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Pulicaria odora essential oil: a potential source of eco- friendly antioxidants and allelochemicals

Manal Zefzoufi, Rabiaa Fdil, Hafida Bouamama, Abdelkarim Mouzdahir, Khadija Sraidi, Amina Abouzaid

Abstract


Several plants are potential sources of natural antioxidants and can also stimulate or inhibit the germination and growth of weeds due to the production of secondary metabolites. Pulicaria odora, medicinal and aromatic plant, spontane­ous and widespread in Morocco, is widely used by the local population for its medicinal properties. In this study, allelopathic effects and antioxidant activities of P. odora roots essential oil (EO), and the main components, at different concentrations were investigated. The EO was isolated by hydrodistillation using a Clevenger apparatus. GC analysis of the EO indicated the presence of 75 volatile compounds. Among them, two accounted for 89.96% of the oil. The EO was then subjected to column chromatography on silica gel. Two major constituents were isolated and identified by 1H NMR, 13C NMR as isobutyric acid 2-isopropyl-4-methyl-phenylester (1), and 2-isopropyl-4-methylphenol (2). Following the results obtained by DPPH, H2O2, and FRAP methods, EO and its main components possess an interesting antioxidant effect.  The significantly (p<0.05) highest antioxidant properties were exhibited by the phenolic compound 2 followed by EO, whereas lowest from compound 1. The allelopathic effect of EO and its main components at different concentrations (7.81-500 μg/mL) was also tested against two forage species. Data obtained showed that EO, compounds 1 and 2 inhibited significantly (p<0.05) seeds growth of both tested plants (M. sativa and M. falcata). A dose-response relationship was found in seed germination and seedling growth inhibition of the two tested plants. Overall, phenolic component 2 exhibited the highest phytotoxicity. Compound 1 and EO have moderate phytotoxic effects on the growth of the two seeds essayed. In addition, results indicated that the phytotoxic effect of the EO (or its main compounds) also depended on the tested species.

Several plants are potential sources of natural antioxidants and can also stimulate or inhibit the germination and growth of weeds due to the production of secondary metabolites. Pulicaria odora, medicinal and aromatic plant, spontane­ous and widespread in Morocco, is widely used by the local population for its medicinal properties. In this study, allelopathic effects and antioxidant activities of P. odora roots essential oil (EO), and the main components, at different concentrations were investigated. The EO was isolated by hydrodistillation using a Clevenger apparatus. GC analysis of the EO indicated the presence of 75 volatile compounds. Among them, two accounted for 89.96% of the oil. The EO was then subjected to column chromatography on silica gel. Two major constituents were isolated and identified by 1H NMR, 13C NMR as isobutyric acid 2-isopropyl-4-methyl-phenylester (1), and 2-isopropyl-4-methylphenol (2). Following the results obtained by DPPH, H2O2, and FRAP methods, EO and its main components possess an interesting antioxidant effect.  The significantly (p<0.05) highest antioxidant properties were exhibited by the phenolic compound 2 followed by EO, whereas lowest from compound 1. The allelopathic effect of EO and its main components at different concentrations (7.81-500 μg/mL) was also tested against two forage species. Data obtained showed that EO, compounds 1 and 2 inhibited significantly (p<0.05) seeds growth of both tested plants (M. sativa and M. falcata). A dose-response relationship was found in seed germination and seedling growth inhibition of the two tested plants. Overall, phenolic component 2 exhibited the highest phytotoxicity. Compound 1 and EO have moderate phytotoxic effects on the growth of the two seeds essayed. In addition, results indicated that the phytotoxic effect of the EO (or its main compounds) also depended on the tested species.

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- L.L. Liu, J.L. Yang, Y.P. Shi, Phytochemicals and Biological Activities of Pulicaria Species, Chem. Biodivers., 2010, 7, 327-349.

- A. Ezoubeiri, C.A. Gadhi, N. Fdil, A. Benharref, M. Jana, M. Vanhaelen, Isolation, and antimicrobial activity of two phenolic compounds from Pulicaria odora L, J. Ethnopharmacol., 2005, 99, 287-292.

