Phytochemical Analysis and Evaluation of Antifungal and Antioxidant Activities of Essential Oil of Fruits from Juniperus oxycedrus L. Obtained from Morocco
DOI:
https://doi.org/10.1590/s2175-97902023e21088%20Keywords:
Juniperus oxycedrus L., Fruits, GC/MS, Antifungal, Antioxidant activitiesAbstract
The present study was aimed at conducting phytochemical analysis and evaluating the in vitro antifungal and antioxidant activities of the essential oil obtained from the fruits of J. oxycedrus L. Hydro-distillation was used to extract the essential oil from the fruits of Juniper oxycedrus. The essential oil was analyzed using gas chromatography with a flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). The antioxidant activity of the essential oil against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals was determined in vitro using varying concentrations of the essential oil and vitamin C as a standard antioxidant compound. A disc diffusion test was employed to evaluate the antifungal activity of the essential oil against two test fungal strains, Penicillium citrinum, and Aspergillus niger. The results revealed that 49 constituents were identified in fruit oil, representing 91.56% of the total oil and the yield was 1.58%. Juniper fruit oil was characterized by having high contents of β-pinene (42.04%), followed by limonene (15.45%), sabinene (9.52%), α-pinene (5.21%), (E)-caryophyllene (3.77%), ρ-cymene (1.56%), caryophyllene oxide (2.02%), and myrcene (1.02%). The radical scavenging activity (% inhibition) of the essential oil was highest (81.87± 2.83%) at a concentration of 200 µg/mL. The essential oil of J. oxycedrus exhibited antifungal activity against A. niger and P. citrinum with minimum inhibitory concentration values (MIC) ranging from 2.89 to 85.01 µl/mL. The findings of the study reveal that the antioxidant and antifungal properties of J. oxycedrus essential oil and their chemical composition are significantly correlated.
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References
Achak N, Romane A, Alifriqui M, Robert PA. Chemical studies of leaf essential oils of three species of Juniperus from Tensift AlHaouz- Marrakech region (Maroc). J Essent Oil Res. 2009;21(4):337-341.
Adams R. Essential oil components by quadrupole GC/MS. Allured Publishing Corp, Carol Stream, IL. 2001.
Adams R. Investigation of Juniperus species of the United States for new sources of cedarwood oil. Econ Bot. 1987;41(1):48-54.
Adiguzel A, Hakan O, Hamdullah K, Bulent C. Screening of antimicrobial activity of essential oil and methanol extract of Satureja hortensis on foodborne bacteria and fungi. Czech J Food Sci. 2002;25(2):81-89.
Akrout A, Chemli R, Chief I, Hammami M. Analysis of the essential oil of Artemisia campestris L. Flav Fragr J. 2001;16(5):337-339.
Albayrak S, Aksoy A, Sagdic O, Hamzaoglu. Compositions, antioxidant and antimicrobial activities of Helichrysum (Asteraceae) species collected from Turkey. Food Chem. 2010;119(1):114-122.
Alotaibi SS, Alshoaibi D, Alamari H, Albogami S, Khan E, Alshanbari A, et al. Potential significance of medicinal plants in forensic analysis: A review. Saudi J Biol Sci. 2021;28(7):3929-3935.
Angioni A, Barra A, Russo MT, Coroneo V, Dessi S, Cabras P. Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity. J AgricFood Chem. 2003;51(10):3073-3078.
Barrero AF, Oltra JE, Altarejos J, Barragán A, Lara A, Laurent R. Minor components in the essential oil of Juniperus oxycedrus L. Wood Flav Frag J. 1993;8(4):185-189.
Belletti N, Ndagijimana M, Sisto C, Guerzoni ME, Lanciotti R, Gardini F. Evaluation of the Antimicrobial Activity of Citrus Essences on Saccharomyces cerevisiae. J Agric Food Chem. 2004;52: 6932-6938.
