Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics
Abstract
:1. Introduction
2. Results and Discussion
2.1. NMR Fingerprinting of Legume Sprouts
2.2. Quantification of Major Metabolites Detected Via 1H-NMR
2.3. 1H-NMR Data Multivariate Data Analyses
2.3.1. Unsupervised Multivariate PCA of Full-Range 1H-NMR Data
2.3.2. Unsupervised Multivariate PCA of the Aromatic 1H-NMR Region Data
2.3.3. Supervised Multivariate OPLS-DA of 1H-NMR Data
3. Materials and Methods
3.1. Plant Material
3.2. Sprouting Procedures
3.3. Chemicals and Reagents
3.4. Extraction Procedure and Sample Preparation for NMR Analysis
3.5. NMR Analysis
3.6. NMR Quantification
3.7. NMR Data Processing and Multivariate Data Analysis
3.8. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
Abbreviations
References
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ID | Metabolite | Assignment | δ1H (ppm) | δ13C in HSQC (ppm) | δ1H in COSY (ppm) | HMBC correlations δ13C (ppm) | C | L | T | V | |
---|---|---|---|---|---|---|---|---|---|---|---|
1–2 | ω-6 and ω-3 Fatty acids | (CH2)n | 1.27–1.39 (br. s) | 30.8 | 0.91 (t-CH3), 1.61 (H-3), 2.07 (allylic CH2) | 30.8 (CH2)n., 131.9 (olefinic C) | + | + | + | + | |
C-2 | 2.31 (m) | 35.5 | 1.61 (H-3) | 26.2 (C-3), 30.8 (CH2)n, 175.8 (C-1) | |||||||
C-3 | 1.61 (m) | 26.2 | 2.31 (H-2), 1.33 (CH2)n | 30.8 (CH2)n, 35.5 (C-2), 175.8 (C-1) | |||||||
Olefinic Cs | 5.30–5.38 (br. m) | 129–132 | 2.77, 2.81 (bis-allylic CH2), 2.07 (allylic CH2) | 26.8 (bis-allylic CH2), 130.2 (olefinic C) | |||||||
allylic CH2 | 2.05–2.09 (m) | 28.2–28.8 | 1.37 (CH2)n, 5.30–5.38 (olefinic Hs) | 14.9 (t-CH3), 30.8 (CH2)n, 130.2, 131.9 (olefinic Cs) | |||||||
1 | ω-6 Fatty acid | bis-allylic CH2 | 2.77 (t, J = 6.6 Hz) | 26.8 | 5.30–5.38 (olefinic Hs) | 130.2, 131.9 (olefinic Cs) | |||||
t-CH3 | 0.91 (t, J = 6.2 Hz) | 14.9 | 1.33 (CH2)n | 23.9 (ω-2 C) | |||||||
2 | ω-3 Fatty acid | bis-allylic CH2 | 2.81 (t, J = 6.9 Hz) | 26.8 | 5.30–5.38 (olefinic Hs) | 130.2, 131.9 (olefinic Cs) | |||||
t-CH3 | 0.97 (t, J = 7.5 Hz) | 14.9 | 2.07 (allylic CH2) | 22.1 (ω-2 C), 133.7 (olefinic C) | |||||||
3 | Sucrose | C-1 | 5.39 (d, J = 3.8 Hz) | 94.5 | 3.42 (H-2) | 73.9 (C-2), 105.6 (C-2′) | + | + | + | + | |
C-2 | 3.42 (dd, J = 9.8, 3.8 Hz) | 73.9 | 5.39 (H-1), 3.71 (H-3) | 75.3 (C-3) | |||||||
C-1′ | 3.61 (s) | 64.7 | - | 79.9 (C-3′), 105.6 (C-2′) | |||||||
4 | Fructose | C-3 | 4.10 | 78.6 | 4.03 (H-3) | 62.0 (C-1), 74.6 (C-4) | + | + | + | + | |
