Abstract
Purpose
This study investigates for the first time the influence of seasonal variation on the chemical composition, antifungal and insecticidal potentials of essential oils extracted from Daucus reboudii growing in Tunisia.
Methods
Essential oils were extracted in summer (vegetative stage) and autumn (flowering-fruiting stage) by hydrodistillation, the corresponding volatiles were identified by gas chromatography coupled with mass spectrometry (GC/MS). The anti-insect potency of the essential oils from D. reboudii collected seasonally was evaluated towards two stored product insects, Tribolium confusum and Sitophilus zeamais. The antifungal effects of these oils were screened against Candida albicans and Candida glabrata yeasts and Trichophyton rubrum and Microsporum canis dermatophytes, fungi with medical interest.
Results
The essential oil highest yield was recorded from the sample collected in October. The phytochemical profiling of D. reboudii volatile oils indicated that monoterpene hydrocarbons (52.2–61.4)% represent the major class of the identified compounds, with -pinene (36.6–40.6)% as the major secondary metabolite through both seasons. Taking into consideration the second most represented class of compounds, a predominance of sesquiterpenes hydrocarbons (25.3%) was observed in summer, versus a predominance of phenyl derivatives (21.1%) in the flowering-fruiting stage. The essential oils showed promising effect in protecting stored grains from T. confusum attacks. The essential oils from D. reboudii showed interesting antifungal potential towards T. rubrum and M. canis. C.
Conclusion
These results may be gainful in choosing the optimal harvest time for the production of D. reboudii active agents, with high value in crops preservation and medication.
Graphic Abstract
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References
Ebadollahi, A., Mahboubi, M.: Insecticidal activity of the essential oil isolated from Azilia eryngioides (Pau) Hedge et lamond against two beetle pests. Chil. J. Agric. Res. 71, 406–411 (2011)
Khemais, A., Acheuk, F., Miladi, M., Omri, G.: Phytochemistry, Biochemical and insecticidal activities of ruta chalepensis essential oils on Tribolium confusum. Agric. For. 64, 31–45 (2018)
Liu, Z.L., Chu, S.S., Jiang, G.H.: Insecticidal Activity and Composition of Essential Oil of Ostericum sieboldii (Apiaceae) Against Sitophilus zeamais and Tribolium castaneum. Rec. Nat. Prod. 2, 74–81 (2011)
Sanglard, D.: Finding the needle in a haystack: Mapping antifungal drug resistance in fungal pathogen by genomic approaches. PLoS. Pathog. 15, e1007478 (2019)
Wang, D., Zhang, J., Jia, X., Xin, L., Zhai, H.: Antifungal Effects and Potential Mechanism of Essential Oils on Collelotrichum gloeosporioides In Vitro and In Vivo. Molecules 24, 3386 (2019). https://doi.org/10.3390/molecules24183386
El Mokni, R., Majdoub, S., Chaieb, I., Jlassi, I., Joshi, K.R., Hammami, S.: Chromatographic analysis, antimicrobial and insecticidal activities of the essential oil of Phlomis floccosa D Don. Biomed. Chromatogr. (2019). https://doi.org/10.1002/bmc.4603
Bona, E., Cantamessa, S., Pavan, M., Novello, G., Massa, N., Rocchetti, A., Berta, G., Gamalero, E.: Sensitivity of Candida albicans to essential oils : are they an alternative to antifungal agents? J. Appl. Microbiol. 121, 1530–1545 (2016)
Ibrahim, S.Y., El-salam, M.M.A.: Anti-dermatophyte efficacy and environmental safety of some essential oils commercial and in vitro extracted pure and combined against four keratinophilic pathogenic fungi. Environ. Health. Prev. Med. 20, 279–286 (2015)
