Chemical and Antimicrobial Evaluation of Supercritical and Conventional Sideritis scardica Griseb., Lamiaceae Extracts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Composition of Investigated Samples
2.2. Antimicrobial Activity
2.3. The Extraction Yields
2.4. The Kinetics of SC-CO2 Extraction
3. Experimental
3.1. Plant Material
3.2. Essential Oil Extraction by Hydrodistillation
3.3. Supercritical Fluid Extraction
3.4. Solvent Extraction (SE)
3.5. Gas Chromatography (GC-FID)
3.6. Gas Chromatography/Mass Spectrometry (GC-MS)
3.7. In Vitro Antimicrobial Activity
4. Conclusions
Acknowledgments
Conflict of Interest
References and Notes
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Sample Availability: Samples of the analyzed samples are available from the authors. |
No | Extraction mode | HD | SC CO2 | SE | |||||
---|---|---|---|---|---|---|---|---|---|
Compound | K.I. a | EO | EO-CO2 | AO-CO2 | A | B | C | D | |
1 | α-thujene | 925.5 | 0.30 | - | - | - | - | - | - |
2 | thuja-2,4(10)-diene | 953.0 | - | 1.33 | - | - | - | - | - |
3 | sabinene | 967.3 | 0.05 | - | - | - | - | - | - |
4 | myrcene | 967.4 | 1.25 | 0.24 | - | - | - | - | - |
5 | n-Decane | 985.5 | 0.07 | - | - | - | - | - | - |
6 | β-phellandrene/limonene | 1021.7 | 0.05 | - | - | - | - | - | - |
7 | 1,8-cineole | 1023.2 | 0.08 | - | - | - | - | - | - |
8 | γ-terpinene | 1052.8 | 0.11 | - | - | - | - | - | - |
9 | isobutyl acetoacetate | 1084.9 | 0.31 | - | - | - | - | - | - |
10 | linalool | 1095.3 | 1.53 | - | - | - | - | - | - |
11 | β-thujone | 1097.8 | 0.45 | - | - | - | - | - | - |
12 | α-thujone | 1098.7 | 0.56 | - | - | - | - | - | - |
13 | trans-pinocarveol | 1130.8 | 0.34 | - | - | - | - | - | - |
14 | camphor | 1134.8 | 0.88 | - | - | - | - | - | - |
15 | trans-verbenol | 1138.8 | t | - | - | - | - | - | - |
16 | iso-menthone | 1145.8 | 1.75 | - | - | - | - | - | - |
17 | borneol | 1157.7 | 1.46 | - | - | - | - | - | - |
18 | menthol | 1165.6 | 4.90 | - | - | - | - | - | - |
19 | terpinen-4-ol | 1169.8 | 0.42 | - | - | - | - | - | - |
20 | α-terpineol | 1186.2 | 0.27 | - | - | - | - | - | - |
21 | myrtenal | 1190.8 | 0.42 | - | - | - | - | - | - |
22 | myrtenol | 1191.2 | 0.64 | - | - | - | - | - | - |
23 | trans-dihydrocarvone | 1199.5 | 0.07 | - | - | - | - | - | - |
24 | β-cyclocitral | 1214.0 | 0.09 | - | - | - | - | - | - |
25 | neoiso-dihydrocarveol | 1224.5 | 0.08 | - | - | - | - | - | - |
26 | thymol methyl ether | 1228.4 | 0.19 | - | - | - | - | - | - |
27 | pulegone | 1233.4 | 0.80 | - | - | - | - | - | - |
