Background
Methods
Plant material
Extraction of essential oils
Analytical GC-FID and GC-MS
GC conditions
Identification and quantification of oils components
Standards compounds
Anti-leishmanial activity
Cytotoxicity assay and selectivity index
Statistical analysis
Results
Chemical profiles of the oils
EO 2013 (Anlz1) | EO 2013 (Anlz2) | EO 2015 (Anlz3) | ||||||||
---|---|---|---|---|---|---|---|---|---|---|
Constituents | l.r.i.a | LEO | SEO | LSEO | LEO | SEO | LSEO | LEO | SEO | LSEO |
ethyl isovalerate | 854 | - | - | - | - | - | - | - | 0.3 | - |
tricyclene | 928 | - | - | - | - | - | 0.1 | - | - | 0.2 |
α-thujene | 933 | - | - | - | - | - | - | - | - | 0.2 |
α-pinene | 941 | 2.9 | 4.6 | 3.9 | 1.4 | 3.4 | 4.6 | 2.1 | 4.6 | 7.2 |
camphene | 955 | 0.9 | 3.0 | 2.5 | 0.6 | 2.1 | 2.8 | 0.8 | 2.5 | 3.2 |
sabinene | 977 | 0.4 | - | 0.7 | 0.2 | 0.3 | 0.6 | 0.3 | 0.5 | 0.9 |
β-pinene | 981 | 1.1 | 3.4 | 2.9 | 0.7 | 2.5 | 3.0 | 0.9 | 3.5 | 3.9 |
myrcene | 993 | 3.3 | 0.8 | 1.3 | 0.7 | 0.4 | 0.9 | 1.0 | 2.1 | 2.6 |
octanal | 1002 | - | - | - | - | - | 0.3 | - | - | - |
α-phellandrene | 1006 | 0.4 | - | 0.7 | - | - | - | - | 2.8 | 3.8 |
α-terpinene | 1020 | - | - | 0.3 | - | - | - | - | - | - |
p-cymene | 1028 | 1.9 | 2.0 | 3.2 | 0.7 | - | 2.3 | 0.9 | 0.8 | 2.2 |
limonene | 1032 | 8.1 | 2.3 | 5.2 | 2.0 | 1.5 | 2.9 | 2.8 | 6.4 | 9.4 |
(E)-β-ocimene | 1052 | - | - | - | - | - | - | - | - | 0.2 |
(E)-2-octen-1-ol | 1071 | 0.4 | - | 0.7 | 0.6 | 0.9 | 0.7 | 0.6 | 0.6 | 0.4 |
1-octanol | 1074 | 0.3 | 1.0 | 0.5 | - | 0.3 | - | - | - | - |
1-nonen-3-ol | 1088 | 0.7 | 1.3 | - | 0.6 | 1.1 | 2.0 | 0.6 | 0.6 | 1.1 |
2-nonanone | 1093 | - | - | 0.3 | - | - | 0.3 | - | - | - |
2-methylbutyl 2-methylbutanoate | 1101 | - | - | - | - | - | - | - | 0.3 | - |
linalool | 1101 | 0.7 | - | 0.9 | 0.5 | - | 0.7 | 0.4 | - | 0.7 |
isopentyl 2-methylbutanoate | 1103 | 0.6 | - | 0.8 | 0.7 | 0.6 | 0.7 | 0.8 | - | - |
isopentyl isovalerate | 1104 | 0.4 | 0.6 | 0.6 | - | - | 0.4 | - | 2.0 | 1.0 |
pentyl isovalerate | 1106 | - | - | - | 0.4 | 0.5 | 0.7 | 0.4 | 1.5 | 0.7 |
cis-p-menth-2-en-1-ol | 1123 | 16.8 | 12.4 | 8.7 | 19.9 | 12.7 | 13.7 | 21.3 | 15.9 | 16.0 |
trans-p-menth-2-en-1-ol | 1142 | 16.2 | 11.2 | 8.2 | 17.8 | 11.2 | 12.2 | 18.8 | 11.8 | 12.6 |
pinocarvone | 1164 | - | - | 0.3 | - | - | 0.3 | - | - | - |
ethyl benzoate | 1172 | - | - | - | - | - | - | - | 0.5 | - |
1-nonanol | 1173 | - | - | - | 0.2 | - | - | - | - | - |
4-terpineol | 1179 | 0.4 | - | 0.8 | - | 0.7 | 0.6 | - | 0.5 | 0.4 |
cryptone | 1186 | - | - | 4.5 | 1.7 | 3.8 | 3.3 | 1.5 | 1.4 | 1.4 |
1-dodecene | 1193 | - | - | - | - | 0.8 | - | - | - | - |
cis-piperitol | 1195 | 4.9 | 4.0 | 2.6 | 5.9 | 3.2 | 2.8 | 5.6 | 4.1 | 3.1 |
trans-piperitol | 1207 | 12.1 | 9.1 | 5.5 | 7.9 | 3.2 | - | 8.0 | 4.2 | - |
1-octyl acetate | 1213 | 5.4 | 7.4 | 8.8 | 10.5 | 11.0 | 15.2 | 9.9 | 8.1 | 12.4 |
3-methyl-3-hexen-1-yl butanoate | 1235 | 0.8 | - | - | - | - | - | - | - | - |
(Z)-3-hexenyl isovalerate | 1238 | - | - | - | 0.2 | - | - | - | - | - |
2-nonyl acetate | 1243 | - | - | - | - | - | 1.0 | 0.7 | 0.3 | 0.5 |
hexyl isovalerate | 1243 | - | - | - | 0.6 | 0.6 | - | - | - | - |
cumin aldehyde | 1244 | - | 0.9 | - | 0.2 | 0.3 | 0.4 | - | - | - |
