Chemical composition and biological activity of the essential oil from Thymus lanceolatus
-
Abdelmounaim Khadir
Abstract
Thymus lanceolatus is a rare species, which grows wild in Algeria and Tunis. It is used traditionally as a drink and to flavor and preserve meat and poultry. The composition of the essential oil was determined by GLC/FID and GLC/MS. Forty-nine components were identified and quantified, accounting for 96.75% of the total detected components in the oil. The oxygenated monoterpenes (74.85%) constitute the major class of volatile secondary metabolites in the oil. Thymol was the most abundant constituent (69.61%) followed by γ-terpinene (8.38%). The antioxidant activity was evaluated using both diphenylpicrylhydrazyl (DPPH˙) reduction and 2-deoxyribose (2-DR) degradation prevention methods. The oil showed a very potent antioxidant activity with IC50 values of 0.20 ± 0.07 and 4.96 ± 0.39 μg/mL for the DPPH˙ and 2-DR methods, respectively. The antimicrobial activity of the oil was assessed using the agar diffusion method, and the in vitro cytotoxicity on five different cancer cells was examined using the MTT assay. The oil revealed promising inhibitory activity against Gram positive bacteria, especially Bacillus subtilis and Streptococcus pyogenes with an MIC value of 62.5 μg/mL. Additionally, the highest cytotoxic activity was observed against the HL-60 cells with an IC50 of 113.5 μg/mL. These results validate some of their traditional uses in food preservation.
References
1. Wink M. Plant secondary metabolism: diversity, function and its evolution. Nat Prod Commun 2008;3:1205–16.10.1177/1934578X0800300801Suche in Google Scholar
2. Başer KH, Buchbauer G. Handbook of essential oils: science, technology, and applications. Boca Raton: CRC Press/Taylor & Francis, 2010.10.1201/9781420063165Suche in Google Scholar
3. Kadereit JW. Flowering plants, dicotyledons: lamiales (except acanthaceae including Avicenniaceae), the families and genera of vascular plants. New York: Springer-Verlag, 2004.10.1007/978-3-642-18617-2Suche in Google Scholar
4. Mabberley DJ. Mabberley’s plant-book: a portable dictionary of plants, their classification and uses, 3rd ed. Cambridge, UK; New York: Cambridge University Press, 2008.Suche in Google Scholar
5. Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 2003;64:3–19.10.1016/S0031-9422(03)00300-5Suche in Google Scholar
6. Stahl-Biskup E, Sáez F. Thyme: the genus Thymus, medicinal and aromatic plants—industrial profiles. London, New York: Taylor and Francis, 2002.10.4324/9780203216859Suche in Google Scholar
7. Hazzit M, Baaliouamer A, Veríssimo AR, Faleiro ML, Miguel MG. Chemical composition and biological activities of Algerian Thymus Oils. Food Chem 2009;116:714–21.10.1016/j.foodchem.2009.03.018Suche in Google Scholar
8. Bekhechi C, Bekkara FA, Abdelouahid DE, Tomi F, Casanova J. Composition and antibacterial activity of the essential oil of Thymus fontanesii Boiss. et Reut. from Algeria. J Essent Oil Res 2007;19:594–6.10.1080/10412905.2007.9699339Suche in Google Scholar
9. Dob T, Dahmane D, Benabdelkader T, Chelghoum C. Studies on the essential oil composition and antimicrobial activity of Thymus algeriensis Boiss. et Reut. Int J Aromather 2006;16:95–100.10.1016/j.ijat.2006.04.003Suche in Google Scholar
10. Hazzit M, Baaliouamer A, Faleiro ML, Miguel MG. Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities. J Agric Food Chem 2006;54:6314–21.10.1021/jf0606104Suche in Google Scholar
11. Bousmaha-Marroki L, Atik-Bekkara F, Tomi F, Casanova J. Chemical composition and antibacterial activity of the essential oil of Thymus ciliatus (Desf.) Benth. ssp. eu-ciliatus maire from Algeria. J Essent Oil Res 2007;19:490–3.10.1080/10412905.2007.9699960Suche in Google Scholar
12. Benbelaïd F, Khadir A, Abdoune MA, Bendahou M. Phytochemical screening and in vitro antimicrobial activity of Thymus lanceolatus Desf. from Algeria. Asian Pac J Trop Dis 2013;3:454–9.10.1016/S2222-1808(13)60100-0Suche in Google Scholar
13. Quézel P, Santa S, Schotter O. Nouvelle flore de l’Algerie et des regions desertiques meridionales. Paris: Centre National de la Recherche Scientifique, 1962.Suche in Google Scholar
14. Adams RP. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy, 4th ed. Carol Stream, Illinois: Allured Pub Corp, 2007.Suche in Google Scholar
15. El-Ahmady SH, Ashour ML, Wink M. Chemical composition and anti-inflammatory activity of the essential oils of Psidium guajava fruits and leaves. J Essent Oil Res 2013;25:475–81.10.1080/10412905.2013.796498Suche in Google Scholar
