Structural analysis of fructans from Agave americana grown in South Africa for spirit production.
Fructans isolated from Agave americana grown in South Africa are currently used for spirit production. Structural studies on water-soluble fructans were performed to facilitate the development of other applications including its use as a prebiotic. Acid hydrolysis followed by HPAEC-PAD analysis confirmed that the fructan was composed of glucose and fructose, and size analysis by HPAEC-PAD and size exclusion chromatography indicated that the saccharides have a DP range from 6 to 50. An average DP of 14 was estimated by (1)H NMR analysis. Linkage analysis and ESI-MS studies suggest that A. americana has a neofructan structure consisting of a central sucrose to which (2 → 1)- and (2 → 6)-linked β-D-Fruf chains are attached. The (2 → 1)-linked units extend from C-1 of Fru and C-6 of glucose, whereas the (2 → 6)-linked β-D-Fruf units are attached to C-6 of the central Fru. This structure accounts for the presence of equimolar amounts of 1,6-linked Glu and 1,2,6-linked Fru found in linkage analysis and the multiplicity of the NMR signals observed. Detailed ESI-MS studies were performed on fructan fractions: native, periodate oxidized/reduced, and permethylated oligomers. These derivatizations introduced mass differences between Glc and Fru following oxidation and between 1,2-, 1,6-, 2,6-, and 1,2,6-linked units after methylation. Thus, ESI-MS showed the presence of a single Glc per fructan chain and that it is predominantly internal, rather than terminal as found in inulin. These structural features were confirmed by the use of 1D and 2D NMR experiments.
Bioanalytical and Vaccine Research, Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa. Neil.Ravenscroft@uct.ac.za
Neil
N
Ravenscroft
Paola
P
Cescutti
Meredith A
MA
Hearshaw
Ronica
R
Ramsout
Roberto
R
Rizzo
Elizabeth M
EM
Timme
D027882:Agave / Q000737:chemistry*; D000434:Alcoholic Beverages; D002236:Carbohydrate Conformation; D002850:Chromatography, Gel; D005511:Food Handling / Q000379:methods; D005630:Fructans / Q000032:analysis* / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013019:South Africa; D021241:Spectrometry, Mass, Electrospray Ionization; D013395:Sucrose / Q000737:chemistry
D005630:Fructans; D005632:Fructose; D013395:Sucrose; D005947:Glucose