Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity
Abstract Secondary metabolic profiling, using UPLC-MSE and molecular networking, revealed the secondary metabolites produced by Serratia marcescens NP10. The NP10 strain co-produced cyclic and open-ring stephensiolides (i.e., fatty acyl chain linked to Thr–Ser–Ser–Ile/Leu–Ile/Leu/Val) and glucosamin...
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| Format: | Article |
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Nature Portfolio
2023-02-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-28502-6 |
| _version_ | 1811166001845239808 |
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| author | Tanya Clements-Decker Marina Rautenbach Wilma van Rensburg Sehaam Khan Marietjie Stander Wesaal Khan |
| author_facet | Tanya Clements-Decker Marina Rautenbach Wilma van Rensburg Sehaam Khan Marietjie Stander Wesaal Khan |
| author_sort | Tanya Clements-Decker |
| collection | DOAJ |
| description | Abstract Secondary metabolic profiling, using UPLC-MSE and molecular networking, revealed the secondary metabolites produced by Serratia marcescens NP10. The NP10 strain co-produced cyclic and open-ring stephensiolides (i.e., fatty acyl chain linked to Thr–Ser–Ser–Ile/Leu–Ile/Leu/Val) and glucosamine derivatives (i.e., fatty acyl chain linked to Val–glucose–butyric/oxo-hexanoic acid), with the structures of sixteen new stephensiolides (L–Y) and three new glucosamine derivatives (L–N) proposed. Genome mining identified sphA (stephensiolides) and gcd (glucosamine derivatives) gene clusters within Serratia genomes available on NBCI using antiSMASH, revealing specificity scores of the adenylation-domains within each module that corroborates MSE data. Of the nine RP-HPLC fractions, two stephensiolides and two glucosamine derivatives exhibited activity against Staphylococcus aureus (IC50 of 25–79 µg/mL). 1H NMR analysis confirmed the structure of the four active compounds as stephensiolide K, a novel analogue stephensiolide U, and glucosamine derivatives A and C. Stephensiolides K and U were found to cause membrane depolarisation and affect the membrane permeability of S. aureus, while glucosamine derivatives A and C primarily caused membrane depolarisation. New members of the stephensiolide and glucosamine derivative families were thus identified, and results obtained shed light on their antibacterial properties and mode of membrane activity. |
| first_indexed | 2024-04-10T15:45:18Z |
| format | Article |
| id | doaj.art-64c13157a1a349d5baa278db58fcaf32 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-10T15:45:18Z |
| publishDate | 2023-02-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-64c13157a1a349d5baa278db58fcaf322023-02-12T12:09:39ZengNature PortfolioScientific Reports2045-23222023-02-0113111410.1038/s41598-023-28502-6Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activityTanya Clements-Decker0Marina Rautenbach1Wilma van Rensburg2Sehaam Khan3Marietjie Stander4Wesaal Khan5Faculty of Health Sciences, University of JohannesburgDepartment of Biochemistry, Faculty of Science, Stellenbosch UniversityDepartment of Biochemistry, Faculty of Science, Stellenbosch UniversityFaculty of Health Sciences, University of JohannesburgDepartment of Biochemistry, Faculty of Science, Stellenbosch UniversityDepartment of Microbiology, Faculty of Science, Stellenbosch UniversityAbstract Secondary metabolic profiling, using UPLC-MSE and molecular networking, revealed the secondary metabolites produced by Serratia marcescens NP10. The NP10 strain co-produced cyclic and open-ring stephensiolides (i.e., fatty acyl chain linked to Thr–Ser–Ser–Ile/Leu–Ile/Leu/Val) and glucosamine derivatives (i.e., fatty acyl chain linked to Val–glucose–butyric/oxo-hexanoic acid), with the structures of sixteen new stephensiolides (L–Y) and three new glucosamine derivatives (L–N) proposed. Genome mining identified sphA (stephensiolides) and gcd (glucosamine derivatives) gene clusters within Serratia genomes available on NBCI using antiSMASH, revealing specificity scores of the adenylation-domains within each module that corroborates MSE data. Of the nine RP-HPLC fractions, two stephensiolides and two glucosamine derivatives exhibited activity against Staphylococcus aureus (IC50 of 25–79 µg/mL). 1H NMR analysis confirmed the structure of the four active compounds as stephensiolide K, a novel analogue stephensiolide U, and glucosamine derivatives A and C. Stephensiolides K and U were found to cause membrane depolarisation and affect the membrane permeability of S. aureus, while glucosamine derivatives A and C primarily caused membrane depolarisation. New members of the stephensiolide and glucosamine derivative families were thus identified, and results obtained shed light on their antibacterial properties and mode of membrane activity.https://doi.org/10.1038/s41598-023-28502-6 |
| spellingShingle | Tanya Clements-Decker Marina Rautenbach Wilma van Rensburg Sehaam Khan Marietjie Stander Wesaal Khan Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity Scientific Reports |
| title | Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| title_full | Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| title_fullStr | Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| title_full_unstemmed | Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| title_short | Secondary metabolic profiling of Serratia marcescens NP10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| title_sort | secondary metabolic profiling of serratia marcescens np10 reveals new stephensiolides and glucosamine derivatives with bacterial membrane activity |
| url | https://doi.org/10.1038/s41598-023-28502-6 |
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