Identification of a Novel Oligosaccharide in Maple Syrup as a Potential Alternative Saccharide for Diabetes Mellitus Patients
Abstract
:1. Introduction
2. Results
2.1. Profile and Characteristics of the Saccharides in Maple Syrup
2.2. Purification and Structural Analysis of the Unidentified Oligosaccharide in Maple Sap
2.3. The Inhibitory Effect of Maplebiose1 on Enzymatic Glycolysis
2.4. Prevention of the Hyperglycemia Induced in Rats Following Oral Administration of a Sucrose Load by Maplebiose1
3. Discussion
4. Material and Methods
4.1. Materials and Animals
4.2. PMP Derivatization of Maple Syrup and Sap
4.3. Capillary Electrophoresis (CE)
4.4. Invertase Digestion of Maple Syrup
4.5. Size Exclusion Chromatography
4.6. High-Performance Liquid Chromatography with Charged Aerosol Detection (HPLC-CAD)
4.7. Hydrolysis of the Unidentified Oligosaccharide
4.8. Liquid Chromatography (LC)-Electrospray Ionization (ESI)-Mass Spectrometry (MS)
4.9. Nuclear Magnetic Resonance (NMR)
4.10. Invertase Inhibition Assay
4.11. Glycosidase Inhibition Assay
4.12. Biochemical Assays Conducted on Blood Samples from Rats
4.13. Oral Sucrose Tolerance Testing
4.14. Statistical Analysis
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
BGE | Background electrolyte |
CAD | Charged aerosol detection |
CE | Capillary electrophoresis |
CID | Collision introduced dissolution |
DM | Diabetes mellitus |
HMBC | 1H-13C heteronuclear multiple-bond correlation spectroscopy |
HPLC | High-performance liquid chromatography |
IC50 | Half-maximal inhibitory concentration |
LC-ESI-MS | Liquid chromatography-electrospray ionization-mass spectrometry |
NMR | Nuclear magnetic resonance |
PMP | 1-phenyl-3-methyl-5-pyrazolone |
UV | Ultraviolet |
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Chemical Shift | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Residue | Position | δC | δH | JH,H | Type | Residue | Position | δC | δH | JH,H | Type |
Glc α | 1 | 94.72 | 5.07 | 3.8 | d | Glc β | 1 | 98.57 | 4.49 | 8.0 | d |
2 | 74.05 | 3.38 | 3.8, 9.8 | dd | 2 | 76.67 | 3.09 | 8.0, 9.3 | dd | ||
3 | 75.25 | 3.54 | - | m | 3 | 78.23 | 3.33 | 9.3, 9.3 | dd | ||
4 | 72.32 | 3.29 | 9.0, 9.0 | dd | 4 | 72.25 | 3.29 | 9.0, 9.0 | dd | ||
5 | 73.27 | 3.77 | 1.9, 9.2, 9.7 | ddd | 5 | 77.58 | 3.40 | 2.1, 8.7, 9.7 | ddd | ||
6 | 63.38 | 3.82 | 2.1, 10.9 | dd | 6 | 63.38 | 3.87 | 2.0, 11.0 | dd | ||
Fru β | 1’ | 62.75 | 3.60 | - | m | Fru β | 1’ | 62.72 | 3.54 | - | m |
2’ | 106.31 | - | - | - | 2’ | 106.34 | - | - | - | ||
3’ | 79.42 | 4.03 | 8.5 | d | 3’ | 79.52 | 4.02 | 8.5 | d | ||
4’ | 77.06 | 3.97 | 8.1, 8.2 | dd | 4’ | 77.21 | 3.96 | 8.0, 8.3 | dd | ||
5’ | 83.75 | 3.72 | 7.4 | t | 5’ | 83.81 | 3.72 | 7.4 | t | ||
6’ | 64.98 | 3.54–3.66 | - | m | 6’ | 65.10 | 3.54–3.66 | - | m |
Glycolytic Enzyme | Inhibitor (µg) | Peak Response (D2) | Peak Response (D3) | Inhibition Rate (%) | IC50 (mmol/L) |
---|---|---|---|---|---|
Invertase | - | 30.5 | - | - | 1.17 |
1 | 18.2 | N.D | 40.3 | ||
10 | 17.2 | N.D | 43.6 | ||
100 | 23.1 | 12.5 | 65.2 | ||
Maltase | - | 44.3 | - | - | 1.72 |
1 | 27 | N.D | 39.1 | ||
10 | 22.4 | N.D | 49.4 | ||
100 | 20.3 | N.D | 54.2 | ||
Isomaltase | - | 31.6 | - | - | - |
1 | 21.1 | N.D | 33.2 | ||
10 | 31.9 | N.D | - | ||
100 | 46.7 | 6.7 | - |
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Sato, K.; Nagai, N.; Yamamoto, T.; Mitamura, K.; Taga, A. Identification of a Novel Oligosaccharide in Maple Syrup as a Potential Alternative Saccharide for Diabetes Mellitus Patients. Int. J. Mol. Sci. 2019, 20, 5041. https://doi.org/10.3390/ijms20205041
Sato K, Nagai N, Yamamoto T, Mitamura K, Taga A. Identification of a Novel Oligosaccharide in Maple Syrup as a Potential Alternative Saccharide for Diabetes Mellitus Patients. International Journal of Molecular Sciences. 2019; 20(20):5041. https://doi.org/10.3390/ijms20205041
Chicago/Turabian StyleSato, Kanta, Noriaki Nagai, Tetsushi Yamamoto, Kuniko Mitamura, and Atsushi Taga. 2019. "Identification of a Novel Oligosaccharide in Maple Syrup as a Potential Alternative Saccharide for Diabetes Mellitus Patients" International Journal of Molecular Sciences 20, no. 20: 5041. https://doi.org/10.3390/ijms20205041