Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation and Structure Characterization of C. aurantifolia Constituents
2.2. GC-MS Analysis
Peak | Compound | RT a | RI b | % c |
---|---|---|---|---|
1 | Tetrahydro-2-methyl-2 H-pyran | 5.25 | 838 | 0.72 |
2 | 4-Hexen-3-one | 5.54 | 855 | 0.51 |
3 | 3-Methyl-3-penten-2-one | 5.61 | 859 | 0.33 |
4 | 3-Hexen-2-one | 5.67 | 862 | 0.48 |
5 | 2,3-Dimethyl-2,3-butanediol | 6.30 | 898 | 1.67 |
6 | Resorcinol | 8.35 | 1016 | 3.65 |
7 | p-Cymene | 8.85 | 1046 | 0.36 |
8 | 1-Methoxycyclohexene | 9.56 | 1089 | 8.00 |
9 | Linalool oxide | 9.97 | 1115 | 1.18 |
10 | Crysantenile acetate | 10.60 | 1156 | 0.40 |
11 | Corylone | 10.92 | 1177 | 6.93 |
12 | Terpinen-4-ol | 11.47 | 1213 | 1.66 |
13 | α-Terpineol | 11.74 | 1232 | 5.97 |
14 | 3-Methyl-1,2-cyclopentanedione | 12.10 | 1257 | 8.27 |
15 | 3,7-Dimethyl-(Z)-2,6-octadienal | 12.36 | 1276 | 1.09 |
16 | Carvone | 12.49 | 1284 | 0.88 |
17 | Geraniol | 12.60 | 1292 | 1.15 |
18 | Citral | 12.77 | 1305 | 2.21 |
19 | 1,8-Dimethyl-4-(1-methylethyl)-spiro[4.5]dec-8-en-7-one | 12.96 | 1318 | 0.56 |
20 | Geranyl formate | 13.11 | 1329 | 0.70 |
21 | Oleic acid | 13.93 | 1390 | 0.69 |
22 | 7-Methyl-(Z)-8-tetradecen-1-ol acetate | 14.20 | 1410 | 2.83 |
23 | Geranyl acetone | 14.78 | 1455 | 1.84 |
24 | Bergamotene | 14.96 | 1470 | 1.00 |
25 | (Z)-8-Methyl-9-tetradecenoic acid | 15.28 | 1494 | 1.24 |
26 | trans-α-Bisabolene | 15.89 | 1545 | 1.02 |
27 | Caryophyllene oxide | 17.05 | 1643 | 3.02 |
28 | Spathulenol | 17.60 | 1691 | 1.95 |
29 | Umbelliferone | 19.06 | 1828 | 4.36 |
30 | (Z)-11(13,14-Epoxy)tetradecen-1-ol acetate | 19.29 | 1849 | 0.59 |
31 | trans-Phytol | 19.52 | 1872 | 0.22 |
32 | 1-Heptatriacontanol | 19.65 | 1884 | 0.42 |
33 | Versalide | 20.08 | 1926 | 0.51 |
34 | Methyl palmitate | 20.45 | 1964 | 0.29 |
35 | Palmitic acid | 21.19 | 2031 | 6.89 |
36 | 5,7-Dimethoxycoumarin | 21.83 | 2083 | 15.80 |
37 | 5-Methoxypsoralen | 22.55 | 2154 | 1.14 |
38 | Linoleic acid | 22.77 | 2179 | 0.96 |
39 | Tricosane | 23.88 | 2305 | 0.31 |
40 | 5,8-Dimethoxypsoralen | 24.12 | 2332 | 6.08 |
41 | Pentacosane | 25.86 | 2506 | 0.46 |
42 | Tetracosanal | 27.80 | 2650 | 0.70 |
43 | Octacosane | 28.78 | 2711 | 0.39 |
44 | Nonacosane | 33.40 | 2915 | 0.50 |
2.3. Antimycobacterial Activity of Constituents from C. aurantifolia
Compound | H37Rv a | H10 b | M15 c | M26 d |
---|---|---|---|---|
5-Geranyloxypsoralen (1) | 50 | 200 | 100 | 100 |
5-Geranyloxy-7-methoxycoumarin (2) | 200 | 200 | 100 | 100 |
5,7-Dimethoxycoumarin (3) | >200 | NT | NT | NT |
5,8-Dimethoxypsoralen (5) | 25 | 25 | >50 | 50 |
4-Hexen-3-one | 50 | >200 | >200 | >200 |
3-Methyl-3-penten-2-one | >200 | NT | NT | NT |
Resorcinol | >200 | NT | NT | NT |
p-Cymene | >200 | NT | NT | NT |
Linalool oxide | >200 | NT | NT | NT |
Terpinen-4-ol | 200 | >200 | >200 | >200 |
3-Methyl-1,2-cyclopentanedione | >200 | NT | NT | NT |
Carvone | 200 | >200 | >200 | >200 |
Geraniol | 200 | >200 | >200 | >200 |
Citral | 50 | >200 | >200 | 200 |
Geranyl formate | >200 | NT | NT | NT |
Oleic acid | 100 | 100 | 100 | 100 |
Methyl palmitate | >200 | NT | NT | NT |
Palmitic acid | 25 | 50 | 50 | 50 |
Linoleic acid | 50 | 100 | 100 | 100 |
Pinacol | >200 | NT | NT | NT |
Ethambutol | 2.0 | 15 | 15 | 15 |
Isoniazid | 0.02 | 5 | 7 | 6 |
Rifampicin | 0.08 | 9 | 10 | 12 |
3. Experimental
3.1. General Experimental Procedures
3.2. Chemicals
3.3. Mycobacterium Tuberculosis Strains
3.4. Plant Material
3.5. Extraction and Isolation of Constituents from C. aurantifolia
3.6. Spectroscopical Data
3.7. GC-MS Analysis
3.8. Antimycobacterial Activity
4. Conclusions
Acknowledgments
Conflict of Interest
References
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Sandoval-Montemayor, N.E.; García, A.; Elizondo-Treviño, E.; Garza-González, E.; Alvarez, L.; Del Rayo Camacho-Corona, M. Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents. Molecules 2012, 17, 11173-11184. https://doi.org/10.3390/molecules170911173
Sandoval-Montemayor NE, García A, Elizondo-Treviño E, Garza-González E, Alvarez L, Del Rayo Camacho-Corona M. Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents. Molecules. 2012; 17(9):11173-11184. https://doi.org/10.3390/molecules170911173
Chicago/Turabian StyleSandoval-Montemayor, Nallely E., Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez, and María Del Rayo Camacho-Corona. 2012. "Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents" Molecules 17, no. 9: 11173-11184. https://doi.org/10.3390/molecules170911173