Kinetics of Glycoxidation of Bovine Serum Albumin by Glucose, Fructose and Ribose and Its Prevention by Food Components
Abstract
:1. Introduction
2. Results
2.1. Kinetics of Glycoxidation
2.2. Protection against Glycoxidation
Additive | AGE | Dityrosine | N'-formylkynurenine | Kynurenine | AOPP |
---|---|---|---|---|---|
BSA, no sugar | 3.55 ± 5.16 * | 3.46 ± 5.61 * | 1.57 ± 5.37 * | 7.27 ± 10.06 * | 17.25 ± 6.58 # |
BSA + glucose, no additive | 100 | 100 | 100 | 100 | 100 |
DMSO | 103.78 ± 10.32 | 100.56 ± 10.59 | 103.45 ± 10.91 | 232.47 ± 23.09 # | 91.11 ± 9.34 |
Standard Antiglycating Agents | |||||
Aminoguanidine | 41.91 ± 2.69 * | 29.39 ± 4.13 * | 38.07 ± 3.07 * | 66.58 ± 10.87 Δ | 41.31 ± 4.87 # |
Metformin | 112.75 ± 3.34 Δ | 116.00 ± 2.79 # | 124.59 ± 3.01 # | 119.83 ± 6.21 Δ | 118.21 ± 9.02 |
Pyridoxine | <0 * | <0 * | <0 * | 193.42 ± 14.04 # | 6.19 ± 4.27 * |
Antioxidants | |||||
Captopril | 34.52 ± 7.55 # | 31.85 ± 6.81 # | 37.62 ± 7.22 # | 87.27 ± 16.74 | 33.66 ± 6.14 # |
Tiron | 31.3 ± 10.73 # | 28.91 ± 10.92 # | 33.12 ± 11.23 # | 72.55 ± 15.79 Δ | 65.87 ± 13.88 |
Metal Chelators | |||||
EDTA | 98.14 ± 2.27 | 92.47 ± 3.40 | 99.53 ± 4.81 | 87.01 ± 7.95 | 106.87 ± 13.37 |
DETAPA | 135.79 ± 2.61 # | 127.51 ± 1.63 Δ | 125.27 ± 4.11 Δ | 94.94 ± 2.24 | 107.18 ± 17.16 |
NTA | 124.59 ± 9.51 Δ | 113.80 ± 8.24 | 112.30 ± 8.92 | 94.03 ± 13.82 | 109.73 ± 8.69 |
Amino Acids and Derivatives, Peptides | |||||
Arginine | 120.14 ± 9.56 | 106.81 ± 9.16 | 108.58 ± 8.69 | 104.33 ± 14.37 | 107.86 ± 14.18 |
Carnosine | 122.00 ± 6.13 Δ | 120.20 ± 6.46 Δ | 135.06 ± 7.29 # | 152.47 ± 9.75 # | 127.47 ± 31.73 |
Cysteamine | 20.19 ± 9.35 # | 19.16 ± 9.82 # | 22.82 ± 10.75 # | 48.48 ± 22.52 Δ | 46.15 ± 10.14 Δ |
Glutathione oxidized | 136.72 ± 10.56 Δ | 140.81 ± 11.13 Δ | 144.95 ± 11.84 Δ | 149.44 ± 20.76 | 110.25 ± 8.37 |
Glutathione reduced | 51.49 ± 13.28 Δ | 49.26 ± 10.97 # | 49.61 ± 10.87 # | 111.08 ± 25.92 | 83.66 ± 8.70 |
Glycine | 140.89 ± 20.65 | 143.49 ± 18.41 | 148.09 ± 21.45 | 148.40 ± 28.52 | 110.04 ± 10.32 |
Organic Acids | |||||
1-Cyano-4-hydroxycinnamic acid | 4.89 ± 1.60 * | 4.59 ± 1.26 * | 6.12 ± 2.29 * | 19.48 ± 5.36 * | 31.62 ± 9.55 # |
4-Hydroxy cinnamic acid | 94.70 ± 7.05 | 97.77 ± 6.09 | 104.29 ± 6.23 | 92.12 ± 12.43 | 89.07 ± 9.50 |
