Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Analysis
Chemical compound | a Retention time | Percentage | b Retention Index |
---|---|---|---|
3-Hexene-2,5-diol | 5.19 | 4.32 | 921 |
3-Methyl-2-cyclopenten-1-one | 6.13 | 1.77 | 960 |
1,3-Benzenediol | 9.21 | 29.59 | 1070 |
1-Methoxycyclohexene | 10.93 | 30.58 | 1217 |
(1 S-(1α,3α,6α))-Bicyclo(4.1.0)hept-4-en-3-ol | 12.60 | 0.59 | 1176 |
6-Hydroxy- exo-(±)-bicyclo(3.2.1)octan-3-one | 13.35 | 2.71 | 1199 |
α-Thujone | 13.68 | 0.94 | 1209 |
4-Ethyl-1,2-dimethylbenzene | 13.84 | 1.30 | 1214 |
2-Hydroxy-3-methyl-2-cyclopenten-1-one | 14.17 | 11.81 | 1224 |
Anethole | 19.82 | 1.18 | 1398 |
Eugenol | 22.45 | 1.73 | 1483 |
Bisabolene | 23.40 | 1.58 | 1515 |
9-Acetoxynonaldehyde | 24.26 | 0.73 | 1544 |
Carotol | 25.73 | 3.73 | 1594 |
Cedrol | 25.90 | 1.56 | 1600 |
2,14-Pentadecadienal | 31.45 | 0.92 | 1804 |
Linoleic acid | 32.12 | 0.50 | 1830 |
Oleic acid | 34.53 | 1.04 | 1926 |
6,10,14-Trimethyl-2-pentadecanone | 35.98 | 3.42 | 1986 |
Chemical compound | a Retention time | Percentage | b Retention Index |
---|---|---|---|
3-Hexen-2-one | 5.14 | 1.66 | 919 |
2-Ethyl-2-butenal | 6.42 | 0.32 | 972 |
2,4-Dimethylpentanal | 7.34 | 0.36 | 908 |
Camphene | 8.31 | 1.38 | 1041 |
3-Hexene-2,5-dione | 8.55 | 1.03 | 1049 |
3-Methyl-2-cyclopenten-1-one | 8.67 | 4.29 | 1052 |
1,3- Benzenediol | 9.17 | 14.91 | 1069 |
o-Cymene | 10.87 | 19.23 | 1215 |
Terpinolene | 12.56 | 0.15 | 1175 |
Isocitronellol | 12.97 | 0.17 | 1187 |
2-Methyl-3-(1-methylethenyl)-,(1α,2α,3α)- cyclohexanol | 13.11 | 0.06 | 1191 |
2-Hydroxy-3-methyl-2-cyclopenten-1-one | 14.07 | 4.14 | 1320 |
1,2,4,5-Tetramethylbenzene | 14.97 | 0.25 | 1248 |
Limonen-10-ol | 16.32 | 9.04 | 1287 |
Fenchyl acetate | 17.00 | 3.85 | 1310 |
Cyclamen aldehyde | 21.78 | 1.38 | 1461 |
6,6,7-Trimethyl-3-octyne-2,5-dione | 21.87 | 1.97 | 1464 |
Linalol isovalerate | 21.99 | 2.48 | 1468 |
Ethyl linalool | 22.08 | 3.16 | 1471 |
Bisaboleno | 23.41 | 2.46 | 1515 |
Methylisovalerate | 23.49 | 1.65 | 1517 |
Apofarnesol | 23.60 | 4.69 | 1521 |
Kessane | 23.85 | 6.31 | 1530 |
Thymohydroquinone | 24.60 | 2.06 | 1555 |
Germacrene D-4-ol | 25.11 | 3.50 | 1575 |
Viridiflorol | 25.69 | 4.05 | 1592 |
Cedrol | 25.92 | 2.48 | 1600 |
Isoeugenol acetate | 26.29 | 2.96 | 1614 |
Chemical compound | a Retention time | Percentage | b Retention Index |
---|---|---|---|
3-Hexene-2,5-diol | 5.19 | 1.44 | 921 |
2,3-Dimethyl-2,3-butanediol (pinacol) | 5.77 | 3.76 | 945 |
3-Methyl-cyclohexanol | 6.12 | 1.32 | 960 |
2-Methyl-2-pentenal | 6.42 | 0.69 | 972 |
2,2-Dimethyl-3-propyl-oxyrane | 7.05 | 2.77 | 979 |
Heptadienol | 7.56 | 4.53 | 1016 |