- F.E. Hanbali, M. Akssira, A. Ezoubeiri, C.E. Gadhi, F. Mellouki, A. Benherraf, A.M. Blazquez, H. Boira, Chemical composition and antibacterial activity of essential oil of Pulicaria odora L, J. Ethnopharmacol., 2005, 99, 399-401.

- S.R. Hussein, M.M. Marzouk, M.M. Soltan, M.M. Ahmed, M.M. Said, A.R. Hamed, Antioxidant protective effects and chemosystematic significances, J. Food. Drug. Anal., 2017, 3, 333-339.

- M.N. Algabr, R. Mekkiou, S. Ameddah, A. Menad, O. Boumaza, R. Seghiri, S. Benayache, F. Benayache, Antioxydant activities from the aerial parts of Pulicaria jaubertii, J. Adv. in Nat. App. Sci., 2010, 4, 63-70.

- M. Gherib, B. Chahrazed, I.A. El-haci, T.M. Chaouche, F. Bekkara, Antioxidant and antibacterial activities of aerial part essential oil and some organic extracts from the Algerian medicinal plant Pulicaria mauritanica coss, Int. J. Pharm. Sci. Res., 2016, 7, 76-84.

- A. Hamdouch, A. Asdadi, F. Achemchem, B. Chebli, M. El Hadek, L.M. Idrissi-Hassani, Phytochemical analysis, Antifungal, antibacterial and antioxidant properties of Pulicaria mauritanica from south-east of Morocco, J. Mater. Env. Sci., 2018, 9, 1762-1770.

- N. Touati, K. Saidani, H. Boudries, H. Hammiche, N. Ouazene, F. Bedjou, Antibacterial activity of phenolic compounds of Pulicaria odora, wild plant in northern Algeria, Inter. Food. Res. J., 2018, 25, 2121-2130.

- M. Zefzoufi, M. Chatir, R. Fdil, H. Bouamama, A. Mouzdahir, K. Sraidi, A. Abouzaid, Antioxydant capacity and allelopathic potential of roots extracts of Pulicaria odora L, Res. J. Pharm. Biol. Chem. Sci., 2018, 9, 872-882.

- V.L. Singleton, J.A. Rossi, Colorimetry of Total Phenolics with Phosphomolybdic-Phosphotungstic Acid Reagent, Am. J. Enology. Vitic., 1965, 16, 144-158.

- G. Sudha, M.S. Priya, R.I. Shree, S. Vadivukkarasi, In vitro free radical scavenging activity of raw Pepino fruit (Solanum muricatum Aiton), Inter. J. Curr. Pharm. Res., 2011, 3, 137-140.

- R.J. Ruch, S.J. Cheng, J.E. Klaunig, Prevention of cytotoxicity and inhibition of intracellular communication by antioxidant catechins isolated from Chinese green tea, Carcinogenesis., 1989, 10, 1003-1008.

- M. Oyaizu, Studies on products of browning reactions, antioxidative activities of products of browning reaction prepared from glucosamine, Jpn. J. Nutr., 1986, 44, 307–315.

- A. Tanveer, M.K. Jabbar, A. Kahliq, A. Matloob, R.N. Abbas, M.M. Javaid, Allelopathic effects of aqueous and organic fractions of Euphorbia dracunculoides lam. On germination and seedling growth of chickpea and wheat, Chil. J. Agr. Res., 2012, 72, 495-501.

- A. Gulzar, M.B. Siddiqui, Allelopathic effect of Calotropis procera on growth and antioxidant activity of Brassica oleracea var. botrytis, J. Saudi. Soc. Agric. Sci., 2017, 16, 375–382.

- N.Q.M. Al-Hajj, H. Rashid, S. Al-Hashedi, R. Thabit, H. X. Wang, Total Phenolic Content and Antioxidant, antimicrobial Activity from Some Yemani Plants, J. Eur. Acad. Res., 2014, 4, 10196-10215.

