Sulfated steroid-amino acid conjugates from the Irish marine sponge Polymastia boletiformis

• Published in: Marine drugs Vol. 13; no. 4; pp. 1632 - 1646
• Main Authors: Smyrniotopoulos, Vangelis, Rae, Margaret, Soldatou, Sylvia, Ding, Yuanqing, Wolff, Carsten W, McCormack, Grace, Coleman, Christina M, Ferreira, Daneel, Tasdemir, Deniz
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 24-03-2015; MDPI
• Subjects: Animals; antifungal activity; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Atlantic Ocean; Candida albicans; Candida albicans - drug effects; Candida albicans - growth & development; Cholestadienes - chemistry; Cholestadienes - isolation & purification; Cholestadienes - pharmacology; Chromatography, High Pressure Liquid; Circular Dichroism; Cladosporium - drug effects; Cladosporium - growth & development; Cladosporium cucumerinum; Communication; Disk Diffusion Antimicrobial Tests; Drug Discovery; Glycine - analogs & derivatives; Glycine - chemistry; Glycine - isolation & purification; Glycine - pharmacology; Ireland; Magnetic Resonance Spectroscopy; Marine; Methylation; Molecular Structure; Polymastia boletiformis; Porifera - chemistry; Porifera - growth & development; Quantum Theory; Spectrometry, Mass, Electrospray Ionization; sponge; Stereoisomerism; sulfated steroid; Sulfur Compounds - chemistry; Sulfur Compounds - isolation & purification; Sulfur Compounds - pharmacology; Atlantic Ocean; Ireland; ANE, Eire
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md13041632

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.