Chemical Fingerprint of ‘Oblačinska’ Sour Cherry (Prunus cerasus L.) Pollen
Abstract
:1. Introduction
2. Materials and Methods
2.1. Sample Collection
2.2. Chemicals
2.3. Sample Preparation
2.4. Analysis of Carbohydrate Content
2.5. Determination of Individual Polyphenols
2.6. Statistical Analysis
3. Results and Discussion
3.1. Carbohydrate Profile
3.2. Phenolic Profile
3.3. Principal Component Analysis
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Name | tR (min) | LOD × 10−3 (µg/mL) | LOQ × 10−3 (µg/mL) | R (%) |
---|---|---|---|---|
Sorbitol | 2.76 | 0.19 | 0.57 | 102 |
Trehalose | 3.55 | 0.25 | 0.76 | 109 |
Arabinose | 4.85 | 0.19 | 0.58 | 98 |
Glucose | 5.55 | 0.06 | 0.17 | 103 |
Fructose | 6.41 | 0.08 | 0.24 | 104 |
Isomaltose | 8.70 | 0.12 | 0.35 | 97 |
Sucrose | 9.20 | 0.09 | 0.26 | 99 |
Turanose | 14.90 | 0.05 | 0.16 | 105 |
Maltose | 17.89 | 0.10 | 0.30 | 101 |
Maltotriose | 23.12 | 0.15 | 0.48 | 95 |
No | Compound | Parent Ion, m/z | Product Ion, m/z (CE, eV) | tR, min | LOD | LOQ | R2 |
---|---|---|---|---|---|---|---|
Benzoic Acid Derivatives | |||||||
1 | Protocatechuic acid | 153.013 | 108.09 (23); 109.10 (14) | 4.44 | 0.10 | 0.34 | 0.9980 |
2 | p-Hydroxybenzoic acid | 137.057 | 93.19 (19); 108.33 (22) | 4.68 | 0.14 | 0.48 | 0.9934 |
3 | Vanillic acid | 167.034 | 153.00 (15); 108.00 (21) | 5.67 | 0.02 | 0.08 | 0.9957 |
4 | Syringic acid | 197.046 | 153.02 (16); 182.02 (21) | 6.07 | 0.04 | 0.13 | 0.9968 |
5 | Ellagic acid | 300.98 | 284.00 (32); 300.04 (30) | 6.76 | 0.11 | 0.37 | 0.9938 |
Cinnamic Acid Derivatives | |||||||
6 | Chlorogenic acid | 353.103 | 191.28 (25) | 5.33 | 0.08 | 0.27 | 0.9980 |
7 | Caffeic acid | 179.004 | 134.00 (13); 135.00 (16) | 5.82 | 0.11 | 0.38 | 0.9951 |
8 | p-Coumaric acid | 163.031 | 93.12 (39); 119.09 (16) | 6.67 | 0.12 | 0.41 | 0.9947 |
9 | Ferulic acid | 193.057 | 134.00 (18); 178.00 (15) | 6.93 | 0.15 | 0.50 | 0.9933 |
10 | Sinapic acid | 223.082 | 149.21 (36) | 6.95 | 0.08 | 0.26 | 0.9984 |
11 | Cinnamic acid | 147.050 | 103.00 (10); 129.00 (10) | 8.73 | 0.07 | 0.22 | 0.9991 |
Flavonoid Glycosides | |||||||
12 | Rutin | 609.197 | 299.98 (42); 301.20 (32) | 6.42 | 0.09 | 0.31 | 0.9976 |
13 | Hyperoside | 463.100 | 300.00 (30); 271.00 (43) | 6.67 | 0.10 | 0.34 | 0.9976 |
14 | Cynaroside | 447.090 | 285.00 (30) | 6.91 | 0.12 | 0.40 | 0.9975 |