C-4 | 4.03 * | 74.6 | 4.10 (H-4) | - | |||||||
5 | α-Glucose | C-1 | 5.11 (d, J = 3.7 Hz) | 94.5 | 3.35 (H-2) | 73.2 (C-5), 74.7 (C-2) | + | + | + | + | |
C-2 | 3.35 (br. s) | 74.7 | 5.11 (H-1), 3.67 (H-3) | - | |||||||
6 | β-Glucose | C-1 | 4.48 (d, J = 7.8 Hz) | 97.9 | 3.13 (H-2) | 75.2 (C-2), 77.3 (C-3) | + | + | + | + | |
C-2 | 3.13 (dd, J = 7.8, 9.0 Hz) | 75.2 | 3.35 (H-3) | 77.3 (C-3) | |||||||
7 | Alanine | C-2 | 3.59 * | 51.9 | 1.46 | 17.6 (C-3), 176.6 (C-1) | + | + | + | + | |
C-3 | 1.46 (d, J = 7.2 Hz) | 17.6 | 3.59 | 51.9 (C-2), 176.6 (C-1) | |||||||
8 | Valine | C-2 | 3.42 * | 61.9 | 2.25 (H-3) | 19.6 (C-5), 30.7 (C-3) | + | + | + | + | |
C-3 | 2.25 (m) | 30.7 | 1.02 (H-4), 1.06 (H-5), 3.42 (H-2) | 180.2 (C-1) | |||||||
C-4 | 1.02 (d, J = 7.0 Hz) | 18.2 | 2.25 (H-3) | 19.6 (C-5), 30.7 (C-3), 61.9 (C-2) | |||||||
C-5 | 1.06 (d, J = 7.0 Hz) | 19.6 | 2.25 (H-3) | 18.2 (C-4), 30.7 (C-3), 61.9 (C-2) | |||||||
9 | Threonine | C-2 | 3.18 * | nd | 4.12 (H-3) | - | + | + | + | + | |
C-3 | 4.12 * | nd | 1.31 (H-4), 3.18 (H-2) | 174.0 (C-1) | |||||||
C-4 | 1.31 * | 21.6 | 4.12 (H-3) | 62.6 (C-2), 67.7 (C-3) | |||||||
10 | 4-Hydroxy-isoleucine | C-2 | 3.81 (d, J = 5.5 Hz) | 58.7 | 1.82 (H-3) | 13.6 (C-6), 43.4 (C-3), 175.1 (C-1) | - | - | + | - | |
C-3 | 1.82 (m) | 43.4 | 3.81 (H-2), 3.79 (H-4) | 13.6 (C-6), 22.9 (C-5), 58.7 (C-2), 72.0 (C-4), 175.1 (C-1) | |||||||
C-4 | 3.79 * | 72.0 | 1.82 (H-3), 1.24 (H-5) | 58.7 (C-2), 72.0 (C-4), | |||||||
C-5 | 1.24 (d, J = 6.3 Hz) | 22.9 | 3.79 (H-4) | 43.4 (C-3), 72.0 (C-4) | |||||||
C-6 | 0.99 (d, J = 7.2 Hz) | 13.6 | 3.79 (H-4) | 43.4 (C-3), 58.7 (C-2), 72.0 (C-4) | |||||||
11 | Asparagine | C-2a | 2.72 (dd, J = 9.3, 17.0 Hz) | 36.2 | 3.84 (H-3) | 53.4 (C-3), 174.7, 176.4 (C-1 and C-4) | + | + | + | + | |
C-2b | 2.94 (dd, J = 3.6, 17.0 Hz) | 36.2 | 3.84 (H-3) | 53.4 (C-3), 174.7, 176.4 (C-1 and C-4) | |||||||
C-3 | 3.84 * | 53.4 | 2.72 (H-2a), 2.94 (H-2b) | 36.2 (C-2), 174.7, 176.4 (C-1 and C-4) | |||||||
12 | Choline | N-(CH3)3 | 3.21 (s) | 55.4 | - | 55.4 (N-CH3), 69.3 (N-CH2) | + | + | + | + | |
N-CH2 | 3.47 * | 69.3 | 4.00 (O-CH2) | 55.4 (N-CH3), 69.3 (N-CH2), 57.3 (O-CH3) | |||||||
O-CH2 | 4.00 * | 57.3 | 3.47 (N-CH2) | - | |||||||
13 | Betaine | N-(CH3)3 | 3.27 (s) | 52.7 | - | 52.7 (N-CH3), 66.7 (C-2), 168.3 (CO) | + | + | + | + | |
N-CH32 | 3.83 (s) | 66.7 | - | 53.7 (N-CH3), 168.3 (CO) | |||||||
14 | Proline | CO | - | 173.6 | - | - | + | + | + | + | |
C-1 | 3.98 * | 62.0 | 2.11 (H-2) | 24.2 (C-3), 29.6 (C-2), 173.6 (CO) | |||||||
