TY - JOUR
T1 - α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]
AU - Kyeremeh, Kwaku
AU - Kwain, Samuel
AU - Tetevi, Gilbert Mawuli
AU - Camas, Anil Sazak
AU - Camas, Mustafa
AU - Dofuor, Aboagye Kwarteng
AU - Deng, Hai
AU - Jaspars, Marcel
N1 - Publisher Copyright:
© 2019 by the authors.
PY - 2019/6
Y1 - 2019/6
N2 - 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 theWestern 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.
AB - 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 theWestern 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.
KW - Antiparasitics
KW - Endophytes
KW - Glycosides
KW - Mangroves
KW - Trypanosomes
UR - http://www.scopus.com/inward/record.url?scp=85071362344&partnerID=8YFLogxK
U2 - 10.3390/M1066
DO - 10.3390/M1066
M3 - Article
AN - SCOPUS:85071362344
SN - 1422-8599
VL - 2019
JO - MolBank
JF - MolBank
IS - 2
M1 - M1066
ER -