Sulfated Steroid–Amino Acid Conjugates from the Irish Marine Sponge Polymastia boletiformis
Vangelis Smyrniotopoulos,
Margaret Rae,
Sylvia Soldatou,
Yuanqing Ding,
Carsten W. Wolff,
Grace McCormack,
Christina M. Coleman,
Daneel Ferreira,
Deniz Tasdemir
Affiliations
Vangelis Smyrniotopoulos
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
Margaret Rae
Ryan Institute, National University of Ireland Galway, University Road, Galway, Ireland
Sylvia Soldatou
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
Yuanqing Ding
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
Carsten W. Wolff
Zoology, Ryan Institute, School of Natural Sciences, National University of Ireland Galway, University Road, Galway, Ireland
Grace McCormack
Zoology, Ryan Institute, School of Natural Sciences, National University of Ireland Galway, University Road, Galway, Ireland
Christina M. Coleman
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
Daneel Ferreira
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
Deniz Tasdemir
School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland
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.
