Table 1.
Compounds | l.r.i. 1 | Relative Abundance (AVG ± SD) | |||||
---|---|---|---|---|---|---|---|
CTRL | [DMIM]DMP 100 | [DMIM]DMP 100 R1 | [DMIM]DMP 90 | [DMIM]DMP 80 | [DMIM]DMP 50 | ||
hexanal | 805 | - 2 | - | 0.1 ± 0.03 | 0.2 ± 0.02 | - | - |
α-pinene 3 | 939 | 2.1 ± 0.71 BC | 2.8 ± 0.03 B | 5.4 ± 1.10 A | 5.4 ± 0.89 A | 0.9 ± 0.30 C | 4.9 ± 0.90 A |
camphene | 954 | - | - | 0.1 ± 0.03 | 0.1 ± 0.02 | - | 0.2 ± 0.05 |
β-pinene | 980 | 0.8 ± 0.28 B | 0.8 ± 0.00 B | 2.1 ± 0.39 A | 2.2 ± 0.34 A | 0.7 ± 0.20 B | 2.4 ± 0.38 A |
myrcene | 991 | 2.1 ± 0.58 B | 2.2 ± 0.05 B | 7.6 ± 1.08 A | 6.7 ± 0.87 A | 1.9 ± 0.60 B | 7.5 ± 1.27 A |
δ-3-carene | 1012 | - | - | 0.1 ± 0.02 | 0.2 ± 0.03 | - | 0.2 ± 0.03 |
p-cymene | 1024 | 0.2 ± 0.04 | 0.2 ± 0.00 | 0.3 ± 0.04 | 0.4 ± 0.06 | 0.2 ± 0.06 | 0.5 ± 0.06 |
limonene | 1031 | 2.2 ± 0.64 B | 2.2 ± 0.03B | 2.9 ± 0.37 A,B | 2.7 ± 0.33 A,B | 1.2 ± 0.35 C | 3.0 ± 0.36 A |
1,8-cineole | 1035 | 0.6 ± 0.18 | 0.8 ± 0.02 | 0.5 ± 0.07 | 0.5 ± 0.06 | 0.3 ± 0.07 | 0.3 ± 0.06 |
(E)-β-ocimene | 1050 | 0.2 ± 0.04 | 0.2 ± 0.01 | 0.4 ± 0.04 | 0.2 ± 0.03 | - | 0.3 ± 0.02 |
γ-terpinene | 1062 | 0.1 ± 0.01 | 0.1 ± 0.08 | - | - | - | - |
cis-sabinene hydrate | 1070 | 0.1 ± 0.08 | - | - | - | - | - |
terpinolene | 1089 | 1.2 ± 0.28 BC | 1.0 ± 0.03C | 2.0 ± 0.18 A | 1.4 ± 0.14 B | 0.5 ± 0.11 D | 1.9 ± 0.13 A |
methyl benzoate | 1091 | - | 0.2 ± 0.01 | - | - | - | - |
linalool | 1100 | 0.3 ± 0.06 | 0.2 ± 0.03 | 0.3 ± 0.00 | 0.4 ± 0.06 | 0.4 ± 0.08 | 0.4 ± 0.03 |
perillene | 1101 | - | - | 0.1 ± 0.07 | 0.1 ± 0.01 | 0.1 ± 0.07 | 0.2 ± 0.03 |
nonanal | 1103 | - | - | 0.1 ± 0.01 | 0.1 ± 0.03 | - | 0.2 ± 0.02 |
fenchol | 1115 | 0.3 ± 0.09 | 0.2 ± 0.01 | 0.3 ± 0.01 | 0.3 ± 0.04 | 0.3 ± 0.05 | 0.4 ± 0.02 |
cis-p-menth-2-en-1-ol | 1123 | 0.2 ± 0.06 | 0.1 ± 0.11 | 0.2 ± 0.01 | 0.2 ± 0.04 | 0.2 ± 0.04 | 0.2 ± 0.00 |
trans-p-mentha-2,8-dien-1-ol | 1125 | - | - | - | 0.2 ± 0.02 | - | - |
cis-p-mentha-2,8-dien-1-ol | 1138 | - | - | 0.2 ± 0.00 | 0.4 ± 0.04 | 0.9 ± 0.18 | 0.4 ± 0.01 |