4,4-Dimethylpent-2-enal | 8.31 | 1.92 | 1041 |
3-Hexen-2,5-dione | 8.55 | 0.73 | 1049 |
3-Methyl-2-cyclopenten-1-one | 8.67 | 7.70 | 1052 |
1,3-Benzenediol | 9.17 | 12.61 | 1069 |
α-Pinene oxide | 10.07 | 1.36 | 1099 |
Sorbic acid | 10.87 | 17.34 | 1123 |
γ-Terpinene | 11.74 | 0.99 | 1150 |
Fenchone | 12.73 | 0.43 | 1180 |
Citronellol epoxide | 13.38 | 0.62 | 1200 |
Fenchyl acetate | 14.10 | 5.04 | 1220 |
3,3,6-Trimethyl-1,5-heptadien-4-one | 15.27 | 0.43 | 1257 |
Estragole | 16.31 | 10.49 | 1288 |
Methyl chavicol | 16.99 | 2.07 | 1309 |
Carvone | 18.36 | 1.54 | 1451 |
2,4-Undecadienal | 18.67 | 1.14 | 1460 |
p-Anisaldehyde | 18.78 | 0.99 | 1463 |
Undecanal | 20.15 | 0.30 | 1408 |
3-Hydroxydodecanoic acid | 21.86 | 0.78 | 1464 |
Caryophyllene | 21.99 | 1.15 | 1466 |
Methyl isovalerate | 23.49 | 1.17 | 1517 |
Tridecanol | 25.10 | 2.31 | 1571 |
Germacrene D-4-ol | 25.25 | 1.17 | 1575 |
Globulol | 25.69 | 2.65 | 1590 |
Trans-β-elemenone | 25.91 | 4.31 | 1602 |
Β-Himachelene oxide | 26.29 | 2.69 | 1614 |
Cedrene-3-one | 27.17 | 1.15 | 1645 |
β-Eudesmol | 27.34 | 1.03 | 1651 |
Sedanenolide | 29.25 | 1.38 | 1720 |
2.2. Antimycobacterial Activity
M. tuberculosis MIC (µg/mL) | ||||
---|---|---|---|---|
Fraction/Chemical compound | H37 Rv | M-10 | M-15 | M-26 |
Fraction 7 | ||||
α-Thujone | >200 | ND | ND | ND |
Anethole | >200 | ND | ND | ND |
Eugenol | 100 | ND | ND | ND |
Oleic acid | 100 | 100 | 100 | 100 |
Linoleic Acid | 100 | 100 | 100 | 100 |
2-Hydroxy-1-methyl-1-cyclopenten-3-one | >200 | ND | ND | ND |
1,3-Benzenediol a | 200 | 200 | 100 | 100 |
Fraction 8 | ||||
Terpinolene | 200 | ND | ND | ND |
o-Cymene | 50–100 | ND | ND | ND |
3-Methyl-2-cyclopenten-1-one | >200 | ND | ND | ND |
Isocitronellol | >200 | ND | ND | ND |
Fraction 9 | ||||
Fenchylacetate | >200 | ND | ND | ND |
Carvone | >200 | ND | ND | ND |
p-Anisaldehyde | 100 | ND | ND | ND |
Fenchone | 200 | ND | ND | ND |
Methylchavicol | >200 | ND | ND | ND |
Estragole | 100–200 | ND | ND | ND |
Undecanal | 100 | 200 | 100 | 50 |
2,4-Undecadienal | 25 | 50 | 25 | 25 |
2,3-Dimethyl-2,3-butanediol | >200 | ND | ND | ND |
Ethambutol | 2.0 | 15 | 15 | 15 |
3. Experimental
3.1. Plant Material
3.2. Chemical and Reagents
3.3. Equipment Utilized
3.4. Extract Preparation and Isolation of 5-Hydroxyfuranocoumarin (1)
3.5. Microorganisms
3.6. Antimycobacterial Assay
4. Conclusions
Acknowledgments
Conflicts of Interest
References
- Global Tuberculosis Control. WHO Report 2011; World Health Organization: Geneva, Switzerland. Available online: http://www.who.int/tb/publications/global-report/2011/gtbr11_full (accessed on 6 June 2012).