15 | Apiin | 563.140 | 465.00 (25); 269.00 (46) | 6.97 | 0.11 | 0.38 | 0.9956 |
16 | Naringin | 579.241 | 151.42 (43); 217.26 (33) | 7.01 | 0.16 | 0.53 | 0.9937 |
17 | Astragalin | 447.090 | 284.00 (33) | 7.03 | 0.14 | 0.46 | 0.9975 |
Flavonoid Aglycones | |||||||
18 | Catechin | 289.094 | 203.00 (23); 245.03 (31) | 5.41 | 0.14 | 0.45 | 0.9953 |
19 | Luteolin | 285.035 | 133.05 (30); 150.95 (24) | 8.45 | 0.10 | 0.32 | 0.9958 |
20 | Apigenin | 269.032 | 117.24 (43); 149.00 (24) | 9.12 | 0.11 | 0.36 | 0.9981 |
21 | Naringenin | 271.036 | 119.10 (25); 151.07 (19) | 9.22 | 0.09 | 0.28 | 09974 |
22 | Kaempferol | 285.074 | 211.00 (32); 227.00 (32) | 9.39 | 0.04 | 0.13 | 0.9961 |
Other Phenolics | |||||||
23 | Aesculin | 339.080 | 133.09 (44); 177.06 (25) | 4.95 | 0.01 | 0.05 | 0.9999 |
24 | Phlorizin | 435.149 | 273.16 (20); 167.16 (34) | 7.37 | 0.05 | 0.15 | 0.9978 |
25 | Coniferyl aldehyde | 177.060 | 162.00 (17); 97.00 (14) | 7.70 | 0.03 | 0.08 | 0.9968 |
26 | Aesculetin | 176.992 | 133.28 (19); 105.25 (20) | 7.71 | 0.10 | 0.34 | 0.9969 |
Carbohydrates/Clones | I/1 | II/2 | II/10 | III/9 | IV/1 | IV/8 | V/P | VII/2P | VIII/1 | IX/1 | IX/P | X/2 | XIII/1 | XIV/3 | XIV/5 |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Sorbitol | 16.00 e | 14.03 d | 9.87 b | 11.28 c | 7.22 a | 8.01 a | 17.41 f | 7.12 a | 22.38 h | 16.68 e,f | 21.03 g | 14.96 d | 14.83 d | 17.30 f | 17.24 f |
Trehalose | 4.03 e | 0.93 a | 1.58 b | 2.36 c | 3.54d e | 3.19 c,d | 2.98 c | 4.73 f | 5.31 g | 2.50 c | 1.84 b | 2.36 c | 1.52 b | 4.23 e,f | 4.56 f |
Arabinose | 0.35 b | 0.48 c | 0.30 b | 0.23 a,b | 0.46 c | 0.20 a | 0.64 d | 0.49 c | 0.17 a | 0.34 b | 0.28 b | 0.18 a | 0.38 b | 0.74 e | 0.49 c |
Glucose (G) | 136.71 k | 89.77 b | 116.71 h | 86.44 a | 95.69 d | 91.46 c | 95.44 d | 102.38 e | 107.47 f | 132.49 j | 92.61 c | 85.83 a | 129.51 i | 95.42 d | 110.68 g |
Fructose (F) | 92.73 j | 68.57 b | 83.52 f,g | 85.04 h | 87.45 i | 71.60 c | 91.69 j | 56.72 a | 74.70 d | 82.17 e,f | 67.25 b | 81.31 e | 86.96 i | 82.46 e,f | 84.45 g,h |
Sucrose | 66.40 j | 75.11 k | 56.12 g | 73.97 k | 50.75 f | 59.38 h | 38.58 b | 63.84 i | 38.64 b | 31.92 a | 36.68 b | 42.58 c | 41.83 c | 46.88 e | 44.78 d |