Lipoic acid | 89.23 ± 2.41 Δ | 89.35 ± 2.42 # | 97.02 ± 3.17 | 97.73 ± 2.80 | 91.71 ± 9.89 |
Para-aminobenzoic acid | 152.04 ± 18.58 Δ | 150.09 ± 16.01 Δ | 163.83 ± 17.49 Δ | 149.39 ± 15.80 Δ | 129.74 ± 25.42 |
Pyruvic acid | 82.29 ± 3.11 # | 84.56 ± 2.68 # | 91.26 ± 2.88 Δ | 73.94 ± 6.16 # | 94.54 ± 2.27 |
Quinic acid | 72.93 ± 8.44 Δ | 75.19 ± 8.59 Δ | 79.49 ± 8.34 Δ | 56.54 ± 12.28 Δ | 88.53 ± 11.99 |
Organic Polybases | |||||
Spermidine | 143.88 ± 4.11 # | 137.43 ± 3.23 # | 151.7 ± 3.39 * | 233.07 ± 8.83 * | 117.47 ± 16.58 |
Spermine | 144.22 ± 19.98 | 139.62 ± 23.29 | 153.53 ± 22.79 | 195.06 ± 35.58 Δ | 118.37 ± 13.14 |
Polyphenols | |||||
Caffeic acid | <0 * | <0 * | <0 * | 180.71 ± 9.74 # | 43.38 ± 14.08 Δ |
Ellagic acid | 96.47 ± 6.16 | 58.82 ± 4.37 # | 92.01 ± 6.56 | 107.71 ± 35.95 | 103.99 ± 41.12 |
Ferulic acid | <0 * | <0 * | 29.34 ± 7.35 # | 156.28 ± 19.39 Δ | 53.27 ± 9.22 Δ |
Gallic acid | 460.03 ± 9.73 * | 249.02 ± 14.12 # | 432.07 ± 11.04 * | 586.37 ± 49.71 # | 615.09 ± 24.62 * |
Genistein | 27.46 ± 0.97 * | 23.86 ± 0.79 * | 27.77 ± 1.43 * | 46.85 ± 1.77 * | 44.43 ± 10.14 Δ |
Kaempferol | 20.77 ± 2.09 * | 13.98 ± 1.58 * | 20.18 ± 2.43 * | 22.12 ± 4.38 * | 45.97 ± 18.44 Δ |
Naringin | 28.90 ± 0.44 * | 22.05 ± 0.17 * | 24.38 ± 0.35 * | 103.39 ± 4.68 | 35.87 ± 11.61 Δ |
Propyl gallate | <0 * | <0 * | <0 * | 198.18 ± 5.78 * | 71.84 ± 20.08 |
Quercitrin | 3.37 ± 0.38 * | 1.11 ± 0.28 * | 1.01 ± 0.17 * | 3.31 ± 0.58 * | 47.35 ± 14.16 Δ |
Rutin | 2.94 ± 0.35 * | 1.15 ± 0.34 * | 1.26 ± 0.23 * | 2.79 ± 0.14 * | 42.26 ± 5.76 # |
Additive | AGE | Dityrosine | N'-formylkynurenine | Kynurenine | AOPP |
---|---|---|---|---|---|
BSA, no sugar | 0.67 ± 0.97 * | 0.65 ± 1.05 * | 0.29 ± 0.99 * | 1.52 ± 2.10 * | 8.91 ± 3.40 * |
BSA + fructose, no additive | 100 | 100 | 100 | 100 | 100 |
DMSO | 68.54 ± 4.64 # | 62.86 ± 3.89 # | 67.52 ± 4.32 # | 134.00 ± 10.30 Δ | 70.55 ± 3.61 # |
Standard Antiglycating Agents | |||||
Aminoguanidine | 19.53 ± 1.58 * | 17.76 ± 0.667 * | 19.20 ± 0.75 * | 39.31 ± 1.96 * | 44.15 ± 3.33 # |
Metformin | 82.45 ± 5.02 Δ | 83.67 ± 5.14 Δ | 87.36 ± 4.91 Δ | 75.52 ± 7.14 Δ | 123.16 ± 13.28 |
Pyridoxine | <0 * | <0 * | <0 * | 181.88 ± 3.75 * | 34.26 ± 4.68 # |
Antioxidants | |||||