- He, W.; Huang, B. A review of chemistry and bioactivities of medicinal spice: Foeniculum vulgare. J. Med. Plants Res. 2011, 5, 3595–3600. [Google Scholar]
- González-Ferrara, M. Plantas Medicinales del Noreste de México, 1st ed; Grupo Vitro: Monterrey N.L., Mexico, 1998; Volume 1, p. 123. [Google Scholar]
- Andrade-Cetto, A. Ethnobotanical study of the medicinal plants from Tlanchinol, Hidalgo, México. J. Ethnopharmacol. 2009, 122, 163–171. [Google Scholar]
- Shahat, A.; Ibrahim, A.; Hendawy, S.; Omer, E.; Hammouda, F.; Abdel-Rahman, F.; Saleh, M. Chemical composition, antimicrobial and antioxidant activities of essential oils from organically cultivated fennel cultivars. Molecules 2011, 16, 1366–1377. [Google Scholar]
- Ghanem, M.T.M.; Radwan, H.M.A.; Mahdy, E.M.; Elkholy, Y.M.; Hassanein, H.D.; Shahat, A.A. Phenolic compounds from Foeniculum vulgare (Subsp. Piperitum) (Apiaceae) herb and evaluation of hepatoprotective antioxidant activity. Pharmacogn. Res. 2012, 4, 104–108. [Google Scholar] [CrossRef]
- Ozbek, H.; Ugras, S.; Dulger, H.; Bayram, I.; Tuncer, I.; Ozturk, G.; Öztürk, A. Hepatoprotective effect of F. vulgare essential oil. Fitoterapia 2003, 74, 317–319. [Google Scholar]
- Albert-Puleo, M. Fennel and anise as estrogenic agents. J. Ethnopharmacol. 1980, 2, 337–344. [Google Scholar] [CrossRef]
- Chainy, G. B.; Manna, S. K.; Chaturvedi, M. M.; Aggarwal, B. B. Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK, and apoptosis. Oncogene 2000, 19, 2943–2950. [Google Scholar]
- Zellagui, A.; Gherraf, N.; Elkhateeb, A.; Hegazy, M.-E.F.; Mohamed, T.A.; Touil, A.; Shahat, A.A.; Rhouati, S. Chemical constituents from Algerian Foeniculum vulgare aerial parts and evaluation of antimicrobial activity. J. Chil. Chem. Soc. 2011, 56, 759–763. [Google Scholar] [CrossRef]
- Miguel, M.G.; Cruz, C.; Faleiro, L.; Simoes, M.T.F.; Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G. Foeniculum vulgare essential oils: Chemical composition, antioxidant and antimicrobial activities. Nat. Prod. Commun. 2010, 5, 319–328. [Google Scholar]
- Cetin, B.; Ozer, H.; Cakir, A.; Polat, T.; Dursun, A.; Mete, E.; Oztürk, E.; Ekinci, M. Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms. J. Med. Food 2010, 13, 196–204. [Google Scholar]
- Araque, M.; Rojas, L.B.; Usubillaga, A. Antibacterial activity of essential oil of Foeniculum vulgare miller against multiresistant gram-negative bacilli from nosocomial infections. Science 2007, 15, 366–370. [Google Scholar]
- Kwon, Y.S.; Choi, W.G.; Kim, W.J.; Kim, W.K.; Kim, M.J.; Kang, W.H.; Kim, C.M. Antimicrobial constituents of Foeniculum vulgare. Arch. Pharm. Res. 2002, 25, 154–157. [Google Scholar] [CrossRef]
- Camacho-Corona, M.R.; Ramírez-Cabrera, M.A.; Santiago, O.G.; Garza-González, E.; Palacios de, P.; Luna-Herrera, J. Activity against drug resistant-tuberculosis strains of plants used in mexican traditional medicine to treat tuberculosis and other respiratory diseases. Phytother. Res. 2008, 22, 82–85. [Google Scholar] [CrossRef]
- Nassar, M.I.Aboutabl, E-S.A.; Makled, Y.A.; El-Khrisy, E-D.A.; Osman, A.F. Secondary metabolites and pharmacology of Foeniculum vulgare Mill. Subsp. Piperitum. Rev. Lat. Quim. 2010, 38, 103–112. [Google Scholar]
- Abdel-Fattah, M.E.; Taha, K.E.; Abdel Aziz, M.H.; Missalem, A.A.; El-Khrisy, E.A.M. Chemical constituents of Citrus Limonia and Foeniculum vulgare. Indian J. Heterocycl. Chem. 2003, 13, 45–48. [Google Scholar]
