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α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]

1
Marine and Plant Research Laboratory of Ghana, Department of Chemistry, School of Physical and Mathematical Sciences, University of Ghana, P.O. Box LG 56, Legon-Accra, Ghana
2
Department of Bioengineering, Munzur University, 62000 Tunceli, Turkey
3
Department of Biochemistry, Cell and Molecular Biology, University of Ghana, P. O. Box LG 54 Legon-Accra, Ghana
4
Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE Scotland, UK
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(2), M1066; https://doi.org/10.3390/M1066
Received: 13 May 2019 / Revised: 14 June 2019 / Accepted: 14 June 2019 / Published: 16 June 2019
(This article belongs to the Section Natural Products)
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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. View Full-Text
Keywords: endophytes; mangroves; glycosides; trypanosomes; antiparasitics endophytes; mangroves; glycosides; trypanosomes; antiparasitics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kyeremeh, K.; Kwain, S.; Tetevi, G.M.; Camas, A.S.; Camas, M.; Dofuor, A.K.; Deng, H.; Jaspars, M. α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]. Molbank 2019, 2019, M1066.

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