α-<span style="font-variant: small-caps">d</span>-Glucopyranosyl-(1→2)-[6-<i>O</i>-(<span style="font-variant: small-caps">l</span>-tryptophanyl)-β-<span style="font-variant: small-caps">d</span>-fructofuranoside]
oleh: Kwaku Kyeremeh, Samuel Kwain, Gilbert Mawuli Tetevi, Anil Sazak Camas, Mustafa Camas, Aboagye Kwarteng Dofuor, Hai Deng, Marcel Jaspars
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2019-06-01 |
Deskripsi
The <i>Mycobacterium</i> sp. BRS2A-AR2 is an endophyte of the mangrove plant <i>Rhizophora racemosa</i> G. Mey., which grows along the banks of the River Butre, in the Western Region of Ghana. Chemical profiling using <sup>1</sup>H-NMR and HRESI-LC-MS of fermentation extracts produced by the strain led to the isolation of the new compound, α-<span style="font-variant: small-caps;">d</span>-Glucopyranosyl-(1→2)-[6-<i>O</i>-(<span style="font-variant: small-caps;">l</span>-tryptophanyl)-β-<span style="font-variant: small-caps;">d</span>−fructofuranoside] or simply tortomycoglycoside (<b>1</b>). Compound <b>1</b> is an aminoglycoside consisting of a tryptophan moiety esterified to a disaccharide made up of β-<span style="font-variant: small-caps;">d</span>-fructofuranose and α-<span style="font-variant: small-caps;">d</span>-glucopyranose sugars. The full structure of <b>1</b> was determined using UV, IR, 1D, 2D-NMR and HRESI-LC-MS data. When tested against <i>Trypanosoma brucei</i> subsp. <i>brucei</i>, the parasite responsible for Human African Trypanosomiasis in sub-Saharan Africa, <b>1</b> (IC<sub>50</sub> 11.25 µM) was just as effective as <i>Coptis japonica</i> (Thunb.) Makino. (IC<sub>50</sub> 8.20 µM). The extract of <i>Coptis japonica</i> (Thunb.) Makino. is routinely used as laboratory standard due to its powerful antitrypanosomal activity. It is possible that, compound <b>1</b> interferes with the normal uptake and metabolism of tryptophan in the <i>T. brucei</i> subsp. <i>brucei</i> parasite.