Ghanaian mangrove wetland endophytic fungus, Penicillium herquei strain BRS2A-AR produces (9Z, 11E)-13-oxooctadeca-9,11-dienoic acid with activity against Trichomonas mobilensis

Abstract

Sub-Sahara Africa is burdened with a high incidence of parasitic infections, including schistosomiasis, trypanosomiasis, trichomoniasis, and leishmaniasis. Currently, there is a rapid widespread development of resistance to prescription drugs for these neglected diseases. Microbes provide the largest chemical and biological diversity in drug discovery screening programs; therefore, our project seeks to explore microbes in the sub-region for new drugs. The oxylipin (9Z,11E)-13-oxooctadeca-9,11-dienoic acid (1) was isolated from the Ghanaian endophytic fungus, Penicillium herquei strain BRS2A-AR obtained from the leaves of a Laguncularia racemosa tree growing on the banks of the River Butre in the Western Regional wetlands of Ghana. Compound 1 was isolated on reverse phase HPLC at tR of 34.3 minutes. The structure of compound 1 was confirmed by a combination of mass spectrometry, 1D and 2D-NMR techniques. Compound 1 showed minimal antiparasitic activity when tested against Plasmodium falciparum 3d7 (IC50>100μM; aretesunate, IC₅₀ 36nm), Trypanosoma brucei brucei (IC₅₀>100μM; Coptis japonica, IC₅₀ 8.20μM), Leishmani donovani (IC₅₀>100μM; amphotericin B, IC₅₀ 0.32μM) and Leishmania major (IC₅₀>100μM; amphotericin B, IC₅₀ 0.31μM). Compound 1 produced IC₅₀ of 44.47μM when tested against Trichomonas mobilensis with metronidazole (IC₅₀ 5.20μM) as standard. These results show the potential to further engineer the structure of compound 1 into a potent anti-Trichomonas scaffold.

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Keywords: Oxylipin, Antiprasitic, Plasmodium, Trypanosome, Leishmania, Trichomonas