Comparative study of essential oils from fennel fruits and anise fruits: Chemical composition and in vitro antimicrobial activity
DOI:
https://doi.org/10.20450/mjcce.2021.2418Keywords:
fennel, anise, essential oil, chemical composition, antimicrobial activity, minimal inhibitory concentrationAbstract
Fennel (Foeniculum vulgare Mill.) and anise (Pimpinella anisum L.) are well-known aromatic plants with traditional use as medicinal and culinary spices and herbs. As part of a broader study, the aim of this investigation was to determine the chemical composition of fennel fruit essential oil (Foeniculi fructus aetheroleum, FFA) and anise fruit essential oil (Anisi aetheroleum, AA) and to assess their antimicrobial potential. Hydrodistilled FFA from fruits gathered in central Macedonia was subjected to physico-chemical analysis, as well as commercial AA, which was obtained from a local vendor. The chemical composition of both essential oils was determined using gas chromatography with mass spectrometric detection. The main component of both essential oils was trans-anethole. The antimicrobial action of both essential oils (FFA and AA) was tested against several bacterial cultures and compared to standard antimicrobial agents. The microorganisms used in this research were Gram-positive bacteria (Bacillus pumilus NCTC 8241, Staphylococcus aureus ATCC 6538,), Gram-negative bacteria (Escherichia coli ATCC 8739 and Pseudomonas aeruginosa ATCC 9027), and fungi (Saccharomyces cerevisiae ATCC 9763 and Candida albicans ATCC 10231). The microdilution test enabled determination of the minimal inhibitory concentration (MIC) of all samples used in the experiment against all of the test microorganisms. It was concluded that FFA and AA have moderate antibacterial activity and affect the growth of the Gram positive and the Gram negative bacteria. On the other, they are potent antifungal agents and affect the growth of S. cerevisiae ATCC 9763 and C. albicans ATCC 10231. AA was observed to have a slightly higher antimicrobial activity when compared to FFA. Based on the chemical composition of the samples, a connection was proposed between the trans-anethole content of the essential oils and their antimicrobial properties.
References
C. F. Carson, K. A. Hammer, Chemistry and bioactivity of essential oils. In: Lipids and Essential Oils as Antimi-crobial Agents, (H. Thormar, ed.), Wiley, 2011, pp 203–238.
DOI: 10.1002/9780470976623.ch9
K. A. Hammer, C. F. Carson, Antibacterial and Antifun-gal Activities of Essential Oils. In Lipids and Essential Oils as Antimicrobial Agents, (H. Thormar, ed.), Wiley, 2011, pp 255–306. DOI: 10.1002/9780470976623.ch11
J.-M. Mérillon, C. Rivière, Natural Antimicrobial Agents. Springer International Publishing AG: Cham, Switzer-land, 2018. DOI: 10.1007/978-3-319-67045-4
Wińska, W. Mączka, J. Łyczko, M. G. Grabarczyk, A. Czubaszek, A. Szumny, Essential oils as antimicrobial agents – myth or real alternative?, Molecules, 24(11), 2130 (2019). DOI: 10.3390/molecules24112130
M. M. Jodral, Illicium, Pimpinella and Foeniculum (Me-dicinal and Aromatic Plants – Industrial Profiles), CRC Press, Boca Raton, Fl, 2004.
E. A. Weiss, Umbelliferae. In: Spice Crops (E. A. Weiss, ed.), CAB International, Wallingford, UK, 2002, pp. 284–298. DOI: 10.1079/9780851996059.0000
Council of Europe EPC, and European Directorate for the Quality of Medicines & Healthcare. European Pharma-copoeia, 10th ed., Council of Europe, Strasbourg, 2019.
R. P. Adams, Identification of Essential Oil Components by Gas Chromatography/ Mass Spectrometry, 4th ed., Allured Publishing, Carol Stream, IL, USA, 2007.
K.-H. Kubeczka, K. Formacek, Essential Oils: Analysis by Capillary Gas Chromatography and Carbon 13-NMR Spectroscopy, 2nd ed., Wiley, 2002.