pinocarveol | 1140 | - | - | - | - | 0.1 ± 0.07 | - |
trans-verbenol | 1145 | - | - | 0.1 ± 0.08 | - | 0.1 ± 0.03 | 0.1 ± 0.01 |
(E)-tagetone | 1146 | 0.1 ± 0.09 | - | - | - | - | - |
borneol | 1167 | 0.1 ± 0.01 | - | - | 0.1 ± 0.10 | 0.1 ± 0.01 | 0.1 ± 0.09 |
4-terpineol | 1178 | 0.4 ± 0.07 | 0.4 ± 0.05 | 0.2 ± 0.01 | 0.5 ± 0.03 | 0.2 ± 0.04 | 0.3 ± 0.00 |
p-cymen-8-ol | 1185 | 0.2 ± 0.01 | - | - | 0.4 ± 0.01 | 0.3 ± 0.05 | 0.2 ± 0.02 |
α-terpineol | 1190 | 0.4 ± 0.04 | 0.2 ± 0.02 | 0.3 ± 0.02 | 0.5 ± 0.03 | 0.4 ± 0.07 | 0.4 ± 0.00 |
carveol | 1228 | - | - | - | 0.1 ± 0.01 | - | - |
α-ylangene | 1372 | - | - | 0.1 ± 0.01 | - | - | - |
isocaryophyllene | 1405 | 0.2 ± 0.01 | 0.3 ± 0.05 | 0.4 ± 0.06 | 0.3 ± 0.01 | 0.3 ± 0.00 | 0.1 ± 0.09 |
β-caryophyllene | 1418 | 32.1 ± 0.68 B | 40.3 ± 1.42 A | 30.3 ± 1.00 B | 22.5 ± 0.54 C | 15.6 ± 1.27 D | 10.2 ± 0.06 E |
trans-α-bergamotene | 1438 | 0.2 ± 0.06 | 0.5 ± 0.04 | 0.5 ± 0.03 | 0.3 ± 0.01 | 0.3 ± 0.00 | - |
α-guaiene | 1440 | 0.3 ± 0.06 | 0.6 ± 0.02 | 0.4 ± 0.01 | 0.3 ± 0.01 | 0.2 ± 0.00 | - |
α-himachalene | 1450 | - | 0.1 ± 0.13 | - | 0.1 ± 0.09 | 0.1 ± 0.00 | - |
α-humulene | 1455 | 13.1 ± 0.13 B | 15.3 ± 0.47 A | 12.4 ± 0.43 C | 10.0 ± 0.22 D | 7.8 ± 0.45 E | 5.3 ± 0.04 F |
(E)-beta-farnesene | 1459 | - | 0.2 ± 0.23 | 0.4 ± 0.06 | 0.3 ± 0.06 | 0.2 ± 0.02 | - |
alloaromadendrene | 1461 | 0.7 ± 0.04 C | 1.1 ± 0.05 A | 0.9 ± 0.04 B | 0.7 ± 0.01 C | 0.6 ± 0.02 D | 0.3 ± 0.00 E |
γ-gurjunene | 1469 | - | - | 0.3 ± 0.01 | 0.2 ± 0.01 | 0.5 ± 0.02 | 0.2 ± 0.02 |
γ-muurolene | 1476 | - | - | 0.1 ± 0.08 | 0.1 ± 0.00 | 0.1 ± 0.00 | - |
β-chamigrene | 1477 | - | - | - | 0.6 ± 0.01 | - | - |
γ-selinene | 1482 | 0.6 ± 0.06 | 0.9 ± 0.04 | 0.7 ± 0.08 | - | 0.5 ± 0.01 | 0.1 ± 0.19 |
β-selinene | 1485 | 2.4 ± 0.13 B | 3.8 ± 0.01 A | 2.6 ± 0.17 B,C | 2.1 ± 0.02 B | 1.8 ± 0.02 B,C | 1.0 ± 0.01C |
valencene | 1492 | 1.9 ± 0.02 C | 3.4 ± 0.03 A | 2.3 ± 0.06 B | 1.7 ± 0.13 C | 1.4 ± 0.01D | 0.7 ± 0.07 E |
