Chemical Composition and Antimicrobial Activity of Bark and Leaf Extracts of Cupressus sempervirens and Juniperus phoenicea Grown in Al- Jabel Al-Akhdar Region, Libya

Mohamed     E.I.   Badawy; Ibrahim     E.A.    Kherallah; Ahmed     S.O.    Mohareb; Mohamed.   Z.M.    Salem; Hameda    A.    Yousef

doi:10.2174/2210315508666180223151210

Abstract

Background: Plant extracts are important products in the world and have been widely used for isolation of important biologically active products. Because of their significant environmental impact, extensive research has been explored to determine the antimicrobial activity of plant extracts.

Methods: Acetone extracts of the bark and leaf of Cupressus sempervirens and Juniperus phoenicea, collected from three different altitudes (125, 391, and 851 m high of sea level) at Al- Jabel Al-Akhdar area, Libya were obtained and analyzed by GC/MS. The antimicrobial activity of the extracts was further evaluated against plant bacteria Rhizobium radiobacter, Erwinia carotovora, Rhodococcus fascians and Ralstonia solanacearum and fungus Botrytis cinerea.

Results: The impact of the altitude from the sea level on the quantity and chemical constituents of the extracts was investigated. The yield was largely dependent on tree species and the highest yield (6.50%) was obtained with C. sempervirens L bark of altitude III (851 m of the sea level), while the lowest (1.17%) was obtained with the leaf extract of C. sempervirens L from altitude I (125 m). The chemical composition analyzed by GC/MS confirmed that the leaf extracts of C. sempervirens and J. phoenicea contained a complex mixture of monoterpene hydrocarbons, sesquiterpenes, diterpenes, diterpenoids, terpenophenolic, steroids and phthalates. However, the bark extracts of both trees contained a mixture of sesquiterpenes, diterpenes, diterpenoids, terpenophenolics, phthalates, retinol and steroids. These constituents revealed some variability among the extracts displaying the highest interesting chemotype of totarol (terpenophenolic) in all extracts (14.63-78.19% of the total extract). The extracts displayed a noteworthy antifungal potency with varying degrees of inhibition of growth with EC50 values ranged from 78.50 to 206.90 mg/L. The extracts obtained from the leaves of C. sempervirens showed that the highest inhibitory activity was obtained with the extract of altitude II (391 m) with MIC 565, 510, 380 and 710 mg/L against E. carotovora, R. fascians, and R. radiobacter and R. solanacearum, respectively.

Conclusion: Based on antimicrobial activity, raw plant extracts can be a cost-effective way to protect crops from microbial pathogens. Because plant extracts contain several antimicrobial compounds, the development of resistant pathogens can be delayed.

Keywords: Cupressus sempervirens, Juniperus phoenicea, GC/MS analyses, antifungal activity, antibacterial activity, microbial pathogens.