28 | carvacrol methyl ether | 1235.5 | 0.36 | - | - | - | - | - | - |
29 | d-carvone | 1242.1 | 0.37 | - | - | - | - | - | - |
30 | piperotone | 1250.7 | 0.27 | - | - | - | - | - | - |
31 | (Z)-chrysanthenyl acetate | 1257.8 | - | - | - | - | - | 1.63 | 4.58 |
32 | isobornyl acetate | 1277.5 | 1.10 | - | - | - | - | - | - |
33 | (E)-anethole | 1281.4 | 2.89 | - | - | - | - | - | - |
34 | menthyl acetate | 1286.4 | - | - | - | - | - | - | |
35 | thymol | 1291.1 | 1.97 | - | - | - | - | - | - |
36 | carvacrol | 1300.5 | 2.05 | - | - | 1.94 | 0.48 | 0.82 | 1.88 |
37 | (E)-dimetoxy citral | 1341.0 | - | - | - | 1.62 | - | - | - |
38 | 3’-metoxy-acetophenone | 1343.0 | 0.02 | - | - | - | - | - | - |
39 | α-cubebene | 1345.0 | 0.02 | - | 0.05 | - | - | - | - |
40 | α-terpenyl acetate | 1342.3 | 0.03 | - | - | - | - | - | - |
41 | decanoic acid | 1364.0 | - | - | - | - | - | 0.10 | 5.47 |
42 | α-copeane | 1365.6 | 0.11 | 0.34 | - | - | - | - | - |
43 | β-bourbonene | 1374.3 | 0.04 | - | - | - | - | - | - |
44 | trans-β-demascenone | 1376.9 | 0.21 | - | - | - | - | - | - |
45 | decyl acetate | 1407.0 | - | - | - | - | - | 2.66 | 12.54 |
46 | α-dihydroionone | 1389.0 | 0.27 | - | - | - | - | - | - |
47 | β-funebrene | 1395.2 | 0.30 | - | - | - | - | - | - |
48 | trans-β-caryophyllene | 1408.0 | 0.60 | 1.39 | - | - | - | - | - |
49 | 2,5-dimethyl-p-cymene | 1417.4 | 0.07 | - | - | - | - | - | - |
50 | trans-α-bergamotene | 1425.9 | 0.06 | - | - | - | - | - | - |
51 | α-humulene | 1442.4 | 0.10 | - | - | - | - | - | - |
52 | (E)-β-farnesene | 1449.2 | 0.21 | - | - | - | - | - | - |
53 | (2E)-dodecanal | 1464.0 | 0.10 | - | - | - | - | - | - |
54 | germacrene D | 1470.3 | 0.52 | - | - | - | - | - | - |
55 | (E)-β-ionone | 1478.0 | 1.15 | - | - | - | - | - | - |
56 | (E)-muurola-4(14),5-diene | 1482.2 | 0.03 | - | - | - | - | - | - |
57 | valencene | 1484.8 | 0.35 | - | - | - | - | - | - |
58 | α-muurolene | 1490.2 | 0.33 | - | - | - | - | - | - |
59 | β-bisabolene | 1499.3 | 0.19 | 0.41 | - | - | - | - | - |
60 | χ-cadinene | 1503.1 | 0.13 | 0.89 | - | - | - | - | - |
61 | 7-epi-α-selinene | 1520.0 | 0.66 | 0.94 | - | - | - | - | - |
62 | (E)-calamenene | 1521.0 | 0.36 | - | - | - | - | - | - |
63 | myristicin | 1522.0 | 5.23 | - | - | - | - | - | - |
64 | δ-cadinene | 1522.0 | 0.10 | - | - | - | - | - | - |
65 | ether-italicane | 1531.1 | t | - | - | - | - | - | - |
66 | α-calacorene | 1532.7 | 1.31 | - | - | - | - | - | - |
67 | β-calacorene | 1553.3 | 1.21 | - | - | - | - | - | - |
68 | (E)-nerolidol | 1557.1 | 0.06 | - | - | - | - | - | - |