piperitone | 1254 | 6.7 | 8.5 | 9.1 | 8.1 | 8.0 | 9.6 | 7.5 | 6.8 | 5.2 |
1-decanol | 1272 | - | - | - | 1.5 | - | - | 1.5 | - | - |
(Z)-3-tridecene | 1282 | - | 1.6 | 2.0 | - | - | - | - | - | - |
isobornyl acetate | 1287 | 2.0 | 13.8 | 7.8 | 3.0 | 15.0 | 9.8 | 2.8 | 9.8 | 7.3 |
2-undecanone | 1293 | 0.4 | 1.0 | 0.9 | 0.4 | 0.6 | 0.5 | 0.4 | 0.5 | 0.2 |
2-undecanol | 1304 | - | - | 0.6 | - | - | - | - | - | - |
neo-iso-isopulegol acetate | 1310 | - | - | 0.7 | - | - | - | - | - | - |
myrtenyl acetate | 1327 | - | - | 0.3 | - | 0.7 | - | - | - | - |
3-oxo-p-menth-1-en-7-al | 1334 | - | - | 0.3 | - | - | - | - | - | - |
trans-piperitol acetate | 1343 | - | 0.9 | 1.0 | 0.6 | 0.9 | 0.9 | 0.6 | 0.6 | 0.4 |
neryl acetate | 1365 | 0.5 | 0.7 | 0.5 | 0.6 | 0.6 | 0.4 | 0.6 | 0.6 | 0.3 |
geranyl acetate | 1383 | - | - | - | 0.3 | 0.2 | - | - | - | - |
1-decyl acetate | 1411 | - | - | - | 0.5 | 0.5 | 0.3 | 0.5 | 0.4 | - |
1-decanol acetate | 1412 | 0.4 | - | 0.8 | - | - | - | - | - | - |
1-octyl 2-methylbutanoate | 1434 | 1.6 | 1.1 | 1.5 | 1.6 | 0.7 | 1.0 | 1.7 | 0.8 | 0.7 |
1-octyl isovalerate | 1440 | 1.2 | 1.9 | 1.4 | 1.1 | 0.8 | 0.8 | 1.0 | 1.0 | 0.6 |
germacrene D | 1482 | - | - | - | - | - | - | - | 0.7 | - |
ar-curcumene | 1483 | 0.6 | - | - | 0.7 | 0.3 | - | 0.6 | - | - |
2-phenylethyl isovalerate | 1490 | - | - | - | 0.2 | - | - | - | - | - |
valencene | 1493 | 0.6 | 0.8 | 0.5 | 0.6 | 0.5 | 0.3 | 0.6 | 0.6 | - |
α-zingiberene | 1496 | - | - | - | - | - | - | - | 0.3 | - |
β-sesquiphellandrene | 1525 | 0.8 | - | - | 0.8 | - | - | 0.7 | 0.5 | - |
kessane | 1526 | - | - | - | - | 0.3 | - | - | - | - |
tetradecanal | 1612 | - | - | - | 0.4 | - | - | 0.3 | - | - |
α-cadinol | 1654 | - | - | - | 0.3 | 0.3 | - | - | 0.3 | - |
γ-dodecalactone | 1677 | - | - | - | 0.3 | 0.3 | - | - | - | - |
cis-14-nor-muurol-5-en-4-one | 1687 | - | - | - | 0.3 | - | - | - | - | - |
pentadecanal | 1716 | 0.9 | - | - | 1.9 | 0.3 | - | 1.5 | 0.3 | - |
Monoterpene hydrocarbons | 19.0 | 16.1 | 20.7 | 6.3 | 10.2 | 17.2 | 8.8 | 23.2 | 33.8 | |
Oxygenated monoterpenes | 60.3 | 61.5 | 46.7 | 64.8 | 56.7 | 51.4 | 65.6 | 54.3 | 46.0 | |
Sesquiterpene hydrocarbons | 2.0 | 0.8 | 0.5 | 2.1 | 0.8 | 0.3 | 1.9 | 2.1 | 0.0 | |
Oxygenated sesquiterpenes | - | - | - | 0.6 | 0.6 | 0.0 | 0.0 | 0.3 | 0.0 | |
Non-terpene derivatives | 13.1 | 15.9 | 23.4 | 23.4 | 22.8 | 27.2 | 21.4 | 18.6 | 19.0 | |
Total identified | 94.4 | 94.3 | 91.3 | 97.2 | 91.1 | 96.1 | 97.7 | 98.5 | 98.8 |
Anti-leishmanial activity
Anti-leishmanial activity – promastigotes (L. mexicana mexicana) | Cytotoxicity -CHO | Selectivity index | |
---|---|---|---|
Samples | IC50 (μg/ml) ± SD | CC50 (μg/ml) ± SD | CHO/Lmm |
LEO 2013 | 16.69±0.35c | 81.20±1.59d | 4.86 |
SEO 2013 | 16.00±0.56c | 49.64±8.56c | 3.10 |
LSEO 2013 | 6.48±0.44b | 27.79±3.73b | 4.29 |
LEO 2015 | 19.44±1.00c | 80.65±1.60d | 4.15 |
SEO 2015 | 50.28±2.13d | 82.56±5.51d | 1.64 |
LSEO 2015 | 61.79±5.05e | 79.06±0.80d | 1.28 |
R- (+)-limonene | 16.59±0.35c | 29.65±0.78b | 1.79 |
S- (-)-limonene | >100 | 75.89±0.88d | - |
1-octanol | >100 | >100 | - |
linalool | >100 | >100 | - |
Amphotericin B | 0.10±0.01a | nd | - |
Camptothecin | nd | 0.74±0.09a | - |