C-2 | 2.11, 2.30 (m) | 29.6 | 3.98 (H-1) | 46.2 (C-4), 62.0 (C-1) | |||||||
C-3 | 1.96 (m) | 24.2 | 3.25, 3.37 (H-4) | 46.2 (C-4), 62.0 (C-1) | |||||||
C-4 | 3.25, 3.37 * | 46.1 | 1.96 (H-3) | 24.2 (C-3), 29.6 (C-2) | |||||||
15 | Phenylalanine | C-3 | 3.33 * | 38.80 | - | 55.9, (C-2), 131.5 (C-3′/C-5′), 138.5 (C-1′) | - | + | + | + | |
C-4′ | 7.33 * | 129.0 | - | 131.5 (C-3′/C-5′) | |||||||
C-3′/C-5′ | 7.33 * | 131.0 | 7.28 (H-2′/H-6′) | 138.5 (C-1′) | |||||||
C-2′/C-6′ | 7.28 (d, J = 6.7 Hz) | 129.0 | 7.33 (H-3′/H-5′) | 38.8 (C-3), 131.5 (C-3′/C-5′) | |||||||
16 | Tyrosine | C-3′/C-5′ | 6.76 * | 112.5 | 7.12 (H-2′/H-6′) | - | - | + | + | + | |
C-2′/C-6′ | 7.12 (d, J = 8.5 Hz) | 131.0 | 6.76 (H-3′/H-5′) | 36.6 (C-3), 157.7 (C-4′) | |||||||
17 | L-Dopa | C-2 | 3.70 * | 56.6 | 2.86, 3.17 (H-3) | 120.9 (C-2′, C-6′), 173.6 (C-1) | - | - | - | + | |
C-3a | 2.86 (dd, J = 14.7, 9.0 Hz) | 36.6 | 3.70 (H-2) | 56.6 (C-2), 116.5 (C-5′), 120.9 (C-2′,C-6′), 127.9 (C-1′), 173.6 (C-1) | |||||||
C-3b | 3.17 (dd, J = 14.7, 4.2 Hz) | 36.6 | 3.70 (H-2) | 56.6 (C-2), 116.5 (C-5′), 120.9 (C-2′,C-6′), 127.9 (C-1′), 173.6 (C-1) | |||||||
C-2′ | 6.73 (br. s) | 120.9 | 6.61 (H-6′) | 36.6 (C-3), 127.9 (C-1′), 145.5 (C-4′) | |||||||
C-5′ | 6.75 * | 116.5 | 6.61 (H-6′) | 36.6 (C-3), 120.9 (C-2′,C-6′), 127.9 (C-1′), 145.5 (C-4′) | |||||||
C-6′ | 6.61 (dd, J = 8.1, 2.1 Hz) | 120.9 | 6.73 (H-2′), 6.75 (H-5′) | 36.6 (C-3), 116.5 (C-5′), 145.5 (C-4′) | |||||||
18 | Tryptophan | C-5 | 7.19 (s) | 125.7 | - | 109.9 (C-4), 129.2 (C-11), 138.9 (C-6) | + | + | + | + | |
C-7 | 7.33 * | 113.1 | 7.10 (H-8) | 121.1 (C-9), 129.2 (C-11) | |||||||
C-8 | 7.10 (t, J = 7.8 Hz) | 123.0 | 7.33 (H-7) | 119.7 (C-10), 138.9 (C-6) | |||||||
C-9 | 7.05 * | 121.1 | 7.63 (H-10) | 113.1 (C-7), 129.2 (C-11) | |||||||
C-10 | 7.63 (d, J = 7.8 Hz) | 119.7 | 7.05 (H-9) | 123.0 (C-8), 138.9 (C-6) | |||||||
19 | Histidine | C-5 | 7.75 (s) | 136.5 | - | 134.2 (H-4), 117.0 (H-6) | + | + | + | + | |
C-6 | 7.01 (s) | 117.0 | - | 134.2 (H-4), 136.5 (H-5) | |||||||
20 | Cytosine | C-5 | 5.70 (d, J = 8.7 Hz) | 97.1 | 8.01 | - | + | + | + | + | |
C-6 | 8.01 (d, J = 8.7 Hz) | 143.6 | 5.70 | 156.4 (C-2), 167.0 (C-4) | |||||||
21 | 4-Aminobutyric acid | C-2 | 2.36 (t, J = 6.9 Hz) | 35.5 | 1.88 (H-3) | 24.9 (C-3), 41.4 (C-4), 180.2 (C-1) | + | + | + | + | |
C-3 | 1.88 (m) | 24.9 | 2.36 (H-2), 2.96 (H-4) | 35.2 (C-2), 41.4 (C-4), 180.2 (C-1) | |||||||