Boti J, Bighelli A, Cavaleiro C, Salgueiro L, Casanova J. Chemical variability of Juniperus oxycedrus ssp. Oxycedrus berry and leaf oils from Corsica, were analyzed by a combination of GC, GC-MS, and 13C-NMR. Flav Frag J. 2006;21:268-273.
Bourkhiss M, Hnach M, Bourkhiss B, Ouhssine M, Chaouch A. Composition chimique et propriétés antimicrobiennes de l’huile essentielle extraite des feuilles de Tetraclinis articulata (Vahl) du Maroc. Afri Sci. 2000;3(2):232-242.
Brand-Williams W, Cuvelier M, Berset C. Use of a free radical method to evaluate antioxidant activity. Lebensm.- Wiss Technol. 1995;28(1):25-30.
Cavaleiro C, Pinto E, Goncalves M, Salgueiro L. Antifungal activity of Juniperus essential oils against dermatophyte, Aspergillus and Candida strains. J Appl Microb. 2000;100(6):1333-1338.
Clevenger J. Apparatus for determination of volatile oil. J America Pharma Assoc. 1928;17(4):341-346.
Coode M, Cullen J. Juniperus L . In: Davis PH (ed.) flora of Turkey and the east Aegean islands. Edinburgh: Edinburgh University Press. 1965;1:78-84.
Consentino S, Berra A, Pisano B, Cabizza M, Pirisi FM, Palmas F. Composition and antimicrobial activity of Sardinian Juniperus oils against foodborne pathogens and spoilage microorganisms. J Food Prot. 2003;66(7):1288-1291.
Cristani M, D’Arrigo M, Mandalari G, Castelli F, Sarpietro MG, Micieli D, et al. Interaction of four monoterpenes contained in essential oils with model membranes: Implications for their antibacterial activity. J Agric Food Chem. 2007;55(15):6300-8.
Deba F, Xuan TD, Yasuda M, Tawata S. Chemical composition and antioxidant; antibacterial and antifungal activities of the essential oils from Bidens pilosa L. var. radiata. Food Control. 2008;19(4):346-352.
Derwich E, Benziane Z, Boukir A. Chemical composition and insecticidal activity of essential oils of three plants Artemisia sp: Artemisia herba-alba, Artemisia absinthium, and Artemisia pontica (Morocco). Electron J Environ Agric Food Chem . 2009;8(11):1202-1211.
Dorman HJD, Deans SG, 2000. Antimicrobial agents from plants: Antibacterial activity of plant volatile oils. J Appl Microb iol. 2000;88(2):308-16.
Edward P, Claus T Varro, Lynn R. Pharmacognosy, sixth edition LEA and Febiger (ed). 1987; 18:184-187. https://doi.org/10.1002/jps.2600600445
» https://doi.org/10.1002/jps.2600600445
El-Abid H, Amaral C, Cunha SC, Augusto TV, Fernandes JO, Correia-da-Silva G, et al. Chemical composition and anti-cancer properties of Juniperus oxycedrus L. essential oils on estrogen receptor-positive breast cancer cells. J Funct Foods. 2019;59:261-271.
El-Ghorab A, Hamdy A, Shaaban T, Khaled F, El-Massry T, Shibamoto T. Chemical composition of volatile extract and biological activities of volatile and less-volatile extracts of Juniper Berry (Juniperus drupacea L.) fruit. J Agric Food Chem . 2008;56(13):5021-5025.
El-Shemy H. Potential of Essential Oils. BoD - Books on Demand. 2018.
El-Massry KF, El-Ghorab AH, Farouk A. Antioxidant activity and volatile components of Egyptian Artemisia judaica L. Food Chem. 2002;79(3):331-336.
Ennajar M, Bouajila J, Lebrihi A, Mathieu F, Abderraba M, Raies A, et al. Chemical composition and antimicrobial and antioxidant activities of essential oils and various extracts of Juniperus phoenicea L. (Cupressacees). J Food Sci. 2009;74(7):364-371.
