Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum
Sy-Cordero, A. A., Figueroa, M., Raja, H. A., Avina, M. E. M., Croatt, M. P., Adcock, A. F., ... Oberlies, N. H. (2015). Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum. Tetrahedron, 71(47), 8899-8904. DOI: 10.1016/j.tet.2015.09.073, 10.1016/j.tet.2015.09.073
Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a solid phase culture of the fungus Scytalidium cuboideum (MSX 68345). The molecular connectivity of 1-3 was determined using NMR spectroscopy and mass spectrometry. The relative configurations of 1 and 2 were determined by NOESY experiments. The absolute configuration of 1 was determined by electronic circular dichroism (ECD) via a combination of experimental measurements and computational calculations. While leporin B was known, it displayed activities that had not been reported previously, including cytotoxicity against three human tumour cell lines and antibacterial activity against Candida albicans and Staphylococcus aureus. (C) 2015 Elsevier Ltd. All rights reserved.