Captopril | 27.87 ± 0.78 * | 25.15 ± 0.78 * | 28.50 ± 0.93 * | 59.26 ± 2.32 * | 16.28 ± 3.17 * |
Tiron | 97.32 ± 0.70 Δ | 104.07 ± 0.78 # | 103.62 ± 0.98 Δ | 105.68 ± 1.72 Δ | 44.98 ± 4.78 # |
Metal Chelators | |||||
EDTA | 98.57 ± 2.99 | 97.09 ± 2.99 | 99.2 ± 1.50 | 99.76 ± 2.01 | 111.12 ± 12.93 |
DETAPA | 63.07 ± 3.04 # | 59.98 ± 2.92 # | 58.47 ± 2.79 # | 49.35 ± 7.83 # | 87.21 ± 4.25 Δ |
NTA | 107.64 ± 3.03 Δ | 102.55 ± 3.12 | 101.09 ± 2.80 | 93.19 ± 4.03 Δ | 109.27 ± 5.26 |
Amino Acids and Derivatives, Peptides | |||||
Arginine | 93.26 ± 3.56 Δ | 87.62 ± 3.70 Δ | 89.68 ± 4.06 Δ | 81.59 ± 4.85 Δ | 107.2 ± 41.66 |
Carnosine | 97.12 ± 5.10 | 96.28 ± 4.74 | 103.05 ± 5.13 | 104.80 ± 8.01 | 109.53 ± 18.10 |
Cysteamine | 54.44 ± 1.83 * | 53.36 ± 1.78 * | 56.81 ± 2.18 * | 71.95 ± 4.41 # | 46.10 ± 13.99 Δ |
Glutathione oxidized | 111.61 ± 1.64 # | 113.09 ± 2.61 # | 115.42 ± 2.35 # | 114.77 ± 3.19 # | 120.90 ± 16.07 |
Glutathione reduced | 78.10 ± 7.50 Δ | 78.39 ± 6.58 Δ | 77.68 ± 6.80 Δ | 69.38 ± 8.54 Δ | 129.12 ± 2.89 # |
Glycine | 118.53 ± 7.88 Δ | 118.7 ± 7.03 Δ | 120.96 ± 6.82 Δ | 120.01 ± 8.89 Δ | 102.15 ± 21.96 |
Organic Acids | |||||
1-Cyano-4-hydroxycinnamic acid | 5.57 ± 0.16 * | 5.14 ± 0.13 * | 6.27 ± 0.16 * | 20.81 ± 0.59 * | 52.02 ± 13.55 Δ |
4-Hydroxycinnamic acid | 88.85 ± 3.17 Δ | 90.26 ± 3.39 Δ | 94.86 ± 3.67 | 93.19 ± 5.23 | 63.30 ± 17.30 |
Lipoic acid | 132.99 ± 4.67 # | 130.7 ± 4.22 # | 137.82 ± 4.29 # | 129.87 ± 4.37 # | 150.17 ± 8.03 # |
Para-aminobenzoic acid | 102.75 ± 4.31 | 97.82 ± 3.74 | 106.23 ± 4.13 | 107.31 ± 4.52 | 111.79 ± 9.52 |
Pyruvic acid | 61.70 ± 7.64 # | 62.90 ± 7.79 # | 65.43 ± 8.03 # | 39.36 ± 9.49 # | 87.62 ± 5.22 |
Quinic acid | 96.86 ± 2.00 | 98.96 ± 1.73 | 104.02 ± 1.80 Δ | 98.33 ± 2.61 | 85.14 ± 6.43 |
Organic Polybases | |||||
Spermidine | 101.10 ± 1.64 | 94.96 ± 3.30 | 102.77 ± 2.56 | 153.21 ± 8.47 # | 93.39 ± 12.04 |
Spermine | 120.74 ± 7.01 Δ | 118.59 ± 7.42 Δ | 125.58 ± 7.11 Δ | 150.61 ± 5.94 # | 98.82 ± 49.59 |
Polyphenols | |||||
Caffeic acid | <0 * | <0 * | <0 * | 239.70 ± 68.36 Δ | 79.04 ± 6.87 Δ |
Ellagic acid | 31.62 ± 4.73 * | 21.03 ± 3.68 * | 29.80 ± 4.41 * | 60.44 ± 7.81 # | 129.61 ± 5.19 Δ |
Ferulic acid | <0 * | <0 * | 0.42 ± 3.25 * | 92.74 ± 5.87 | 43.52 ± 3.32 # |
Gallic acid | 59.54 ± 1.65 * | 33.05 ± 1.20 * | 55.43 ± 1.18 * | 217.27 ± 2.94 * | 92.99 ± 21.89 |