S. Azeez, Fennel. In: Chemistry of Spices (V. A. Par-thasaraty, B. Chempakam, T. J. Zachariah, eds.), CAB In-ternational, New Delhi, 2008, pp 227–241.
B. Muckensturm, D. Foechterlen, J.-P. Reduron, P. Dan-ton, M. Hildenbrand, Phytochemical and chemotaxonom-ic studies of Foeniculum vulgare, Biochem. Syst. Ecol., 25(4), 353–358 (1997).
DOI: 10.1016/S0305-1978(96)00106-8
R. Piccaglia, M. Marotti, Characterization of some Italian types of wild fennel (Foeniculum vulgare Mill.), J. Agric. Food. Chem., 49(1), 239–244 (2001).
DOI: 10.1021/jf000636+
O. Barazani, Y. Cohen, A. Fait, S. Diminshtein, N. Dudai, U. Ravid, E. Putievsky, J. Friedman, Chemotypic differentiation in indigenous populations of Foeniculum vulgare var. vulgare in Israel, Biochem. Syst. Ecol., 30(8), 721–731 (2002).
DOI: 10.1016/S0305-1978(02)00019-4
J. Barnes, L. A. Anderson, J. D. Phillipson, Herbal Med-icines. 3rd ed., Pharmaceutical Press, London, United Kingdom, 2007.
N. K. Leela, T. M. Vipin, Aniseed. In: Chemistry of Spic-es, (V. A. Parthasaraty, B. Chempakam, T. J. Zachariah, eds.), CAB International, New Delhi, 2008, pp 331–341.
N. Tabanca, B. Demirci, T. Ozek, N. Kirimer, K. H. C. Baser, E. Bedir, I. A. Khan, D. E. Wedge, Gas chromato-graphic-mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey, J. Chromatogr. A, 1117(2), 194–205 (2006). DOI:10.1016/j.chroma.2006.03.075
A. Velasco-Negueruela, M. J. Perez-Alonso, P. L. de Paz Perez, J. Pala-Paul, J. Sanz, Analysis by gas chromatog-raphy–mass spectrometry of the essential oils from the aerial parts of Pimpinella anagodendron Bolle and Pimpi-nella rupicola Svent., two endemic species to the Canary Islands, Spain, J. Chromatogr. A, 1095(1), 180–184 (2005). DOI: 10.1016/j.chroma.2005.09.074
M. Özgüven, 7 – Aniseed. In: Handbook of Herbs and Spices, 2nd ed.: (K. V. Peter, ed.), Woodhead Publishing, Sawston, Cambrigde, UK, 2012, pp 138–150.
C. K. George, 24 – Star anise. In: Handbook of Herbs and Spices, 2nd ed. (K. V. Peter, ed.), Woodhead Publish-ing, Sawston, Cambrigde, UK, 2012, pp 487–503.
B. Khameneh, M. Iranshahy, V. Soheili, B. S. Fazly Bazzaz, Review on plant antimicrobials: a mechanistic viewpoint, Antimicrob. Resist. Infect. Control, 8(1), 118 (2019). DOI: 10.1186/s13756-019-0559-6
Y.-S. Ku, C. A. Contador, M.-S. Ng, J. Yu, G. Chung, H.-M. Lam, The effects of domestication on secondary metabolite composition in legumes, Front. Genet., 11(2020, Sep. 18), 581357 (2020).
DOI: 10.3389/fgene.2020.581357
I. H. N. Bassolé, J. H. Rodolfo, Essential oils in combi-nation and their antimicrobial properties, Molecules, 17(4), 3989–4006 (2012).
DOI: 10.3390/molecules17043989
A. Sartoratto, A. L. M. Machado, C. Delarmelina, G. M. Figueira, M. C. T. Duarte, V. L. G. Rehder, Composition and antimicrobial activity of essential oils from aromatic plants used in Brazil, Braz. J. Microbiol., 35(4), 275–280 (2004). DOI: 10.1590/S1517-83822004000300001
S. B. Badgujar, V. V. Patel, A. H. Bandivdekar, Foenicu-lum vulgare Mill: a review of its botany, phytochemistry, pharmacology, contemporary application, and toxicology, Biomed. Res. Int., 2014, 842674 (2014).