69 | dodecanoic acid | 1565.0 | - | - | - | 17.05 | 6.96 | 25.56 | 35.78 |
70 | spathulenol | 1577.0 | 1.97 | - | - | - | - | - | - |
71 | caryophyllene oxide | 1582.0 | 4.84 | 2.44 | 0.07 | - | - | - | - |
72 | viridiflorol | 1592.0 | 1.23 | - | - | - | - | - | - |
73 | carotol | 1593.5 | t | - | - | - | - | - | - |
74 | ledol | 1594.3 | 0.99 | - | - | - | - | - | - |
75 | diepi-α-cedrenepoxide | 1607.0 | t | - | - | - | - | - | - |
76 | humulene epoxide II | 1608.0 | 0.56 | - | - | - | - | - | - |
77 | ledene | 1613.0 | 0.32 | - | - | - | - | - | - |
78 | (E)-isolongifolanene | 1618.8 | 0.56 | - | - | - | - | - | - |
79 | α-colocalene | 1622.0 | 0.14 | - | - | - | - | - | - |
80 | muurola-4,10(14)-dien-1-β-ol | 1630.0 | 0.61 | 0.21 | - | - | - | - | - |
81 | caryophylla-4(12),8(13)-dien-5-β-ol | 1639.0 | 0.51 | - | - | - | - | - | - |
82 | τ-muurolol | 1640.6 | 3.62 | - | - | - | - | - | - |
83 | α-muurolol | 1645.7 | 0.19 | - | - | - | - | - | - |
84 | α-selin-11-en-4-ol | 1658.1 | 1.65 | - | - | - | - | - | - |
85 | (E)-calamenen-10-ol | 1668.2 | 1.45 | - | - | - | - | - | - |
86 | valeranone | 1674.4 | 2.15 | 1.06 | - | - | - | - | - |
87 | cadelene | 1675.0 | 1.51 | - | - | - | - | - | - |
88 | α-germacra-4(15),5,10(14)-trien-1-ol | 1685.3 | 1.21 | - | - | - | - | - | - |
89 | α-bisabolol | 1685.7 | 0.32 | 0.27 | - | - | - | - | - |
90 | acorenone | 1692.0 | 0.26 | - | - | - | - | - | - |
91 | 2-(E)-tridecanol acetate | 1703.0 | 2.50 | 0.65 | 0.19 | - | - | - | - |
92 | (E)-coniferyl alcohol | 1735.6 | - | - | - | - | - | 11.81 | 18.69 |
93 | benzyl benzoate | 1761.8 | 0.02 | - | - | - | - | - | - |
94 | β-bisabolenal | 1768.9 | 0.22 | - | - | - | - | - | - |
95 | β-bisabolenol | 1786.1 | 1.40 | 0.53 | - | - | - | - | - |
96 | (2Z,6E)-farnesyl acetate | 1821.0 | - | 0.44 | - | - | - | - | - |
97 | cyclopentadecanolide | 1826.6 | - | - | - | 4.01 | 0.34 | 15.35 | - |
98 | (Z)-lanceol acetate | 1858.0 | - | 0.66 | - | - | - | - | - |
99 | hexadecanol | 1878.8 | - | - | - | - | - | 0.63 | 0.42 |
100 | (5E,9E)-farnesyl acetone | 1907.9 | 0.45 | - | 0.12 | - | - | - | - |
101 | methyl hexadecanoate | 1922.0 | - | - | 0.27 | - | - | - | - |
102 | ent-rosa-5,15-diene | 1933.9 | 0.15 | - | - | - | - | - | - |
103 | pimaradiene | 1948.8 | 0.05 | 1.52 | 2.84 | - | - | - | - |
104 | hexadecanoic acid | 1966.6 | 12.92 | 18.59 | 43.22 | 46.57 | 8.53 | 29.89 | 0.38 |
105 | ethyl hexadecanoate | 1992.0 | 0.20 | 11.82 | - | 4.13 | 1.23 | 7.64 | - |
106 | kaur-15-ene | 1997.0 | 1.88 | 0.55 | - | - | - | - | - |
107 | 13-epi-manool oxide | 2009.9 | 0.62 | - | - | - | - | - | - |