α-bulnesene | 1505 | 0.4 ± 0.04 | 0.8 ± 0.02 | 0.4 ± 0.02 | 0.3 ± 0.01 | 0.2 ± 0.04 | 0.1 ± 0.09 |
α-farnesene | 1507 | - | - | 0.5 ± 0.04 | 0.3 ± 0.03 | - | 0.1 ± 0.08 |
β-bisabolene | 1509 | - | 0.3 ± 0.04 | - | - | 0.1 ± 0.06 | - |
trans-γ-cadinene | 1514 | - | - | - | 0.1 ± 0.07 | 0.1 ± 0.11 | - |
7-epi-α-selinene | 1517 | 0.3 ± 0.01 | 0.5 ± 0.02 | 0.5 ± 0.13 | 0.4 ± 0.01 | 0.5 ± 0.04 | 0.1 ± 0.19 |
β-cadinene | 1520 | - | 0.2 ± 0.00 | - | 0.2 ± 0.00 | - | - |
δ-cadinene | 1523 | - | 0.2 ± 0.00 | 0.2 ± 0.21 | - | 0.1 ± 0.16 | - |
selina-3,7(11)-diene | 1542 | 1.8 ± 0.35 D,E | 2.4 ± 0.04 D | 2.1 ± 0.07C | 1.8 ± 0.04 B | 1.6 ± 0.11 A | 1.2 ± 0.09 E |
α-calacorene | 1546 | - | 0.2 ± 0.04 | - | 0.1 ± 0.13 | - | - |
elemol | 1549 | 0.4 ± 0.04 | 0.3 ± 0.01 | 0.3 ± 0.03 | 0.6 ± 0.01 | 0.8 ± 0.07 | 0.8 ± 0.04 |
(E)-nerolidol | 1565 | 0.3 ± 0.06 | - | 0.3 ± 0.08 | 0.7 ± 0.01 | 1.1 ± 0.09 | 1.0 ± 0.11 |
palustrol | 1568 | 0.5 ± 0.09 | - | 0.4 ± 0.13 | 0.5 ± 0.01 | - | 0.8 ± 0.06 |
caryophyllene alcohol | 1569 | - | - | - | - | 0.9 ± 0.09 | - |
caryophyllene oxide | 1582 | 12.8 ± 0.78 D | 7.3 ± 0.44 F | 10.2 ± 0.50 E | 15.9 ± 0.37 C | 23.6 ± 0.35 A | 22.0 ± 0.25 B |
viridiflorol | 1590 | - | - | - | 0.2 ± 0.25 | 0.5 ± 0.13 | 0.2 ± 0.31 |
humulene oxide | 1606 | 4.3 ± 0.16 D | 2.5 ± 0.09 F | 3.2 ± 0.16 E | 4.9 ± 0.04 C | 7.8 ± 0.10 A | 7.2 ± 0.15 B |
selin-6-en-4-ol | 1618 | 1.7 ± 0.18 B | 1.0 ± 0.14 D | 0.9 ± 0.05 D | 1.3 ± 0.02 C | 1.8 ± 0.14 B | 2.4 ± 0.18 A |
1-epi-cubenol | 1629 | 0.2 ± 0.22 | - | 0.2 ± 0.06 | 0.1 ± 0.11 | 0.7 ± 0.03 | - |
caryophylla-4(14),8(15)-dien-5-ol | 1636 | 3.8 ± 0.37 B | 1.9 ± 0.37 C | 1.9 ± 0.21 D | 2.9 ± 0.07 C | 5.2 ± 0.25 A | 4.9 ± 0.35 A |
β-eudesmol | 1649 | - | - | - | - | - | 0.2 ± 0.28 |
α-eudesmol | 1653 | 0.4 ± 0.01 | - | - | - | - | - |
neointermedeol | 1660 | 1.5 ± 0.09 A | 0.8 ± 0.21 B | 0.5 ± 0.05 B | 0.9 ± 0.02 B | 1.8 ± 0.16 A | 1.9 ± 0.47 A |