- P.G. Pietta, Flavonoids as Antioxidants, J. Nat. Prod., 2000, 63, 1035-1042.

- A. Wojdyło, J. Oszmian´ski, R. Czemerys, Antioxidant activity and phenolic compounds in 32 selected herbs, Food. Chem., 2007, 105,

–949.

- G. Clarke, K.N. Ting, C. Wiart, J. Fry, High Correlation of 2,2-diphenyl-1-picrylhydrazyl (DPPH) Radical Scavenging, Ferric Reducing Activity Potential, and Total Phenolic Content Indicates Redundancy in Use of All Three Assays to Screen for Antioxidant Activity of Extracts of Plants from the Malaysian Rainforest, J. Antioxidants., 2013, 2, 1-10.

- N. Shariatifar, A. Kamkar, M.R. Shamse-Ardekani, A. Misagi, A. Akhonzade, A.H. Jamshidi, Composition and antioxidant activities of Iranian Pulicaria gnaphalodes essential oil in Soybean oil, Pak. J. Pharm. Sci., 2014, 27, 807-812.

- N. Djermane, N. Gherraf, R. Arhab, A. Zellagui, K. Rebbas, Chemical composition, antioxidant and antimicrobial activities of the essential oil of Pulicaria arabica (L.), Pharm. Lett., 2016, 8, 1-6.

- S. Dudonné, X. Vitrac, P. Coutière, M. Woillez, J.M. Mérillon, Comparative study of antioxidant properties and total phenolic content of 30 plant extracts of industrial interest using DPPH, ABTS, FRAP, SOD, and ORAC assays, J. Agric. Food. Chem., 2009, 57, 1768-1774.

- B.J. Xu, S.H. Yuan, S.K. Chang, Comparative analyses of phenolic composition, antioxidant capacity, and color of cool-season legumes and other selected food legumes, J. Food. Sci., 2007, 72, 167-177.

- S. Burt, Essential oils their antibacterial properties and potential applications in foods, Int. J. Food. Microbiol., 2004, 94, 223-253.

- M. Olszowy, A.L. Dawidowicz, Essential oils as antioxidants: their evaluation by DPPH, ABTS, FRAP, CUPRAC, and β-carotene bleaching methods, Monatsh. Chem., 2016, 147, 2083–2091.

- L. De Martino, E. Mancini, A. Marandino, L. Fernando-Rolim, V. De Feo, Chemistry, and Antigerminative Activity of Essential Oils and Monoterpenoids from Mediterranean Plants, Curr. Bioact. Compd., 2012, 8, 13-49.

- H.R.A. Ghareib, M.S. Abdelhamed, O.H. Ibrahim, Antioxidative effects of the acetone fraction and vanillic acid from Chenopodium murale on tomato plants, Weed. Biol. Manag., 2010, 10, 64–72.

- S.U. Chon, J.H. Coutts, C.J. Nelson, Effects of light, growth media, and seedling orientation on bioassays of alfalfa autotoxicity, Agron. J., 2000, 92, 715–720.

- S. Azirak, S. Karaman, Allelopathic effect of some essential oils and components on germination of weed species, Acta. Agric. Scand. B-S P., 2008, 51, 88-92.

- I. Amri, L. Hamrouni, M. Hanana, B. Jamoussi, Reviews on phytotoxic effects of essential oils and their individual components: news approach for weeds management, Int. J. Appl. Biol. Pharm., 2013, 4, 96-114.

- S. Kaur, H.P. Singh, S. Mittal, D.R. Batish, R.K. Kohli, Phytotoxic effects of volatile oil from Artemisia scoparia against weeds and its possible use as a bioherbicide, Ind. Crops. Prod., 2010, 32, 54-61.

- L.F. Rolim de Almeida, F. Frei, E. Mancini, L. De Martino, V. De Feo, Phytotoxic activities of Mediterranean essential oils, Molecules., 2010, 15, 4309-4323.

