Table 4.
Quantification (μg/g d.w.) of the phenolic compounds identified in raw and bioprocessed hemp. H, untreated hemp dough; HX, hemp dough treated with xylanase Depol 761P (1% wt/wt of fiber); HP, hemp dough treated with protease VeronPS (2.5% wt/wt of protein); HF, hemp dough fermented by Lactiplantibacillus plantarum 18S9 and Leuconostoc mesenteroides 12MM1 (ratio 1:1, final cell density of circa 7 log10 cfu/g). All treated samples were incubated at 30 °C for 24 h.
| H | HX | HP | HF | |
|---|---|---|---|---|
| Free phenolics | ||||
| Protocatechuic acid-glucoside | 27.0 ± 0.1 a | 3.7 ± 0.2 c | 6.1 ± 0.1 b | n.d |
| Protocatechuic acid-glucoside | 33.5 ± 0.8 a | 4.99 ± 0.06 c | 8.66 ± 0.07 b | 5.9 ± 0.6 c |
| Catechol | n.d. | 2.94 ± 0.08 a | 2.95 ± 0.01 a | 2.60 ± 0.09 b |
| 4-vinyl catechol | n.d. | n.d. | n.d. | 4.01 ± 0.01 |
| Tuberonic acid glucoside | 3.43 ± 0.05 a | 2.26 ± 0.03 b | 2.30 ± 0.11 b | 1.92 ± 0.01 c |
| 4-vinyl guaiacol | 2.14 ± 0.06 a | n.d. | 1.98 ± 0.01 b | 1.88 ± 0.01 b |
| Tuberonic acid glucoside | 3.09 ± 0.06 a | 1.99 ± 0.02 b | 2.08 ± 0.06 b | 1.89 ± 0.01 b |
| 3-(3-Hydroxyphenyl) propionic acid | 1.96 ± 0.02 c | 3.95 ± 0.07 b | 3.18 ± 0.08 b | 10.48 ± 0.04 a |
| 4-vinyl phenol | 1.87 ± 0.02 c | 2.53 ± 0.00 b | 2.28 ± 0.06 b | 4.70 ± 0.06 a |
| Tuberonic acid glucoside | 3.37 ± 0.01 a | 1.94 ± 0.01 b | 2.13 ± 0.06 b | 1.88 ± 0.01 c |
| Tuberonic acid glucoside | 19.4 ± 0.2 a | 3.32 ± 0.01 c | 5.6 ± 0.3 b | 2.67 ± 0.02 d |
| Tuberonic acid glucoside | 2.23 ± 0.03 a | 2.04 ± 0.04 b | 2.08 ± 0.06 b | 1.81 ± 0.01 c |
| N-caffeoyltyramine | 32.2 ± 0.5 a | 24 ± 2 b | 33 ± 2 a | 31.2 ± 0.6 a |
| Luteolin | <LOQ | <LOQ | <LOQ | <LOQ |
| N-caffeoyltyramine | 29 ± 2 b | 36 ± 1 a | 34 ± 4 a | 26.2 ± 0.9 b |
| Cannabisin B | 0.81 ± 0.05 b | 1.02 ± 0.06 a | 1.0 ± 0.1 a | 0.86 ± 0.05 b |
| Cannabisin B | 20.4 ± 0.4 a | 20 ± 2 a | 21.0 ± 0.1 a | 19.6 ± 0.5 a |
| Cannabisin B | 1.16 ± 0.02 b | 1.51 ± 0.09 a | 1.4 ± 0.2 a | 0.98 ± 0.03 c |
| Cannabisin B | 0.92 ± 0.09 a | 1.11 ± 0.02 a | 1.1 ± 0.2 a | 0.61 ± 0.08 b |
| Cannabisin C | 6.3 ± 0.1 ab | 6.72 ± 0.06 a | 6.5 ± 0.2 a | 5.7 ± 0.2 b |
| Cannabisin C | 5.60 ± 0.02 a | 5.7 ± 0.4 a | 5.9 ± 0.3 a | 5.0 ± 0.4 a |
| Cannabisin C | 3.0 ± 0.2 ab | 3.3 ± 0.3 a | 3.7 ± 0.3 a | 2.61 ± 0.03 b |