108 | manool | 2041.7 | 0.54 | - | - | - | - | - | - |
109 | 13-epi-manool | 2059.0 | 0.53 | - | - | - | - | - | - |
110 | octadecanol | 2077.0 | 0.21 | 6.20 | 1.84 | t | t | - | - |
111 | methyl linoleate | 2095.0 | 0.01 | 1.34 | 0.11 | - | - | - | - |
112 | methyl oleate | 2104.0 | - | - | 0.18 | t | - | - | - |
113 | linoleic acid | 2132.0 | 0.12 | 0.71 | 24.80 | - | t | - | - |
114 | oleic acid | 2141.0 | - | 0.80 | - | - | - | - | - |
115 | phytol acetate | 2170.6 | - | - | 0.46 | - | - | - | - |
116 | ugandensodial | 2190.0 | - | - | - | 1.36 | - | - | - |
117 | 7α-hydroxy manool | 2237.0 | 0.41 | 0.61 | - | - | - | - | - |
118 | 3β-sandaracopimardienol | 2269.0 | 0.20 | - | - | t | t | - | - |
119 | sandaracopimarinol | 2269.0 | 0.37 | 1.26 | 1.26 | - | - | - | - |
120 | tricosane | 2300.0 | 0.38 | 0.40 | - | - | t | - | - |
121 | isopimarol | 2310.4 | 0.22 | 1.49 | - | - | - | - | - |
122 | (E) -ferruginol acetate | 2357.0 | - | 11.73 | 11.22 | 8.25 | 65.47 | - | - |
123 | methyl strictate | 2387.0 | - | 1.70 | - | - | - | - | - |
124 | 9-octadecen-1-ol | 2396.4 | - | 1.05 | - | - | - | - | - |
125 | (Z) -ferruginol acetate | 2406.0 | - | - | - | 4.26 | 1.04 | - | - |
126 | pentacosane | 2486.0 | 0.41 | 1.23 | - | - | - | - | - |
127 | dihydroxysandaracopimar-8(14),15-diene b | 2506.0 | - | 14.89 | 11.49 | 10.79 | 6.25 | - | - |
128 | hexacosane | 2600 | - | t | - | - | - | - | - |
129 | heptacosane | 2700.0 | 1.28 | t | t | - | - | - | - |
130 | octacosane | 2800.0 | - | t | t | - | - | - | - |
131 | nonacosane | 2900.0 | - | t | - | - | - | - | - |
132 | triacontane | 3000.0 | 0.08 | - | - | - | - | - | - |
133 | dotriacontane | 3200.0 | 0.01 | - | - | - | - | - | - |
Total | 89.12 | 87.69 | 98.12 | 99.98 | 90.30 | 96.09 | 79.74 | ||
Monoterpene hydrocarbons | 1.83 | 1.57 | - | - | - | - | - | ||
Oxygenated monoterpenes | 30.01 | - | - | 3.56 | 0.48 | 14.26 | 25.15 | ||
Sesquiterpene hydrocarbons | 8.63 | 3.97 | 0.05 | - | - | - | - | ||
Oxygenated sesquiterpenes | 25.54 | 5.61 | 0.19 | - | - | - | - | ||
Diterpenes | 4.97 | 33.75 | 26.81 | 23.30 | 72.76 | - | - | ||
Fatty acids&esters&aldehydes&alcohols | 15.96 | 41.16 | 71.07 | 67.75 | 16.72 | 66.48 | 54.59 | ||
Hydrocarbones | 2.16 | 1.63 | t | - | t | - | - | ||
Others | 0.02 | - | - | 5..37 | 0.34 | 15.35 | - |
Strain | MIC VALUES µg/mL | |||||||
---|---|---|---|---|---|---|---|---|
EO | EO-CO2 | AO-CO2 | A | B | C | D | Gentamicin | |
Gram-positive bacteria | ||||||||
Streptococcus pyogenes 1, tonsils swab | 1280 | 640 | 640 | 1280 | 640 | 1280 | 1280 | ≤4 |
