title: 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.
authors.affiliation: a Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Hainan Normal University , Haikou , 571158 , China.
authors.forename: Feng
authors.initials: F
authors.lastname: Zhu
authors.forename: Guangying
authors.initials: G
authors.lastname: Chen
authors.forename: Jingshu
authors.initials: J
authors.lastname: Wu
authors.forename: Jiahui
authors.initials: J
authors.lastname: Pan
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D018920:Coculture Techniques; D018360:Crystallography, X-Ray; D004952:Esters / Q000633:toxicity*; D005658:Fungi / Q000737:chemistry*; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D007769:Lactams / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004952:Esters; D007769:Lactams; D015363:Quinolones; C584632:marinamide