| Cannabisin D | 4.4 ± 0.1 a | 4.3 ± 0.5 a | 4.32 ± 0.05 a | 4.0 ± 0.3 a |
| Cannabisin D | 0.93 ± 0.07 a | 1.3 ± 0.3 a | 1.4 ± 0.6 a | 0.38 ± 0.06 b |
| Cannabisin D | 4.80 ± 0.09 b | 4.2 ± 0.4 b | 6.2 ± 0.3 a | 5.9 ± 0.2 a |
| Cannabisin D | 3.1 ± 0.1 b | 5.1 ± 0.2 a | 4.5 ± 0.5 a | 2.1 ± 0.2 c |
| Cannabisin D | 3.3 ± 0.2 a | 4.1 ± 0.6 a | 3.7 ± 0.5 a | 2.37 ± 0.04 b |
| Cannabidiolic acid glucoside | 7.62 ± 0.01 a | 3.3 ± 0.2 b | 4.0 ± 0.2 b | 3.77 ± 0.05 b |
| Cannabielsoic acid | 13.3 ± 0.2 a | 2.9 ± 0.2 d | 4.35 ± 0.01 b | 3.90 ± 0.09 c |
| Cannabielsoic acid | 9.86 ± 0.01 a | 2.7 ± 0.1 d | 3.5 ± 0.1 b | 3.24 ± 0.01 c |
| Cannabielsoic acid | 4.63 ± 0.04 a | 1.90 ± 0.01 c | 2.06 ± 0.01 b | 2.05 ± 0.04 b |
| Cannabielsoic acid | 6.81 ± 0.02 a | 1.96 ± 0.03 d | 2.40 ± 0.01 b | 2.27 ± 0.01 c |
| Cannabielsoic acid | 4.57 ± 0.02 a | 1.96 ± 0.03 d | 2.64 ± 0.09 b | 2.22 ± 0.01 c |
| Cannabielsoic acid | 16.2 ± 0.1 a | 3.0 ± 0.1 b | 3.8 ± 0.1 b | 3.42 ± 0.07 b |
| Cannabielsoic acid | 30 ± 2 a | 3.5 ± 0.4 c | 4.8 ± 0.4 b | 4.6 ± 0.2 b |
| Total | 307 ± 6 a | 170 ± 6 c | 194 ± 4 b | 173 ± 2 c |
| Bound phenolics | ||||
| Salicylic acid derivative | 14.4 ± 0.5 c | 59 ± 2 a | 32 ± 2 b | 7.2 ± 0.5 d |
| Benzoic acid aldehyde | 26 ± 3 a | 7.20 ± 0.20 c | 6.60 ± 0.2 c | 13 ± 1 b |
| Xerocomic acid | 1.37 ± 0.01 c | 3.60 ± 0.20 b | 3.60 ± 0.1 b | 4.10 ± 0.11 a |
| trans p-Coumaric acid | 0.98 ± 0.03 a | 0.91 ± 0.02 a | 0.98 ± 0.02 a | 1.02 ± 0.06 a |
| cis p-Coumaric acid | 0.56 ± 0.02 a | 0.49 ± 0.01 b | 0.54 ± 0.01 a | 0.56 ± 0.01 a |
| Coumaric acid derivative | 0.84 ± 0.05 a | 0.50 ± 0.01 c | 0.68 ± 0.01 b | 0.90 ± 0.01 a |
| Coumaric acid derivative | 1.89 ± 0.07 a | 0.95 ± 0.07 c | 0.85 ± 0.02 c | 1.47 ± 0.02 b |
| Flavodic acid | 0.37 ± 0.02 a | 0.30 ± 0.02 b | 0.32 ± 0.01 b | 0.43 ± 0.01 a |
| Flavodic acid | 0.80 ± 0.10 c | 2.45 ± 0.06 a | 2.03 ± 0.08 b | 2.1 ± 0.10 b |
| Flavodic acid | 0.48 ± 0.01 c | 1.52 ± 0.10 a | 1.14 ± 0.04 b | 1.21 ± 0.04 b |
| N-caffeoyltyramine | 11.04 ± 0.02 c | 24 ± 2 a | 21.0 ± 0.6 b | 23.3 ± 0.9 a |
| Flavodic acid derivative | 0.70 ± 0.03 ab | 0.81 ± 0.07 a | 0.61 ± 0.04 b | 0.75 ± 0.04 a |
| Flavodic acid derivative | 0.23 ± 0.02 a | 0.26 ± 0.03 a | 0.16 ± 0.01 b | 0.24 ± 0.01 a |