Alsohaili, S.: Seasonal Variation in the Chemical Composition and Antimicrobial Activity of Essential Oil Extracted from Achillea fragrantissima Grown in Northern-Eastern Jordanian Desert. J. Essent. Oil-Bear. Plants 21, 139–145 (2018)
Liu, J., Shi, L., Han, J., Li, G., Lu, H., Hou, J., Zhou, X., Meng, F., Downie, S.R.: Identification of species in the angiosperm family Apiaceae using DNA barcodes. Mol. Ecol. Resour. 14, 1231–1238 (2014)
Majdoub, S., El Mokni, R., Muradalieviche, A.A., Piras, A., Porcedda, S., Hammami, S.: Effect of pressure variation on the efficiency of supercritical fluid extraction of wild carrot (Daucus carota subsp. maritimus) extracts. J. Chromatogr. B 1125, 121713 (2019). https://doi.org/10.1016/j.jchromb.2019.121713
Zaibet, W., Laouer, H., Amira, S., Flamini, G., Ramdani, M., Akkal, S.: Chemical composition and biological activities of Daucus aureus essential oils from eastern algeria. J. Chil. Chem. Soc. 60, 2986–2993 (2016). https://doi.org/10.4067/S0717-97072015000400017
Hammami, S., Elshamy, A.I., El Mokni, R., Snene, A., Iseki, K., Dhaouadi, H., Okamoto, Y., Suenaga, M., Noji, M., Umeyama, A., Asakawa, Y.: Chemical Constituents of the Aerial Parts of Daucus carota subsp. hispidus Growing in Tunisia. Nat. Prod. Commun. (2019). https://doi.org/10.1177/1934578X19863512
Snene, A., Sirignano, C., Rigano, D., Formisano, C., El Mokni, R., Ercolano, G., Dhaouadi, H., Ianaro, A., Hammami, S., Taglialatela-Scafati, O.: Antiproliferative metabolites from the Northern African endemic plant Daucus virgatus (Apiaceae). Phytochemistry 143, 194–198 (2017). https://doi.org/10.1016/j.phytochem.2017.08.010
Alla, F.M.A., Abdelshafeek, K.A., El-sollb, A.M., ELsayed, W.M.: Volatile oils lipid constitutes and the antimicrobial activity of Daucus syrticus growing in Libya. J. Arab. Soc. Med. Res. 8, 96–103 (2013). https://doi.org/10.4103/1687-4293.123793
Benyelles, B., Allali, H., El Amine Dib, M., Djabou, N., Paolini, J., Costa, J.: Chemical composition variability of essential oils of Daucus gracilis Steinh. from Algeria. Chem. Biodivers. 14, e1600490 (2017). https://doi.org/10.1002/cbdv.201600490
Pottier-Alapetite, G.: Flore de la Tunisie: Angiospermes-dicotylédones.1, Apétales-dialypétales, Impremerie officielle de la république Tunisienne, (1979).
APD (African Plant Database) Daucus reboudii Coss. ex Batt. (Apiaceae)-In: African Plant Database3 http://www.ville ge.ch/musinfo/bd/cjb/africa/details.php?langue=an&id=154630 (2020). Accessed 15 February 2020
Djarri, L., Medjroubi, K., Akkal, S., Elomri, A.: Composition of the essential oil of aerial parts of an endemic species of the Apiaceae of Algeria, Daucus reboudii Coss. Flavour Frag. J. 21, 647–649 (2006)
Adams, R.P.: Identification of essential oil components by gas chromatography/mass spectorscopy. Allured Pub. Corp, USA (2007)
Stein, S.E., Mikaia, A., White, E., Zaikin, V., Zhu, D., Milman, B., Babushok, V., Zenkevich, I., Linstrom, P., Mirokhin, Y., Tchekhovskoi, D., Mallard, W.G., Sparkman, O.D., Sparkman, J.A.: NIST Standard Reference Database 1A NIST/EPA/NIH Mass Spectral Library (NIST 08) and NIST Mass Spectral Search Program (Version 2.0f) for Use with Microsoft, (2008).
McDonald, L.L., Guy, R.H., Speirs, R.D.: Preliminary evaluation of new candidate materials as toxicants, repellents, and attractants against stored product insects. Marketing Research Report No. 882, Agriculture Research Service, USDA Washington, DC, 8, (1970).