Genistein | 14.88 ± 0.61 * | 12.64 ± 0.34 * | 14.97 ± 0.49 * | 20.47 ± 0.25 * | 69.88 ± 10.88 Δ |
Kaempferol | 14.36 ± 1.15 * | 9.98 ± 0.77 * | 13.63 ± 1.10 * | 18.55 ± 2.11 * | 64.21 ± 7.72 Δ |
Naringin | 27.03 ± 0.30 * | 21.53 ± 0.38 * | 24.90 ± 0.97 * | 99.74 ± 3.01 | 76.34 ± 4.21 Δ |
Propyl gallate | <0 * | <0 * | <0 * | 54.36 ± 6.62 # | 41.08 ± 11.75 Δ |
Quercitrin | 2.62 ± 0.26 * | 1.77 ± 0.22 * | 2.08 ± 0.30 * | 1.84 ± 0.23 * | 43.63 ± 2.57 * |
Rutin | 2.48 ± 0.11 * | 1.82 ± 0.07 * | 2.20 ± 0.10 * | 1.82 ± 0.09 * | 50.28 ± 7.56 # |
Additive | AGE | Dityrosine | N'-formylkynurenine | Kynurenine | AOPP |
---|---|---|---|---|---|
BSA, no sugar | 0.67 ± 0.97 * | 0.65 ± 1.05 * | 0.29 ± 0.99 * | 1.52 ± 2.10 * | 1.82 ± 0.70 * |
BSA + ribose, no additive | 100 | 100 | 100 | 100 | 100 |
DMSO | 92.02 ± 0.64 # | 92.38 ± 0.67 # | 93.92 ± 0.84 # | 113.33 ± 0.96 * | 109.68 ± 0.87 # |
Standard Antiglycating Agents | |||||
Aminoguanidine | 78.07 ± 1.53 * | 70.13 ± 0.32 * | 79.71 ± 0.44 * | 80.21 ± 2.06 * | 64.35 ± 4.39 # |
Metformin | 99.66 ± 1.77 | 100.52 ± 1.67 | 105.57 ± 1.63 Δ | 91.19 ± 3.96 | 80.84 ± 4.72 Δ |
Pyridoxine | <0 * | <0 * | <0 * | 95.09 ± 2.42 | 10.02 ± 3.45 * |
Antioxidants | |||||
Captopril | 93.66 ± 0.41 * | 94.57 ± 0.80 # | 98.39 ± 0.69 Δ | 102.39 ± 2.97 | 91.08 ± 2.02 Δ |
Tiron | 97.32 ± 0.70 Δ | 104.07 ± 0.78 # | 103.62 ± 0.98 Δ | 105.68 ± 1.72 Δ | 51.85 ± 4.39 # |
Metal Chelators | |||||
EDTA | 98.67 ± 0.59 | 97.64 ± 6.72 | 99.29 ± 7.77 | 100.31 ± 8.44 | 96.71 ± 0.74 |
DETAPA | 104.09 ± 0.48 # | 99.73 ± 0.62 | 100.59 ± 0.78 | 978.65 ± 1.79 | 76.42 ± 3.41 # |
NTA | 111.73 ± 0.79 * | 107.94 ± 1.07 # | 107.87 ± 0.80 # | 104.63 ± 2.52 | 86.01 ± 2.59 Δ |
Amino Acids and Derivatives, Peptides | |||||
Arginine | 89.83 ± 0.86 # | 89.06 ± 0.80 * | 87.61 ± 0.96 * | 97.67 ± 1.91 | 86.78 ± 4.06 Δ |
Carnosine | 93.56 ± 0.43 * | 93.68 ± 0.35 * | 99.28 ± 0.24 Δ | 102.90 ± 0.77 | 77.96 ± 3.48 # |
Cysteamine | 78.55 ± 1.87 # | 79.47 ± 1.85 # | 82.13 ± 1.98 # | 104.22 ± 3.52 | 93.21 ± 1.68 Δ |
Glutathione oxidized | 83.63 ± 4.11 # | 91.42 ± 3.07 Δ | 87.73 ± 4.38 Δ | 106.09 ± 4.06 | 95.55 ± 3.30 |
Glutathione reduced | 85.58 ± 1.45 # | 91.99 ± 1.15 # | 86.17 ± 1.16 # | 103.70 ± 3.42 | 109.26 ± 3.92 |
