Abstract
Reducing carbohydrates in maple syrup and maple sugar were separated by capillary electrophoresis using derivatization with 1-phenyl-3-methyl-5-pyrazolone (PMP) and the characteristics of these samples were studied. Reducing carbohydrate standards including nine monosaccharides and five disaccharides as PMP derivatives could be easily resolved by using 200 mM borate buffer (pH 10.5) as a background electrolyte. Glucose was the most abundant reducing sugar in both maple samples, and mannose was abundant relative to the other sugars. The other monosaccharides (xylose, arabinose, ribose, galactose and N-acetylglucosamine) were also detected. When maple syrup and maple sugar were treated with invertase, which removed fructose residues from the reducing ends of fructosyl saccharides, melibiose was detected, suggesting that raffinose exists in both samples. The differences of carbohydrate contents between maple syrup and maple sugar were also discussed.
Similar content being viewed by others
Abbreviations
- BGE:
-
Background electrolyte
- PMP:
-
1-Phenyl-3-methyl-5-pyrazolone
- Lac:
-
Lactose
- Mal:
-
Maltose
- Gen:
-
Gentiobiose
- Mel:
-
Melibiose
- Cel:
-
Cellobiose
- Gal:
-
Galactose
- Man:
-
Mannose
- Glc:
-
Glucose
- Rib:
-
Ribose
- Lyx:
-
Lyxose
- Xyl:
-
Xylose
- Ara:
-
Arabinose
- GalNAc:
-
N-Acetylgalactosamine
- GlcNAc:
-
N-Acetylglucosamine
- LC:
-
Liquid chromatography
- GC:
-
Gas chromatography
- ESI:
-
Electrospray ionization
- MS:
-
Mass spectrometry
- UV:
-
Ultraviolet
- r :
-
Correlation coefficient
- RSD:
-
Relative standard deviation
- S/N:
-
Signal to noise ratio
- LOD:
-
Limit of detection
- CE:
-
Capillary electrophoresis
- CZE:
-
Capillary zone electrophoresis
- MEKC:
-
Micellar electrokinetic chromatography
- IEKC:
-
Ion exchange electrokinetic chromatography
- CEC:
-
Capillary electrochromatography
- ACE:
-
Affinity capillary electrophoresis
References
Medeiros PM, Conte MH, Weber JC, Simoneit BRT (2006) Sugars as source indicators of biogenic organic carbon in aerosols collected above the Howland Experimental Forest, Maine. Atmos Environ 40:1694–1705
Slavin JL (2005) Dietary fiber and body weight. Nutrition 21:411–418
Brooks SPJ, Mongeau R, Deeks JR, Lampi BJ, Brassard R (2006) Dietary fiber in baby foods of major brands sold in Canada. J Food Compos Anal 19:59–66
Rawitscher M, Mayer J (1979) Sugar: an expensive source of calories. Food Policy 4:138–139
Poget SF, Legge GB, Proctor MR, Jonathan P, Butler G, Bycroft M, Williams RL (1999) The structure of tunicate C-type lectin from Polyandrocarpa misakiensis complexed with d-galactose. J Mol Biol 290:867–879
Tanaka N, Awai A, Bhuiyan MSA, Fujita K, Fukui H, Takegawa K (1999) Cell surface galactosylation is essential for nonsexual flocculation in Schizosaccharomyces pombe. J Bacteriol 181:1356–1359
Zajonc DM, Savage PB, Bendelac A, Wilson IA, Teyton L (2008) Crystal structures of mouse CD1d-iGb3 complex and its cognate Vα14 T cell receptor suggest a model for dual recognition of foreign and self glycolipids. J Mol Biol 377:1104–1116
Nyholm P-G, Pascher I (1993) Steric presentation and recognition of the saccharide chains of glycolipids at the cell surface: favoured conformations of the saccharide-lipid linkage calculated using molecular mechanics (MM3). Int J Biol Macromol 15:43–51
Baumann H, Doyle D (1980) Metabolic fate of cell surface glycoproteins during immunoglobulin-induced internalization. Cell 21:897–907
Bozzaro S (1985) Cell surface carbohydrates and cell recognition in Dictyostelium. Cell Differ 17:67–82
Yeh S-L, Lin M-S, Chen H-L (2010) Partial hydrolysis enhances the inhibitory effects of konjac glucomannan from Amorphophallus konjac C. Koch on DNA damage induced by fecal water in Caco-2 cells. Food Chem 119:614–618
Imahori Y, Kitamura N, Kobayashi S, Takihara T, Ose K, Ueda Y (2010) Changes in fructooligosaccharide composition and related enzyme activities burdock root during low-temperature storage. Postharvest Biol Technol 55:15–20
