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^*, 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

School of Computing, Engineering and Physical Sciences

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

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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
DOIs	https://doi.org/10.1093/jambio/lxad158
Publication status	Published - 21 Jul 2023

Keywords

Aspergillus sydowii
deap-sea
(S)-sydosine
HRMS
dereplication
molecular modelling

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10.1093/jambio/lxad158Licence: CC BY 4.0

2023 07 20 Qader et al Discovery finalFinal published version, 1.48 MBLicence: CC BY 4.0

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

@article{dfa9ec11a9984673a8a0e50b8373fae7,

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

abstract = "AimsThis 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 resultsMBC15-11F 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.ConclusionFermentation 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.",

keywords = "Aspergillus sydowii, deap-sea, (S)-sydosine, HRMS, dereplication, molecular modelling",

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.}",

year = "2023",

month = jul,

day = "21",

doi = "10.1093/jambio/lxad158",

language = "English",

volume = "134",

journal = "Journal of Applied Microbiology",

issn = "1364-5072",

publisher = "Oxford University Press",

number = "8",

}

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

Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher, and molecular modelling analyses. / Qader, Mallique; Mweetwa, Larry L.; Rämä, Teppo et al.
In: Journal of Applied Microbiology, Vol. 134, No. 8, lxad158, 21.07.2023.

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

TY - JOUR

T1 - Discovery and structural assignment of (S)-sydosine from amphipod-derived Aspergillus sydowii MBC15-11F through HRMS, advanced Mosher, and molecular modelling analyses

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.

PY - 2023/7/21

Y1 - 2023/7/21

N2 - AimsThis 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 resultsMBC15-11F 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.ConclusionFermentation 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 - AimsThis 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 resultsMBC15-11F 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.ConclusionFermentation 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.

KW - Aspergillus sydowii

KW - deap-sea

KW - (S)-sydosine

KW - HRMS

KW - dereplication

KW - molecular modelling

U2 - 10.1093/jambio/lxad158

DO - 10.1093/jambio/lxad158

M3 - Article

SN - 1364-5072

VL - 134

JO - Journal of Applied Microbiology

JF - Journal of Applied Microbiology

IS - 8

M1 - lxad158

ER -

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

Abstract

Keywords

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