Unknown

Dataset Information

0

Isolation of Smenopyrone, a Bis-?-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea.

ABSTRACT: The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two ?-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.

SUBMITTER: Esposito G 

PROVIDER: S-EPMC6117678 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge <i>Smenospongia aurea</i>.

Esposito Germana G   Teta Roberta R   Della Sala Gerardo G   Pawlik Joseph R JR   Mangoni Alfonso A   Costantino Valeria V  

Marine drugs 20180817 8

The organic extract of the Caribbean sponge <i>Smenospongia aurea</i> has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NM  ...[more]

Similar Datasets

Unknown Isolation and assessment of the in vitro anti-tumor activity of smenothiazole A and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea.
| S-EPMC4306946 | biostudies-literature
Unknown Smenamides A and B, chlorinated peptide/polyketide hybrids containing a dolapyrrolidinone unit from the Caribbean sponge Smenospongia aurea. Evaluation of their role as leads in antitumor drug research.
| S-EPMC3853738 | biostudies-literature
Unknown Neopetrosiamine A, biologically active bis-piperidine alkaloid from the Caribbean sea sponge Neopetrosia proxima.
| S-EPMC2939202 | biostudies-literature
Unknown Isolation and structural elucidation of euryjanicins B-D, proline-containing cycloheptapeptides from the Caribbean marine sponge Prosuberites laughlini.
| S-EPMC5328627 | biostudies-literature
Unknown Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa.
| S-EPMC4685874 | biostudies-other
Unknown A joint molecular networking study of a Smenospongia sponge and a cyanobacterial bloom revealed new antiproliferative chlorinated polyketides.
| S-EPMC6927677 | biostudies-literature
Unknown New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum.
| S-EPMC3999825 | biostudies-literature
Unknown Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from <i>Smenospongia aurea</i>: Total Synthesis of <i>ent</i>-Smenamide A and 16-<i>epi</i>-Smenamide A.
| S-EPMC6044836 | biostudies-literature
Unknown Ulososides and urabosides--triterpenoid saponins from the Caribbean marine sponge Ectyoplasia ferox.
| S-EPMC6270507 | biostudies-literature
Unknown Cytotoxic Furanoditerpenes from the Sponge Spongia tubulifera Collected in the Mexican Caribbean.
| S-EPMC6669439 | biostudies-literature