α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]

Kwaku Kyeremeh*, Samuel Kwain, Gilbert Mawuli Tetevi, Anil Sazak Camas, Mustafa Camas, Aboagye Kwarteng Dofuor, Hai Deng, Marcel Jaspars

*Corresponding author for this work

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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 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.

Original languageEnglish
Article numberM1066
Number of pages11
JournalMolBank
Volume2019
Issue number2
DOIs
Publication statusPublished - 16 Jun 2019

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Coptis
parasites
Trypanosoma brucei brucei
tryptophan
Tryptophan
Inhibitory Concentration 50
Parasites
Rhizophoraceae
Ghana
Nuclear magnetic resonance
African Trypanosomiasis
Endophytes
Banks (bodies of water)
nuclear magnetic resonance
fermentation
Africa South of the Sahara
Disaccharides
Aminoglycosides
metabolism
Mycobacterium

Keywords

  • Antiparasitics
  • Endophytes
  • Glycosides
  • Mangroves
  • Trypanosomes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Kyeremeh, K., Kwain, S., Tetevi, G. M., Camas, A. S., Camas, M., Dofuor, A. K., ... Jaspars, M. (2019). α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]. MolBank, 2019(2), [M1066]. https://doi.org/10.3390/M1066

α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]. / Kyeremeh, Kwaku; Kwain, Samuel; Tetevi, Gilbert Mawuli; Camas, Anil Sazak; Camas, Mustafa; Dofuor, Aboagye Kwarteng; Deng, Hai; Jaspars, Marcel.

In: MolBank, Vol. 2019, No. 2, M1066, 16.06.2019.

Research output: Contribution to journalArticle

Kyeremeh, K, Kwain, S, Tetevi, GM, Camas, AS, Camas, M, Dofuor, AK, Deng, H & Jaspars, M 2019, 'α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]', MolBank, vol. 2019, no. 2, M1066. https://doi.org/10.3390/M1066
Kyeremeh K, Kwain S, Tetevi GM, Camas AS, Camas M, Dofuor AK et al. α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]. MolBank. 2019 Jun 16;2019(2). M1066. https://doi.org/10.3390/M1066
Kyeremeh, Kwaku ; Kwain, Samuel ; Tetevi, Gilbert Mawuli ; Camas, Anil Sazak ; Camas, Mustafa ; Dofuor, Aboagye Kwarteng ; Deng, Hai ; Jaspars, Marcel. / α-D-glucopyranosyl-(1→2)-[6-O-(L-tryptophanyl)-β-D-fructofuranoside]. In: MolBank. 2019 ; Vol. 2019, No. 2.
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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 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.",
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author = "Kwaku Kyeremeh and Samuel Kwain and Tetevi, {Gilbert Mawuli} and Camas, {Anil Sazak} and Mustafa Camas and Dofuor, {Aboagye Kwarteng} and Hai Deng and Marcel Jaspars",
note = "Funding: K.K. wishes to thank the Centre for African Wetlands (CAW), University of Ghana, for providing seed funding to enable the collection of soil samples for microbe isolation and a TWAS Research Grant Award_17-512 RG/CHE/AF/AC_G. K.K. is also very grateful to the Cambridge-Africa Partnership for Research Excellence (CAPREx), which is funded by the Carnegie Corporation of New York, for a Postdoctoral Fellowship. K.K. also appreciates the Cambridge-Africa ALBORADA Research Fund for support and MRC African Research Leaders MR/S00520X/1 Award. S.K. wishes to thank the Carnegie BANGA-Africa Project Award for a PhD scholarship. Acknowledgments: All the authors extend their gratitude to the Department of Chemistry, UG for providing NMR facility. Conflicts of Interest: The authors declare no conflicts of interests. Author Contributions: K.K. collected mangrove plant parts and isolated the strain BRS2A-AR2. A.S.C. and M.C. identified the exact taxonomy of the strain. M.J. and H.D. provided access to facilities for mass spectrometry and data interpretation. K.K. performed chemical profiling to identify the major metabolite. S.K. and G.M.T. performed seed culture, large scale culture, isolation and purification of compound. A.K.D. performed all the biological assays. K.K. measured all NMR, IR and UV, analyzed the results and integration of data to give the complete structure of the compound. K.K. wrote the article.",
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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 - Funding: K.K. wishes to thank the Centre for African Wetlands (CAW), University of Ghana, for providing seed funding to enable the collection of soil samples for microbe isolation and a TWAS Research Grant Award_17-512 RG/CHE/AF/AC_G. K.K. is also very grateful to the Cambridge-Africa Partnership for Research Excellence (CAPREx), which is funded by the Carnegie Corporation of New York, for a Postdoctoral Fellowship. K.K. also appreciates the Cambridge-Africa ALBORADA Research Fund for support and MRC African Research Leaders MR/S00520X/1 Award. S.K. wishes to thank the Carnegie BANGA-Africa Project Award for a PhD scholarship. Acknowledgments: All the authors extend their gratitude to the Department of Chemistry, UG for providing NMR facility. Conflicts of Interest: The authors declare no conflicts of interests. Author Contributions: K.K. collected mangrove plant parts and isolated the strain BRS2A-AR2. A.S.C. and M.C. identified the exact taxonomy of the strain. M.J. and H.D. provided access to facilities for mass spectrometry and data interpretation. K.K. performed chemical profiling to identify the major metabolite. S.K. and G.M.T. performed seed culture, large scale culture, isolation and purification of compound. A.K.D. performed all the biological assays. K.K. measured all NMR, IR and UV, analyzed the results and integration of data to give the complete structure of the compound. K.K. wrote the article.

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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

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