14-hydroxy-9-epi-(E)-caryophyllene | 1665 | 1.7 ± 0.24 C | 0.7 ± 0.14 D | 0.8 ± 0.08 D | 1.4 ± 0.03 C | 3.0 ± 0.29 A | 2.6 ± 0.29 B |
α-bisabolol | 1685 | 0.7 ± 0.08 | 0.5 ± 0.05 | 0.4 ± 0.01 | 0.5 ± 0.03 | 0.9 ± 0.13 | 0.8 ± 0.11 |
juniper camphor | 1695 | 0.5 ± 0.07 | 0.3 ± 0.05 | 0.2 ± 0.01 | 0.4 ± 0.01 | 0.6 ± 0.04 | 0.6 ± 0.06 |
hexahydrofarnesyl acetone | 1845 | - | - | 0.8 ± 0.12 | 0.8 ± 0.05 | 0.9 ± 0.14 | 0.4 ± 0.00 |
cannabidiol | 2431 | 3.4 ± 0.49 B | 0.9 ± 0.13 C | 0.6 ± 0.04 C | 1.1 ± 0.01 C | 6.0 ± 0.90 A | 6.7 ± 0.39 A |
Δ9-tetrahydro-cannabinol | 2468 | 0.1 ± 0.04 B | - B | - B | - B | 0.1 ± 0.08 B | 1.3 ± 0.66 A |
Monoterpene hydrocarbons | 8.8 ± 2.59 B | 9.5 ± 0.16 B | 21.0 ± 3.26 A | 19.3 ± 2.70 A | 5.5 ± 1.62 B | 20.8 ± 3.18 A | |
Oxygenated monoterpenes | 2.7 ± 0.67 A,B,C | 1.9 ± 0.20 C | 2.1 ± 0.06 B,C | 3.7 ± 0.45 A | 3.3 ± 0.76 A | 2.9 ± 0.09 A,B | |
Sesquiterpene hydrocarbons | 54.0 ± 0.11B | 71.1 ± 1.55 A | 55.1 ± 2.11 B | 42.2 ± 1.16 C | 32.0 ± 1.23 D | 19.3 ± 0.81 E | |
Oxygenated sesquiterpenes | 28.7 ± 2.39 C | 15.4 ± 1.23 E | 19.3 ± 1.27 D | 30.1 ± 0.83 C | 48.8 ± 1.16 A | 45.3 ± 2.17 B | |
Apocarotenoids | - D | - D | 0.8 ± 0.12 B | 0.8 ± 0.05 A,B | 0.9 ± 0.14 A | 0.4 ± 0.00 C | |
Cannabinoids | 3.5 ± 0.54 C | 0.9 ± 0.13 D | 0.6 ± 0.04 D | 1.1 ± 0.01 D | 6.1 ± 0.98 B | 8.0 ± 0.27 A | |
Other non-terpene derivatives | - C | 0.2 ± 0.01 B | 0.2 ± 0.02 B | 0.3 ± 0.05 A | - C | 0.2 ± 0.02 B | |
Total identified (%) | 97.8 ± 0.44 | 99.1 ± 0.18 | 99.0 ± 0.11 | 97.5 ± 1.26 | 96.6 ± 1.33 | 96.9 ± 0.58 | |
Distillation yield (% w/w) | 0.03 ± 0.01 B | 0.06 ± 0.01 A | 0.07 ± 0.01 A | 0.06 ± 0.00 A | 0.01 ± 0.00 C | 0.01 ± 0.00 C |
1 Linear retention index on a HP-5MS capillary column; 2 Not detected; 3 For all elements reported in bold (compounds > 1% in at least one sample, all the detected chemical classes, and distillation yields), uppercase superscript letters (A–F) indicate statistically significant differences (established according to Tukey’s HSD post-hoc test, with p ≤ 0.05) among the samples.