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Open AccessCommunication
Mar. Drugs 2015, 13(4), 1632-1646; doi:10.3390/md13041632

Sulfated Steroid–Amino Acid Conjugates from the Irish Marine Sponge Polymastia boletiformis

1
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
2
Ryan Institute, National University of Ireland Galway, University Road, Galway, Ireland
3
Marine Biodiscovery Laboratory, Marine Institute, Rinville, Oranmore, Co. Galway, Ireland
4
Department of BioMolecular Sciences, Division of Pharmacognosy, and the National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
5
Zoology, Ryan Institute, School of Natural Sciences, National University of Ireland Galway, University Road, Galway, Ireland
*
Author to whom correspondence should be addressed.
Academic Editor: Miguel O. Mitchell
Received: 12 December 2014 / Revised: 23 February 2015 / Accepted: 16 March 2015 / Published: 24 March 2015
(This article belongs to the Special Issue Marine Anti-infective Agents)
View Full-Text   |   Download PDF [611 KB, uploaded 24 March 2015]   |  

Abstract

Antifungal bioactivity-guided fractionation of the organic extract of the sponge Polymastia boletiformis, collected from the west coast of Ireland, led to the isolation of two new sulfated steroid-amino acid conjugates (1 and 2). Extensive 1D and 2D NMR analyses in combination with quantum mechanical calculations of the electronic circular dichroism (ECD) spectra, optical rotation, and 13C chemical shifts were used to establish the chemical structures of 1 and 2. Both compounds exhibited moderate antifungal activity against Cladosporium cucumerinum, while compound 2 was also active against Candida albicans. Marine natural products containing steroidal and amino acid constituents are extremely rare in nature. View Full-Text
Keywords: marine; sponge; Polymastia boletiformis; sulfated steroid; antifungal activity marine; sponge; Polymastia boletiformis; sulfated steroid; antifungal activity
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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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MDPI and ACS Style

Smyrniotopoulos, V.; Rae, M.; Soldatou, S.; Ding, Y.; Wolff, C.W.; McCormack, G.; Coleman, C.M.; Ferreira, D.; Tasdemir, D. Sulfated Steroid–Amino Acid Conjugates from the Irish Marine Sponge Polymastia boletiformis. Mar. Drugs 2015, 13, 1632-1646.

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