Chemical Analysis, Antioxidant, Antimicrobial and Enzyme Inhibitory Effects of Daucus Virgatus (Poir.) Maire Essential oil from Algeria

Document Type: Research Paper

Authors

1 Departement de chimie, Faculté des sciences, Université Ferhat Abbas Setif Algeria

2 département de chimie faculté des sciences université ferhat abbas sétif

3 bLaboratory of Applied Biochemistry, Faculty of Life and Nature Sciences, University of Ferhat Abbas Setif 1, 19000, Algeria

4 Department of pharmacy, University of Pisa, Via Bonanno 6, 56126 Pisa, Italy.

5 Laboratory of Microbial Biotechnologies, AgroScience and Environment (BioMAgE), Faculty of Sciences Semlalia (FSSM), University Cadi Ayyad Marrakesh, Morocco.

6 Laboratory of Natural and Biological Resources Valorization, Faculty of Life and Nature Sciences, University of Ferhat Abbas Setif 1, 19000, Algeria

7 Laboratory of Chemistry, Engineering, Materials and Nanostructure, University of Ferhat Abbas Setif 1, 19000, Algeria

10.22036/abcr.2020.235500.1516

Abstract

Essential oils (EO) represent an important source of bioactive molecules and are widely used for their great efficacy relating to their different therapeutic properties. Maire, an aromatic and native plant spontaneously growing in the North-Eastern regions of Algeria, by analyzing the chemical composition of its essential oil and evaluating the antioxidant and antimicrobial activities, together with the assay of the enzyme inhibitory effects against α-glucosidase and cholinesterase. Daucus virgatus EO was extracted by hydrodistillation and analyzed by gaschromatography-mass spectroscometry analysis (GC–MS). Twenty-one constituents accounting for 98% of the whole components were identified. β- pinene (77.9%) and α-pinene (7.6%) were the most abundant components. The antimicrobial activity against the pathogen microorganisms Listeria innocua, Salmonella typhimurium, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli and Candida albicans was investigated. The best antimicrobial effect was observed against S. typhimurium and C. albicans, which showed high sensitivity, with inhibition zones ranging between 27.3 and 25 mm; the minimum inhibitory concentrations were 15.63 and 31.25 μg ml-1, respectively. In the DPPH test, the essential oil showed a moderate antioxidant effect, with an IC50 value of 39.61 mg ml-1. D.virgatus EO exhibited an interesting inhibitory effect against α-glucosidase enzyme (IC50= 0.35 mg ml-1) compared with the positive control Acarbose (IC50= 0.24 mg ml-1), and a moderate inhibitory effect against cholinesterases enzymes, with IC50 values of 0.33 and 0.20 mg ml-1 for acetylcholinesterase and butyrylcholinesterase, respectively. D. virgatus EO might be used as a promising source of natural products with potential antimicrobial, antihyperglycemic and anti-Alzheimer effects.