Christophe, K.K., Tia, V.E., Cynthia Ochou, G.E., Kouakou, M., Norbert Bini, K.K., Dagnogo, M., Dick, A.E., Ochou, O.G.: Comparaison du potentiel insecticide des huiles essentielles de Ocimum gratissimum L. et de Ocimum canum Sims sur Pectinophora gossypiella Saunders (Lepidoptera : Gelechiidae), insecte ravageur du cotonnier en Côte d’Ivoire. Eur. Sci. J. 14, 286–301 (2018). https://doi.org/10.19044/esj.2018.v14n21p286
Risslegger, B., Lass-Flörl, C., Blum, G., Lackner, M.: Evaluation of a modified EUCAST fragmented-mycelium inoculum method for in vitro susceptibility testing of dermatophytes and the activity of novel antifungal agents. Antimicrob. Agents Chemother. 59, 3675–3682 (2015). https://doi.org/10.1128/AAC.04381-14
Matias, E.F.F., Alves, E.F., Silva, M.K.N., Carvalho, V.R.A., Figueredo, F.G., Ferreira, J.V.A., Coutinho, H.D.M., Silvaa, J.M.F.L., Ribeiro-Filhoa, J., Costa, J.G.M.: Seasonal variation, chemical composition and biological activity of the essential oil of Cordiaverbenacea DC (Boraginaceae) and the sabinene. Ind. Crops Prod. 87, 45–53 (2016). https://doi.org/10.1016/j.indcrop.2016.04.028
Bendiabdellah, A., El Amine Dib, M., Meliani, N., Muselli, A., Nassim, D., Boufeldja Tabti, B., Costa, J.: Antibacterial activity of Daucus crinitus essential oils along the vegetative life of the plant. J. Chem. 2013, 7 (2014). https://doi.org/10.1155/2013/149502
Flamini, G., Smaili, T., Zellagui, A., Gherraf, N., Cioni, P.L.: Effect of growth stage on essential-oil yield and composition of Daucus sahariensis. Chem. Biodivers. 10, 2014–2020 (2014)
Hussain, A.I., Anwar, F., Sherazi, S.T.H., Przybylski, R.: Chemical composition, antioxidant and antimicrobial activities of basil (Ocimum basilicum) essential oils depends on seasonal variations. Food chem. 108, 986–995 (2008). https://doi.org/10.1016/j.foodchem.2007.12.010
Hussain, A.I., Anwar, F., Nigam, P.S., Ashraf, M., Gilani, A.H.: Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species. J. Sci. Food Agric. 90, 1827–1836 (2010). https://doi.org/10.1002/jsfa.4021
Silva, P.T., Santos, H.S., Teixeira, A.M.R., Bandeira, P.N., Holanda, C.L., Vale, J.P.C., Pereira, E.J.P., Menezes, J.E.S.A., Rodrigues, T.H.S., Souza, E.B., Silva, H.C., Santiago, G.M.P.: Seasonal variation in the chemical composition and larvicidal activity against Aedes aegypti of essential oils from Vitex gardneriana Schauer. South African J. Bot. 124, 329–332 (2019). https://doi.org/10.1016/j.sajb.2019.04.036
Chizzola, R.: Composition of the essential oil from Daucus carota ssp. carota growing wild in Vienna. J. Essent. Oil Bear. Plants 2014, 37–41 (2013). https://doi.org/10.1080/0972060X.2010.10643785
Ben Chaaban, S., Hamdi, S.H., Mahjoubi, K., Ben Jemâa, J.M.: Composition and insecticidal activity of essential oil from Ruta graveolens, Mentha pulegium and Ocimum basilicum against Ectomyelois ceratoniae Zeller and Ephestia kuehniella Zeller (Lepidoptera : Pyralidae). J. Plant Dis. Prot. 126, 237–246 (2019). https://doi.org/10.1007/s41348-019-00218-8
Traboulsi, A.F., Taoubi, K., Samih El-Haj, S., Bessiere, J.M., Rammal, S.: Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera : Culicidae). Pest Manag. Sci. 495, 491–495 (2002)
Valente, J., Zuzarte, M., Resende, R., Gonçalves, M.J., Cavaleiro, C., Pereira, C.F., Cruzb, M.T., Salgueiro, L.: Daucus carota subsp. gummifer essential oil as a natural source of antifungal and anti-inflammatory drugs. Ind. Crops Prod. 65, 361–366 (2015). https://doi.org/10.1016/j.indcrop.2014.11.014
Bouaziz, M., Yangui, T., Sayadi, S., Dhouib, A.: Disinfectant properties of essential oils from Salvia officinalis L. cultivated in Tunisia. Food Chem. Toxicol. 47, 2755–2760 (2009). https://doi.org/10.1016/j.fct.2009.08.005
Valente, J., Resende, R., Zuzarte, M., Gonçalves, M.J., Lopes, M.C., Cavaleiro, C., Pereira, C., Salgueiro, L., Cruz, M.T.: Bioactivity and safety profile of Daucus carota subsp. maximus essential oil. Ind. Crops Prod. 77, 218–224 (2015). https://doi.org/10.1016/j.indcrop.2015.08.037
Aijaz, A., Amber, K., Luqman, A.K., Nikhat, M.: In vitro synergy of eugenol and methyleugenol with fluconazole against clinical Candida isolates. J. Med. Microbiol. 59, 1178–1184 (2010). https://doi.org/10.1099/jmm.0.020693-0