16. Youssef FS, Hamoud R, Ashour ML, Singab AN, Wink M. Volatile oils from the aerial parts of Eremophila maculata and their antimicrobial activity. Chem Biodivers 2014;11:831–41.10.1002/cbdv.201300366Suche in Google Scholar
17. Ayoub IM, Youssef FS, El-Shazly M, Ashour ML, Singab AN, Wink M. Volatile constituents of Dietes bicolor (Iridaceae) and their antimicrobial activity. Z Naturforsch C 2015;70:217–25.10.1515/znc-2015-0164Suche in Google Scholar
18. Brandwilliams W, Cuvelier ME, Berset C. Use of a free-radical method to evaluate antioxidant activity. LWT-Food Sci Technol 1995;28:25–30.10.1016/S0023-6438(95)80008-5Suche in Google Scholar
19. Halliwell B, Gutteridge JM, Aruoma OI. The deoxyribose method: a simple “Test-Tube” assay for determination of rate constants for reactions of hydroxyl radicals. Anal Biochem 1987;165:215–9.10.1016/0003-2697(87)90222-3Suche in Google Scholar
20. Clinical and Laboratory Standards Institute. Performance standards for antimicrobial disk susceptibility tests: approved standards, M7–A7, 2006.Suche in Google Scholar
21. Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: approved standard, M27–A2, 2012.Suche in Google Scholar
22. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.10.1016/0022-1759(83)90303-4Suche in Google Scholar
23. Ghannadi A, Sajjadi SE, Kabouche A, Kabouche Z. Thymus fontanesii boiss. & reut.—a potential source of thymol-rich essential oil in North Africa. Z Naturforsch C 2004;59:187–9.10.1515/znc-2004-3-410Suche in Google Scholar PubMed
24. Nouasri A, Dob T, Toumi M, Dahmane D, Krimat S, Lamari L, et al. Chemical composition and antimicrobial activity of the essential oil of Thymus lanceolatus Desf., an endemic thyme from Algeria. J Essent Oil Bear Plants 2015;18:1246–52.10.1080/0972060X.2014.981591Suche in Google Scholar
25. Houmani Z, Azzoudj S, Naxakis G, Skoula M. The essential oil composition of Algerian Zaâtar: Origanum spp. and Thymus spp. J Herbs Spices Med Plants 2002;9:275–80.10.1300/J044v09n04_03Suche in Google Scholar
26. Giordani R, Hadef Y, Kaloustian J. Compositions and antifungal activities of essential oils of some algerian aromatic plants. Fitoterapia 2008;79:199–203.10.1016/j.fitote.2007.11.004Suche in Google Scholar PubMed
27. Hadef Y, Kaloustian J, Chefrour A, Mikail C, Abou L, Giodani R, et al. Chemical composition and variability of the essential oil of Thymus numidicus Poir. from Algeria. Acta Bot Gall 2007;154:265–74.10.1080/12538078.2007.10516056Suche in Google Scholar
28. El-Readi MZ, Eid HH, Ashour ML, Eid SY, Labib RM, Sporer F, et al. Variations of the chemical composition and bioactivity of essential oils from leaves and stems of Liquidambar styraciflua (Altingiaceae). J Pharm Pharmacol 2013;65:1653–63.10.1111/jphp.12142Suche in Google Scholar PubMed
29. Hamdan D, Ashour ML, Mulyaningsih S, El-Shazly A, Wink M. Chemical composition of the essential oils of variegated pink-fleshed lemon (Citrus x limon L. Burm. f.) and their anti-inflammatory and antimicrobial activities. Z Naturforsch C 2013;68:275–84.10.1515/znc-2013-7-804Suche in Google Scholar
30. Tsai ML, Lin CC, Lin WC, Yang CH. Antimicrobial, antioxidant, and anti-inflammatory activities of essential oils from five selected herbs. Biosci Biotechnol Biochem 2011;75:1977–83.10.1271/bbb.110377Suche in Google Scholar PubMed
31. Dawidowicz AL, Olszowy M. Does antioxidant properties of the main component of essential oil reflect its antioxidant properties? the comparison of antioxidant properties of essential oils and their main components. Nat Prod Res 2014;28:1952–63.10.1080/14786419.2014.918121Suche in Google Scholar PubMed
32. Başer SH. Biological and pharmacological activities of carvacrol and carvacrol bearing essential oils. Curr Pharm Des 2008;14:3106–19.10.2174/138161208786404227Suche in Google Scholar PubMed
33. Quiroga PR, Asensio CM, Nepote V. Antioxidant effects of the monoterpenes carvacrol, thymol and sabinene hydrate on chemical and sensory stability of roasted sunflower seeds. J Sci Food Agric 2015;95:471–9.10.1002/jsfa.6744Suche in Google Scholar PubMed
34. Kim YS, Hwang JW, Kang SH, Kim EH, Jeon YJ, Jeong JH, et al. Thymol from Thymus quinquecostatus Celak. Protects against tert-butyl hydroperoxide-induced oxidative stress in Chang cells. J Nat Med 2014;68:154–62.10.1007/s11418-013-0786-8Suche in Google Scholar PubMed