Graphical Abstract

[1] 
Al-Idrissi, M.; Sbeita, A.; Jebriel, A.; Zintani, A.; Shreidi, A.; Ghawawi, H.; Tazi, M.   Libya: Country report to the Fao international
	technical conference on plant genetic resources. 1996. Available
	from: 
                    http://www.fao.org/fileadmin/templates/agphome/docu ments/PGR/SoW1/east/LIBYA.pdf
[2] 
Hegazy, A.; Boulos, L.; Kabiel, H.; Sharashy, O. Vegetation and species altitudinal distribution in Al-jabal Al-akhdar landscape, Libya. Pak. J. Bot.,  2011, 43(4), 1885-1898.
[3] 
Elshatshat, S.; Mansour, A. Disturbance of flora and vegetation composition of Libya by human impacts: Costal region of Al-Jabal Al-Akhdar area as model. J. Appl. Sci. Res.,  2014, 5(5), 286-292.
[4] 
Attitalla, I.H.; Alhasin, A.M.; Nasib, M.; Ghazali, A.; Zakaria, L.; Jais, H.; Balal, I.; Salleh, B. Occurrence and microbiological characteristics of azospirillum strains associated with leguminous and non-leguminous plants in Al Jabal Al Akhdar eco-region, Libya. Am.-Eurasian J. Agric. Environ. Sci.,  2010, 8, 617-625.
[5] 
Hamad, H.; Ibrahim, H.; Mariam, H.; Mojahidul, I. Comparative phytochemical and antimicrobial investigation of some plants growing in Al Jabal Al-Akhdar. J. Nat. Prod. Plant Resour.,  2011, 1, 15-23.
[6] 
Al-Sodany, Y.M.; Shehata, M.; Shaltout, K.H. Vegetation along an elevation gradient in Al-Jabal Al-Akhdar, Libya. Ecol. Mediter.,  2003, 29, 125-138.
[7] 
Krüssmann, G.; Warda, H.D. Manual of cultivated conifers, 2nd ed; Timber Press, 1985. 
[8] 
Bagnoli, F.; Vendramin, G.G.; Buonamici, A.; Doulis, A.G.; González-Martínez, S.C.; La Porta, N.; Magri, D.; Raddi, P.; Sebastiani, F.; Fineschi, S. Is Cupressus sempervirens native in Italy? An answer from genetic and palaeobotanical data. Mol. Ecol.,  2009, 18(10), 2276-2286.
[http://dx.doi.org/10.1111/j.1365-294X.2009.04182.x] [PMID:  19389173] 
[9] 
Rawat, P.; Khan, M.F.; Kumar, M.; Tamarkar, A.K.; Srivastava, A.K.; Arya, K.R.; Maurya, R. Constituents from fruits of Cupressus sempervirens. Fitoterapia,  2010, 81(3), 162-166.
[http://dx.doi.org/10.1016/j.fitote.2009.08.014] [PMID:  19686818] 
[10] 
Ismail, A.; Lamia, H.; Mohsen, H.; Samia, G. Bassem, J. Chemical composition, Bio-herbicidal and antifungal activities of essential oils isolated from tunisian common cypress (Cupressus sempervirens l.). J. Med. Plants Res.,  2013, 7(16), 1070-1080.
[11] 
Adams, R.P.; Barrero, A.; Lara, A. Comparisons of the leaf essential oils of Juniperus phoenicea, j. Phoenicea subsp. Eu-mediterranea lebr. & thiv. and j. Phoenicea var. Turbinata (guss.) parl. J. Essent. Oil Res.,  1996, 8(4), 367-371.
[http://dx.doi.org/10.1080/10412905.1996.9700642] 
[12] 
Meloni, M.; Perini, D.; Filigheddu, R.; Binelli, G. Genetic variation in five Mediterranean populations of Juniperus phoenicea as revealed by Inter-Simple Sequence Repeat (ISSR) markers. Ann. Bot.,  2006, 97(2), 299-304.
[http://dx.doi.org/10.1093/aob/mcj024] [PMID:  16311272] 
[13] 
El-Sawi, S.A.; Motawae, H.M.; Ali, A.M. Chemical composition, cytotoxic activity and antimicrobial activity of essential oils of leaves and berries of Juniperus phoenicea L. grown in Egypt. Afr. J. Tradit. Complement. Altern. Med.,  2007, 4(4), 417-426.
[http://dx.doi.org/10.4314/ajtcam.v4i4.31236] [PMID:  20161910] 
[14] 
Derwich, E.; Benziane, Z.; Boukir, A. Chemical composition of leaf essential oil of Juniperus phoenicea and evaluation of its antibacterial activity. Int. J. Agric. Biol.,  2010, 12, 199-204.
[15] 
Otto, A.; Wilde, V. Sesqui-, di-, and triterpenoids as chemosystematic markers in extant conifers. A review. Bot. Rev.,  2001, 67(2), 141-238.
[http://dx.doi.org/10.1007/BF02858076] 
[16] 
