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

Nat Prod Res. 2013;27(21):1960-4. doi: 10.1080/14786419.2013.800980. Epub 2013 May 24.

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.

MeSH terms

  • Alkaloids / chemistry*
  • Cell Survival / drug effects
  • Coculture Techniques
  • Crystallography, X-Ray
  • Esters / toxicity*
  • Fungi / chemistry*
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Lactams / chemistry
  • Lactams / toxicity*
  • Molecular Structure
  • Quinolones / chemistry

Substances

  • Alkaloids
  • Esters
  • Lactams
  • Quinolones
  • marinamide