Glycine | 99.46 ± 0.55 | 103.24 ± 0.24 * | 104.19 ± 0.99 # | 109.24 ± 2.23 # | 89.25 ± 3.25 Δ |
Organic Acids | |||||
1-Cyano-4-hydroxycinnamic acid | 18.29 ± 0.11 * | 16.46 ± 0.04 * | 18.54 ± 0.05 * | 35.31 ± 0.19 * | 33.38 ± 5.90 # |
4-Hydroxycinnamic acid | 102.44 ± 0.28 # | 104.63 ± 0.40 # | 110.93 ± 0.26 * | 97.48 ± 0.27 # | 96.52 ± 3.52 |
Lipoic acid | 105.45 ± 0.61 # | 102.81 ± 0.83 Δ | 108.73 ± 0.35 * | 111.00 ± 2.01 # | 83.08 ± 5.73 Δ |
Para-aminobenzoic acid | 85.53 ± 1.05 * | 80.87 ± 1.05 * | 87.46 ± 0.93 * | 99.43 ± 1.78 | 82.13 ± 3.72 Δ |
Pyruvate | 104.70 ± 2.98 | 105.50 ± 3.08 | 111.00 ± 3.13 Δ | 99.18 ± 4.47 | 98.48 ± 8.42 |
Quinic acid | 108.40 ± 0.90 # | 110.98 ± 0.90 # | 116.92 ± 1.11 * | 107.96 ± 0.80 # | 105.43 ± 3.09 |
Organic Polybases | |||||
Spermidine | 38.84 ± 0.37 * | 36.07 ± 0.21 * | 40.85 ± 0.39 * | 87.18 ± 0.65 * | 44.69 ± 5.23 # |
Spermine | 32.06 ± 1.86 * | 29.54 ± 1.80 * | 33.71 ± 1.87 * | 71.84 ± 0.59 * | 67.50 ± 3.97 # |
Polyphenols | |||||
Caffeic acid | 45.63 ± 22.36 Δ | 56.37 ± 24.57 Δ | 48.62 ± 12.47 # | 96.67 ± 6.67 | 64.26 ± 0.88 * |
Ellagic acid | 74.18 ± 2.54 # | 74.19 ± 2.95 # | 74.74 ± 2.85 # | 44.32 ± 1.84 * | 77.97 ± 6.66 Δ |
Ferulic acid | 14.04 ± 0.52 * | 28.05 ± 0.49 * | 18.08 ± 0.51 * | 99.22 ± 1.05 | 41.60 ± 2.21 * |
Gallic acid | 73.48 ± 1.87 * | 86.01 ± 1.52 # | 79.09 ± 1.49 * | 64.21 ± 1.38 * | 81.57 ± 3.22 Δ |
Genistein | 29.40 ± 0.99 * | 28.48 ± 1.02 * | 30.75 ± 0.93 * | 33.91 ± 0.82 * | 17.42 ± 3.80 * |
Kaempferol | 29.23 ± 1.95 * | 24.84 ± 1.96 * | 29.68 ± 1.88 * | 19.98 ± 1.81 * | 84.23 ± 6.49 |
Naringin | 53.60 ± 1.21 * | 50.86 ± 1.11 * | 53.28 ± 1.20 * | 68.38 ± 0.70 * | 58.63 ± 4.45 # |
Propyl gallate | 66.71 ± 1.60 * | 55.39 ± 2.09 * | 65.65 ± 1.77 * | 81.82 ± 1.30 * | 55.23 ± 3.53 # |
Quercitrin | 14.20 ± 0.15 * | 12.13 ± 0.13 * | 14.19 ± 0.18 * | 8.37 ± 0.07 * | 50.17 ± 3.76 # |
Rutin | 15.79 ± 0.30 * | 13.40 ± 0.35 * | 15.78 ± 0.35 * | 7.88 ± 0.14 * | 64.22 ± 6.26 Δ |
Additive | Glucose | Fructose | Ribose |
---|---|---|---|
BSA + sugar, no additive | 100 | 100 | 100 |
DMSO | 101.31 ± 2.37 | 99.90 ± 2.09 | 101.58 ± 1.89 |
Standard Antiglycating Agents | |||
Aminoguanidine | 74.41 ± 0.44 * | 70.63 ± 1.683 * | 88.98 ± 1.00 * |
Metformin | 96.57 ± 0.46 # | 97.74 ± 2.836 | 99.35 ± 0.54 |
