Structure revision and cytotoxic activity of marinamide and its methyl ester, novel alkaloids produced by co-cultures of two marine-derived mangrove endophytic fungi

Abstract

Marinamide (1) and its methyl ester (2) have been previously reported as pyrrolyl 1-isoquinolone alkaloids, which were produced by co-cultures of two marine-derived mangrove endophytic fungi from the South China Sea coast. Recrystallisation of methyl marinamide (2) from pyridine forms the known pesticide, quinolactacide (3). Treatment of 3 with methyl iodide to afford N-methyl quinolactacide (4) was identified by X-ray crystallography. Thus, the structures of 1 and 2 were revised from the previously reported pyrrolyl 1-isoquinolone structures to pyrrolyl 4-quinolone analogues. In the MTT assays, both 1 and 2 exhibited potent cytotoxic activity against HepG2, 95-D, MGC832 and HeLa tumour cell lines.