Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses

Mallique Qader; Larry L Mweetwa; Teppo Rämä; Bathini Thissera; Bruce F Milne; Usama R Abdelmohsen; Raha Orfali; Ahmed Tawfike; Manal Esheli; Emmanuel T Oluwabusola; Lalith Jaysainghe; Marcel Jaspars; Mostafa E Rateb

doi:10.1093/jambio/lxad158

Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses

Mallique Qader^* (Corresponding Author), Larry L Mweetwa, Teppo Rämä, Bathini Thissera, Bruce F Milne, Usama R Abdelmohsen, Raha Orfali, Ahmed Tawfike, Manal Esheli, Emmanuel T Oluwabusola, Lalith Jaysainghe, Marcel Jaspars, Mostafa E Rateb

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

AIMS: This study aims to prioritize fungal strains recovered from under-explored habitats that produce new metabolites. HRMS dereplication is used to avoid structure redundancy and molecular modelling is used to assign absolute configuration.

METHODS AND RESULTS: MBC15-11F was isolated from an amphipod and identified using ITS, 28S, and β-tubulin phylogeny as Aspergillus sydowii. Chemical profiling using taxonomic-based dereplication identified structurally diverse metabolites, including unreported ones. Large-scale fermentation led to the discovery of a new N-acyl adenosine derivative: (S)-sydosine (1) which was elucidated by NMR and HRESIMS analyses. Two known compounds were also identified as predicted by the initial dereplication process. Due to scarcity of 1, molecular modelling was used to assign its absolute configuration without hydrolysis, and is supported by advanced Mosher derivatization. When the isolated compounds were assessed against a panel of bacterial pathogens, only phenamide (3) showed anti-Staphylococcus aureus activity.

CONCLUSION: Fermentation of A. sydowii yielded a new (S)-sydosine and known metabolites as predicted by HRESIMS-aided dereplication. Molecular modelling prediction of the absolute configuration of 1 agreed with advanced Mosher analysis.

Original language	English
Article number	lxad158
Number of pages	12
Journal	Journal of Applied Microbiology
Volume	134
Issue number	8
Early online date	21 Jul 2023
DOIs	https://doi.org/10.1093/jambio/lxad158
Publication status	Published - Aug 2023

Bibliographical note

Funding
The authors extend their appreciation to the Researchers Supporting Project number (RSP2023R431), King Saud University, Riyadh, Saudi Arabia, for funding this research work. M.Q. would like to thank the support of the EU-Erasmus Mundus-gLINK project (552099-EM-1–2014-1-UK-ERA) for offering the research scholarship to carry out research at the UWS, UK. T.R. would like to thank the Centre for New Antibacterial Strategies (CANS) at UiT the Arctic University of Norway for funding.

Data Availability Statement

The original contributions presented in the study are included in the article/Supplementary Material, further inquiries can be directed to the corresponding author.

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10.1093/jambio/lxad158Licence: Unspecified

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Cite this

Qader, M., Mweetwa, L. L., Rämä, T., Thissera, B., Milne, B. F., Abdelmohsen, U. R., Orfali, R., Tawfike, A., Esheli, M., Oluwabusola, E. T., Jaysainghe, L., Jaspars, M., & Rateb, M. E. (2023). Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses. Journal of Applied Microbiology, 134(8), Article lxad158. https://doi.org/10.1093/jambio/lxad158

Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses. / Qader, Mallique (Corresponding Author); Mweetwa, Larry L; Rämä, Teppo et al.
In: Journal of Applied Microbiology, Vol. 134, No. 8, lxad158, 08.2023.

Research output: Contribution to journal › Article › peer-review

Qader, M, Mweetwa, LL, Rämä, T, Thissera, B, Milne, BF, Abdelmohsen, UR, Orfali, R, Tawfike, A, Esheli, M, Oluwabusola, ET, Jaysainghe, L, Jaspars, M & Rateb, ME 2023, 'Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses', Journal of Applied Microbiology, vol. 134, no. 8, lxad158. https://doi.org/10.1093/jambio/lxad158

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title = "Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses",

abstract = "AIMS: This study aims to prioritize fungal strains recovered from under-explored habitats that produce new metabolites. HRMS dereplication is used to avoid structure redundancy and molecular modelling is used to assign absolute configuration.METHODS AND RESULTS: MBC15-11F was isolated from an amphipod and identified using ITS, 28S, and β-tubulin phylogeny as Aspergillus sydowii. Chemical profiling using taxonomic-based dereplication identified structurally diverse metabolites, including unreported ones. Large-scale fermentation led to the discovery of a new N-acyl adenosine derivative: (S)-sydosine (1) which was elucidated by NMR and HRESIMS analyses. Two known compounds were also identified as predicted by the initial dereplication process. Due to scarcity of 1, molecular modelling was used to assign its absolute configuration without hydrolysis, and is supported by advanced Mosher derivatization. When the isolated compounds were assessed against a panel of bacterial pathogens, only phenamide (3) showed anti-Staphylococcus aureus activity.CONCLUSION: Fermentation of A. sydowii yielded a new (S)-sydosine and known metabolites as predicted by HRESIMS-aided dereplication. Molecular modelling prediction of the absolute configuration of 1 agreed with advanced Mosher analysis.",