Sasidharan, S.; Chen, Y.; Saravanan, D.; Sundram, K.M.; Yoga Latha, L. Extraction, isolation and characterization of bioactive compounds from plants’ extracts. Afr. J. Tradit. Complement. Altern. Med.,  2011, 8(1), 1-10.
[PMID:  22238476] 
[17] 
Badawy, M.E.; Abdelgaleil, S.A. Composition and antimicrobial activity of essential oils isolated from Egyptian plants against plant pathogenic bacteria and fungi. Ind. Crops Prod.,  2014, 52, 776-782.
[http://dx.doi.org/10.1016/j.indcrop.2013.12.003] 
[18] 
Fatope, M.; Adoum, O.; Takerda, Y. Palmitate Ximenia americana. Pharm. Biol.,  2001, 38(5), 391-393.
[http://dx.doi.org/10.1076/phbi.38.5.391.5972] 
[19] 
Shahidi, F.; Mc Donald, J.; Chandrasekara, A.; Zhong, Y. Phytochemicals of foods, beverages and fruit vinegars: Chemistry and health effects. Asia Pac. J. Clin. Nutr.,  2008, 17(Suppl. 1), 380-382.
[PMID:  18296384] 
[20] 
Harborne, J.B.   The chemical basis of plant defense. Plant defenses
	against mammalian herbivory., 1991, 45-59.
[21] 
Ayoola, G.; Coker, H.; Adesegun, S.; Adepoju-Bello, A.; Obaweya, K.; Ezennia, E.; Atangbayila, T. Phytochemical screening and antioxidant activities of some selected medicinal plants used for malaria therapy in southwestern Nigeria. Trop. J. Pharm. Res.,  2008, 7, 1019-1024.
[22] 
Muthee, J.; Gakuya, D.; Mbaria, J.; Mulei, C. Phytochemical screening and cytotoxicity of selected plants used as anthelmintics in loitoktok sub-county, Kenya. Phytopharmacology,  2016, 5(1), 15-19.
[23] 
Badawy, M.E.; Kherallah, I.E.; Mohareb, A.S.; Salem, M.; Yousef, H.A. Chemical composition and antifungal activity of essential oils isolated from Cupressus sempervirens l. And Juniperus phoenicea l. Grown in Al-Jabel Al-Akhdar region, libya against botrytis cinerea. Nat. Prod. J.,  2017, 7, 298-308.
[http://dx.doi.org/10.2174/2210315507666170530092645] 
[24] 
Mazari, K.; Bendimerad, N.; Bekhechi, C. Chemical composition and antimicrobial activity of essential oils isolated from algerian Juniperus phoenicea l. and Cupressus sempervirens l. J. Med. Plants Res.,  2010, 4(10), 959-964.
[25] 
Ali, H.M.; Salem, M.Z.; Mohamed, N.H. Evaluation of extracts from different parts of some tree species against the growth of human bacterial pathogens. J. Pure Appl. Microbiol.,  2014, 8, 149-154.
[26] 
Anäs, E.; Ekman, R.; Holmbom, B. Composition of nonpolar extractives in bark of norway spruce and scots pine. J. Wood Chem. Technol.,  1983, 3(2), 119-130.
[http://dx.doi.org/10.1080/02773818308085155] 
[27] 
Ekman, R.; Holmbom, B. Analysis by gas chromatography of the wood extractives in pulp and water samples from mechanical pulping of spruce. Nordic. Pulp Paper Res. J.,  1989, 4(1), 16-24.
[http://dx.doi.org/10.3183/npprj-1989-04-01-p016-024] 
[28] 
Davies, N. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicon and carbowax 20 m phases. J. Chromatogr. A,  1990, 503, 1-24.
[http://dx.doi.org/10.1016/S0021-9673(01)81487-4] 
[29] 
Adams, R. Identification of essential oil components by gas chromatography. Mass Spectrom. (Tokyo),  1995, 237-243.
[30] 
Badawy, M.E.; Rabea, E.I.; Taktak, N.E. Antimicrobial and inhibitory enzyme activity of N-(benzyl) and quaternary N-(benzyl) chitosan derivatives on plant pathogens. Carbohydr. Polym.,  2014, 111, 670-682.
[http://dx.doi.org/10.1016/j.carbpol.2014.04.098] [PMID:  25037402] 
[31] 
Finney, D.J. Probit analysis, 3rd ed; Cambridge University Press: New York, 1971. 
[32] 
Oztürk, M.; Tümen, İ.; Uğur, A.; Aydoğmuş-Öztürk, F.; Topçu, G. Evaluation of fruit extracts of six Turkish Juniperus species for their antioxidant, anticholinesterase and antimicrobial activities. J. Sci. Food Agric.,  2011, 91(5), 867-876.
[http://dx.doi.org/10.1002/jsfa.4258] [PMID:  21384354] 
