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The compounds quinolactacin A2 (2) and citrinadin A (13) which are originally considered to be the compounds of fungi genus Penicillium, were co-isolated for the first time from the new fungal strain Cladosporium oxysporum strain BRS2A-AR2F (Genebank number KX257257) which is an endophyte of the Ghanaian mangrove plant Rhizophora racemosa. A derivative of citrinadin A, which was named butrecitrinadin (12) was also isolated from fermentation cultures of this new fungal strain. The structures of quinolactacin A2 (2), citrinadin A (13) and butrecitrinadin (12) were determined using a combination of mass spectrometry with 1D and 2D NMR data analysis. The antiproliferative activities of the three compounds 2, 12 and 13 were tested using human cancer cell lines HL-60, Jurkat cells, LNCap, PC3, HepG2, and MCF7. The compounds were found to show some level of anti-proliferative activity against some of the cell lines compared to curcumin as a positive control. The three compounds however, showed no activity against Jurkat and PC-3 cells. Compounds 2, 12 and 13 were also tested against the chloroquine sensitive Plasmodium falciparum 3D7 strain for anti-plasmodial activity. Only 2 showed antiplasmodial activity within the concentration range tested with an EC50 value of 24.80 μM compared to artesunate 0.074. Since this represents the first study of the anti-plasmodial activity of quinolactacin A2 (2), the apoptotic activity of 2 on 3D7 plasmodia strain was evaluated by studying the effect of the compound on the mitochondrion membrane potential of the parasite. The results indicated the dissipation of the mitochondrial membrane potential (ΔΨm) and abolition of probe accumulation in a concentration dependent manner. Hence 2 may provide a drug development scaffold for apoptotic death in the stages of Plasmodium falciparum development. The three compounds 2, 12 and 13 were also tested for anti-buruli ulcer activity on Mycobacterium ulcerans MN209 characterized isolates but, were found to be inactive.

journal of chemistry and applications

Anti-Proliferative and Anti-Plasmodia Activity of Quinolactacin A2, Citrinadin A and Butrecitrinadin co-isolated from a Ghanaian Mangrove Endophytic Fungus Cladosporium oxysporum strain BRS2A-AR2F