The effect of extraction methods on the yields, chemical composition and antifungal activity of sawdust Cedrus atlantica Manetti essential oils

Abstract

The aim of this work is to determine the effect of the extraction method on the yield, the chemical composition, and the antifungal activity of cedarwood essential oils (EOs) from sawdust of Moroccan Cedrus atlantica (C. atlantica). EOs were extracted by different methods: hydrodistillation, soxhlet, maceration, and ultrasound. The chemical composition was determined using gas chromatography mass spectrometry (GC-MS) analysis. The yields of EOs were 5.60%, 11.68%, 4.82% and 9.33% for hydrodistillation, soxhlet, maceration and ultrasound, respectively. GC-MS revealed a diversity of chemical compounds depending on extraction methods. Indeed, the main compound of EOs obtained by soxhlet, maceration, and ultrasound was copalic acid methyl ester by a rate of 28.41%, 20.24%, and 24.17%, respectively. However, -himachalene (21.32%) followed by -himachalene (9.40%), β-Copaen-4α-ol (7.71%) and longifolene (6.74%) are the main compounds of EO extracted by hydrodistillation. The antifungal activity of cedarwood EO was tested in vitro on two pathogenic fungi: Fusarium culmorum (F. Culmorum) and Botrytis cineria (B. Cinerea). The minimum inhibitory concentration (MIC) was determined by successive dilutions of the stock solutions. The extracted EOs by soxhlet, maceration and ultrasound showed the important inhibitory effect against B. cinerea (MIC=1.25 mL/L). However, F. culmorum showed resistance towards all tested EOs. The finding of this study showed clearly that the volatile composition of EOs can be variable according to extraction. methods. Moreover, antifungal effects are depending on chemical composition of EOs but also to tested staris.

Keywords

• Cedrus atlantica
• Essential oils
• Fusarium culmorum
• Botrytis cinerea
• Antifungal activity

References

1. Aberchane, M., Fechtal, M., Chaouch, A., & Bouayoune, T. (2001). Influence de la durée et de la technique d’extraction sur le rendement et la qualité des huiles essentielles du cèdre de l’atlas (Cedrus atlantica Manetti) [Influence of duration and extraction technique on the yield and quality of essential oils of Atlas cedar (Cedrus atlantica Manetti)]. J Ann. Rech. For. Maroc, 34, 110-118.
2. Abers, M., Schroeder, S., Goelz, L., Sulser, A., St Rose, T., Puchalski, K., & Langland, J. (2021). Antimicrobial activity of the volatile substances from essential oils. BMC Complementary Medicine and Therapies, 21(1), 1-14
3. Ainane, A., Khammour, F., Charaf, S., Elabboubi, M., Elkouali, M., Talbi, M., ... & Ainane, T. (2019). Chemical composition and insecticidal activity of five essential oils: Cedrus atlantica, Citrus limonum, Rosmarinus officinalis, Syzygium aromaticum and Eucalyptus globules. Materials Today Proceedings, 13, 474 485. https://doi.org/10.1016/j.matpr.2019.04.004
4. Al-Rimawi, F., Jaradat, N., Qneibi, M., Hawash, M., & Emwas, N. (2020). Free radicals and enzymes inhibitory potentials of the traditional medicinal plant Echium angustifolium. European Journal of Integrative Medicine, 38, 101196.
5. Belkacem, N., Khettal, B., Hudaib, M., Bustanji, Y., Abu-Irmaileh, B., & Amrine, C.S.M. (2021). Antioxidant, antibacterial, and cytotoxic activities of Cedrus atlantica organic extracts and essential oil. European Journal of Integrative Medicine, 42, 101292.
6. Benkherara, S., Bordjiba, O., & Djahra, A.B. (2011). Etude de l’activité antibactérienne des huiles essentielles de la Sauge officinale: Salvia officinalis L. sur quelques entérobactéries pathogènes [Study of the antibacterial activity of essential oils of Sage officinalis: Salvia officinalis L. on some pathogenic enterobacteria]. Synthèse: Revue des Sciences et de la Technologie, 23, 72-80.
7. Bouchra, C., Mohamed, A., Mina, I.H., & Hmamouchi, M. (2003). Antifungal activity of essential oils from several medicinal plants against four postharvest citrus pathogens. Phytopathologia Mediterranea, 42, 251–256.
8. Bourkhiss, M., Hnach, M., Bourkhiss, B., Ouhssine, M., & Chaouch, A. (2007). Composition chimique et propriétés antimicrobiennes de l’huile essentielle extraite des feuilles de Tetraclinis articulata (Vahl) du Maroc [Chemical composition and antimicrobial properties of the essential oil extracted from the leaves of Tetraclinis articulata (Vahl) from Morocco]. Afrique Science: Revue Internationale des Sciences et Technologie, 3(2).