DOI: 10.1155/2014/842674
W. Sun, M. H. Shahrajabian, Q. Cheng, Anise (Pimpinel-la anisum L.), a dominant spice and traditional medicinal herb for both food and medicinal purposes, Cogent Biol-ogy, 5(1), 1673688 (2019).
DOI: 10.1080/23312025.2019.1673688
N. Khalil, M. Ashour, S. Fikry, A. N. Singab, O. Salama, Chemical composition and antimicrobial activity of the es-sential oils of selected Apiaceous fruits, Future J. Pharm. Sci,, 4(1), 88–92 (2018).
DOI: 10.1016/j.fjps.2017.10.004
A. Shahat, A. Ibrahim, S. Hendawy, E. Omer, F. Ham-mouda, F. Abdel-Rahman, M. Saleh, Chemical composi-tion, antimicrobial and antioxidant activities of essential oils from organically cultivated fennel cultivars, Mole-cules, 16(2), 1366–1377 (2011).
DOI: 10.3390/molecules16021366
W.-R. Diao, Q.-P. Hu, H. Zhang, J.-G. Xu, Chemical composition, antibacterial activity and mechanism of ac-tion of essential oil from seeds of fennel (Foeniculum vulgare Mill.), Food Control, 35(1), 109–116 (2014). DOI: 10.1016/j.foodcont.2013.06.056
A. S. Mota, M. R. Martins, S. Arantes, V. R. Lopes, E. Bettencourt, S. Pombal, A. C. Gomes, L. A. Silva, Anti-microbial activity and chemical composition of the essen-tial oils of Portuguese Foeniculum vulgare fruits, Nat. Prod. Commun., 10(4), 673–676 (2015).
DOI: 10.1177/1934578x1501000437
H. Mahmoudi, M. R. Arabestani, M. Molavi, K. Kara-molah, N. Fahim, The study effects antimicrobial of Foe-niculum vulgare Mill. and Achilles Mill. folium Plant on Bacterial Pathogens Causing Urinary Tract Infections and nosocomial infection, Int. J. Pharmacognosy and Phyto-chem. Res. 8(9), 1549–1554 (2016).
S. A. AbduRahim, B. Elamin, A. A. A. Bashir, A. Al-magboul, In vitro test of antimicrobial activity of Foenicu-lum vulgare Mill. (fennel) essential oil, J. Multidiscip. Eng. Sci. Stud. (JMESS), 3(4), 1609–1614 (2017).
I. Kosalec, S. Pepeljnjak, D. Kustrak, Antifungal activity of fluid extract and essential oil from anise fruits (Pimpi-nella anisum L., Apiaceae), Acta Pharmaceutica (Zagreb, Croatia), 55(4), 377–385 (2006).
M. Özcan, J.-C. Chalchat, Chemical composition and antifungal effect of anise (Pimpinella anisum L.) fruit oil at ripening stage, Annals of Microbiology, 56(4), 353–358 (2006). DOI: 10.1007/bf03175031
A. Sosa, N. Girardi, L. Rosso, F. Salusso, M. Etchever-ry, M. Passone, In vitro compatibility of Pimpinella ani-sum and Origanum vulgare essential oils with nematoph-agous fungi and their effects against Nacobbus aberrans, J. Pest Sci., 93, 1381–1395 (2020).
DOI: 10.1007/s10340-020-01252-4
Y. Huang, J. Zhao, L. Zhou, J. Wang, Y. Gong, X. Chen, Z. Guo, Q. Wang, W. Jiang, Antifungal activity of the es-sential oil of Illicium verum fruit and its main component trans-anethole, Molecules, 15(11), 7558–7569 (2010). DOI: 10.3390/molecules15117558
C. Yu, J. Zhang, T. Wang, Star anise essential oil: chemi-cal compounds, antifungal and antioxidant activities: a re-view, J. Essent. Oil Res., 33(1), 1–22 (2021).
