Abstract
The Mycobacterium sp. BRS2A-AR2 is an endophyte of the mangrove plant Rhizophora racemosa G. Mey., which grows along the banks of the River Butre, in the Western Region of Ghana. Chemical profiling using 1H-NMR and HRESI-LC-MS of fermentation extracts produced by the strain led to the isolation of the new compound, α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d–fructofuranoside] or simply tortomycoglycoside (1). Compound 1 is an aminoglycoside consisting of a tryptophan moiety esterified to a disaccharide made up of β-d-fructofuranose and α-d-glucopyranose sugars. The full structure of 1 was determined using UV, IR, 1D, 2D-NMR and HRESI-LC-MS data. When tested against Trypanosoma brucei subsp. brucei, the parasite responsible for Human African Trypanosomiasis in sub-Saharan Africa, 1 (IC50 11.25 µM) was just as effective as Coptis japonica (Thunb.) Makino. (IC50 8.20 µM). The extract of Coptis japonica (Thunb.) Makino. is routinely used as laboratory standard due to its powerful antitrypanosomal activity. It is possible that, compound 1 interferes with the normal uptake and metabolism of tryptophan in the T. brucei subsp. brucei parasite.
Highlights
Carbohydrate-based natural products constitute a very potent group of compounds with promising prospects as future drugs [1]
We have previously reported for the first time ever that, strain BRS2A-AR2 biosynthesizes gold nanoparticles that are cytotoxic to HUVEC and HeLa cell lines [42]
HPLC of WB-SF4 led to the isolation of the potent glycoside antitrypanosomal data, indirectly confirms the disposition of the protons in both the β-D-fructofuranose and α-Dcompound (Figure 1), α-d-glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d–fructofuranoside] or glucopyranose rings
Summary
Carbohydrate-based natural products constitute a very potent group of compounds with promising prospects as future drugs [1]. Mey. from unexplored unique and extreme environments in the Ghanaian Western, Volta, and Brong Ahafo Regional wetlands From these samples, we have isolated many cultivable strains of endophytic microbes (e.g., Penicillium herquei strain BRS2A-AR, Cladosporium oxysporum strain BRS2A-AR2F, etc.) from the different plant parts that in turn produce culture extracts, which show antiparasitic activity against the neglected tropical parasites Trypanosoma brucei subsp. We have isolated many cultivable strains of endophytic microbes (e.g., Penicillium herquei strain BRS2A-AR, Cladosporium oxysporum strain BRS2A-AR2F, etc.) from the different plant parts that in turn produce culture extracts, which show antiparasitic activity against the neglected tropical parasites Trypanosoma brucei subsp. To H-1′′ helped to solve the rest of the structure, which was shown to be an α- D-glucopyranose ring strain an endophyte of a mangrove produced a very distinct rRNA gene sequence, afterissimilar examination of the sugarplant ring, that which is explained above. HPLC of WB-SF4 led to the isolation of the potent glycoside antitrypanosomal data, indirectly confirms the disposition of the protons in both the β-D-fructofuranose and α-Dcompound (Figure 1), α-d-glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d–fructofuranoside] or glucopyranose rings
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