Fadel H, Benayache F, Chalchat JC, Figueredo G, Chalard P, Hazmoune H, et al. Essential oil constituents of Juniperus oxycedrus L. and Cupressus sempervirens L. (Cupressaceae) growing in Aures region of Algeria. Nat Prod Res. 2019;35(15):2616-2620.
Farjon A. Monograph of Cupressaceae and Sciadopitys. Royal Botanic Gardens, Kew. 2005.
Fretz T, Sydnor T, Cobbs M. Monoterpene composition of foliage of 9 Juniperus species. Scienta Horticulture. 1976;5(1):85-91.
Gaussen H. Les Cupressacées Fasc. Xin Les Gymnospermes, Actuelles et Fossiles. Lab Forest. Unive. Toulouse, France. 1968.
Gul HI, Ojanen T, Hanninen O. Antifungal evaluation of Bis Mannich bases derived from acetophenones and their corresponding piperidinols and stability studies. Biol Pharm Bull. 2002;25(10):1307-1310.
Koukos P, Papadopoulou K, Papagiannopoulos A, Patiaka D. Variation in the chemical composition of the berrey oil of Juniperus oxycedrus L Grown in North and West Greece. Holz als Roh- und Werkstoff. 2002;60(2):152-153.
Leung A, Foster S. Encyclopedia of common natural ingredients. New York: Wiley. 1996.
Llorens-Molina JA, Ygueravide B, Vacas S. Essential oil composition of berries of Juniperus oxycedrus L. ssp. oxycedrus according to their ripening stage. J Essent Oil Res. 2019;31(4):276-285.
Loizzo M, Tundis R, Conforti F, Saab A, Statti A, Menichini F. Comparative chemical composition, antioxidant and hypoglycaemic activities of Juniperus oxycedrus ssp. oxycedrus L. berry and wood oils from Lebanon. Food Chem. 2007;105(2):572-578.
Małgorzata K, Krystyna B, Jose Maria M, Yakov D, Angel R, Daniel G, et al. Morphological variation of Juniperus oxycedrus subsp. Oxycedrus (Cupressaceae) in the Mediterranean region. Flora. 2007;202(2):133-147.
Marongiu B, Porcedda S, Caredda A, De Gioannis B, Vargiu L, La Colla P. Extraction of Juniperus oxycedrus ssp. Oxycedrus essential oil by supercritical carbon dioxide: Influence of some process parameters and biological activity. Flav Fragr J. 2003;18(5):390-397.
Massei G, Watkins R, Hartley SE. Sex-related growth and secondary compounds in Juniperus oxycedrus macrocarpa. Acta Oecologica. 2006;29(2):135-140.
McLafferty and Stauffer, 1989 F.W. McLafferty, D.B. Stauffer The Wiley/NBS Registry of Mass Spectral Data J Wiley and Sons, New York (1989)
Milos M, Radonic A. Gas chromatography-mass spectral analysis of free and glycosidically bound volatile compounds from Juniperus oxycedrus L. growing wild in Croatia. Food Chem . 2000;68(3):333-338.
Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolke RH. Manual of Clinical Microbiology, 6th edition. ASM, Washington, DC. 1995.
Nazzaro F, De Martino L, Fratianni F, De Feo V. Chapter 49 - Essential oils from Mediterranean aromatic plants, in: Preedy, VR, Watson RR . (Eds.), The Mediterranean Diet (Second Edition). Academic Press. 2020. p. 555-564.
Omidbeygi M, Barzegar M, Hamidi Esfahani Z, Naghdibadi H. Antifungal activity of thyme, summer savory and clove essential oils against Aspergillus Xavus in liquid medium and tomato paste. Food Control. 2007;18:1518-1523.
Orhan N, Berkkan A, Deliorman Orhan D, Aslan M, Ergun F. Effects of Juniperus oxycedrus ssp. oxycedrus on tissue lipid peroxidation, trace elements (Cu, Zn, Fe), and blood glucose levels in experimental diabetes. J Ethnopharmacol. 2011;133(2):759-764.