9. Bouyahia, C., Slaoui, M., Gouiti, M., Ouassor, I., Harhar, H., & El Hajjaji, S. (2022). Total phenolic, flavonoid contents and antioxidant activity of cedrus atlantica extracts. Polish Journal of Natural Sciences, 37(1), 63–74. https://doi.org/10.31648/pjns.7395
10. Bouzouita, N., Kachouri, F., Ben Halima, M., & Chaabouni, M.M. (2008). Composition chimique et activités antioxydante, antimicrobienne et insecticide de l’huile essentielle de Juniperus phoenicea [Chemical composition and antioxidant, antimicrobial and insecticidal activities of essential oil of Juniperus phoenicea]. Journal de la Société Chimique de Tunisie, 10, 119-125.
11. Chebli, B., Hmamouchi, M., Achouri, M., & Hassani, L.I. (2004). Composition and in vitro fungitoxic activity of 19 essential oils against two post-harvest pathogens. Journal of Essential Oil Research, 16(5), 507-511. https://doi.org/10.1080/10412905.2004.9698783
12. Da Porto, C., & Decorti, D. (2009). Ultrasound-assisted extraction coupled with under vacuum distillation of flavour compounds from spearmint (carvone-rich) plants: comparison with conventional hydrodistillation. Ultrasonics Sonochemistry, 16(6), 795 799. https://doi.org/10.1016/j.ultsonch.2009.03.010
13. Derwich, E., Benziane, Z., & Boukir, A. (2010b). Chemical composition and in vitro antibacterial activity of the essential oil of Cedrus atlantica. International Journal of Agriculture and Biology, 12(3), 381-385.
14. Derwich, E., Benziane, Z., Taouil, R., Senhaji, O., & Touzani, M. (2010a). Aromatic plants of morocco: GC/MS analysis of the essential oils of leaves of Mentha piperita. Advances in Environmental Biology, 80-86.
15. Duval, L. (2012). Les huiles essentielles à l’officine [Essential oils in the pharmacy]. [Doctoral dissertation, Rouen University].
16. El Guilli, M., Achbani, E., Fahad, K., & Jijakli, H. (2009, May). Biopesticides: Alternatives à la lutte chimique. In Symposium international “Agriculture durable en région Méditerranéenne (AGDUMED)”, Rabat, Maroc (14-16 mai) (pp. 266-280).
17. Emer, A.A., Donatello, N.N., Batisti, A.P., Belmonte, L.A.O., Santos, A.R., & Martins, D.F. (2018). The role of the endocannabinoid system in the antihyperalgesic effect of Cedrus atlantica essential oil inhalation in a mouse model of postoperative pain. Journal of ethnopharmacology, 210, 477-484. https://doi.org/10.1016/j.jep.2017.09.011
18. Fidah, A. (2016) Etude de la durabilité naturelle des bois de Cedrus atlantica (Manetti) et de Tetraclinis articulata (Vahl) et évaluation de la bioactivité de leurs huiles essentielles sur les champignons basidiomycètes lignivores [Study of the Natural Durability of Cedrus atlantica (Manetti) and Tetraclinis articulata (Vahl) Masters Woods and Evaluation of the Bioactivity of their Essential Oils on Basidiomycetes Lignivores]. [Doctoral dissertation, Mohammed V University].
19. Fitsiou, E., & Pappa, A. (2019). Anticancer activity of essential oils and other extracts from aromatic plants grown in Greece. Antioxidants, 8(8), 290.
20. Govrin, E.M., & Levine, A. (2000). The hypersensitive response facilitates plant infection by the necrotrophic pathogen Botrytis cinerea. Current Biology, 10(13), 751-757. https://doi.org/10.1016/S0960-9822(00)00560-1
21. Habybellah. W. (2016) Contrôle de la rouille jaune et la rouille brune du blé tendre par l’huile essentielle du Thym (Thymus satureioides) lors des deux campagnes agricoles 2014/2015 et 2015/2016 [Control of stripe rust and brown rust of common wheat by essential oil of thyme (Thymus satureioides) during the two agricultural campaigns 2014/2015 and 2015/2016]. [Master Thesis, Université Hassan Ier].
