Isomers of the Tomato Glycoalkaloids α-Tomatine and Dehydrotomatine: Relationship to Health Benefits
Abstract
:1. Introduction
2. Results
3. Discussion
3.1. Health Benefits
3.1.1. Antibiotic Effects
3.1.2. Preventive Effects against Hyperlipidemia, Atherosclerosis, Obesity, and Osteoporosis
3.1.3. Cancer-Preventive Properties In Vitro and In Vivo
4. Materials and Methods
4.1. Materials
4.2. Sample Preparation
4.3. LC/MS Analysis
4.4. LC-(Q) TOF/MS Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound | Stereochemistry | Molecular Weight |
---|---|---|
Dehydrotomatine (tetrasaccharide) | Tomatidenol-3-O-[β-d-glucopyranosyl-(1→2)-β-d-xylopyranosyl-(1→3)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside | 1032.2 |
α-Tomatine (tetrasaccharide) | Tomatidine-3-O-[β-d-glucopyranosyl-(1→2)-β-d-xylopyranosyl-(1→3)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside | 1034.2 |
β1-Tomatine (trisaccharide) | Tomatidine-3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)]-β-d-galactopyranoside | 902.05 |
β2-Tomatine (trisaccharide) | Tomatidine-3-O-[β-d-xylopyranosyl-(1→3)-β-d-glucopyranosyl-(1→4)]-β-d-galactopyranoside | 872.03 |
γ-Tomatine (disaccharide) | Tomatidine-3-O-[β-d-glucopyranosyl-1→4)-β-galactopyranoside] | 739.90 |
δ-Tomatine (monosaccharide) | Tomatidine-3-O-β-d-galactopyranoside | 577.75 |
Tomatidine | 5α-tomatidan-3β-Ol |
Samples | Peak No. on HPLC and LC-MS | Retention a Time (min) | Peak Area (%) b (208 nm) | Peak Area (%) c [TIC Count (cps)] | [M-H]− (m/z) | MS/MS Fragments | Identification |
---|---|---|---|---|---|---|---|
Tomatine sample A | 1 | 7.52 | 0.97 (1.00) d | 0.32 (1.00) e | 1031.7 | nd c | Dehydrotomatine isomer |
2 | 8.61 | 1.12 (1.15) | 1.76 (5.50) | 1032.8 | 1033.4, 870.7, 739.8, 576.3 | α-Tomatine isomer | |
3 | 16.37 | 48.83 (50.34) | 15.68 (49.00) | 1030.8 | 1031.5, 899.8, 869.4, 737.4, 575.4 | Dehydro-tomatine | |
4 | 20.02 | 49.08 (50.60) | 82.24 (257.00) | 1033.7 | 1033.6, 901.7, 871.6, 739.5, 577.3 | α-Tomatine | |
Tomatine sample D | 1 | 7.41 | 2.78 (1.00) | 1.46 (1.00) | 1030.7 | 868.2, 574.2 | Dehydro-tomatine isomer |
2 | 8.47 | 1.81 (0.65) | 8.50 (5.82) | 1032.7 | 1033.7, 901.4, 870.5, 738.5, 576.4 | α-Tomatine isomer | |
3 | 15.82 | 38.25 (13.76) | 12.62 (8.64) | 1030.6 | 1030.9, 898.7, 869.8, 736.6, 574.2 | Dehydro-tomatine | |
4 | 19.39 | 57.16 (20.56) | 77.42 (53.03) | 1032.8 | 1033.8, 871.7, 738.5, 576.2 | α-Tomatine |
Samples | Peak No. on HPLC and LC-MS | Retention a Time (min) | Peak Area (%) b (208 nm) | Peak Area (%) c [TIC count (cps)] | [M-H]− (m/z) | MS/MS Fragments | Identification |
---|---|---|---|---|---|---|---|
Tomatine sample B | 1 | 6.75 | 0.64 (1.00) d | 0.46 (1.00) e | 1030.8 | 898.8, 868.9, 737.3, 574.2 | Dehydrotomatine isomer |