Keywords


[1]       A. Snene, R. El Mokni, H. Jmii, I. Jlassi, H. Jaïdan, D. Falconieri, A. Piras, H. Dhaouadi,S. Porcedda, S. Hammami, Ind. Crops. Prod. 109 (2017) 109.
[2]       P. Quezel, S. Santa, Nouvelle Flore d’Algérie et des Régions Désertiques Méridionales, CNRS Paris, France, 1963.
[3]       M. El Hadi, F.J. Zhang, F.F. Wu, C.H. Zhou, J. Tao, Molecules 18 (2013) 8200.
[4]       J. Kula, K. Izydorczyk, A. Czajkowska, R. Bonikowski, Flavour Fragr. J. 21 (2006) 667.
[5]       H.E.A. Saad, S.H. El-Sharkawy, A.F. Halim, Pharm. Acta Helv. 70 (1995) 79.
[6]       A. Jabrane, H. Jannet, F. Harzallah-Skhiri, M. Mastouri, J. Casanova, Z. Mighri, Chem.Biodivers 6 (2009) 881.
[7]       M. Staniszewska, J. Kula, M. Wieczorkiewicz, D. Kusewicz, J. Essent. Oil Res. 17 (2005) 579.
[8]       V. Kilibarda, N. Nanusević, N. Dogović, R. Ivanić, K. Savin, Pharmazie 51 (1996) 777.
[9]       H. Marzouki, A. Khaldi, D. Falconieri, A. Piras, B. Marongiu, P. Molicotti, S. Zanetti, Nat. Prod. Commun. 5 (2010) 1955.
[10]    R. Chizzola, J. Essent. Oil-Bear. Plants. 13 (2010) 19.
[11]    A. Maxia, B. Marongiu, A. Piras, S. Porcedda, E. Tuveri, M. Gonçalves, C. Cavaleiro, L. Salgueiro, Fitoterapia 80 (2009) 57.
[12]    F. Mojab, A. Hamedi, B. Nickavar, K. Javidnia, B. Shaheed, J. Essent. Oil-Bear. Plants. 11 (2008) 271.
 
 
[13]    G. Flamini, E. Cosimi, P.L. Cioni, I. Molfetta, A. Braca, Chem. Biodivers. 11 (2014) 1022.
[14]    M. Staniszewska, J. Kula, M. Wieczorkiewicz, D. Kusewicz, J. Essent. Oil Res. 17 (2005) 579.
[15]    M. Staniszewska, J. Kula, J. Essent. Oil Res. 13 (2001) 439.
[16]    P.G. Rossi, L. Bao, A. Luciani, J. Panighi, J.M. Desjober, J. Costa, J. Casanova, J.M. Bolla, L. Berti, J. Agric. Food Chem. 55 (2007) 7332.
[17]    L. Djarri, K. Medjroubi, S. Akkal, A. Elomri, E. Seguin, P. Vérité, Flavour Fragr. J. 21 (2006) 647.
[18]    A. Bendiabdellah, M. Dib, N. Djabou, H. Allali, B. Tabti, A. Muselli, J. Costa, Chem. Cent. J. 6 (2012) 1.
[19]    M. Dib, N. Djabou, J.M. Desjobert, H. Allali, B. Tabti, A. Muselli, J. Costa, Chem. Cent. J. 4 (2010)1.
[20]    D.A. Lanfranchi, H. Laouer, M. El Kolli, S. Prado, C. Maulay-Bailly, N. Baldovini,    J. Agric. Food Chem. 58 (2010) 2174.
[21]    M. El Kolli, H. Laouer, H. El Kolli, S. Akkal, F. Sahli, Asian Pac. J. Trop. Biomed. 6 (2016) 8.
[22]    N. Sakhraoui, R.  Boussouak, S. Metallaoui, A. Chefrour, A. Hadef, Acta Botanica Malacitana 45 (2020) 6138.
[23]    Bull. Soc. Hist. Nat. Afrique N. 23: C.1244, 187, 1932.                        
[24]    A. Snene, C. Sirignano, D. Rigano, C. Formisano, R. ElMokni, G. Ercolano, H. Dhaouadi, A. Ianaro, S. Hammami, O. Taglialatela-Scafati, Phytochemistry 143 (2017) 194.
[25]    C. Sirignano, A. Snene, A.R. Tenoh, R. El Mokni, D. Rigano, A. Habluetzel, S. Hammami, O. Taglialatela-Scafatia, Fitoterapia 137 (2019) 104188.
[26]    C. Sirignano, A. Snene, D. Rigano, S. Tapanelli, C. Formisano, P. Luciano, R. El Mokni, S. Hammami, A.R. Tenoh, A. Habluetzel, O. Taglialatela-Scafati, J. Nat. Prod. 80 (2017) 2787.
[27]    Z. Yu, B. Wang, F. Yang, Q. Sun, Z. Yang, L. Zhu, Iran. J. Pharm. Res. 10 (2011) 265.
[29]    G. Flamini, A. Bader, P.L. Cioni, A. Kabeh-Bader, I. Morelli, J. Agric. Food Chem. 52 (2004) 572.
[30]    R.P.    Adams,     Identification     of     Essential     Oil
 