- Figueroa, M.; Rivero-Cruz, I.; Rivero-Cruz, B.; Byeb, R.; Navarrete, A.; Mata, R. Constituents, biological activities and quality control parameters of the crude extract and essential oil from Arracacia tolucensis var. Multifida. J. Ethnopharmacol. 2007, 113, 125–131. [Google Scholar] [CrossRef]
- Adams, R.P. Identification of Essential Oils Components by Gas Chromatography/Mass Spectrometry, 4th ed; Allured Business Media: Carol Stream, IL, USA, 2007; pp. 1–804. [Google Scholar]
- Conforti, F.; Statti, G.; Uzonov, D.; Menichini, F. Comparative chemical composition and antioxidant activities of wild and cultivated Laurus nobilis L. leaves and Foeniculum vulgare subsp. piperitum (Ucria) Coutinho seeds. Biol. Pharm. Bull. 2006, 29, 2056–2064. [Google Scholar] [CrossRef]
- Kubo, I.; Fujita, K.; Kubo, A.; Nihei, K.; Ogura, T. Antibacterial activity of coriander volatile compounds against Salmonella choleraesuis. J. Agric. Food Chem. 2004, 52, 3329–3332. [Google Scholar]
- Bisignano, G.; Lagana, M.; Trombetta, D.; Arena, S.; Nostro, A.; Uccella, N.; Mazzanti, G.; Saija, A. In vitro antibacterial activity of some aliphatic aldehydes from Olea europea L. FEMS Microbiol. Lett. 2001, 198, 9–13. [Google Scholar]
- Kazumori, M. Bactericidal action of oleic acid for tubercle bacilli: II. Morphological Response. J. Bacteriol. 1957, 73, 345–352. [Google Scholar]
- Kabara, R. Antimicrobial lipids natural and synthetic. Fatty acids and monoglycerides. Lipids 1977, 12, 9–12. [Google Scholar]
- Seidel, V.; Taylor, P. In vitro activity of extracts and constituents of Pelagonium against rapidly growing mycobacteria. Int. J. Antimicrob. Agents 2004, 23, 613–619. [Google Scholar] [CrossRef]
- Zheng, C.J.; Yoo, J.S.; Lee, T.G.; Cho, H.Y.; Kim, Y.H.; Kim, W.G. Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Lett. 2005, 579, 5157–5162. [Google Scholar]
- Karakousis, P.C.; Bishai, W.R.; Dorman, S.E. Mycobacterium tuberculosis cell envelope lipids and the host immune response. Rev. Cell Microbiol. 2004, 6, 105–116. [Google Scholar] [CrossRef]
- Chang, C.P.; Chang, H.S.; Peng, C.F.; Lee, S.J.; Chen, I. S. Antitubercular resorcinol analogs and benzenoid C-glucoside from the roots of Ardisia cornudentata. Planta Med. 2011, 77, 60–65. [Google Scholar] [CrossRef]
- Okunade, A.; Elvin-Lewis, M.; Lewis, W.H. Natural antimycobacterial metabolites: Current status. Phytochemistry 2004, 65, 1017–1032. [Google Scholar]
- Copp, B.R. Antimycobacterial natural compounds. Nat. Prod. Rep. 2003, 20, 535–557. [Google Scholar] [CrossRef]
- Sample Availability: Not available.
© 2012 by the authors; licensee MDPI, Basel, Switzerland. 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/).
Share and Cite
Esquivel-Ferriño, P.C.; Favela-Hernández, J.M.J.; Garza-González, E.; Waksman, N.; Ríos, M.Y.; Camacho-Corona, M.d.R. Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico. Molecules 2012, 17, 8471-8482. https://doi.org/10.3390/molecules17078471
Esquivel-Ferriño PC, Favela-Hernández JMJ, Garza-González E, Waksman N, Ríos MY, Camacho-Corona MdR. Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico. Molecules. 2012; 17(7):8471-8482. https://doi.org/10.3390/molecules17078471
Chicago/Turabian StyleEsquivel-Ferriño, Patricia C., Juan Manuel J. Favela-Hernández, Elvira Garza-González, Noemí Waksman, María Yolanda Ríos, and María del Rayo Camacho-Corona. 2012. "Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico" Molecules 17, no. 7: 8471-8482. https://doi.org/10.3390/molecules17078471