2 | 7.62 | 1.04 (1.63) | 2.19 (4.76) | 1033.2 | 1032.8, 900.7, 870.7, 738.5, 576.5 | α-Tomatine isomer | |
3 | 14.29 | 37.88 (59.19) | 14.63 (31.80) | 1031.4 | 1030.8, 898.5, 868.6, 736.6, 574.4 | Dehydrotomatine | |
4 | 18.77 | 60.45 (94.45) | 82.72 (179.82) | 1032.9 | 1032.6, 900.9, 870.9, 738.7, 576.5 | α-Tomatine | |
Tomatine sample C | 1 | 6.77 | 1.02 (1.00) | 0.74 (1.00) | 1030.8 | 898.8, 736.6, 574.2 | Dehydrotomatine isomer |
2 | 7.75 | 2.17 (2.13) | 2.49 (3.36) | 1032.7 | 1032.5, 900.4, 870.4, 738.7, 576.2 | α-Tomatine isomer | |
3 | 14.20 | 45.28 (44.39) | 17.03 (23.01) | 1031.5 | 1030.6, 898.6, 868.8, 736.8, 574.6 | Dehydrotomatine | |
4 | 18.65 | 51.53 (50.52) | 79.74 (107.76) | 1033.6 | 1033.6, 901.7, 871.8, 739.6, 577.4 | α-Tomatine |
Samples | Peak No. on HPLC and LC-MS | Retention a Time (min) | Peak Area (%) b (208 nm) | Peak Area (%) c [TIC Count (cps)] | [M-H]− (m/z) | MS/MS Fragments | Identification |
---|---|---|---|---|---|---|---|
New α-tomatine | 1 | 10.78 | 2.18 (1.00) d | 0.24 (1.00) e | 1030.6 | 1030.6, 899.0, 868.8, 736.7, 574.4 | Dehydrotomatine isomer |
2 | 12.32 | 1.22 (0.56) | 2.17 (9.04) | 1033.5 | 1032.7, 900.5, 870.6, 738.6, 576.4 | α-Tomatine isomer | |
3 | 22.78 | 37.15 (17.04) | 7.95 (33.13) | 1031.5 | 1031.6, 896.6, 869.6, 736.7, 574.7 | Dehydrotomatine | |
4 | 28.60 | 59.45 (27.27) | 89.64 (373.50) | 1033.7 | 1032.6, 900.7, 870.9, 738.8, 576.7 | α-Tomatine | |
Old α-tomatine | 1 | 10.65 | 0.91 (1.00) | 0.18 (1.00) | 1031.4 | 1031.4, 899.3, 869.2 | Dehydrotomatine isomer |
2 | 12.18 | 1.39 (1.53) | 2.36 (13.11) | 1032.7 | 900.4, 870.4, 738.8, 576.4 | α-Tomatine isomer | |
3 | 23.73 | 55.83 (61.35) | 15.59 (86.61) | 1030.8 | 1030.6, 898.6, 868.5, 736.5, 574.3 | Dehydrotomatine | |
4 | 29.36 | 41.87 (46.01) | 81.87 (454.83) | 1033.4 | 1032.5, 900.7, 870.8, 738.6, 576.6 | α-Tomatine |
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Kozukue, N.; Kim, D.-S.; Choi, S.-H.; Mizuno, M.; Friedman, M. Isomers of the Tomato Glycoalkaloids α-Tomatine and Dehydrotomatine: Relationship to Health Benefits. Molecules 2023, 28, 3621. https://doi.org/10.3390/molecules28083621
Kozukue N, Kim D-S, Choi S-H, Mizuno M, Friedman M. Isomers of the Tomato Glycoalkaloids α-Tomatine and Dehydrotomatine: Relationship to Health Benefits. Molecules. 2023; 28(8):3621. https://doi.org/10.3390/molecules28083621
Chicago/Turabian StyleKozukue, Nobuyuki, Dong-Seok Kim, Suk-Hyun Choi, Masashi Mizuno, and Mendel Friedman. 2023. "Isomers of the Tomato Glycoalkaloids α-Tomatine and Dehydrotomatine: Relationship to Health Benefits" Molecules 28, no. 8: 3621. https://doi.org/10.3390/molecules28083621