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

doi:10.3390/M1066

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

by

Kwaku Kyeremeh

^1,*

,

Samuel Kwain

¹,

Gilbert Mawuli Tetevi

¹,

Anil Sazak Camas

²,

Mustafa Camas

²

,

Aboagye Kwarteng Dofuor

³

,

Hai Deng

⁴

and

Marcel Jaspars

⁴

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

Submission received: 13 May 2019 / Revised: 14 June 2019 / Accepted: 14 June 2019 / Published: 16 June 2019

(This article belongs to the Section Natural Product Chemistry)

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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.

Keywords: endophytes; mangroves; glycosides; trypanosomes; antiparasitics

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MDPI and ACS Style

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. https://doi.org/10.3390/M1066

AMA Style

Kyeremeh K, Kwain S, Tetevi GM, Camas AS, Camas M, Dofuor AK, Deng H, Jaspars M. α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]. Molbank. 2019; 2019(2):M1066. https://doi.org/10.3390/M1066

Chicago/Turabian Style

Kyeremeh, Kwaku, Samuel Kwain, Gilbert Mawuli Tetevi, Anil Sazak Camas, Mustafa Camas, Aboagye Kwarteng Dofuor, Hai Deng, and Marcel Jaspars. 2019. "α-d-Glucopyranosyl-(1→2)-[6-O-(l-tryptophanyl)-β-d-fructofuranoside]" Molbank 2019, no. 2: M1066. https://doi.org/10.3390/M1066

APA Style

Kyeremeh, K., Kwain, S., Tetevi, G. M., Camas, A. S., Camas, M., Dofuor, A. K., Deng, H., & 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

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

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