Mucosin: a new bicyclic eicosanoid from the mediterranean sponge Reniera mucosa

Casapullo, Agostino; Scognamiglio, Gennaro; Cimino, Guido

doi:10.1016/s0040-4039(97)00690-4

Cited by 19 publications

(60 citation statements)

References 10 publications

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“…10 In 1997 (−)-mucosin 1, a novel bicyclic eicosanoid was isolated from the marine sponge Reniera mucosa in the Mediterranean. 1 The structure of its methyl ester 2 was determined using mass, infrared and high field NMR spectroscopy. The relative stereochemistry was determined using a series of 2D NMR 15 experiments.…”

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confidence: 99%

“…19 Conversion of acid 1 to its methyl ester 2 using diazomethane allowed comparison with the reported data demonstrating excellent agreement. 1 The optical rotation of the synthetic mucosin methyl ester (90% ee) was 15 [α] In conclusion the absolute stereochemistry of the natural product (−)-mucosin has been established and the first total synthesis of its enantiomer (+)-mucosin has been completed in 14 steps and 7% overall yield. (−)-Mucosin could easily be made by using quinine in the enantioselective ring opening of 9.…”

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confidence: 99%

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The first total synthesis of (+)-mucosin

et al. 2012

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The first total synthesis of (+)-mucosin

et al. 2012

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“…Recently, cladocroic acid and the diastereomer 3-epicladocroic acid were also isolated from H. fulva (Genta-Jouve and Thomas 2013). H. mucosa (subgenus Soestella) is known to produce sesquiterpenes hydroquinones from the panicein family (Zubía et al 1994) and the bicyclic eicosanoid mucosin (Casapullo et al 1997). Thus, these two species, phylogenetically related and living in the same environment, produce totally different families of specialized metabolites.…”

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confidence: 99%

Metabolome variability for two Mediterranean sponge species of the genus Haliclona: specificity, time, and space

et al. 2018

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In this study, the intraspecific (temporal and spatial) variability of two Mediterranean Haliclona sponges (H. fulva and H. mucosa) was investigated through an untargeted and then targeted metabolomics approach and further compared to their interspecific variability. Methods Samples of both species were collected monthly during 1 year in the coralligenous habitat of the Northwestern Mediterranean sae at Marseille and Nice. Their metabolomic profiles were obtained by UHPLC-QqToF analyses. Results Marked variations were noticed in April and May for both species including a decrease in Shannon's diversity and concentration in specialized metabolites together with an increase in fatty acids and lyso-PAF like molecules. Spatial variations across different sampling sites could also be observed for both species, however in a lesser extent. Conclusions Synchronous metabolic changes possibly triggered by physiological factors like reproduction and/or environmental factors like an increase in the water temperature were highlighted for both Mediterranean Haliclona species inhabiting close habitats but displaying different biosynthetic pathways. Despite significative intraspecific variations, metabolomic variability remains minor when compared to interspecific variations for these congenerous species, therefore suggesting the predominance of genetic information of the holobiont in the observed metabolome.

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“…Ostensibly, mucosin ( 1 ) is a natural product that was isolated from the Mediterranean sponge Reniera mucosa as methyl ester 2 [ 35 ]. Formally classified as an eicosanoid, it has been conjectured to originate from arachidonic acid ( 3 ), based on the C 20 -architechture ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin

et al. 2017

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A stereodivergent total synthesis has been executed based on the plausibly misassigned structure of the unusual marine hydrindane mucosin (1). The topological connectivity of the four contiguous all-carbon stereocenters has been examined by selective permutation on the highlighted core. Thus, capitalizing on an unprecedented stereofacial preference of the cis-fused bicycle[4.3.0]non-3-ene system when a Michael acceptor motif is incorporated, copper-mediated conjugate addition furnished a single diastereomer. Cued by the relative relationship reported for the appendices in the natural product, the resulting anti-adduct was elaborated into a probative target structure 1*.

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Mucosin: a new bicyclic eicosanoid from the mediterranean sponge Reniera mucosa

Cited by 19 publications

References 10 publications

The first total synthesis of (+)-mucosin

The first total synthesis of (+)-mucosin

Metabolome variability for two Mediterranean sponge species of the genus Haliclona: specificity, time, and space

Stereopermutation on the Putative Structure of the Marine Natural Product Mucosin

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