22. Huang, X.F., Chang, K.F., Lee, S.C., Sheu, G.T., Li, C.Y., Weng, J.C., ... & Tsai, N.M. (2020). Extract derived from Cedrus atlantica acts as an antitumor agent on hepatocellular carcinoma growth in vitro and in vivo. Molecules, 25(20), 4608.
23. Hung, P.H., Hsieh, M.C., Lee, S.C., Huang, X.F., Chang, K.F., Chen, S.Y., ... & Tsai, N.M. (2020). Effects of Cedrus atlantica extract on acute myeloid leukemia cell cycle distribution and apoptosis. Molecular Biology Reports, 47, 8935-8947.
24. Jaouadi, W., Mechergui, K., Ammari, Y., Hamrouni, L., Hanana, M., & Khouja, M.L. (2016). Étude ethnobotanique et ethnopharmacologique d’Acacia tortilis (Forssk) Hayne subsp. raddiana (Savi) de la steppe arborée du Nord de l'Afrique [Ethnobotanical and ethnopharmacological study of Acacia tortilis (Forssk) Hayne subsp. raddiana (Savi) from the wooded steppe of North Africa]. Phytothérapie, 14(5), 285-292. https://doi.org/10.1007/s10298-015-0951-1
25. Kang, Z., & Buchenauer, H. (2000). Cytology and ultrastructure of the infection of wheat spikes by Fusarium culmorum. Mycological Research, 104(9), 1083 1093. https://doi.org/10.1017/S0953756200002495
26. Kellouche, A., & Soltani, N. (2004). Activité biologique des poudres de cinq plantes et de l'huile essentielle d'une d'entre elles sur Callosobruchus maculatus (F.) [Biological activity of the powders of five plants and the essential oil of one of them on Callosobruchus maculatus (F.)]. International Journal of Tropical Insect Science, 24(2), 184 191. https://doi.org/10.1079/IJT200420
27. Kordali, S., Cakir, A., Ozer, H., Cakmakci, R., Kesdek, M., & Mete, E. (2008). Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene. Bioresource Technology, 99(18), 8788-8795. https://doi.org/10.1016/j.biortech.2008.04.048
28. Lahlou, M. (2003). Composition and molluscicidal properties of essential oils of five Moroccan Pinaceae. Pharmaceutical Biology, 41(3), 207 210. https://doi.org/10.1076/phbi.41.3.207.15097
29. Laib, I. (2012). Etude des activités antioxydante et antifongique de l’huile essentielle des fleurs sèches de Lavandula officinalis: application aux moisissures des légumes secs [Study of the antioxidant and antifungal activities of the essential oil of the dry flowers of Lavandula officinalis: application to the molds of pulses]. Revue Nature et Technologie, 4(2), 44-52. https://www.asjp.cerist.dz/en/article/41687
30. Lecompte, F., Abro, M.A., & Nicot, P.C. (2013). Can plant sugars mediate the effect of nitrogen fertilization on lettuce susceptibility to two necrotrophic pathogens: Botrytis cinerea and Sclerotinia sclerotiorum?. Plant and Soil, 369, 387-401
31. Li, Y.L., Yeung, C.M., Chiu, L.C., Cen, Y.Z., & Ooi, V.E.C. (2009). Chemical composition and antiproliferative activity of essential oil from the leaves of a medicinal herb, Schefflera heptaphylla. Phytotherapy Research, 23(1), 140-142. https://doi.org/10.1002/ptr.2567
32. Loizzo, M.R., Saab, A.M., Tundis, R., Statti, G.A., Menichini, F., Lampronti, I., ... & Doerr, H.W. (2008). Phytochemical analysis and in vitro antiviral activities of the essential oils of seven Lebanon species. Chemistry & Biodiversity, 5(3), 461 470. https://doi.org/10.1002/cbdv.200890045
33. Mancianti, F., & Ebani, V.V. (2020). Biological activity of essential oils. Molecules, 25(3), 678.
