Chaetomugilins, New Selectively Cytotoxic Metabolites, Produced by a Marine Fish-derived Chaetomium Species

Abstract

Chaetomugilins AϳF have been isolated from a strain of Chaetomium globosum originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures have been elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, some chemical transformations and an X-ray analysis. These compounds exhibited significant growth inhibition against cultured P388 cells and HL-60 cells. In addition, chaetomugilins A, C and F showed selective cytotoxic activities against 39 human cancer cell lines.

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

“…Chaetomugilins A-F (85-90), six chlorinated azaphilones, have been isolated from a strain of C. globosum OUPS-T106B-6 originally found in the marine fish Mugil cephalus, and their structures were elucidated on the basis of 1D and 2D NMR techniques, and chemical transformations [89,90]. The absolute structure of 86 was determined through singlecrystal X-ray analysis and CD spectrum.…”

NW-G03, a related cyclic hexapeptide compound of NW-G01, produced by Streptomyces alboflavus 313

“…[11][12][13][14][15] As summarized in Table 4, the in vitro compound inhibited the growth of cell lines BEL-7402, HCT-116 and H460 in the concentration of 30 mg ml À1 .…”

Two phytotoxic azaphilone derivatives fromChaetomium globosum, a fungal endophyte isolated fromAmaranthus viridisleaves

“…The isolation of chaetomugilin D ( 1 ) from the fungal endophyte C. globosum was reported previously (Muroga et al 2008; Qin et al 2009). This is the second report of the isolation of chaetomugilin J ( 2 ) (Muroga et al 2009).…”

“…This is the second report of the isolation of chaetomugilin J ( 2 ) (Muroga et al 2009). Chaetomugilin-type compounds are known to have potent cytotoxic (including against brine shrimp larvae), antibacterial and antifungal activities (Muroga et al 2008, 2009; Qin et al 2009). Phytotoxic activities of 1 and 2 are reported for the first time in the present study, suggesting a potential use of the two compounds as a herbicide or weedicide to replace or reduce the use of hazardous synthetic compounds.…”