Isomaltotriose | 0.91 e | 1.16 f | 0.49 a | 0.78 d | 0.67 c | 0.94 e | 0.92 e | 0.69 c,d | 0.48 a | 1.34 g | 0.65 c | 0.56 b | 1.92 i | 1.20 f | 1.81 h |
Turanose | 0.38 c | 0.39 c,d | 0.16 a | 0.44 d | 0.60 f | 0.85 g | 0.27 b | 0.28 b | 0.47 d,e | 0.35 b,c | 0.60 f | 0.36 b,c | 0.54 e,f | 0.38 c | 0.55 e,f |
Maltose | 7.17 e | 8.60 f | 5.27 c | 7.48 e | 6.27 d | 6.54 d | 5.64 c | 2.31 a | 6.05 c | 3.84 b | 5.61 c | 4.23 b | 5.94 c | 4.36 b | 4.02 b |
Maltotriose | 0.18 a | 0.38 c | 0.26 b | 0.47 d | 0.24 b | 0.18 a | 0.32 c | 0.19 a | 0.54 e | 0.30 b,c | 0.20 a | 0.40 c,d | 0.22 a,b | 0.28 b,c | 0.44 d |
G/F ratio | 1.47 | 1.31 | 1.40 | 1.02 | 1.09 | 1.28 | 1.04 | 1.81 | 1.44 | 1.61 | 1.38 | 1.06 | 1.49 | 1.16 | 1.31 |
Total | 324.86 | 259.42 | 274.28 | 268.49 | 252.89 | 242.35 | 253.89 | 238.75 | 256.21 | 271.93 | 226.75 | 232.77 | 283.65 | 253.25 | 269.02 |
No | Phenolic Compounds/Clones | I/1 | II/2 | II/10 | III/9 | IV/1 | IV/8 | V/P | VII/2P | VIII/1 | IX/1 | IX/P | X/2 | XIII/1 | XIV/3 | XIV/5 | ||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Benzoic Acid Derivatives | ||||||||||||||||||
1 | Protocatechuic acid | 0.42 d | – | – | – | – | 0.10 b | – | 0.11 b | 0.54 e | 0.04 a | 0.12 b | 0.08 a,b | 0.34 c | 0.64 f | 0.04 a | ||
2 | p-Hydroxybenzoic acid | 4.45 e | 1.70 b | 2.91 c | 3.62 d | 2.37 c | 5.57 f | 0.75 a | 3.63 d | 7.80 g | 2.46 c | 3.62 d | 2.86 c | 7.85 g | 5.50 f | 3.81 d,e | ||
3 | Vanillic acid | 10.68 g | 1.52 b | 1.75 b | 2.16 c | 2.58 c | 3.47 d | 0.57 a | 4.54 e | 10.68 g | 1.35 b | 2.16 c | 1.39 b | 10.92 g | 7.74 f | 2.82 c | ||
4 | Syringic acid | 0.65 b | 0.58 b | 0.61 b | 0.95 e | 0.64 b | 1.22 f | 0.20 a | 0.55 b | 0.65 b | 0.54 b | 0.73 c | 0.80 d | 0.72 c | 0.72 c | 0.59 b | ||
5 | Ellagic acid | – | 0.37 d | – | – | – | – | 0.02 a | 0.04 a | 1.75 e | 0.17 b | 0.08 a | 0.28 c | – | 0.06 a | – | ||
Total | 16.20 | 4.17 | 5.27 | 6.73 | 5.59 | 10.36 | 1.54 | 8.87 | 21.42 | 4.56 | 6.71 | 5.41 | 19.83 | 14.66 | 7.26 | |||
Cinnamic Acid Derivatives | ||||||||||||||||||
6 | Chlorogenic acid | 43.70 f | 29.28 c | 23.64 b | 59.93 j | 34.24 d | 42.57 f | 7.27 a | 37.23 e | 58.93 j | 33.21 d | 38.46 e | 47.66 g | 53.33 h | 56.85 i | 24.92 b | ||
7 | Caffeic acid | 5.51 c | 1.99 a | 3.56 b | 5.03 c | 3.18 b | 15.95 f | 1.36 a | 3.78 b | 15.35 f | 2.99 b | 3.98b c | 4.23 c | 6.17 d | 12.94 e | 3.46 b | ||