Pyridoxine | 43.35 ± 2.55 * | 43.08 ± 0.16 * | 71.85 ± 1.86 * |
Antioxidants | |||
Captopril | 84.93 ± 1.02 * | 86.56 ± 1.46 * | 98.45 ± 1.92 |
Tiron | 83.10 ± 0.76 * | 94.41 ± 0.86 # | 98.14 ± 1.73 |
Metal Chelators | |||
NTA | 95.35 ± 1.61 Δ | 97.78 ± 0.51 | 100.31 ± 0.71 |
Amino Acids and Derivatives, Peptides | |||
Arginine | 97.16 ± 5.84 | 98.35 ± 3.39 | 98.79 ± 0.58 Δ |
Carnosine | 93.19 ± 2.04 # | 92.55 ± 1.84 # | 95.36 ± 1.44 # |
Cysteamine | 82.25 ± 0.94 * | 86.00 ± 0.84 * | 88.43 ± 1.93 * |
Glutathione oxidized | 95.69 ± 0.69 # | 99.24 ± 1.27 | 100.73 ± 0.67 |
Glutathione reduced | 88.75 ± 2.77 # | 93.19 ± 3.52 Δ | 96.71 ± 0.93 Δ |
Glycine | 95.61 ± 1.16 # | 99.62 ± 1.35 | 97.51 ± 1.22 Δ |
Organic Acids | |||
1-Cyano-4-hydroxycinnamic acid | 66.41 ± 2.25 * | 72.08 ± 1.89 * | 89.86 ± 0.61 * |
4-Hydroxycinnamic acid | 100.64 ± 3.46 | 97.73 ± 0.98 | 101.17 ± 3.11 |
Lipoic acid | 100.51 ± 8.54 | 96.19 ± 1.23 Δ | 100.78 ± 3.55 |
Para-aminobenzoic acid | 102.88 ± 2.92 | 93.71 ± 4.11 | 105.51 ± 0.58 * |
Pyruvic acid | 84.34 ± 1.06 * | 87.07 ± 0.27 * | 98.94 ± 0.50 Δ |
Quinic acid | 97.05 ± 3.35 | 99.05 ± 2.67 | 98.35 ± 1.87 |
Organic Polybases | |||
Spermidine | 103.5 ± 0.65 Δ | 96.48 ± 2.82 | 92.4 ± 0.20 * |
Polyphenols | |||
Caffeic acid | 46.8 ± 1.39 * | 61.52 ± 1.31 * | 86.04 ± 0.42 * |
Ellagic acid | 94.53 ± 0.31 # | 89.76 ± 2.97 # | 100.05 ± 0.55 |
Ferulic acid | 56.83 ± 3.53 * | 60.96 ± 0.87 * | 85.12 ± 2.72 * |
Gallic acid | 115.89 ± 4.67 # | 94.30 ± 1.88 Δ | 95.66 ± 1.55 # |
Genistein | 61.43 ± 2.95 * | 66.39 ± 0.23 * | 86.23 ± 1.10 * |
Naringin | 57.83 ± 4.10 * | 69.61 ± 1.03 * | 92.52 ± 0.42 * |
Propyl gallate | 57.38 ± 1.53 * | 63.13 ± 1.83 * | 83.97 ± 1.15 * |
Rutin | 62.11 ± 3.98 * | 67.99 ± 0.64 * | 77.25 ± 0.61 * |
Additive | Glucose | Fructose | Ribose |
---|---|---|---|
BSA + sugar, no additive | 100 | 100 | 100 |
DMSO | 98.68 ± 0.76 Δ | 99.18 ± 2.79 | 99.03 ± 0.87 |
Standard Antiglycating Agents | |||
Aminoguanidine | 75.38 ± 0.31 * | 79.34 ± 0.85 * | 79.1 ± 4.69 # |
Metformin | 100.01 ± 2.20 | 98.58 ± 0.32 Δ | 99.39 ± 2.77 |
Pyridoxine | 53.24 ± 0.69 * | 72.82 ± 1.18 * | 74.48 ± 2.69 * |
Antioxidants | |||
Captopril | 88.08 ± 0.06 * | 89.35 ± 2.01 * | 98.06 ± 5.92 |
Tiron | 94.79 ± 0.48 * | 95.00 ± 2.73 Δ | 95.44 ± 2.47 Δ |