C-4 | 2.96 * | 41.4 | 1.88 (H-3) | 24.9 (C-3), 35.2 (C-2) | |||||||
22 | Acetic acid | CH3 | 1.92 (s) | 22.8 | - | 174.0 (CO) | - | + | - | - | |
23 | Fumaric acid | C-2/C-3 | 6.67 (s) | 136.9 | - | 173.2 (C-1, C-4) | + | + | + | + | |
24 | β-Sitosterol | C-6 | 5.34 * | 123.0 | - | - | + | + | + | + | |
C-18 | 0.72 (s) | 14.9 | - | 41.4 (C-12), 44.0 (C-13), 58.9 (C-14) | + | + | + | + | |||
C-19 | 1.02* | 20.2 | - | 143.3 (C-5) | |||||||
C-26/C-27 | 0.83 * | 19.6 | - | 47.5 (C-24) | |||||||
25 | Trigonelline | C-2 | 9.23 (s) | 148.2 | - | 49.4 (N-CH3), 141.0 (C-3), 146.9 (C-4), 168.4 (CO) | + | + | + | + | |
C-4 | 8.91 (d, J = 8.1 Hz) | 146.9 | 8.07 (H-5) | 147.6 (C-6), 168.4 (CO) | |||||||
C-5 | 8.07 (dd, J = 8.1, 6.2 Hz) | 129.0 | 8.91 (H-4), 8.88 (H-6) | 141.0 (C-3), 146.9 (C-4) | |||||||
C-6 | 8.88 d (J = 6.2 Hz) | 147.6 | 8.07 (H-5) | 49.4 (N-CH3), 129.0 (C-5), 148.2 (C-2) | |||||||
N-CH3 | 4.44 (s) | 49.4 | - | 147.6 (C-6) | |||||||
26–31 | Isoflavone derivatives | C-3′/C-5′ | 6.99 * | 115.7 | 7.49 (H-3′/H-5′) | 124–128 (C-3, C-1′), 131.8 (C-2′/C-6′), 161.7 (C-4′) | + | - | - | - | |
C-2′/C-6′ | 7.49 * | 132.3 | 6.99 (H-2′/H-6′) | 115.7 (C-3′/C-5′), 124–128 (C-3, C-1′), 161.7 (C-4′) | |||||||
26–28 | Genistein derivatives | C-2 | 8.08 (s) | 155.5 | - | 124–128 (C-3, C-1′), 160.9 (C-9), 182.9 (C-4) | + | - | - | - | |
8.17 (s) | 156.2 | - | 124–128 (C-3, C-1′), 159.9 (C-9), 183.7 (C-4) | ||||||||
8.20 (s) | 156.6 | - | 124–128 (C-3, C-1′), 159.9 (C-9), 183.7 (C-4) | ||||||||
29–31 | Daidzein derivatives | C-2 | 8.15 (s) | 155.6 | - | 124–128 (C-3, C-1′), 159.9 (C-9), 179.3 (C-4) | + | - | - | - | |
8.23 (s) | 156.2 | - | 124–128 (C-3, C-1′), 179.3 (C-4) | ||||||||
8.27 (s) | 156.2 | - | 124–128 (C-3, C-1′), 159.9 (C-9), 179.3 (C-4) | ||||||||
26 | Biochanin-A | C-6 | 6.23 (d, J = 2.1 Hz) | 101.2 | 6.35 (H-8) | 107.2 (C-10), 167.0 (C-7) | + | - | - | - | |
C-8 | 6.35 (d, J = 2.1 Hz) | 95.1 | 6.23 (H-6) | 101.2 (C-6), 160.9 (C-9), 167.0 (C-7) | |||||||
O-CH3 | 3.83 (s) | 56.0 | - | 161.7 (C-4′) | |||||||
27 | Genistin | C-6 | 6.52 (d, J = 2.1 Hz) | 101.8 | 6.71 (H-8) | 96.5 (C-8), 109.0 (C-10), 164.6 (C-5) | + | - | - | - | |
C-8 | 6.71 (d, J = 2.1 Hz) | 96.5 | 6.52 (H-6) | 101.8 (C-6), 109.0 (C-10), 159.9 (C-9), 165.3 (C-7) | |||||||
C-1″ | 5.06 (d, J = 7.8 Hz) | 102.5 | 3.50 (H-2″) | 78.3 (C-2″), 165.3 (C-7) | |||||||
28 | Malonyl-genistin | C-6 | 6.50 (d, J = 2.3 Hz) | 101.8 | 6.72 (H-8) | 96.5 (C-8), 109.0 (C-10), 164.6 (C-5) | + | - | - | - | |