[33] 
Hayouni, E.A.; Abedrabba, M.; Bouix, M.; Hamdi, M. The effects of solvents and extraction method on the phenolic contents and biological activities in vitro of Tunisian Quercus coccifera l. and Juniperus phoenicea l. fruit extracts. Food Chem.,  2007, 105(3), 1126-1134.
[http://dx.doi.org/10.1016/j.foodchem.2007.02.010] 
[34] 
Mangoni, L.; Belardini, M. Components of Cupressus sempervirens resin. I. Communic acid, cupressic acid, and isocupressic acid. Gazz. Chim. Ital.,  1964, 94, 1108-1121.
[35] 
Selim, S.A.; Adam, M.E.; Hassan, S.M.; Albalawi, A.R. Chemical composition, antimicrobial and antibiofilm activity of the essential oil and methanol extract of the Mediterranean cypress (Cupressus sempervirens L.). BMC Complement. Altern. Med.,  2014, 14, 179.
[http://dx.doi.org/10.1186/1472-6882-14-179] [PMID:  24890383] 
[36] 
Al-Snafi, A.E. Medical importance of Cupressus sempervirens. A review. IOSR J. Pharm.,  2016, 6, 66-76.
[37] 
Al-Othman, A.M.; Hussain, I.; Khan, H.; Rehman, M.U.; Abdeltawab, A.A.; Ullah, R.; Noor, S.; Talha, M. Phytochemical analysis and biological activities of selected medicinal plants. J. Med. Plants Res.,  2012, 6, 4005-4010.
[38] 
Krishnaveni, M.; Amsavalli, L.; Chandrasekar, R.; Madhaiyan, P.; Durairaj, S. Antioxidant activity of plants at Govt. College of Engineering campus, Salem, Tamil Nadu, India. Int. J. Pharm. Sci. Rev. Res.,  2013, 21, 160-163.
[39] 
Tumen, I.; Sezer Senol, F.; Orhan, I.E. Evaluation of possible in vitro neurobiological effects of two varieties of Cupressus sempervirens (mediterranean cypress) through their antioxidant and enzyme inhibition actions. Turk. J. Biochem.,  2012, 37, 5-13.
[http://dx.doi.org/10.5505/tjb.2012.92400] 
[40] 
Shahid, W.; Durrani, R.; Iram, S.; Durrani, M.; Khan, F.A. Antibacterial activity in vitro of medicinal plants. Sky J. Microb. Res.,  2013, 1, 5-21.
[41] 
Thomas, B. Chemistry of order araucariales. 4. Bled resins of Agathis australis. Acta Chem. Scand.,  1966, 20, 1074.
[http://dx.doi.org/10.3891/acta.chem.scand.20-1074] 
[42] 
Arya, V. Isolation of communic acid from some juniper barks. In: 21. Natl Inst Science Communication Dr Ks Krishnan Marg, New Delhi; India, 1962, p. 201.
[43] 
Arya, V.; Enzell, C.; Erdtman, H. Communic acid, a new diterpene
	acid from Juniperus communis l. In: 15. Munksgaard. Int Publ Ltd
	35 Norre Sogade: PO Box 2148, Dk-1016; Copenhagen, Denmark,
	1961, pp. 225-226. 
[http://dx.doi.org/10.3891/acta.chem.scand.15-0225] 
[44] 
Hartwell, J.L.; Johnson, J.M.; Fitzgerald, D.B.; Belkin, M. Silicicolin, a new compound isolated from Juniperus silicicola. J. Am. Chem. Soc.,  1952, 74, 4470-4470.
[http://dx.doi.org/10.1021/ja01137a524] 
[45] 
Noguchi, K.; Kawanami, M. The active components of the umbelliferae. X. Components of Anthricus sylvestris. J. Pharm. Soc. J.,  1940, 60, 629-636.
[46] 
Hartwell, J.; Schrecker, A. The chemistry of podophyllum. Fortschritte der chemie organischer naturstoffe/progress in the chemistry of organic natural products/progrès dans la chimie des substances organiques naturelles; Springer: Vienna, 1958, pp. 83-166.
[47] 
Hartwell, J.L.; Schrecker, A.W.; Johnson, J.M. The structure of silicicolin1a. J. Am. Chem. Soc.,  1953, 75, 2138-2140.
[http://dx.doi.org/10.1021/ja01105a034] 
[48] 
Elmhdwi, M.F.; Attitalla, I.H.; Khan, B.A. Evaluation of antibacterial activity and antioxidant potential of different extracts from the leaves of Juniperus phoenicea. J. Plant Pathol. Microb.,  2015, 6(300), 2.
[http://dx.doi.org/10.4172/2157-7471.1000300] 
[49] 
Mansouri, N.; Satrani, B.; Ghanmi, M.; El-Ghadraoui, L.; Aaf, A. Chemical and biological study of essential oils of Moroccan Juniperus phoenicea ssp. Lycia and Juniperus phoenicea ssp. Turbinata. Biotechnol. Agron. Soc. Environ.,  2011, 15, 415-424.