DOI: 10.1080/10412905.2020.1813213
P. Kwiatkowski, A. Pruss, H. Masiuk, M. Mnichowska-Polanowska, M. Kaczmarek, S. Giedrys-Kalemba, B. Do-legowska, H. Zielinska-Blizniewska, J. Olszewski, M. Sienkiewicz, The effect of fennel essential oil and trans-anethole on antibacterial activity of mupirocin against Staphylococcus aureus isolated from asymptomatic carri-ers, Advances in Dermatology and Allergology (Postepy Dermatologii i Alergologii), 36, 308–314 (2019). DOI: 10.5114/ada.2018.76425
A. J. Drummond, R. Waigh, in: Recent Research Devel-opments in Phytochemistry (S. Pandalai, ed.), Research Signpost, Trivandrum, India, 2000, Vol. 4, pp. 143–152.
M. Najdoska-Bogdanov, J. B. Bogdanov, M. Stefova, Simultaneous determination of essential oil components and fatty acids in fennel using gas chromatography with a polar capillary column, Nat. Prod. Commun., 10(9), 1619–1626 (2015).
DOI: 10.1177/1934578x1501000933
M. Najdoska-Bogdanov, J. B. Bogdanov, M. Stefova, Changes in volatile compounds during aging of sweet fennel fruits – comparison of hydrodistillation and static headspace sampling methods, Nat. Prod. Commun., 11(3), 423–429 (2016).
DOI: 10.1177/1934578x1601100326
M. Najdoska-Bogdanov, PhD Thesis, Ss. Cyril and Methodius University, Skopje, 2016.
I. Telci, I. Demirtas, A. Sahin, Variation in plant proper-ties and essential oil composition of sweet fennel (Foe-niculum vulgare Mill.) fruits during stages of maturity, Industrial Crops and Products, 30(1), 126–130 (2009). DOI: 10.1016/j.indcrop.2009.02.010
B. Cosge, B. Gürbüz, H. Kendir, A. Ipek, Composition of essential oil in sweet fennel (Foeniculum vulgare Mill. var. dulce) lines originated from Turkey, Asian J. Chem., 20(2), 1137–1142 (2008).
S. T. Katsiotis, Study of different parameters influencing the composition of hydrodistilled sweet fennel oil, Fla-vour Fragrance J., 4(4), 221–224 (1989).
DOI: 10.1002/ffj.2730040413
E. Miraldi, Comparison of the essential oils from ten Foeniculum vulgare Miller samples of fruits of different origin, Flavour Fragrance J., 14(6), 379–382 (1999).
DOI: 10.1002/(SICI)1099-1026(199911/12)14:6<379::AID -FFJ833>3.0.CO;2-8
J. Bernáth, E. Németh, A. Kattaa, É. Héthelyi, Morpho-logical and chemical evaluation of fennel (Foeniculum vulgare Mill.) populations of different origin, J. Essent. Oil Res., 8(3), 247–253 (1996).
DOI: 10.1080/10412905.1996.9700610
B. M. Lawrence, Progress in essential oils, Perfume. Flavor., 19, 31–32 (1994).
A. Raal, A. Orav, E. Arak, Essential oil composition of Foeniculum vulgare Mill. fruits from pharmacies in dif-ferent countries, Nat. Prod. Res., 26(13), 1173–1178 (2012). DOI: 10.1080/14786419.2010.535154
M. Acimovic, V. Tesevic, M. Todosijevic, J. Djisailov, S. Oljaca, Compositional characteristics of the essential oil of Pimpinella anisum and Foeniculum vulgare grown in Serbia, Botanica Serbica, 39(1), 9–14 (2015).
N. Arslan, A. Bayrak, A. Akgul, The yield and compo-nents of essential oil in fennels of different origin (Foe-niculum vulgare Mill.) grown in Ankara conditions, Herba Hungarica, 28(3), 27–31 (1989).
B. Coşge, M. Kiralan, B. Gürbüz, Characteristics of fatty acids and essential oil from sweet fennel (Foeniculum vulgare Mill. var. dulce) and bitter fennel fruits (F. vul-gare Mill. var. vulgare) growing in Turkey, Nat. Prod. Res., 22(12), 1011–1016 (2008).
