Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Isolation of Smenopyrone, a Bis-g-Pyrone Polypropionate from the Caribbean Sponge Smenospongia Aurea.

Germana Esposito
ORCID logo ,
Roberta Teta
,
Gerardo Della Sala
ORCID logo ,
Joseph R. Pawlik
,
Alfonso Mangoni
,
Valeria Costantino
* ORCID logo
Version 1 : Received: 27 July 2018 / Approved: 27 July 2018 / Online: 27 July 2018 (17:00:51 CEST)

A peer-reviewed article of this Preprint also exists.

Esposito, G.; Teta, R.; Della Sala, G.; Pawlik, J.R.; Mangoni, A.; Costantino, V. Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea. Mar. Drugs 2018, 16, 285. Esposito, G.; Teta, R.; Della Sala, G.; Pawlik, J.R.; Mangoni, A.; Costantino, V. Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea. Mar. Drugs 2018, 16, 285.

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. Here we report the presence of a biogenetically different compound, smenopyrone (1), a polypropionate containing two -pyrone rings. The structure of smenopyrone, including its relative and absolute stereochemistry, was determined by spectroscopic analysis (NMR, MS, ECD) supported by comparison with model compounds from the literature. 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. As 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.

Keywords

Smenospongia aurea, -pyrone, polypropionate, marine sponges, secondary metabolites, signaling molecules.

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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