Wang X, Chen XH, Yang XY, Geng MY, Wang LM (2007) Acidic oligosaccharide sugar chain, a marine-derived oligosaccharide, activates human glial cell line-derived neurotrophic factor signaling. Neurosci Lett 417:176–180
Martínez-Villaluenga C, Fías J, Gulewicz P, Gulewicz K, Vidal-Valverde C (2008) Food safety evaluation of broccoli and radish sprouts. Food Chem Toxicol 46:1635–1644
Nasi A, Picariello G, Ferranti P (2009) Proteomic approaches to study structure, functions and toxicity of legume seeds lectins. Perspectives for the assessment of food quality and safety. J Proteomics 72:527–538
Lynch BC, Tischler AS, Capen C, Munro IC, McGirr LM, McClain MR (1996) Low digestible carbohydrates (polyols and lactose): significance of adrenal medullary proliferative lesions in the rat. Regul Toxicol Pharmacol 23:256–297
Engel K-H, Blaas WK, Gabriel B, Beckman M (1996) Modern biotechnology in plant breeding: analysis of glycoalkaloids in transgenic potatoes. ACS Symp Ser 637:249–260
Adachi S (1965) Thin-layer chromatography of carbohydrates in the presence of bisulfate. J Chromatogr 17:295–299
Sakho M, Chassagne D, Crouzet J (1997) African mango glycosidically bound volatile compounds. J Agric Food Chem 45:883–888
Gunata Z, Blondeel C, Valuer MJ, Lepoutre JP, Sapis JC, Watanabe N (1998) An endoglycosidase from Grape berry skin of Cv. M. Alexandria hydrolyzing potentially aromatic disaccharide glycosides. J Agric Food Chem 46:2748–2753
Reiffová K, Nemcová R (2006) Thin-layer chromatography analysis of fructooligosaccharides in biological samples. J Chromatogr A 1110:214–221
Honda S, Yamauchi N, Kakehi K (1979) Rapid gas chromatographic analysis of aldoses as their diethyl dithioacetal trimethylsilylates. J Chromatogr 169:287–293
Honda S, Nagata M, Kakehi K (1981) Rapid gas chromatographic of partially methylated aldoses as trimethylsilylated diethyl dithioacetals. J Chromatogr 209:299–305
Kaine LA, Wolnik KA (1998) Detection of counterfeit and relabled infant formulas by high-pH anion-exchange chromatography-pulsed amperometric detection for the determination of sugar profiles. J Chromatogr A 804:279–287
Corradini C, Bianchi F, Matteuzzi D, Amoretti A, Rossi M, Zanoni S (2004) High-performance anion-exchange chromatography coupled with pulsed amperometric detection and capillary zone electrophoresis with indirect ultra violet detection as powerful tools to evaluate prebiotic properties of fructooligosaccharides and inulin. J Chromatogr A 1054:165–173
Zhang Z, Linhardt RJ (2009) Sequence analysis of native oligosaccharides using negative ESI tandem MS. Curr Anal Chem 5:225–237
Solakyildirim K, Zhang Z, Linhardt RJ (2010) Ultraperformance liquid chromatography with electrospray ionization ion trap mass spectrometry for chondroitin disaccharide analysis. Anal Biochem 397:24–28
Zhang X, Cao Y, Ye J (2001) Determination of lactose in sugar-free milk powder by capillary electrophoresis with electrochemical detection. Food Chem 72:385–388
Cao Y, Wang Y, Chen X, Ye J (2004) Study on sugar profile of rice during ageing by capillary electrophoresis with electrochemical detection. Food Chem 86:131–136
Zemann AJ (1997) Sub-minute separations of organic and inorganic anions with co-electroosmotic capillary electrophoresis. J Chromatogr A 787:243–251
Sanz ML, Martínez-Castro I (2007) Recent developments in sample preparation for chromatographic analysis of carbohydrates. J Chromatogr A 1153:74–89
Hichcock AM, Bowman MJ, Staples GO, Zaia J (2008) Improved workup for glycosaminoglycan disaccharide analysis using CE with LIF detection. Electrophoresis 29:4538–4548
Tseng HM, Gattolin S, Pritchard J, Newbury HJ, Barrett DA (2009) Analysis of mono-, di-, and oligosaccharides by CE using a two-stage derivatization method and LIF detection. Electrophoresis 30:1399–1405