 
Components by Gas Chromatography/Mass Spectroscopy, 4th ed., Carol Stream, IL: Allured Publishing Corporation, 1995.
[31]    A.A. Swigar, R.M. Silverstein, Monoterpènes, Infrared, Mass, NMR Spectra and Kovats Indices, Aldrich Chem. Co. Milwaukee, WI, USA, 1981.
[32]    N.W. Davies, J. Chromatogr. 503 (1990) 1.
[33]    D. Joulain, W.A. König, the Atlas of Spectral Data of Sesquiterpene Hydrocarbons, EB-Verlag, Hamburg, Germany, 1999.
[34]    R. Mahmoudi, S. Aghaei, Z. Salehpour, A. Mousavizadeh, S.S. Khoramrooz, M.T. Sisakht, G. Christiansen, M. Baneshi, B. Karimi, H. Bardania, Appl. Organometal. Chem. (2019) 5394.
[35]    S. Que, M. Linchun, P. Xin, Food Res Int. 39 (2006) 581.
[36]    G. Singh, P. Marimuthu, C.S. Heluani, C.A. Catalan, J. Agric. Food. Chem. 54 (2006) 81.
[37]    H. Bardania, R. Mahmoudi, H. Bagheri, Z. Salehpour, M.H. fouani, B. Darabian, S.S. Khoramrooz, A. Mousavizadeh, M. Kowsari, S.E. Moosavifard, G. christiansen, D. Javeshghani, M. Alipour, M. Akrami, Scientific Reports 10 (2020) 6129.
[38]    A.W. Bauer, W.M. Kirby, J.C. Sherris, M. Turck, Am. J. Clin. Path. 45 (1966) 493.
[39]    Clinical and Laboratory Standards Institute (CLSI), Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard-ninth Edition. Wayne, USA, 2012.
[40]    G.L. Ellman, K.D. Courtney, V. Andres, R.M. Featherstone, Biochem. Pharmacol. 7 (1961) 88.
[41]    A. Schäfer, P. Högger, Diabetes Res. Clin. Pract. 77 (2007) 41.
[42]    C. Remigius, J.E.O.P. 13 (2010) 12.
[43]    A. Benyelles, H. Allali, M.E.A. Dib, N. Djabou, J. Paolini, J. Costa, Chembiodivers 14 (2017) 1.
[44]    M.N. Boukhatem, F.M. Amine, A. Kameli, F. Saidi, K. Walid, S.B. Mohamed, Int. Lett. Chem. Phys. Astron. 17 (2014) 303.
[45]    K.A. Khalid, J.A.T. da Silva, Scientia Horticulturae 126 (2010) 297.
[46]    K. Razmjoo, P. Heydarizadeh, M.R. Sabzalian, Int. J. Agric. Biol. 10 (2008) 451.
[47]    M. Danute, N. Ona, J. Essent. Oil Res. 16 (2004) 277.
 