Streptococcus pyogenes 2, tonsils swab | 1280 | 640 | 640 | 1280 | 1280 | 1280 | 2560 | ≤4 |
Streptococcus canis, tonsils swab dog | 2560 | 2560 | 2560 | 2560 | 2560 | 2560 | >2560 | ≤4 |
Moraxella catarrhalis, tonsils swab | 1280 | 2560 | 2560 | 1280 | 1280 | 1280 | 2560 | ≤4 |
Staphylococcus aureus, ATCC 25923 | >2560 | >2560 | >2560 | 1280 | 1280 | 1280 | 1280 | ≤4 |
Staphylococcus aureus, CI, tonsils swab | >2560 | 2560 | 2560 | 1280 | 1280 | 640 | 1280 | ≤4 |
MRSA ATCC 43300 | >2560 | 2560 | 2560 | 1280 | 1280 | 640 | 640 | ≤4 |
Corynebacterium pseudotuberculosis, tonsils swab | 640 | 320 | 320 | 160 | 320 | 80 | 80 | ≤4 |
Enterococcus faecalis, tonsils swab | 2560 | 2560 | 2560 | >2560 | >2560 | >2560 | 1280 | ≤4 |
Gram-negative bacteria | ||||||||
Escherichia coli, ATCC 25922 | 2560 | >2560 | >2560 | 2560 | >2560 | >2560 | 2560 | ≤4 |
Escherichia coli, CI, skin swab | >2560 | >2560 | >2560 | 2560 | >2560 | >2560 | 2560 | ≤4 |
Pseudomonas aeruginosa, tonsils swab | 2560 | 2560 | 2560 | 2560 | >2560 | >2560 | 2560 | ≤4 |
Klebsiella pneumoniae, tonsils swab | >2560 | >2560 | >2560 | 2560 | >2560 | >2560 | 2560 | ≤4 |
Pasteurella multocida tonsils swab, dog | 1280 | 1280 | 1280 | 640 | 640 | 320 | 320 | ≤4 |
Haemophilus sp., nose swab | 640 | 640 | 640 | 320 | 320 | 40 | 80 | ≤4 |
Yeast | ||||||||
Candida albicans, tonsils swab | 2560 | 2560 | 2560 | 2560 | >2560 | >2560 | 2560 | - |
Investigated samples | Yield of extraction (%) |
---|---|
EO | 0.03 |
EO-CO2 | 1.04 |
AO-CO2 | 0.63 |
A | 16.70 |
B | 0.50 |
C | 0.20 |
D | 0.70 |
© 2012 by the author. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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Tadić, V.; Bojović, D.; Arsić, I.; Đorđević, S.; Aksentijevic, K.; Stamenić, M.; Janković, S. Chemical and Antimicrobial Evaluation of Supercritical and Conventional Sideritis scardica Griseb., Lamiaceae Extracts. Molecules 2012, 17, 2683-2703. https://doi.org/10.3390/molecules17032683
Tadić V, Bojović D, Arsić I, Đorđević S, Aksentijevic K, Stamenić M, Janković S. Chemical and Antimicrobial Evaluation of Supercritical and Conventional Sideritis scardica Griseb., Lamiaceae Extracts. Molecules. 2012; 17(3):2683-2703. https://doi.org/10.3390/molecules17032683
Chicago/Turabian StyleTadić, Vanja, Dragica Bojović, Ivana Arsić, Sofija Đorđević, Ksenija Aksentijevic, Marko Stamenić, and Slobodan Janković. 2012. "Chemical and Antimicrobial Evaluation of Supercritical and Conventional Sideritis scardica Griseb., Lamiaceae Extracts" Molecules 17, no. 3: 2683-2703. https://doi.org/10.3390/molecules17032683