Table 1.
1H-NMR assignments of major metabolites in P. harmala extracts.
| No. | Metabolite | δ H (multiplicity, J) | Sample |
|---|---|---|---|
| 1 | Isoleucine | 1.02 (d, 7.06), 0.95 (t, 7.15) | Bb |
| 2 | Valine | 1.05 (d, 7.0), 0.99 (d, 7.0) | Bb |
| 3 | Threonine | 4.25 (m), 1.33 (d, 6.55) | Ab |
| 4 | Alanine | 3.57 (m), 1.48 (d, 7.3) | Bb |
| 5 | Lysine | 3.6 (m), 1.65, 1.89 (m), 2.25 (m), 3.02, 3.4 (m) | Fb |
| 6 | Acetic acid | 1.92 (s) | Ab |
| 7 | Proline | 3.30–3.35 (m), 2.31–2.37 (m), 1.95–2.00 (m), 4.12 (dd, 8.63, 6.56) | Ab |
| 8 | 4-Hydroxyisoleucine | 4.25 (m), 2.167 (m), 3.835 (m), 2.22, 1.98 (m), 1.88 (m) | Ea |
| 9 | Succinic acid | 2.43 (s), 2.43 (s) | Fb |
| 10 | Malic acid | 2.71 (dd, 2.9, 15.62), 4.31 (dd, 3.1, 10.2) | Fb |
| 11 | Asparagine | 4.03 (dd, 4.4, 7.25), 2.94 (m), 2.84 (m) | Eb |
| 12 | Choline | 4.07, 3.21 (s) | Cb |
| 13 | Phosphorylcholine | 3.23 (s) | Ab |
| 14 | Betaine | 3.27 (s) | Bb |
| 15 | Sucrose | 3.69 (s), 4.22 (d, 8.65), 4.06 (t, 8.89), 3.91 (m), 3.87 (d, 3.15), 5.42 (d, 3.8), 3.59 (m), 3.78 (t, 9.48), 3.49 (t, 9.28), 3.91(m) | Ab |
| 16 | β-Glucose | 4.65 (d, 8.0) | Ab |
| 17 | Vasicine | 3.77, 3.69 (m),2.15, 2.71 (m), 5.22 (t, 8.80), 7.11 (m), 7.36 (m), 7.28 (m), 7.19 (d, 7.5) | Ea |
| 18 | α-Glucose | 5.24 (d, 3.83) | Cb |
| 19 | Maleic acid | 6.01 (s) | Bb |
| 20 | Harmine | 6.64 (d, 1.9), 6.69 (dd, 8.75, 2.25), 7.84 (d, 5.64), 2.55 (s), 7.69 (d, 5.42), 7.61 (d, 8.59), 3.84 (s) | Da |
| 21 | Harmaline | 6.46 (dd, 8.85, 1.94), 6.37 (d, 1.66), 7.0 (d, 8.64), 2.47 (s), 2.96(t, 8.83), 3.22(t, 8.83), 3.81(s) | Da |
| 22 | Vasicinone | 4.11, 3.91 (m), 1.99, 2.45 (m), 4.99 (t, 6), 7.71 (m), 7.93 (m), 7.64 (m), 8.25 (d, 6) | Fa |
| 23 | Formic acid | 8.46 (s) | Ab |
Note. “a” was determined by the 1H-NMR, COSY, HSQC, and HMBC spectra. “b” was determined by the 1H-NMR and HSQC spectra. s, singlet; d, doublet; t, triplet; m, multiplet; A, root; B, leaf; C, flower; D, seed; E, testa; F, stem.