 
[48]    M. Gonny, X. Bradesi, J. Casanova, Flavour Fragr. J. 19 (2004) 424.
[49]    R. Habegger, W.H. Schnitzler, J. Appl. Bot. Food Qual. 81 (2007) 132.
[51]    B. Mercier, J. Prost, M. Prost, Int. J. Occup. Med. Environ. Health. 22 (2009) 42.
[52]    R. Mahmoudi, M. Tajali Ardakani, B.H Verdom, A. Bagheri, H. Mohammad-beigi, F. Aliakbari, Z. Salehpour, M. Alipour, S. Afrouz, Hassan Bardania, Bull. Mater. Sci. 42 (2019) 131.
[53]    A.A. Mostafa, A.A. Al-Askar, K.S. Almaary, T.M. Dawoud, E.N. Sholkamy, M.M. Bakri, Saudi. J. Biol. Sci. 25 (2018) 361.
[54]    S.B. Glisic, S.Ž. Milojević, S.I. Dimitrijević, A.M. Orlović,  J. Serb. Chem. Soc. 72 (2007) 311.
[55]    M. Bouchekrit, H. Laouer, M. Hajji, M. Nasri, S.A. Haroutounian, S. Akkal, Asian Pac. J. Trop. Biomed. 6 (2016) 851.
[56]    K.A. Hammer, C.F. Carson, T.V. Riley, J. Appl. Microbiol. 95 (2003) 853.
[57]    B. Joy, A. Rajan, E. Abraham, Phytother Res. 21 (2007) 43.
[58]    A. Ahmad, A. Khan, P. Kumar, R.P. Bhatt, N. Manzoor, Yeast. 28 (2011) 611.
[59]    A.P. Martins, L.R. Salgueiro, M.J. Gonçalves, A. Proença da Cunha, R. Vila, S. Cañigueral, Planta Med. 69 (2003) 9.
[60]    M. Krauze-Baranowska, M. Mardarowicz, M. Wiwart, L. Pobłocka, M. Dynowska,  Z Natur for schC. 57 (2002) 478.
[61]    S. Uribe, J. Ramirez, A. Peña, J. Bacteriol. 161 (1985) 1195.
[62]    M.L. Magwa, M. Gundidza, N. Gweru, G. Humphrey, J. Ethnopharmacol. 103 (2006) 89.
[63]    A. Sonboli, B. Babakhani, A.R. Mehrabian, Z Naturforsch C 61 (2006) 160.
[64]    A.C. Rivas da Silva, P.M. Lopes, M.M. Barros de Azevedo, D.C. Costa, C.S. Alviano, D.S. Alviano, Molecules 17 (2012) 6305.
[65]    A.C. deMacêdo Andrade, P.L. Rosalen, I.A. Freires, L. Scotti, M.T. Scotti, S.G. Aquino, R.D. de Castro, Curr. Top. Med. Chem.18 (2018) 2481.
 
 
[66]    A.M. Leite, E.D.O. Lima, E.L. DeSouza, M.D.F.F.M. Diniz, V.N. Trajano, I.A. De Medeiros, J. Pharm. Sci. 43 (2007) 121.
[67]    F. Bakkali, S. Averbeck, D. Averbeck, M. Idaomar, Food Chem. Toxicol. 46 (2008) 446.
[68]    A. Ultee, M.H.J. Bennik, R. Moezelaar, Appl. J.  Environ. Microbiol. 68 (2002) 1561.
[69]    C.F. Carson, B.J. Mee, T.V. Riley, Antimicrob. Agents Chemother. 46 (2002) 1914.
[70]    M.J. Howes, P.J. Houghton, Int. J. Biomed. Pharm. Sci. 3 (2009) 67.
[71]    D.  Załuski,  Z.  Janeczko,  Nat.  Prod.  Res.  29 (2015)
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
2207.
[72]    N.S.L. Perry, P.J. Houghton, A. Theobald, P. Jenner, E.K. Perry, J. Pharm. Pharmacol. 52 (2000) 895.
[73]    M. Miyazawa, C. Yamafuji, Flavour. Fragr .Chem. 21 (2006) 198.
[74]    I.E. Orhan, M. Kartal, Y. Kan, B. Sener, Z. Naturforsch Sect. C 63 (2008) 547.
[75]    M. Hideyuki, A.Chikako, K. Masanori, M. Junya, Biosci. Biotechnol. Biochem. 66 (2002) 1576.
[76]    W. Benalla, S. Bellahcen, M. Bnouham, Curr. Diabetes. Rev. 6 (2010) 247.