- L.G. Angelini, G. Carpanese, P.L. Cioni, I. Morelli, M. Macchia, G. Flamini, Essential Oils from Mediterranean Lamiaceae as Weed Germination Inhibitors, J. Agr. Food. Chem., 2003, 51, 6158-6164.

- T. Tworkoski, Herbicide effects of essential oils, Weed. Sci., 2002, 50, 425-431.

- N. Dudai, A. Poljakoff-Mayber, A.M. Mayer, E. Putievsky, H.R. Lerner, Essential oils as allelochemicals and their potential use as bioherbicides, J. Chem. Ecol., 1999, 25, 1079-1089.

- A. Synowiec, D. Kalemba, E. Drozdek, J. Bocianowski, Phytotoxic potential of essential oils from temperate climate plants against the germination of selected weeds and crops, J. Pest. Sci., 2016, 90, 407-419.

- I.B.H. Jilani, S. Chebil, R. Khiari, I. Melki, S. LimamBenSaad, A. Daoud-Bouattour, Z. Gammar-Ghrabi, Allelopathic potential of some essential oils vis-à-vis three noxious weed species invading cereals, Inter. J. Agro. Agric. Res., 2014, 4, 77-97.

- D. Vokou, P. Douvli, G.J. Blionis, J.M. Halley, Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth, J. Chem. Ecol., 2003, 29, 2281-2301.

- S. Kordali, A. Cakir, S. Sutay, Inhibitory effects of monoterpenes on seed germination and seedling growth, Z Naturforsch C., 2007, 62, 207-214.

- L. De Martino, E. Mancini, R. de Almeida, L.F. De Feo, the Antigerminative Activity of Twenty-Seven Monoterpenes, Molecules., 2010, 15, 6630-6637.

- S. Mutlu, Ö. Atici, N. Esim, Bioherbicidal effects of essential oils of Nepeta meyeri Benth on weed spp, Allelopathy. J., 2010, 26, 291–300.

- M.L. López, N.E. Bonzani, J.A. Zygadlo, Allelopathic potential of Tagetes minuta terpenes by a chemical, anatomical and phytotoxic approach, Biochem. Syst. Ecol., 2009, 36, 882–890.

-M. Verdeguer, M.A. Blazquez, H. Boira, Phytotoxic effects of Lantana camara, Eucalyptus camaldulensis, and Eriocephalus africanus essential oils in weeds of Mediterranean summer crops, Biochem. Syst. Ecol., 2009, 37, 362–369.

- E. Rolli, M. Marieschi, S. Maietti, G. Sacchetti, R. Bruni, Comparative phytotoxicity of 25 essential oils on pre and postemergence development of Solanum lycopersicum L.: a multivariate approach, Ind. Crops. Prod., 2014, 60, 280–290.

- D. Abrahim, W.L. Braguini, A.M. Kelmer-Bracht, E.L. IshiiIwamoto, Effects of four monoterpenes on germination, primary root growth, and mitochondrial respiration of maize, J. Chem. Ecol., 2000, 26, 611-624.

- H.P. Singh, D.R. Batish, S. Kaur, H. Ramezani, R.K. Kohli, Comparative phytotoxicity of four monoterpenes against Cassia occidentalis, Ann. Appl. Biol., 2002, 141, 111-116.

- H.P. Singh D.R. Batish, S. Kaur, K. Arora, R.K. Kohli, α-pinene inhibits growth and induces oxidative stress in roots, Ann. Bot., 2006, 98,

-1269.

- M. Perricone, E. Arace, M.R. Corbo, M. Sinigaglia, A. Bevilacqua, Bioactivity of essential oils, a review on their interaction with food components, Front. Microbiol., 2015, 6, 76.

- D. Vokou, Essential oils as allelochemicals: research advances in Greece. In Narwal SS (ed) Allelopathy Update Basic and Applied Aspects, Science., New York, 1999, 2, 47-63.




DOI: http://dx.doi.org/10.13171/mjc10602006301405rf

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