Salimabromide: Unexpected Chemistry from the Obligate Marine Myxobacterium <i>Enhygromyxa salina</i>

Felder, Stephan; Dreisigacker, Sandra; Kehraus, Stefan; Neu, Edith; Bierbaum, Gabriele; Wright, Patrick R.; Menche, Dirk; Schäberle, Till F.; König, Gabriele M.

doi:10.1002/chem.201301379

Cited by 57 publications

(72 citation statements)

References 30 publications

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“…Myxobacteria have rarely been found in marine habitats (Reichenbach, 1999). Myxobacteria are prolific producers of natural products, and the first marine obligate halophilic myxobacteria-derived natural products were only reported very recently (Felder et al, 2013). Didemnum sp.…”

Section: Bacterial Composition Of Ascidiansmentioning

confidence: 99%

Species specificity of symbiosis and secondary metabolism in ascidians

et al. 2014

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Ascidians contain abundant, diverse secondary metabolites, which are thought to serve a defensive role and which have been applied to drug discovery. It is known that bacteria in symbiosis with ascidians produce several of these metabolites, but very little is known about factors governing these 'chemical symbioses'. To examine this phenomenon across a wide geographical and species scale, we performed bacterial and chemical analyses of 32 different ascidians, mostly from the didemnid family from Florida, Southern California and a broad expanse of the tropical Pacific Ocean. Bacterial diversity analysis showed that ascidian microbiomes are highly diverse, and this diversity does not correlate with geographical location or latitude. Within a subset of species, ascidian microbiomes are also stable over time (R ¼ À 0.037, P-value ¼ 0.499). Ascidian microbiomes and metabolomes contain species-specific and location-specific components. Location-specific bacteria are found in low abundance in the ascidians and mostly represent strains that are widespread. Location-specific metabolites consist largely of lipids, which may reflect differences in water temperature. By contrast, species-specific bacteria are mostly abundant sequenced components of the microbiomes and include secondary metabolite producers as major components. Species-specific chemicals are dominated by secondary metabolites. Together with previous analyses that focused on single ascidian species or symbiont type, these results reveal fundamental properties of secondary metabolic symbiosis. Different ascidian species have established associations with many different bacterial symbionts, including those known to produce toxic chemicals. This implies a strong selection for this property and the independent origin of secondary metabolite-based associations in different ascidian species. The analysis here streamlines the connection of secondary metabolite to producing bacterium, enabling further biological and biotechnological studies.

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Section: Bacterial Composition Of Ascidiansmentioning

confidence: 99%

Species specificity of symbiosis and secondary metabolism in ascidians

et al. 2014

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“…1 It presents one of the first secondary metabolites isolated from a marine myxobacterium. 2 Salimabromide has a structurally novel tetracyclic carbon skeleton with no apparent resemblance to any known natural products.…”

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confidence: 99%

Concise Synthesis of the Tricyclic Core of Salimabromide

Schmalzbauer

Menche

2015

Org. Lett.

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A concise synthesis of the tricyclic core 2 of the structurally unique marine myxobacterial natural product salimabromide has been developed. Compound 2 contains the tetraline subunit including the two quaternary centers and the eight-membered ring of salimabromide. Major features for its synthesis include a Lewis base catalyzed Denmark-crotylation for stereoselective construction of the highly hindered quaternary stereocenter, an innovative iodine/selectfluor induced endo-carbocylization, and a unique chemoselective carbonylative lactonization of the eight-membered ring.

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“…The relative configuration of salimabromide 27, a tetracyclic antibiotic compound possessing a brominated benzene ring, a furano lactone residue, and a cyclohexane ring, bridged by a seven-membered cyclic unit, was proved by the NOE connectivities and the (Z)-configuration of the C3 = C9 double bond was assigned by NOE correlation between H-3 and H-9 and also supported by the 1 H-1 H NMR coupling constant (J H-3,H-9 13.1 Hz) [26] (Figure 7.9). The relative configuration of other marine natural products were elucidated by a combination of NOESY experiments and comparison with the 1 H and 13 C NMR data of known compounds [27], or using other techniques such as circular dichroism (CD) [28] and overall optical rotation [29].…”

Section: Stereochemistrymentioning

confidence: 88%