HRESIMS fragmentation experiments. Antibacterial assays revealed that skyllamycin D possessed improved activity against B. subtilis E168 compared to previously reported congeners.
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