C-8 | 6.72 (d, J = 2.3 Hz) | 96.5 | 6.50 (H-6) | 101.8 (C-6), 109.0 (C-10), 159.9 (C-9), 165.3 (C-7) | |||||||
Malonyl CH2 | 3.17 (s) | 42.1 | - | - | |||||||
29 | Formononetin | C-5 | 8.05 (d, J = 9.0 Hz) | 129.0 | 6.94 (H-6) | 160.9 (C-9), 165.3 (C-7), 179.3 (C-4) | + | - | - | - | |
C-6 | 6.94 (dd, J = 9.0, 2.3 Hz) | 117.0 | 6.86 (H-8), 8.05 (H-5) | 103.8 (C-8), 118.7 (C-10) | |||||||
C-8 | 6.86 (d, J = 2.3 Hz) | 103.8 | 6.94 (H-6) | 117.0 (C-6), 118.7 (C-10), 160.9 (C-9), 165.3 (C-7) | |||||||
O-CH3 | 3.83 (s) | 56.0 | - | 161.7 (C-4′) | |||||||
30 | Daidzin | C-5 | 8.14 (d, J = 8.7 Hz) | 129.0 | 7.25 (H-8) | 105.8 (C-8), 159.9 (C-9), 164.6 (C-7) | + | - | - | - | |
C-6 | 7.19 (dd, J = 8.7, 2.2 Hz) | 117.7 | 8.14 (H-5) | 105.8 (C-8), 164.4 (C-7) | |||||||
C-8 | 7.25 (d, J = 2.2 Hz) | 105.8 | 7.19 (H-6), 8.14 (H-5) | 117.7 (C-6), 159.9 (C-9), 164.4 (C-7) | |||||||
C-1″ | 5.10 * | 102.5 | 3.52 (H-2″) | 78.3 (C-3″), 164.6 (C-7) | |||||||
31 | Malonyl-daidzin | C-6 | 7.22 (dd, J = 8.7, 2.2 Hz) | 117.7 | 8.14 (H-5) | 105.8 (C-8), 164.4 (C-7) | + | - | - | - | |
C-8 | 7.27 (d, J = 2.4 Hz) | 105.8 | 7.22 (H-6), 8.14 (H-5) | 117.7 (C-6), 159.9 (C-9), 164.4 (C-7) | |||||||
Malonyl CH2 | 3.17 (s) | 42.1 | - | - | |||||||
32 | Cicerin | OCH2O | 5.98 * | 103.2 | - | 150.3 (C-4′) | + | - | - | - | |
C-6 | 5.98 * | 94.5 | - | - | |||||||
C-8 | 5.96 (br. s) | 91.9 | - | - | |||||||
C-3′ | 6.37 * | 98.5 | - | 150.3 (C-4′), 156.5 (C-2′) | |||||||
C-6′ | 6.80 * | 106.4 | - | 150.3 (C-4′), 156.5 (C-2′) |
ID | Compound | Amount µg/mg Dry Matter | |||
---|---|---|---|---|---|
C | L | T | V | ||
1 | ω-6 Fatty acid | 51.19 ± 4.58 a | 41.32 ± 4.26 bc | 38.16 ± 1.78 c | 47.77 ± 4.12 ab |
2 | ω-3 Fatty acid | 20.12 ± 1.76 a | 11.96 ± 0.85 b | 21.69 ± 0.49 a | 13.00 ± 1.30 b |
3 | Sucrose | 239.82 ± 6.98 a | 144.67 ± 5.87 c | 178.74 ± 3.39 b | 172.96 ± 7.80 b |
4 | Fructose | 148.39 ± 3.67 a | 82.91 ± 2.50 d | 103.72 ± 1.55 b | 95.60 ± 3.81 c |
5 | α-Glucose | 36.89 ± 5.11 c | 73.43 ± 5.28 b | 94.92 ± 1.76 a | 71.06 ± 7.58 b |
6 | β-Glucose | 43.15 ± 3.33 c | 76.31 ± 5.11 b | 89.00 ± 7.70 a | 81.72 ± 4.15 ab |
7 | Alanine | 31.46 ± 1.88 b | 23.51 ± 2.51 c | 44.59 ± 1.88 a | 25.01 ± 1.19 c |
8 | Valine | 12.61 ± 0.63 b | 14.59 ± 0.95 a | 12.57 ± 0.75 b | 10.26 ± 0.83 c |
10 | 4-Hydroxyisoleucine | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 51.13 ± 3.53 a | 0.0 ± 0.0 b |
11 | Asparagine | 61.05 ± 4.51 b | 73.46 ± 8.09 b | 93.43 ± 4.29 a | 72.71 ± 9.68 b |
