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Mar. Drugs 2018, 16(8), 285; https://doi.org/10.3390/md16080285

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

1
The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via D. Montesano 49, 80131 Napoli, Italy
2
Laboratory of Pre-clinical and Translational Research, IRCCS-CROB, Referral Cancer Center of Basilicata, 85028 Rionero in Vulture, Italy
3
Department of Biology and Marine Biology, University of North Carolina Wilmington, Center for Marine Science, 5600 Marvin K Moss Lane, Wilmington, NC 28409, USA
*
Author to whom correspondence should be addressed.
Received: 27 July 2018 / Revised: 7 August 2018 / Accepted: 15 August 2018 / Published: 17 August 2018
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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 γ-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. View Full-Text
Keywords: Smenospongia aurea; γ-pyrone; polypropionate; marine sponges; secondary metabolites; signaling molecules Smenospongia aurea; γ-pyrone; polypropionate; marine sponges; secondary metabolites; signaling molecules
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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. (CC BY 4.0).

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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.

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