Metal Chelators | |||
NTA | 101.66 ± 0.10 * | 100.86 ± 0.69 | 105.87 ± 2.26 |
Amino Acids and Derivatives, Peptides | |||
Arginine | 100.65 ± 2.44 | 97.34 ± 2.49 | 95.61 ± 0.72 # |
Carnosine | 101.20 ± 3.82 | 87.54 ± 0.41 * | 92.33 ± 4.76 |
Cysteamine | 93.64 ± 1.32 # | 94.56 ± 1.41 # | 92.99 ± 8.31 |
Glutathione oxidized | 101.24 ± 0.43 Δ | 99.79 ± 2.77 | 102.68 ± 1.00 Δ |
Glutathione reduced | 98.65 ± 2.79 | 96.47 ± 1.39 Δ | 91.23 ± 3.57 Δ |
Glycine | 97.25 ± 0.01 * | 96.67 ± 1.15 Δ | 98.33 ± 3.85 Δ |
Organic Acids | |||
1-Cyano-4-hydroxycinnamic acid | 86.38 ± 0.27 * | 82.21 ± 0.46 * | 82.88 ± 2.30 * |
4-Hydroxycinnamic acid | 102.02 ± 2.58 | 102.53 ± 1.71 | 97.06 ± 5.98 |
Lipoic acid | 98.40 ± 0.12 * | 97.9 ± 3.49 | 98.98 ± 0.04 |
Para-aminobenzoic acid | 104.78 ± 1.51 # | 97.53 ± 1.20 Δ | 102.57 ± 0.59 Δ |
Pyruvic acid | 98.20 ± 1.71 | 91.35 ± 0.87 * | 102.62 ± 0.69 Δ |
Quinic acid | 97.65 ± 0.63 # | 98.50 ± 2.12 | 97.62 ± 2.64 |
Organic Polybases | |||
Spermidine | 99.73 ± 1.04 | 97.32 ± 3.51 | 93.11 ± 0.53 # |
Polyphenols | |||
Caffeic acid | 50.43 ± 0.19 * | 66.40 ± 1.82 * | 79.48 ± 0.99 * |
Ellagic acid | 101.48 ± 0.472 # | 94.17 ± 2.664 Δ | 101.90 ± 0.74 |
Ferulic acid | 59.00 ± 0.16 * | 62.31 ± 2.63 * | 81.26 ± 1.52 * |
Gallic acid | 116.07 ± 0.13 * | 100.52 ± 0.46 | 92.50 ± 4.35 Δ |
Genistein | 77.97 ± 1.69 * | 86.8 ± 0.28 * | 84.08 ± 1.92 * |
Naringin | 78.20 ± 0.06 * | 72.53 ± 2.96 * | 91.43 ± 0.11 * |
Propyl gallate | 53.15 ± 0.20 * | 65.76 ± 1.01 * | 73.83 ± 1.42 * |
Rutin | 69.32 ± 0.30 * | 70.28 ± 0.18 * | 79.61 ± 4.06 # |
Parameters of Glycoxidation | AGEs (E) | AGEs (F) | Dityrosine (F) | N'-formylkynurenine (F) | Kynurenine (F) | Protein Carbonyls (F) |
---|---|---|---|---|---|---|
Glucose | ||||||
AGEs (F) | 0.926 * | |||||
Dityrosine (F) | 0.963 * | 0.962 * | ||||
N'-formylkynurenine (F) | 0.450 | 0.598 | 0.636 | |||
Kynurenine (F) | 0.000 | −0.037 | −0.074 | 0.090 | ||
AOPP (S) | 0.107 | −0.037 | 0.074 | 0.378 | 0.750 | |
Carbonyl protein (F) | 0.857 ∆ | 0.815 ∆ | 0.852 ∆ | 0.504 | −0.143 | |
Glycated albumin (E) | 0.857 ∆ | 0.963 * | 0.926 # | 0.738 | −0.071 | 0.821 ∆ |
Fructose | ||||||
AGEs (F) | 0.926 # | |||||
Dityrosine (F) | 0.926 # | 1.000 * | ||||
N'-formylkynurenine (F) | 0.901 # | 0.972 * | 0.972 * | |||
