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Expanding the Described Metabolome of the Marine Cyanobacterium Moorea producens JHB through Orthogonal Natural Products Workflows.

Boudreau PD, Monroe EA, Mehrotra S, Desfor S, Korobeynikov A, Sherman DH, Murray TF, Gerwick L, Dorrestein PC, Gerwick WH - PLoS ONE (2015)

Bottom Line: In the current study, mass spectrometry-based 'molecular networking' was used to visualize the metabolome of Moorea producens JHB, and both guided and enhanced the isolation workflow, revealing additional metabolites in these compound classes.Further, we developed additional insight into the metabolic capabilities of this strain by genome sequencing analysis, which subsequently led to the isolation of a compound unrelated to the jamaicamide and hectochlorin families.Another approach involved stimulation of the biosynthesis of a minor jamaicamide metabolite by cultivation in modified media, and provided insights about the underlying biosynthetic machinery as well as preliminary structure-activity information within this structure class.

View Article: PubMed Central - PubMed

Affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California, 92093, United States.

ABSTRACT
Moorea producens JHB, a Jamaican strain of tropical filamentous marine cyanobacteria, has been extensively studied by traditional natural products techniques. These previous bioassay and structure guided isolations led to the discovery of two exciting classes of natural products, hectochlorin (1) and jamaicamides A (2) and B (3). In the current study, mass spectrometry-based 'molecular networking' was used to visualize the metabolome of Moorea producens JHB, and both guided and enhanced the isolation workflow, revealing additional metabolites in these compound classes. Further, we developed additional insight into the metabolic capabilities of this strain by genome sequencing analysis, which subsequently led to the isolation of a compound unrelated to the jamaicamide and hectochlorin families. Another approach involved stimulation of the biosynthesis of a minor jamaicamide metabolite by cultivation in modified media, and provided insights about the underlying biosynthetic machinery as well as preliminary structure-activity information within this structure class. This study demonstrated that these orthogonal approaches are complementary and enrich secondary metabolomic coverage even in an extensively studied bacterial strain.

No MeSH data available.


Related in: MedlinePlus

Hectochlorin (1) isotope pattern within the M. producens JHB network.The presence of 35Cl or 37Cl within specific hectochlorin molecules yielded different parent masses and fragment spectra. The species with both 35Cl atoms has an m/z of 665, the species with one 35Cl and one 37Cl atom has and m/z of 667, and the species with 37Cl atoms has an m/z of 669. Because of this the fragment spectra share only masses from those fragments without chlorine atoms, and those fragments bearing the chlorine atoms show the same mass differences as their parent masses.
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pone.0133297.g003: Hectochlorin (1) isotope pattern within the M. producens JHB network.The presence of 35Cl or 37Cl within specific hectochlorin molecules yielded different parent masses and fragment spectra. The species with both 35Cl atoms has an m/z of 665, the species with one 35Cl and one 37Cl atom has and m/z of 667, and the species with 37Cl atoms has an m/z of 669. Because of this the fragment spectra share only masses from those fragments without chlorine atoms, and those fragments bearing the chlorine atoms show the same mass differences as their parent masses.

Mentions: The network was interrogated for the [M+H]+ ions from the known major metabolites from this cyanobacterial strain, 1 and 2. In both cases, this revealed a cluster of parent masses from related analogs in the same family of compounds (Figs 3 and 4). One important caveat of the molecular networking process is that a single compound can give rise to multiple nodes. For example ions deriving from different adducts, from differing isotope composition, as well as source fragments, are all observed in the molecular network when present in sufficient intensity for the spectrometer to collect their MS2 spectra. The hectochlorin cluster is clearly an illustration of a single molecule producing multiple nodes from different halogen isotopes. The presence of heavy chlorine atoms in some of the hectochlorin molecules results in three nodes with mass differences of two Daltons within the hectochlorin cluster (Fig 3).


Expanding the Described Metabolome of the Marine Cyanobacterium Moorea producens JHB through Orthogonal Natural Products Workflows.

Boudreau PD, Monroe EA, Mehrotra S, Desfor S, Korobeynikov A, Sherman DH, Murray TF, Gerwick L, Dorrestein PC, Gerwick WH - PLoS ONE (2015)

Hectochlorin (1) isotope pattern within the M. producens JHB network.The presence of 35Cl or 37Cl within specific hectochlorin molecules yielded different parent masses and fragment spectra. The species with both 35Cl atoms has an m/z of 665, the species with one 35Cl and one 37Cl atom has and m/z of 667, and the species with 37Cl atoms has an m/z of 669. Because of this the fragment spectra share only masses from those fragments without chlorine atoms, and those fragments bearing the chlorine atoms show the same mass differences as their parent masses.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4519256&req=5

pone.0133297.g003: Hectochlorin (1) isotope pattern within the M. producens JHB network.The presence of 35Cl or 37Cl within specific hectochlorin molecules yielded different parent masses and fragment spectra. The species with both 35Cl atoms has an m/z of 665, the species with one 35Cl and one 37Cl atom has and m/z of 667, and the species with 37Cl atoms has an m/z of 669. Because of this the fragment spectra share only masses from those fragments without chlorine atoms, and those fragments bearing the chlorine atoms show the same mass differences as their parent masses.
Mentions: The network was interrogated for the [M+H]+ ions from the known major metabolites from this cyanobacterial strain, 1 and 2. In both cases, this revealed a cluster of parent masses from related analogs in the same family of compounds (Figs 3 and 4). One important caveat of the molecular networking process is that a single compound can give rise to multiple nodes. For example ions deriving from different adducts, from differing isotope composition, as well as source fragments, are all observed in the molecular network when present in sufficient intensity for the spectrometer to collect their MS2 spectra. The hectochlorin cluster is clearly an illustration of a single molecule producing multiple nodes from different halogen isotopes. The presence of heavy chlorine atoms in some of the hectochlorin molecules results in three nodes with mass differences of two Daltons within the hectochlorin cluster (Fig 3).

Bottom Line: In the current study, mass spectrometry-based 'molecular networking' was used to visualize the metabolome of Moorea producens JHB, and both guided and enhanced the isolation workflow, revealing additional metabolites in these compound classes.Further, we developed additional insight into the metabolic capabilities of this strain by genome sequencing analysis, which subsequently led to the isolation of a compound unrelated to the jamaicamide and hectochlorin families.Another approach involved stimulation of the biosynthesis of a minor jamaicamide metabolite by cultivation in modified media, and provided insights about the underlying biosynthetic machinery as well as preliminary structure-activity information within this structure class.

View Article: PubMed Central - PubMed

Affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, California, 92093, United States.

ABSTRACT
Moorea producens JHB, a Jamaican strain of tropical filamentous marine cyanobacteria, has been extensively studied by traditional natural products techniques. These previous bioassay and structure guided isolations led to the discovery of two exciting classes of natural products, hectochlorin (1) and jamaicamides A (2) and B (3). In the current study, mass spectrometry-based 'molecular networking' was used to visualize the metabolome of Moorea producens JHB, and both guided and enhanced the isolation workflow, revealing additional metabolites in these compound classes. Further, we developed additional insight into the metabolic capabilities of this strain by genome sequencing analysis, which subsequently led to the isolation of a compound unrelated to the jamaicamide and hectochlorin families. Another approach involved stimulation of the biosynthesis of a minor jamaicamide metabolite by cultivation in modified media, and provided insights about the underlying biosynthetic machinery as well as preliminary structure-activity information within this structure class. This study demonstrated that these orthogonal approaches are complementary and enrich secondary metabolomic coverage even in an extensively studied bacterial strain.

No MeSH data available.


Related in: MedlinePlus