8 | p-Coumaric acid | 29.89 e | 10.52 b | 19.84 c | 26.54 d | 18.19 c | 51.20 h | 4.82 a | 24.58 d | 53.99 h | 18.60 c | 23.49 d | 18.45 c | 42.94 g | 39.03 f | 24.29 d | ||
9 | Ferulic acid | 35.22 g | 10.68 b | 19.01 d | 24.83 f | 16.81 c | 56.70 i | 7.11 a | 21.99 e | 43.93 h | 16.87 c | 18.71 d | 21.68 e | 43.60 h | 42.46 h | 20.76 d,e | ||
10 | Sinapic acid | 1.79 d,e | – | – | 1.59 c,d | – | 5.21 f | 0.22 a | – | – | – | – | 0.83 b | 1.42 c | 2.28 e | – | ||
11 | Cinnamic acid | 2.44 g | 0.59 b | 0.90 c | 1.04 c | 1.22 d | 1.61 e | 0.19 a | 1.18 d | 2.75 h | 0.99 c | 1.00 c | 1.00 c | 1.95 f | 1.54 e | 1.16 d | ||
Total | 118.55 | 53.06 | 66.95 | 118.96 | 73.64 | 173.24 | 20.97 | 88.76 | 174.95 | 72.66 | 81.66 | 93.85 | 149.41 | 155.10 | 74.59 | |||
Flavonoid Glycosides | ||||||||||||||||||
12 | Rutin | 92.96 b | 93.51 b | 118.96 e | 181.12 i | 113.01 d | 157.95 h | 50.28 a | 114.38 d | 112.89 d | 106.34 c | 117.42 e | 139.47 f | 119.42 e | 144.43 g | 107.03 c | ||
13 | Hyperoside | 9.68 b | 9.44 b | 11.07 c | 18.10 d | 11.08 c | 17.85 b | 4.82 a | 12.07 c | 11.05 c | 10.44 c | 12.15 c,d | 13.31 d | 11.66 c | 13.91 d | 11.03 c | ||
14 | Cynaroside | 6.14 f | 0.34 a | – | 1.15 c | 0.76 a,b | 5.22 e | – | 0.91 b | – | 2.41 d | – | – | 5.83 e,f | 2.58 d | 0.91 b | ||
15 | Apiin | 0.08 c | 0.01 a | 0.04 b | 0.04 b | – | 0.09 c | – | 0.05 b | 0.16 d | 0.04 b | 0.05 b | 0.03 a,b | – | 0.06 b | 0.05 b | ||
16 | Naringin | 0.22 c | 0.08 a | 0.14 b | 0.17 b | 0.13 b | 0.28 d | 0.05 a | 0.15 b | 0.34 e | 0.14 b | 0.16 b | 0.17 b | 0.24 c | 0.21 c | 0.15 b | ||
17 | Astragalin | 15.04 b | 14.05 b | 18.32 d | 22.82 e | 14.17 b | 31.17 f | 7.40 a | 15.38 b | 16.90 b | 14.75 b | 16.98 b | 20.42 d,e | 16.86 b | 19.10 d | 14.84 b | ||
Total | 124.12 | 117.43 | 148.53 | 223.40 | 139.15 | 212.56 | 62.55 | 142.94 | 141.34 | 134.12 | 146.76 | 173.40 | 154.01 | 180.29 | 134.01 | |||
Flavonoid Aglycones | ||||||||||||||||||
18 | Catechin | 5.07 bc | 4.98 bc | 4.47 b | 8.87 d | 4.63 b | 5.99 c | – | 5.62 c | 5.07 bc | 4.57 b | 4.90 bc | 5.58 c | 5.20 bc | 5.21 bc | 3.11 a | ||
19 | Luteolin | 0.26 b | 0.35 d | 0.40 e | 0.44 e | – | 0.31 c | 0.20 a | 0.34 d | – | 0.30 c | – | 0.43 e | 0.40 e | – | 0.32 c | ||