Kynurenine (F) | −0.107 | 0.074 | 0.074 | 0.036 | ||
AOPP (S) | 0.393 | 0.630 | 0.630 | 0.559 | 0.679 | |
Carbonyl protein (F) | 0.964 * | 0.926 # | 0.926 # | 0.847 ∆ | 0.000 | |
Glycated albumin (E) | 0.786 ∆ | 0.926 # | 0.926 # | 0.847 ∆ | 0.074 | 0.857 ∆ |
Ribose | ||||||
AGEs (F) | 0.786 ∆ | |||||
Dityrosine (F) | 0.536 | 0.857 ∆ | ||||
N'-formylkynurenine (F) | 0.714 | 0.964 * | 0.893 # | |||
Kynurenine (F) | −0.143 | −0.071 | 0.250 | 0.143 | ||
AOPP (S) | 0.679 | 0.500 | 0.571 | 0.393 | −0.107 | |
Carbonyl protein (F) | 0.357 | 0.536 | 0.607 | 0.607 | −0.036 | |
Glycated albumin (E) | 0.321 | 0.214 | 0.143 | 0.250 | −0.321 | 0.821 ∆ |
2.3. Validity of Fluorometric and Spectrophotometric Measures of Glycoxidation
3. Discussion
4. Experimental Section
4.1. Reagents
4.2. Glycation Conditions
4.3. Fluorometric Estimates of Glycoxidation
4.4. Amadori Product
4.5. AOPP and Thiol Assay
4.6. ELISA-Based AGEs, Carbonyl Groups and Bovine Glycated Albumin Assays
4.7. Prevention of Glycoxidation
4.8. Statistics
5. Conclusions
Acknowledgments
Author Contributions
Abbreviations
AGEs | advanced glycation end products |
AOPP | advanced oxidation protein products |
BSA | bovine serum albumin |
EDTA | ethylenediaminetetraacetic acid |
DETAPA | diethylenetriaminepentaacetic acid |
DMSO | dimethylsulfoxide |
NBT | nitroblue tetrazolium |
NTA | nitrilotriacetic acid |
ROS | reactive oxygen species |
Conflicts of interest
References
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Sadowska-Bartosz, I.; Galiniak, S.; Bartosz, G. Kinetics of Glycoxidation of Bovine Serum Albumin by Glucose, Fructose and Ribose and Its Prevention by Food Components. Molecules 2014, 19, 18828-18849. https://doi.org/10.3390/molecules191118828
Sadowska-Bartosz I, Galiniak S, Bartosz G. Kinetics of Glycoxidation of Bovine Serum Albumin by Glucose, Fructose and Ribose and Its Prevention by Food Components. Molecules. 2014; 19(11):18828-18849. https://doi.org/10.3390/molecules191118828
Chicago/Turabian StyleSadowska-Bartosz, Izabela, Sabina Galiniak, and Grzegorz Bartosz. 2014. "Kinetics of Glycoxidation of Bovine Serum Albumin by Glucose, Fructose and Ribose and Its Prevention by Food Components" Molecules 19, no. 11: 18828-18849. https://doi.org/10.3390/molecules191118828