35. Kabouche Z, Boutaghane N, Laggoune S, Kabouche A, Ait-Kaki Z, Benlabed K. Comparative antibacterial activity of five lamiaceae essential oils from Algeria. Int J Aromather 2005;15:129–33.10.1016/j.ijat.2005.03.006Suche in Google Scholar
36. Giweli AA, Džamić AM, Soković MD, Ristić MS, Marin PD. Chemical composition, antioxidant and antimicrobial activities of essential oil of Thymus algeriensis wild-growing in Libya. Cent Eur J Biol 2013;8:504–11.10.2478/s11535-013-0150-0Suche in Google Scholar
37. Hamoud R, Zimmermann S, Reichling J, Wink M. Synergistic interactions in two-drug and three-drug combinations (Thymol, EDTA and Vancomycin) against multi drug resistant bacteria including E. coli. Phytomedicine 2014;21:443–7.10.1016/j.phymed.2013.10.016Suche in Google Scholar PubMed
38. Wink M, Ashour ML, El-Readi MZ. Secondary metabolites from plants inhibiting ABC transporters and reversing resistance of cancer cells and microbes to cytotoxic and antimicrobial agents. Front Microbiol 2012;3:130–45.10.3389/fmicb.2012.00130Suche in Google Scholar PubMed PubMed Central
39. Sertel S, Eichhorn T, Plinkert PK, Efferth T. Cytotoxicity of Thymus vulgaris essential oil towards human oral cavity squamous cell carcinoma. Anticancer Res 2011;31:81–7.Suche in Google Scholar
40. Berrington D, Lall N. Anticancer activity of certain herbs and spices on the cervical epithelial carcinoma (HeLa) cell line. Evid Based Complement Alternat Med 2012;2012:564927, 11 pages.10.1155/2012/564927Suche in Google Scholar PubMed PubMed Central
41. Gordo J, Maximo P, Cabrita E, Lourenco A, Oliva A, Almeida J, et al. Thymus mastichina: chemical constituents and their anti-cancer activity. Nat Prod Commun 2012;7: 1491–4.10.1177/1934578X1200701120Suche in Google Scholar
42. Villa TG, Veiga-Crespo P. Antimicrobial compounds: current strategies and new alternatives. Heidelberg, New York: Springer-Verlag, 2014.10.1007/978-3-642-40444-3Suche in Google Scholar
43. Wink M. Evolutionary advantage and molecular modes of action of multi-component mixtures used in phytomedicine. Curr Drug Metab 2008;9:996–1009.10.2174/138920008786927794Suche in Google Scholar PubMed
44. Van Wyk B-E, Wink M. Medicinal plants of the world: an illustrated scientific guide to important medicinal plants and their uses, 1st ed. Portland, OR: Timber Press, 2004.Suche in Google Scholar
©2016 by De Gruyter
Artikel in diesem Heft
- Frontmatter
- Editorial
- ZNC opens a new chapter focussing on the emerging field of natural and natural-like compounds
- Research Articles
- Design, synthesis and evaluation of antitumor activity of new rotundic acid acylhydrazone derivatives
- Synthesis and in vitro anti-HIV-1 activity of a series of N-arylsulfonyl-3-propionylindoles
- Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera
- The effect of coniine on presynaptic nicotinic receptors
- Nematicidal effect of plumbagin on Caenorhabditis elegans: a model for testing a nematicidal drug
- Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil
- Phytochemical investigation of the bioactive extracts of the leaves of Ficus cyathistipula Warb.
- Chemical composition and biological activity of the essential oil from Thymus lanceolatus
- Ascidian bioresources: common and variant chemical compositions and exploitation strategy – examples of Halocynthia roretzi, Styela plicata, Ascidia sp. and Ciona intestinalis
- Structural and evolutionary relationships among RuBisCOs inferred from their large and small subunits
Artikel in diesem Heft
- Frontmatter
- Editorial
- ZNC opens a new chapter focussing on the emerging field of natural and natural-like compounds
- Research Articles
- Design, synthesis and evaluation of antitumor activity of new rotundic acid acylhydrazone derivatives
- Synthesis and in vitro anti-HIV-1 activity of a series of N-arylsulfonyl-3-propionylindoles
- Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera
- The effect of coniine on presynaptic nicotinic receptors
- Nematicidal effect of plumbagin on Caenorhabditis elegans: a model for testing a nematicidal drug
- Synthesis and biological evaluation of novel pyrimidines derived from 6-aryl-5-cyano-2-thiouracil
- Phytochemical investigation of the bioactive extracts of the leaves of Ficus cyathistipula Warb.
- Chemical composition and biological activity of the essential oil from Thymus lanceolatus
- Ascidian bioresources: common and variant chemical compositions and exploitation strategy – examples of Halocynthia roretzi, Styela plicata, Ascidia sp. and Ciona intestinalis
- Structural and evolutionary relationships among RuBisCOs inferred from their large and small subunits
