Demethoxyfumitremorgin C and tryprostatin B are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. Demethoxyfumitremorgin C inhibits the proliferation of PC3 human prostate cancer cells via the intrinsic (mitochondrial) and extrinsic pathway, followed by downstream events leading to apoptotic cell death, it could therefore, serve as a useful agent to treat human advanced prostate cancer.
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Apoptotic effect of demethoxyfumitremorgin C from marine fungus Aspergillus fumigatus on PC3 human prostate cancer cells.[Pubmed: 28359723
Demethoxyfumitremorgin C, a secondary metabolite of the marine fungus, Aspergillus fumigatus, had been reported to demonstrate cytotoxic effect on mouse tsFT210 cells. However, no information is available regarding its functional mechanism and the chemo-sensitization effects on different kinds of human cancer cells.
METHODS AND RESULTS:
We found that treatment of Demethoxyfumitremorgin C inhibited the cell viability of PC3 human advanced prostate cancer cells, induced apoptosis as determined by Annexin V/propidium iodide double staining, and decreased mitochondrial membrane potential. Demethoxyfumitremorgin C induced apoptosis was associated with downregulation of anti-apoptotic proteins: Ras, PI3K, Akt, Bcl-xL, and Bcl-2, and upregulation of pro-apoptotic Bax. Demethoxyfumitremorgin C activated caspase-3, -8, and -9, leading to PARP cleavage. Additionally, caspase inhibitors blocked Demethoxyfumitremorgin C-induced apoptosis of PC3 cells.
These results suggest that Demethoxyfumitremorgin C from Aspergillus fumigatus inhibits the proliferation of PC3 human prostate cancer cells via the intrinsic (mitochondrial) and extrinsic pathway, followed by downstream events leading to apoptotic cell death. Demethoxyfumitremorgin C could therefore, serve as a useful agent to treat human advanced prostate cancer.
J Med Chem. 2000 Apr 20;43(8):1577-85.
Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues.[Pubmed: 10780915
Tryprostatin B and Demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition.
METHODS AND RESULTS:
N-Alkyl derivatives of the L-Trp-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of Demethoxyfumitremorgin C.
The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the Demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.