Table 1.
Metabolites identified in the 600.13 MHz 1 H-NMR spectra of the Bligh-Dyer hydroalcoholic extracts of Cannabis sativa L. inflorescences dissolved in 400 mM phosphate buffer/D2O containing TSP 1 mM.
| Compound | Assignment | 1H (ppm) | Multiplicity [J(Hz)] | 13C (ppm) |
|---|---|---|---|---|
| Sugars | ||||
| α-d-Fructofuranose | CH-3 | 4.14 | 83.1 | |
| CH-5 | 4.07 * | 82.6 | ||
| β-d-Fructofuranose | CH-3 | 4.12 | 76.9 | |
| CH-4 | 4.12 | 75.9 | ||
| CH-5 | 3.85 | 81.7 | ||
| β-d-Fructopyranose | CH-3 | 3.81 | 67.1 | |
| CH-5 | 4.05 * | 66.8 | ||
| CH2-6,6′ | 3.71; 4.03 | 64.4 | ||
| α-Galactose | CH-1 | 5.28 | d [3.8] | 90.2 |
| CH-2 | 3.78 | |||
| CH-3 | 3.83 | |||
| CH-4 | 3.87 | |||
| CH-5 | 4.08 | |||
| β-Galactose | CH-1 | 4.60 | d [8.0] | 97.4 |
| CH-2 | 3.51 | |||
| CH-3 | 3.67 | |||
| CH-4 | 3.95 | |||
| CH-5 | 4.05 | |||
| CH-6 | 3.78 | |||
| α-Glucose | CH-1 | 5.25 * | d [3.8] | 93.1 |
| CH-2 | 3.56 | 72.2 | ||
| CH-3 | 3.74 | 73.8 | ||
| CH-4 | 3.45 | 70.7 | ||
| CH-5 | 3.84 | 72.5 | ||
| CH2-6,6′ | 3.86; 3.79 | 60.1 | ||
| β-Glucose | CH-1 | 4.66 * | d [8.0] | 97.0 |
| CH-2 | 3.27 | 75.2 | ||
| CH-3 | 3.51 | 76.8 | ||
| CH-4 | 3.43 | 70.7 | ||
| CH-5 | 3.48 | 75.1 | ||
| CH2-6,6′ | 3.90; 3.74 | 61.9 | ||
| Myo-Inositol | CH-2,5 | 3.56 | ||
| CH-3,6 | 3.65 | |||
| CH-4 | 3.30 * | 74.2 | ||
| Sucrose | CH-1 (Glucose) | 5.41 * | d [3.8] | 93.3 |
| CH-2 | 3.57 | 71.8 | ||
| CH-3 | 3.78 | 73.6 | ||
| CH-4 | 3.49 | 70.2 | ||
| CH-5 | 3.85 | 73.5 | ||
| CH2-6 | 3.83 | 63.5 | ||
| CH2-1′ (Fructose) | 3.69 | d [3.3] | 60.6 | |
| CH-3′ | 4.23 | d [8.7] | 77.5 | |
| CH-4′ | 4.06 | t [8.7] | 75.1 | |
| CH-5′ | 3.9 | 82.4 | ||
| CH2-6′ | 3.82 | 61.2 | ||
| Raffinose | CH-1 (Galactose) | 5.01 | d [3.8] | 99.4 |
| CH-2 | 3.85 | |||
| CH-3 | 3.91 | |||
| CH-4 | 4.03 | |||
| CH-1 (Glucose) | 5.44 | d [3.9] | ||
| CH-2 | 3.59 | |||
| CH-3 | 3.78 | |||
| CH-5 | 4.08 | |||
| CH-3 (Fructose) | 4.24 | d [8.7] | ||
| Organic acids | ||||
| Acetic acid | CH3 | 1.93 | s | 24.7 |
| COOH | 180.3 | |||
| Citric acid | α,γ-CH | 2.56 * | d [15.9] | 46.2 |
| α,γ′-CH | 2.69 | 46.2 | ||
| β-C | 74.2 | |||
| 1,5-COOH | 177.7 | |||
| 6-COOH | 180.2 | |||
| Formic acid | HCOOH | 8.47 * | s | |
| Fumaric Acid | α,β-CH=CH | 6.53 | s | |
| Malic acid | α-CH | 4.31 * | dd [9.8; 3.2] | 71.4 |
| β-CH | 2.70 | dd [15.6; 3.2] | 43.9 | |
| β′-CH | 2.39 | dd [15.6; 9.8] | 43.9 | |
| Succinic acid | α,β-CH2 | 2.42 * | s | 35.2 |
| Amino acids | ||||
| Alanine | α-CH | 3.81 | 51.6 | |
| β-CH3 | 1.49 * | d [7.3] | 17.2 | |
| COOH | 174.5 | |||
| Asparagine | α-CH | 4.02 | 52.3 | |
| β,β′-CH2 | 2.89; 2.97 * | 35.8 | ||
| Aspartate | α-CH | 3.91 | 52.3 | |
| β,β′-CH2 | 2.72; 2.82 * | dd [3.9; 17.4] | 37.5 | |
| γ-Aminobutyrate | α-CH2 | 2.31 * | t [7.4] | 37.2 |
| β-CH2 | 1.92 | 24.6 | ||
| γ-CH2 | 3.04 | t [7.6] | 40.2 | |
| Glutamine | α-CH | 3.78 | 55.9 | |
| β,β′-CH2 | 2.18 | m | 27.3 | |
| γ-CH | 2.46 * | m | 31.8 | |
| Isoleucine | α-CH | 3.69 | ||
| β-CH | 1.98 | |||
| γ-CH3 | 1.02 * | d [7.0] | 15.8 | |
| δ-CH3 | 0.94 | |||
| Leucine | α-CH | 3.77 | ||
| β-CH2 | 1.74 | |||
| γ-CH | 1.71 | |||
| δ-CH3 | 0.97 | 23.1 | ||
| δ′-CH3 | 0.96 | 22.0 | ||
| Phenylalanine | CH-2,6 | 7.34 | 130.5 | |
| CH-4 | 7.38 | 128.7 | ||
| CH-3,5 | 7.43 * | m | 130.2 | |
| Proline | α-CH | 4.14 | 62.4 | |
| γ-CH2 | 2.01 * | m | 24.9 | |
| Threonine | α-CH | 3.62 | 61.4 | |
| β-CH | 4.28 | 68.1 | ||
| γ-CH3 | 1.34 * | d [6.6] | 18.9 | |
| Tryptophan | CH-4 | 7.71 | d [7.8] | 119.6 |
| CH-7 | 7.52 * | d [7.8] | 113.0 | |
| Tyrosine | CH-3,5 | 7.19 | 131.7 | |
| CH-2,6 | 6.90 | 116.9 | ||
| Valine | α-CH | 3.63 | ||
| β-CH | 2.28 | 30.1 | ||
| γ-CH3 | 1.00 | d [7.03] | 17.8 | |
| γ′-CH3 | 1.05 * | d [7.03] | 19.1 | |
| Miscellaneous metabolites | ||||
| Choline | +N(CH3)3 | 3.21 * | s | 54.8 |
| Trigonelline | CH-1 | 9.11 * | s | |
| CH-3,5 | 8.84 | |||
| CH-4 | 8.11 |
Asterisks (*) indicate signals selected for integration.