Orhan N. Juniperus Species: Features, Profile, and Applications to Diabetes, in Bioactive Food as Dietary Interventions for Diabetes. Elsevier, 2019. p. 447-459.
Papadoupoulou K, Kokous P. Seasonal variation of essential oils in fruits of Juniperus oxycedrus L. Geotecnis Scientific Issue. 1995;6:7-10.
Picking D. The Global Regulatory Framework for Medicinal Plants, in Pharmacognosy. Elsevier, 2017. p. 663-675.
Ramy M, Sayed A, Ghada M. Chemical compositions, antiviral and antioxidant activities of seven essential oils. J Appl Sci Res. 2010;6(1):50-62.
Rodrigues PR, Gonçalves SA, Vieira RP. Organocatalyzed β-pinene polymerization in UV light: Assessment of reaction conditions and material characterization. Eur Polym J. 2021;147:110303.
Ruberto G, Baratta MT. Antioxidant activity of selected essential oil components in two lipid model systems. Food Chem. 2000;69(2):167-174.
Salehi B, Upadhyay S, Orhan IE, Jugran AK, LD Jayaweera S, Dias AD, et al. Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature. Biomolecules. 2019;9(11):738.
Salido S, Altarejos J, Nogueras M, Sánchez A, Pannecouque C, Witvrouw M, et al. Chemical studies of essential oils of Juniperus oxycedrus ssp badia. J Ethnopharmacol. 2002;81(1):129-134.
Semerdjieva I, Zheljazkov VD, Radoukova T, Radanović D, Marković T, Dincheva I, et al. Essential oil yield, composition, bioactivity and leaf morphology of Juniperus oxycedrus L. from Bulgaria and Serbia. Biochem Syst Ecol. 2019;84:55-63.
Sezik E, Kocakulak E, Baser K, Ozek T. Composition of the essential oils of Juniperus oxycedrus Subsp. macrocarpa from Turkey. Chem Nat Com. 2005;41(3):352-354.
Silva ACR da, Lopes PM, Azevedo MMB de, Costa DCM, Alviano CS, Alviano DS. Biological Activities of a-Pinene and β-Pinene Enantiomers. Molecules. 2012;17(6):6305- 6316.
Stassi V, Verykokidou E, Loukis A, Harvala C, Philianos S. The antimicrobial activity of the essential oils of four Juniperus species growing wild in Greece. Flav Fragr J. 1996;11(1):71-74.
Tepe B, Sokmen M, Akpulat H A, Sokmen A. In vitro antioxidant activities of the methanol extracts of five Allium species from Turkey. Food Chem. 2005;92(1):89-92
Topçu G, Gören AC, Bilsel G, Bilsel M, Çakmak O, Schilling J, et al. Cytotoxic activity and essential oil composition of leaves and berries of Juniperus excels. J Pharm Biology. 2005;43(2):125-128.
Tsuda T, Ohshima K, Kawakishi S, Osawa T. Antioxidative pigments isolated from the seeds of Phaseolus Vulgaris L. J Agr Food Chem. 1994;42(2):248-251.
Velasco-Negueruela A, Perez-Alonso MJ, Pala-paul J, Inigo A. Essential oil analyses of the leaves and berries of Juniperus oxycedrus L. subsp. Badia (H. Gay) Debeaux. Botanica, Complutensis. 2003;27(27):147-54.
Wang W, Wu N, Zu YG, Fu YJ. Antioxidative activity of Rosmarinus officinalis L. essential oil compared to its main components. Food Chem. 2008;108(3):1019-1022.
FUNDING AND SUPPORT This research was funded by the Laboratory of Natural Substances, Pharmacology, Environment, Modeling, Health and Quality of Life, Department of Biology, Faculty of Sciences, Sidi Mohamed Ben Abdellah University, Fez, Morocco
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