12 | Choline | 19.06 ± 0.54 a | 16.91 ± 1.09 b | 9.06 ± 0.20 c | 9.94 ± 0.95 c |
13 | Betaine | 12.98 ± 0.62 b | 10.06 ± 0.87 bc | 5.06 ± 1.10 c | 109.16 ± 5.49 a |
15 | Phenylalanine | 0.0 ± 0.0 b | 8.61 ± 0.62 a | 8.69 ± 0.94 a | 9.07 ± 1.45 a |
16 | Tyrosine | 0.0 ± 0.0 c | 8.59 ± 0.53 b | 8.93 ± 0.68 b | 15.57 ± 2.69 a |
17 | L-Dopa | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 112.40 ± 13.16 a |
18 | Tryptophan | 24.16 ± 5.02 a | 22.82 ± 3.70 a | 22.05 ± 2.32 a | 10.36 ± 2.99 b |
19 | Histidine | 4.23 ± 0.25 c | 11.22 ± 1.77 a | 7.43 ± 1.91 b | 11.07 ± 1.77 a |
20 | Cytosine | 9.39 ± 1.95 a | 6.16 ± 1.30 b | 5.53 ± 0.72 b | 7.30 ± 1.45 ab |
22 | Acetic acid | 0.0 ± 0.0 b | 10.51 ± 0.46 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
23 | Fumaric acid | 2.18 ± 0.19 c | 2.51 ± 0.25 bc | 3.11 ± 0.16 a | 2.84 ± 0.34 ab |
24 | β-Sitosterol | 8.95 ± 0.67 b | 10.12 ± 0.78 ab | 8.56 ± 1.03 b | 10.77 ± 0.90 a |
25 | Trigonelline | 18.03 ± 0.97 b | 8.11 ± 1.02 d | 24.73 ± 1.02 a | 11.59 ± 1.34 c |
26 | Biochanin A | 32.04 ± 2.12 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
27 | Genistin | 43.86 ± 4.87 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
28 | Malonyl-genistin | 78.88 ± 1.46 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
29 | Formononetin | 35.52 ± 2.00 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
30 | Daidzin | 49.27 ± 3.10 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
31 | Malonyl-daidzin | 80.22 ± 3.56 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
32 | Cicerin | 33.19 ± 2.84 a | 0.0 ± 0.0 b | 0.0 ± 0.0 b | 0.0 ± 0.0 b |
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Farag, M.A.; Sharaf El-Din, M.G.; Selim, M.A.; Owis, A.I.; Abouzid, S.F.; Porzel, A.; Wessjohann, L.A.; Otify, A. Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics. Molecules 2021, 26, 761. https://doi.org/10.3390/molecules26030761
Farag MA, Sharaf El-Din MG, Selim MA, Owis AI, Abouzid SF, Porzel A, Wessjohann LA, Otify A. Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics. Molecules. 2021; 26(3):761. https://doi.org/10.3390/molecules26030761
Chicago/Turabian StyleFarag, Mohamed A., Mohamed G. Sharaf El-Din, Mohamed A. Selim, Asmaa I. Owis, Sameh F. Abouzid, Andrea Porzel, Ludger A. Wessjohann, and Asmaa Otify. 2021. "Nuclear Magnetic Resonance Metabolomics Approach for the Analysis of Major Legume Sprouts Coupled to Chemometrics" Molecules 26, no. 3: 761. https://doi.org/10.3390/molecules26030761