Honda S, Okeda J, Iwanaga H, Kawakami S, Taga A, Suzuki S, Imai K (2000) Ultramicroanalysis od reducing carbohydrates by capillary electrophoresis with laser-induced fluorescence detection as 7-nitro-2,3,1-benzoxadiazole-tagged N-methylglycamine derivatives. Anal Biochem 286:99–111
Honda S, Iwase S, Makino A, Fujiwara S (1989) Simultaneous determination of reducing monosaccharides by capillary zone electrophoresis as the borate complex of N-2-pyridylglycamines. Anal Biochem 176:72–77
Honda S, Suzuki S, Nose A, Yamamoto K, Kakehi K (1991) Capillary zone electrophoresis of reducing mono- and oligo-saccharides as the borate complexes of their 3-methyl-1-phenyl-2-pyrazoline-5-one derivatives. Carbohydr Res 215:193–198
Chen J, He L, Abo M, Zhang J, Sato K, Okuno A (2009) Influence of borate complexation on the electrophoretic behavior of 2-AA derivatized saccharides in capillary electrophoresis. Carbohydr Res 344:1141–1145
Taga A, Suzuki S, Honda S (2001) Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary derivatization with 1-phenyl-3-methyl-5-pyrazolone. J Chromatogr A 911:259–267
Stinson EE, Dooley CJ, Purcell JM, Ard IS (1967) Quebrachitol—a new component of maple sap and syrup. J Agric Food Chem 15:394–397
Stuckel JG, Low NH (1996) The chemical composition of 80 pure maple syrup samples produced in North America. Food Res Int 29:373–379
Martin GG, Martin Y-L, Naulet N, McManns HJD (1996) Application of 2H SNIF-NMR and 13C SIR-MS analyses to maple syrup: detection of added sugars. J Agric Food Chem 44:3206–3213
Paradkar MM, Sakhamuri S, Irudayaraj J (2002) Comparison of FTIR, FT-Raman, and NIR spectroscopy in a maple syrup adulteration study. J Food Sci 67:2009–2015
Honda S, Akao E, Suzuki S, Okuda M, Kakehi K, Nakamura J (1989) High-performance liquid chromatography of reducing carbohydrates as strongly ultraviolet-absorbing and electrochemically sensitive 1-phenyl-3-methyl-5-pyrazolone derivatives. Anal Biochem 180:351–357
Sharma ML, Newbrun E (1973) Continuous spectrophotometric assay of glucosyltransferase and β-fructofuranosidase activity. Carbohydr Res 29:165–172
Villaluenga CM, Frías J, Gómez R, Valverde CV (2006) Influence of addition of raffinose family oligosaccharides on probiotic survival in fermented milk during refrigerated storage. Int Dairy J 16:768–774
Toyota S, Fukushi Y, Katoh S, Orikasa S, Suzuki Y (1989) Anti-bacterial defence mechanism of the urinary bladder: role of mannose in urine. Jpn J Urol 80:1816–1823
Pätzold R, Brückner H (2005) Mass spectrometric detection and formation of d-amino acids in processed plant saps, syrups, and fruit juice concentrates. J Agric Food Chem 53:9722–9729
Chiesa C, Oefner PJ, Zieske LR, O’Neill RA (1995) Micellar electrokinetic chromatography of monosaccharides derivatized with 1-phenyl-3-methyl-2-pyrazoline-5-one. J Capill Electrophor 2:175–183
Honda S, Togashi K, Uegaki K, Taga A (1998) Enhancement of the zone electrophoretic separation of 1-phenyl-3-methyl-5-pyrazolone derivatives of aldoses as borate complexes by concerted ion-interaction electrokinetic chromatography with Polybrene. J Chromatogr A 805:277–284
Suzuki S, Yamamoto M, Kuwahara Y, Makiura K, Honda S (1998) Separation of 1-phenyl-3-methyl-5-pyrazolone derivatives of monosaccharides by capillary chromatography. Electrophoresis 19:2682–2688
Guček M, Pihlar B (2000) Capillary electrochromatography of 1-phenyl-3-methyl-5-pyrazolone derivatives of some mono- and disaccharides. Chromatographia 51:S139–S142
Taga A, Yabisako Y, Kitano A, Honda S (1998) Separation of disaccharides by affinity capillary electrophoresis in lectin-containing electrophoretic solutions. Electrophoresis 19:2645–2649
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Taga, A., Kodama, S. Analysis of Reducing Carbohydrates and Fructosyl Saccharides in Maple Syrup and Maple Sugar by CE. Chromatographia 75, 1009–1016 (2012). https://doi.org/10.1007/s10337-012-2199-3
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10337-012-2199-3