Hichri, F., Omri, A., Hossan, A.S.M., Flamini, G., Ben Jannet, H.: Chemical composition and biological evaluation of the Tunisian Achillea cretica L. essential oils. J. Essent. Oil Res. (2017). https://doi.org/10.1080/10412905.2017.1391720
Lamamra, M., Laouer, H., Adjaoud, A., Sahli, F., Amira, S., Akkal, S.: Daucus aristidis Coss. essential oil: Volatile constituents and antimicrobial activity in pre-flowering stage. Asian Pacific J. Trop. Dis. 6, 882–886 (2016). https://doi.org/10.1016/S2222-1808(16)61151-9
Silva, A.C.R.D., Lopes, P.M., Azevedo, M.M.B.D., Costa, D.C.M., Alviano, C.S., Alviano, D.S.: Biological Activities of α-Pinene and β-Pinene Enantiomers. Molecules 7, 6305–6316 (2012). https://doi.org/10.3390/molecules17066305
Kula, J., Izydorczyk, K., Czajkowska, A., Radoslaw, B.: Chemical composition of carrot umbel oils from Daucus carota L. ssp. sativus cultivated in Poland. Flavour Frag, J. 21, 667–669 (2006)
Flamini, G., Cioni, P., Maccioni, S., Baldini, R.: Composition of the essential oil of Daucus gingidium L. ssp. Gingidium. Food Chem. 103, 1237–1240 (2007)
Lamamra, M., Hocine Laouer, H., Amira, S., Orhan, I.E., Senol, F.S., Demirci, B., Akkal, S.: Chemical composition and cholinesterase inhibitory activity of different parts of Daucus aristidis Coss. Essential oils from two locations in Algeria. Rec. Nat. Prod. 11, 147–156 (2017)
Bendiabdellah, A., El Amine Dib, M., Djabou, N., Allali, H., Tabti, B., Muselli, A., Jean Costa, J.: Biological activities and volatile constituents of Daucus muricatus L. from Algeria. Chem. Cent. J. 6, 1–10 (2012)
Cosimi, E., Cioni, P.L., Molfetta, I.: Essential-oil composition of Daucus carota ssp. major (Pastinocello Carrot) and nine different commercial varieties of Daucus carota ssp. sativus Fruits. Chem. Biodivers. 11, 1022–1033 (2014)
Jawdat, D., Al-faoury, H., Odeh, A., Al-safadi, B.: Essential oils in seeds of Daucus spp.: Insights into the development of potential new cultivars. Ind. Crops Prod. 74, 867–874 (2015). https://doi.org/10.1016/j.indcrop.2015.04.050
Maxia, A., Marongiu, B., Piras, A., Porcedda, S., Tuveri, E., Gonçalves, M.J., Carlos, C.C., Salgueiro, L.: Chemical characterization and biological activity of essential oils from Daucus carota L. subsp. carota growing wild on the Mediterranean coast and on the Atlantic coast. Fitoterapia 80, 57–61 (2009). https://doi.org/10.1016/j.fitote.2008.09.008
Behidj-Benyounes, N., Benyounes, K., Dahmene, T., Chebouti, N., Gana, S.: Physicochemical Profile of Essential Oil of Daucus carota.. Int. J. Biol. Biom. Agri. Food Biot. Engi. 9, 200–203 (2015)
Stojanovic, Z., Ðor, N., Radulovic, N.: Volatiles of the Balkan endemic Daucus guttatus ssp. zahariadii and cultivated and wild-growing D .carota—A comparison study. Food chem. 125, 35–43 (2011). https://doi.org/10.1016/j.foodchem.2010.08.028
Staniszewska, M., Kula, J.: Composition of the essential oil from wild carrot composition of the essential oil from wild carrot umbels (Daucus carota L. ssp. carota) growing in Poland. J. Essent. Oil Res. 13, 439–441 (2011). https://doi.org/10.1080/10412905.2001.9699720
Verma, R.S., Padalia, R.C., Chauhan, A.: Chemical composition variability of essential oil during ontogenesis of Daucus carota L. subsp. sativus (Hoffm.) Arcang. Ind. Crops Prod. 52, 809–814 (2014). https://doi.org/10.1016/j.indcrop.2013.12.012
Acknowledgements
The authors wish to express their sincere thanks to Professor Hatem DHAOUADI, Director of the Research Unit “Applied Chemistry and Environment (UR13ES63)”, Faculty of Sciences of Monastir, University of Monastir, Tunisia, for the scientific support.
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S.H supervised the project. R.E.M provided the plant. S.H and S.M prepared the essential oils. S.M and S.H drafted the manuscript. R.C.B, H.B, Z.M, S.M and I.C performed the antifungal and insecticidal tests. A.P, D.F and S.P analyzed the chemical composition of the essential oils. All authors read and approved the final manuscript.
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Majdoub, S., Chaabane-Banaoues, R., Mokni, R.E. et al. Seasonal Variation in the Chemical Profile, Antifungal and Insecticidal Activities of Essential Oils from Daucus reboudii. Waste Biomass Valor 13, 1859–1871 (2022). https://doi.org/10.1007/s12649-021-01594-9
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DOI: https://doi.org/10.1007/s12649-021-01594-9