author = "Mallique Qader and Mweetwa, {Larry L} and Teppo R{\"a}m{\"a} and Bathini Thissera and Milne, {Bruce F} and Abdelmohsen, {Usama R} and Raha Orfali and Ahmed Tawfike and Manal Esheli and Oluwabusola, {Emmanuel T} and Lalith Jaysainghe and Marcel Jaspars and Rateb, {Mostafa E}",

note = "Funding The authors extend their appreciation to the Researchers Supporting Project number (RSP2023R431), King Saud University, Riyadh, Saudi Arabia, for funding this research work. M.Q. would like to thank the support of the EU-Erasmus Mundus-gLINK project (552099-EM-1–2014-1-UK-ERA) for offering the research scholarship to carry out research at the UWS, UK. T.R. would like to thank the Centre for New Antibacterial Strategies (CANS) at UiT the Arctic University of Norway for funding.",

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AU - Qader, Mallique

AU - Mweetwa, Larry L

AU - Rämä, Teppo

AU - Thissera, Bathini

AU - Milne, Bruce F

AU - Abdelmohsen, Usama R

AU - Orfali, Raha

AU - Tawfike, Ahmed

AU - Esheli, Manal

AU - Oluwabusola, Emmanuel T

AU - Jaysainghe, Lalith

AU - Jaspars, Marcel

AU - Rateb, Mostafa E

N1 - Funding The authors extend their appreciation to the Researchers Supporting Project number (RSP2023R431), King Saud University, Riyadh, Saudi Arabia, for funding this research work. M.Q. would like to thank the support of the EU-Erasmus Mundus-gLINK project (552099-EM-1–2014-1-UK-ERA) for offering the research scholarship to carry out research at the UWS, UK. T.R. would like to thank the Centre for New Antibacterial Strategies (CANS) at UiT the Arctic University of Norway for funding.

PY - 2023/8

Y1 - 2023/8

N2 - AIMS: This study aims to prioritize fungal strains recovered from under-explored habitats that produce new metabolites. HRMS dereplication is used to avoid structure redundancy and molecular modelling is used to assign absolute configuration.METHODS AND RESULTS: MBC15-11F was isolated from an amphipod and identified using ITS, 28S, and β-tubulin phylogeny as Aspergillus sydowii. Chemical profiling using taxonomic-based dereplication identified structurally diverse metabolites, including unreported ones. Large-scale fermentation led to the discovery of a new N-acyl adenosine derivative: (S)-sydosine (1) which was elucidated by NMR and HRESIMS analyses. Two known compounds were also identified as predicted by the initial dereplication process. Due to scarcity of 1, molecular modelling was used to assign its absolute configuration without hydrolysis, and is supported by advanced Mosher derivatization. When the isolated compounds were assessed against a panel of bacterial pathogens, only phenamide (3) showed anti-Staphylococcus aureus activity.CONCLUSION: Fermentation of A. sydowii yielded a new (S)-sydosine and known metabolites as predicted by HRESIMS-aided dereplication. Molecular modelling prediction of the absolute configuration of 1 agreed with advanced Mosher analysis.

AB - AIMS: This study aims to prioritize fungal strains recovered from under-explored habitats that produce new metabolites. HRMS dereplication is used to avoid structure redundancy and molecular modelling is used to assign absolute configuration.METHODS AND RESULTS: MBC15-11F was isolated from an amphipod and identified using ITS, 28S, and β-tubulin phylogeny as Aspergillus sydowii. Chemical profiling using taxonomic-based dereplication identified structurally diverse metabolites, including unreported ones. Large-scale fermentation led to the discovery of a new N-acyl adenosine derivative: (S)-sydosine (1) which was elucidated by NMR and HRESIMS analyses. Two known compounds were also identified as predicted by the initial dereplication process. Due to scarcity of 1, molecular modelling was used to assign its absolute configuration without hydrolysis, and is supported by advanced Mosher derivatization. When the isolated compounds were assessed against a panel of bacterial pathogens, only phenamide (3) showed anti-Staphylococcus aureus activity.CONCLUSION: Fermentation of A. sydowii yielded a new (S)-sydosine and known metabolites as predicted by HRESIMS-aided dereplication. Molecular modelling prediction of the absolute configuration of 1 agreed with advanced Mosher analysis.

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Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher and molecular modelling analyses

Abstract

Bibliographical note

Data Availability Statement

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