34. Moukrim, S., Lahssini, S., Rifai, N., Menzou, K., Mharzi-Alaoui, H., Labbaci, A., ... & Rhazi, L. (2020). Modelling the potential distribution of Cedrus atlantica Manetti in Morocco and impacts of climate change. Bois et Forets des Tropiques, 344, 3-16.
35. Nakamura, M.T., Endo, E.H., Sousa, J.P.B.D., Callejon, D.R., Ueda-Nakamura, T., Dias, B.P., ... & Lopes, N.P. (2017). Copaiba oil and its constituent copalic acid as chemotherapeutic agents against dermatophytes. Journal of the Brazilian Chemical Society, 28, 1377-1383. https://doi.org/10.21577/0103-5053.20160309
36. Newman, D.J., & Cragg, G.M. (2020). Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. Journal of Natural Products, 83(3), 770-803.
37. Pateiro, M., Barba, F.J., Domínguez, R., Sant'Ana, A.S., Khaneghah, A.M., Gavahian, M., ... & Lorenzo, J.M. (2018). Essential oils as natural additives to prevent oxidation reactions in meat and meat products: A review. Food Research International, 113, 156-166.
38. Rhafouri, R., Strani, B., Zair, T., Ghanmi, M., Aafi, A., El Omari, M., & Bentayeb, A. (2014). Chemical composition, antibacterial and antifungal activities of the Cedrus atlantica (Endl.) Manettiex Carrière seeds essential oil. Mediterranean Journal of Chemistry, 3(5), 1034-1043. https://doi.org/10.13171/mjc.3.5.2014.10.14.23.44
39. Ribeiro, V.P., Arruda, C., Abd El-Salam, M., & Bastos, J. K. (2018). Brazilian medicinal plants with corroborated anti-inflammatory activities: a review. Pharmaceutical Biology, 56(1), 253-268.
40. Stahl-Biskup, E., & Sáez, F. (Eds.). (2002). Thyme: the genus Thymus. CrC press.
41. Uwineza, M.S., Essahli, M., & Lamiri, A. (2016). Corrosion inhibition of aluminium in 2 M phosphoric acid using the essential oil of mentha pulegium leaves. Portugaliae Electrochimica Acta, 34(1), 53-62.
42. Tasei, J.N. (1996). Impact des pesticides sur les Abeilles et les autres pollinisateurs [Pesticide impact on honey bees and other pollinators]. Le Courrier de l'environnement de l'INRA, 29(29), 9-18.
43. Wang, H.W., Liu, Y.Q., Wei, S.L., Yan, Z.J., & Lu, K. (2010). Comparison of microwave-assisted and conventional hydrodistillation in the extraction of essential oils from mango (Mangifera indica L.) flowers. Molecules, 15(11), 7715 7723. https://doi.org/10.3390/molecules15117715
44. Yesil-Celiktas, O., Girgin, G., Orhan, H., Wichers, H.J., Bedir, E., & Vardar-Sukan, F. (2007). Screening of free radical scavenging capacity and antioxidant activities of Rosmarinus officinalis extracts with focus on location and harvesting times. European Food Research and Technology, 224, 443-451.
45. Yu, C.., Wang, W.X., Zhang, A.F., Gu., C.Y., Zhou, M.G., & Gao, T.C. (2011). Activity of the fungicide JS399-19 against Fusarium head blight of wheat and the risk of resistance. Agricultural Sciences in China, 10(12), 1906-1913. https://doi.org/10.1016/S1671-2927(11)60191-0
46. Zoubi, Y.E., Fouad, E.A., Farah, A., Taghzouti, K., & Lalami, A.E.O. (2017). Chemical composition and larvicidal activity of Moroccan atlas cedar (Cedrus atlantica Manetti) against Culex pipiens (diptera: culicidae). Journal of Applied Pharmaceutical Science, 7(7), 030-034. https://doi.org/10.7324/JAPS.2017.70704
47. Zrira, S., & Ghanmi, M. (2016). Chemical composition and antibacterial activity of the essential of Cedrus atlantica (Cedarwood oil). Journal of Essential Oil Bearing Plants, 19(5), 1267-1272. https://doi.org/10.1080/0972060X.2015.1137499