DOI: 10.1080/14786410801980675
A. Orav, A. Raal, E. Arak, Essential oil composition of Pimpinella anisum L. fruits from various European coun-tries, Nat. Prod. Res., 22(3), 227–232 (2008).
DOI: 10.1080/14786410701424667
P. M. Santos, A. C. Figueiredo, M. M. Oliveira, J. G. Barroso, L. G. Pedro, S. G. Deans, A. K. M. Younus, J. J. C. Scheffer, Essential oils from hairy root cultures and from fruits and roots of Pimpinella anisum, Phytochemis-try, 48(3), 455–460 (1998).
DOI: 10.1016/S0031-9422(98)00022-3
G. Figueredo, M. M. Özcan, P. Chalard, M. M. Özcan, N. Uslu, F. Al Juhaimi, Chemical composition of essen-tial oil of anise (Pimpinella anisum), cumin (Cuminum cyminum), fennel (Foeniculum vulgare) and parsley (Pe-troselinum crispum Mill.) seeds, J. Agroaliment. Pro-cesses Technol., 26(1), 01–05 (2020).
International Organization for Standardization, ISO 3475:2020(E), Essential oil of aniseed (Pimpinella ani-sum L.), ISO, Vernier, Geneva, Switzerland, 2020.
A. M. Clark, T. M. Jurgens, C. D. Hufford, Antimicrobi-al activity of juglone, Phytother. Res., 4(1), 11–14 (1990). DOI: 10.1002/ptr.2650040104
M. Gulfraz, S. Mehmood, N. Minhas, N. Jabeen, R. Kausar, D. Jabeen, G. Arshad, Composition and antimi-crobial properties of essential oil of Foeniculum vulgare, Afr. J. Biotechnol., 7(24), 4364–4368 (2008).
DOI: 10.5897/AJB08.715
M. H. H. Roby, M. A. Sarhan, K. A.-H. Selim, K. I. Khalel, Antioxidant and antimicrobial activities of essen-tial oil and extracts of fennel (Foeniculum vulgare L.) and chamomile (Matricaria chamomilla L.), Ind. Crops. Prod., 44, 437–445 (2013).
DOI: 10.1016/j.indcrop.2012.10.012
S. H. Park, I. Seong, Antifungal effects of the extracts and essential oils from Foeniculum vulgare and Illicium verum against Candida albicans, Korean J. Med. Mycol., 15(4), 157–164 (2010).
I. Dadalioǧlu, G. A. Evrendilek, Chemical compositions and antibacterial effects of essential oils of Turkish orega-no (Origanum minutiflorum), bay laurel (Laurus nobilis), Spanish Lavender (Lavandula stoechas L.), and fennel (Foeniculum vulgare) on common foodborne pathogens, J. Agric. Food. Chem., 52(26), 8255–8260 (2004). DOI: 10.1021/jf049033e
F. A. Al-Bayati, Synergistic antibacterial activity between Thymus vulgaris and Pimpinella anisum essential oils and methanol extracts, J. Ethnopharmacol., 116(3), 403–406 (2008). DOI: 10.1016/j.jep.2007.12.003
A. Zellagui, N. Gherraf, A. Elkhateeb, M. E. Hegazy, T. Mohamed, T. Ahmed, A. Shahat, S. Rhouati, Chemical constituents from Algerian Foeniculum vulgare aerial parts and evaluation of antimicrobial activity, J. Chil. Chem. Soc., 56(3), 759–763 (2011).
DOI: 10.4067/s0717-97072011000300008
H. Baydar, O. Sağdiç, G. Özkan, T. Karadoğan, Antibac-terial activity and composition of essential oils from Ori-ganum, Thymbra and Satureja species with commercial importance in Turkey, Food Control, 15(3), 169–172 (2004). DOI: 10.1016/S0956-7135(03)00028-8
Downloads
Published
How to Cite
Issue
Section
License
The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material
- for any purpose, even commercially.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- NonCommercial — You may not use the material for commercial purposes.