20 | Apigenin | 0.08 a | 0.10 b | 0.11 b | 0.17 d | 0.11 b | 0.17 d | 0.07 a | 0.18 d | 0.16 cd | 0.12 b | 0.07 a | 0.11 b | 0.15 c | 0.15 c | 0.17 d | ||
21 | Naringenin | 0.07 b | 0.13 d | 0.12 d | 0.18 ef | 0.10 c | 0.18 ef | 0.16 de | 0.21 f | 0.13 d | 0.12 d | 0.04 a | 0.13 d | 0.13 d | 0.15 de | 0.10 c | ||
22 | Kaempferol | 0.97 b | 0.95 b | 1.53 g | 1.59 g | 1.16 bc | 27.01 h | 0.68 a | 1.09 bc | 1.24 d | 0.97 b | 1.18 c | 1.32 e | 1.18 c | 1.31 e | 1.38 f | ||
Total | 6.45 | 6.51 | 6.63 | 11.25 | 6.00 | 33.66 | 1.11 | 7.44 | 6.60 | 6.08 | 6.19 | 7.57 | 7.06 | 6.82 | 4.76 | |||
Other Phenolics | ||||||||||||||||||
23 | Aesculin | 9.53 c | 7.61 b | 9.74 c | 12.61 d | 9.93 c | 13.45 d | 3.43 a | 11.31 d | 29.25 f | 9.31 c | 10.52 c | 10.17 c | 12.50 d | 17.14 e | 9.38 c | ||
24 | Phlorizin | 0.51 b | 0.78 c | 0.75 c | 1.63 f | 1.00 de | 0.99 de | 0.25 a | 0.94 d | 0.89 d | 0.51 b | 0.59 b | 1.04 e | 0.93 d | 1.08 e | 0.79 c | ||
25 | Coniferyl aldehyde | 0.42 d | 0.16 b | 0.39 cd | 0.56 e | 0.31 c | 0.75 f | 0.08 a | 0.39 cd | 1.19 g | 0.27 bc | 0.51 e | 0.23 b | 1.13 g | 0.26 bc | 0.53 e | ||
26 | Aesculetin | 0.32 d | 0.14 b | 0.30 d | 0.47 e | 0.25 cd | 0.59 f | 0.07 a | 0.32 d | 0.98 g | 0.24 cd | 0.44 e | 0.16 b | 0.94 g | 0.20 bc | 0.43 e | ||
Total | 10.78 | 8.69 | 11.18 | 15.27 | 11.49 | 15.78 | 3.80 | 12.96 | 32.31 | 10.33 | 12.06 | 11.60 | 15.50 | 18.68 | 11.13 | |||
Total of all | 276.09 | 189.84 | 238.55 | 375.62 | 235.87 | 445.57 | 89.98 | 260.96 | 376.62 | 227.73 | 257.34 | 291.83 | 345.78 | 375.53 | 232.07 |
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Fotirić Akšić, M.; Gašić, U.; Dragana, D.Z.; Sredojević, M.; Tosti, T.; Natić, M.; Meland, M. Chemical Fingerprint of ‘Oblačinska’ Sour Cherry (Prunus cerasus L.) Pollen. Biomolecules 2019, 9, 391. https://doi.org/10.3390/biom9090391
Fotirić Akšić M, Gašić U, Dragana DZ, Sredojević M, Tosti T, Natić M, Meland M. Chemical Fingerprint of ‘Oblačinska’ Sour Cherry (Prunus cerasus L.) Pollen. Biomolecules. 2019; 9(9):391. https://doi.org/10.3390/biom9090391
Chicago/Turabian StyleFotirić Akšić, Milica, Uroš Gašić, Dabić Zagorac Dragana, Milica Sredojević, Tomislav Tosti, Maja Natić, and Mekjell Meland. 2019. "Chemical Fingerprint of ‘Oblačinska’ Sour Cherry (Prunus cerasus L.) Pollen" Biomolecules 9, no. 9: 391. https://doi.org/10.3390/biom9090391