Isolation and Characterisation of Some Microalgae Bioactive Molecules

Emeka Ugoala, George Ndukwe, Rachael Ayo

Abstract


This study involved the isolation, structure elucidation, and biological screening of secondary metabolites in freshwater microalgae for bioactive and chemically novel compounds. Isolates were fractionated and purified from the methanol, ethyl acetate, dichloromethane, petroleum ether and aqueous extracts of microalgae via column chromatography technique over silica gel using a gradient mixture of solvents. The chemical structures of isolated compounds have been elucidated using Solid-state cross polarization (CP) and magic angle spinning (MAS) 13C-NMR spectroscopic technique at spectrometer frequency at a field strength corresponding to 91.3695 MHz for 13C and 363.331 MHz for 1H. Of the nine compounds isolated, eight have a glycan skeleton with attached amino acids units. Two of the eight contain beta amino acids units. These are not very common metabolites but hold promise as drug leads. The elements of diversity in the isolates were the gluco and manno configurations of the pyranose ring, the α-configurations at the anomeric centre, and the positions of the carbohydrate and amino acid sectors in the ring. These molecules are not easily available through gene technology since they are post translational products resulting from the activity of glycosyl hydrolases and transferases. The chemical shifts were rationalized in terms of the number of sugar residues, the sugar ring structures, the positions and anomeric configurations of the inter-sugar linkages. Considering all the NMR data, it was concluded that the compounds were glycylglycylglycylglycine, α-D-glucopyranosyl-2-amino-4-methylpentanoic acid, α-D-glucopyranosyl-2-methylamino-4-methylpentanoic acid, α-D-glucopyranosyl-2-amino-4-methylpentanoate, α-D-glucopyranosyl-glycylglycine, α-D-glucopyranosyl-3-aminobutanoic acid, α-D-glucopyranosyl-2,4,7-triaminooctantrioic acid, α-D-mannopyranosyl-2-amino-3-methylbutanoic acid and α-D-mannopyranosyl-3-aminobutanoic acid.


Keywords


Solid-state NMR, CP/MAS, Glycoamino acids, Carbohydrate, Chemical shift, Carbon resonance

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DOI: http://dx.doi.org/10.5281/zenodo.200210

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