| Cannabisin B isomer 1 | 0.17 ± 0.01 c | 0.58 ± 0.02 a | 0.53 ± 0.01 a | 0.26 ± 0.02 b |
| Cannabisin B isomer 2 | 2.01 ± 0.21 b | 4.4 ± 0.50 a | 3.6 ± 0.3 a | 2.4 ± 0.2 b |
| N-trans-feryroyltyramine | 3.51 ± 0.40 a | 3.21 ± 0.00 a | 3.11 ± 0.04 a | 3.5 ± 0.1 a |
| Cannabisin B isomer 3 | 1.12 ± 0.10 c | 1.56 ± 0.01 a | 1.37 ± 0.07 b | 1.55 ± 0.05 a |
| Cannabisin B isomer 4 | 0.14 ± 0.01 d | 0.74 ± 0.09 a | 0.49 ± 0.03 b | 0.32 ± 0.02 c |
| Cannabisin B isomer 5 | 0.61 ± 0.01 c | 1.33 ± 0.03 a | 1.12 ± 0.08 b | 0.9 ± 0.1 b |
| Cannabisin C isomer 1 | 1.17 ± 0.07 b | 2.41 ± 0.10 a | 2.22 ± 0.20 a | 2.30 ± 0.05 a |
| Cannabisin B isomer 6 | 0.16 ± 0.00 c | 0.33 ± 0.02 a | 0.28 ± 0.02 a | 0.23 ± 0.02 b |
| Cannabisin C isomer 2 | 0.37 ± 0.03 a | 1.70 ± 0.10 a | 1.60 ± 0.05 a | 1.26 ± 0.03 b |
| Cannabisin C isomer 3 | 0.53 ± 0.04 a | 0.59 ± 0.04 a | 0.53 ± 0.03 a | 0.54 ± 0.00 a |
| Cannabisin C isomer 4 | 2.21 ± 0.10 b | 2.89 ± 0.11 a | 2.63 ± 0.07 a | 2.72 ± 0.10 a |
| Cannabisin D isomer 1 | 1.92 ± 0.02 a | 1.71 ± 0.05 b | 1.64 ± 0.10 b | 1.68 ± 0.04 b |
| Cannabisin B isomer 7 | 0.36 ± 0.02 c | 1.14 ± 0.04 a | 1.00 ± 0.04 ab | 0.85 ± 0.02 b |
| Cannabisin B isomer 8 | 0.15 ± 0.01 c | 0.47 ± 0.02 a | 0.45 ± 0.02 a | 0.26 ± 0.01 b |
| Cannabisin D isomer 2 | 1.03 ± 0.05 a | 1.01 ± 0.01 a | 0.99 ± 0.03 a | 0.98 ± 0.02 a |
| Cannabisin E isomer 1 | 0.82 ± 0.01 a | 0.61 ± 0.05 b | 0.68 ± 0.01 b | 0.56 ± 0.01 c |
| Cannabisin E isomer 2 | 0.41 ± 0.02 a | 0.39 ± 0.03 a | 0.38 ± 0.03 a | 0.32 ± 0.03 a |
| Cannabisin C isomer 5 | 0.31 ± 0.01 a | 0.32 ± 0.02 a | 0.28 ± 0.01 a | 0.25 ± 0.02 b |
| Cannabisin D isomer 3 | 1.62 ± 0.10 a | 1.29 ± 0.05 b | 1.29 ± 0.04 b | 1.3 ± 0.10 b |
| Cannabisin C isomer 6 | 0.39 ± 0.01 b | 0.44 ± 0.04 a | 0.36 ± 0.01 b | 0.30 ± 0.03 c |
| Cannabisin D isomer 4 | 0.34 ± 0.04 b | 0.45 ± 0.00 a | 0.40 ± 0.04 a | 0.15 ± 0.02 c |
| Cannabisin D isomer 5 | 1.12 ± 0.09 b | 1.28 ± 0.09 a | 1.37 ± 0.07 a | 0.79 ± 0.05 c |
| Total | 81 ± 5 c | 130 ± 6 a | 97 ± 5 b | 80 ± 4 c |
Data are the means of three independent experiments analyzed twice. a–d Values in the same row with different superscript letters differ significantly (p < 0.05). n.d., not detected; LOQ, limit of quantification.