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

doi:10.3390/M1066

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

Research output: Contribution to journal › Article › peer-review

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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 language	English
Article number	M1066
Number of pages	11
Journal	MolBank
Volume	2019
Issue number	2
DOIs	https://doi.org/10.3390/M1066
Publication status	Published - 16 Jun 2019

Bibliographical 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.

Keywords

Antiparasitics
Endophytes
Glycosides
Mangroves
Trypanosomes

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Kveremeh_ADGlucoyranosyl_VOR
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Cite this

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

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.",

keywords = "Antiparasitics, Endophytes, Glycosides, Mangroves, Trypanosomes",

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. ",

year = "2019",

month = jun,

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doi = "10.3390/M1066",

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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.

PY - 2019/6/16

Y1 - 2019/6/16

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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UR - http://www.mendeley.com/research/%CE%B1dglucopyranosyl126oltryptophanyl%CE%B2dfructofuranoside

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M1 - M1066

ER -

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

Abstract

Bibliographical note

Keywords

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