[50] 
Nasri, N.; Tlili, N.; Elfalleh, W.; Cherif, E.; Ferchichi, A.; Khaldi, A.; Triki, S. Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Nat. Prod. Res.,  2011, 25(18), 1733-1742.
[http://dx.doi.org/10.1080/14786419.2010.523827] [PMID:  21707254] 
[51] 
Comte, G.; Allais, D.P.; Chulia, A.J.; Vercauteren, J.; Pinaud, N. Three phenylpropanoids from Juniperus phoenicea. Phytochemistry,  1997, 44, 1169-1173.
[http://dx.doi.org/10.1016/S0031-9422(96)00684-X] 
[52] 
Comte, G.; Allais, D.P.; Chulia, A.J.; Vercauteren, J.; Delage, C. Two furanone glucoside derivatives from Juniperus phoenicea. Phytochemistry,  1996, 41, 1329-1332.
[http://dx.doi.org/10.1016/0031-9422(95)00730-X] 
[53] 
Carpenter, C.D.; O’Neill, T.; Picot, N.; Johnson, J.A.; Robichaud, G.A.; Webster, D.; Gray, C.A. Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis. J. Ethnopharmacol.,  2012, 143(2), 695-700.
[http://dx.doi.org/10.1016/j.jep.2012.07.035] [PMID:  22877928] 
[54] 
Marino, A.; Bellinghieri, V.; Nostro, A.; Miceli, N.; Taviano, M.F.; Güvenç, A.; Bisignano, G. In vitro effect of branch extracts of Juniperus species from Turkey on Staphylococcus aureus biofilm. FEMS Immunol. Med. Microbiol.,  2010, 59(3), 470-476.
[http://dx.doi.org/10.1111/j.1574-695X.2010.00705.x] [PMID:  20584079] 
[55] 
Sati, S.; Joshi, S. Antibacterial potential of leaf extracts of Juniperus communis l. from kumaun himalaya. Afr. J. Microbiol. Res.,  2010, 4, 1291-1294.
[56] 
Mohareb, A.S.O.; Kherallah, I.E.A.; Badawy, M.E.I.; Salem, M.Z.M.; Faraj, H.A.Y. Chemical composition and antibacterial activity of essential oils isolated from leaves of different woody trees grown in al-jabel al-akhdar region, Libya. Alexandria Sci. Exchange J.,  2016, 37, 358-371.
[57] 
Dellavalle, P.D.; Cabrera, A.; Alem, D.; Larrañaga, P.; Ferreira, F.; Dalla Rizza, M. Antifungal activity of medicinal plant extracts against phytopathogenic fungus alternaria spp. Chil. J. Agric. Res.,  2011, 71, 231.
[http://dx.doi.org/10.4067/S0718-58392011000200008] 
[58] 
Filip, R.; Davicino, R.; Anesini, C. Antifungal activity of the aqueous extract of Ilex paraguariensis against Malassezia furfur. Phytother. Res.,  2010, 24(5), 715-719.
[PMID:  19827026] 
[59] 
Clarke, C. Examining the antimicrobial activity of plant extracts. In: Student Research Week Proceedings, 2016, pp. 1.
[60] 
Kähkönen, M.P.; Hopia, A.I.; Vuorela, H.J.; Rauha, J-P.; Pihlaja, K.; Kujala, T.S.; Heinonen, M. Antioxidant activity of plant extracts containing phenolic compounds. J. Agric. Food Chem.,  1999, 47(10), 3954-3962.
[http://dx.doi.org/10.1021/jf990146l] [PMID:  10552749] 
[61] 
Lee, O.H.; Lee, B.Y. Antioxidant and antimicrobial activities of individual and combined phenolics in Olea europaea leaf extract. Bioresour. Technol.,  2010, 101(10), 3751-3754.
[http://dx.doi.org/10.1016/j.biortech.2009.12.052] [PMID:  20106659] 
[62] 
Kuiate, J.R.; Bessière, J.M.; Zollo, P.H.A.; Kuate, S.P. Chemical composition and antidermatophytic properties of volatile fractions of hexanic extract from leaves of Cupressus lusitanica Mill. from Cameroon. J. Ethnopharmacol.,  2006, 103(2), 160-165.
[http://dx.doi.org/10.1016/j.jep.2005.07.022] [PMID:  16169171] 

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DOI https://dx.doi.org/10.2174/2210315508666180223151210	Print ISSN 2210-3155
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Chemical Composition and Antimicrobial Activity of Bark and Leaf Extracts of Cupressus sempervirens and Juniperus phoenicea Grown in Al- Jabel Al-Akhdar Region, Libya

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