Chemical composition and antioxidant activities of essential oils and extracts from cones of Tetraclinis articulata (Vahl) Masters

Abstract

This study was carried out to evaluate the in vitro antioxidant activity and the chemical composition of essential oils and organic extracts of Moroccan Tetraclinis articulata cones (Khemisset region). The GC–MS analysis of essential oils identified a total 23 volatile components. The major constituents of the oil were α-pinene (18.33%), cis-verbenone (10.02%), and L-pinocarveol (8. 32%). For phytosterols analysis of hexane extract, β-sitosterol constitutes the majority with a percentage of 77.74%. The amount of total phenolic and flavonoid contents was high in the methanol extract (78.54±2.8 mg GAE / g and 41.11± 4.5 mg QE/g, respectively) and the Antioxidant capacity determined by DPPH method showed a strongest radical scavenging activity exhibition by the methanol extract (IC50=0.038±0.006 mg/mL). The results indicated that T. articulata contains bioactive compounds which are responsible for its antioxidant activity. Therefore, this plant could be potential candidates for the preparation of a natural antioxidant drug or an additive preparation.

Keywords

• Tetraclinis articulata
• Cones
• Essential oils
• Sterols
• Antioxidant activity

References

1. Ababsa, Z. E. A., Derouiche, M. T., Medjroubi, K., & Akkal, S. (2019). In-vivo Antidiarrhoeal and anti-ulcerative activities of the Tetraclinis articulata species of the Cupressaceae family. Acta Scientifica Naturalis, 6, 50‑53. https://doi.org/10.2478/asn-2019-0007
2. Ait Lahcen, S., El Hattabi, L., Benkaddour, R., Chahboun, N., Ghanmi, M., Satrani, B., Tabyaoui, M., & Zarrouk, A. (2020). Chemical composition, antioxidant, antimicrobial and antifungal activity of Moroccan Cistus Creticus leaves. Chemical Data Collections, 26, 100346. https://doi.org/10.1016/j.cdc.2020.100346
3. Bekro, Y.-A., Rosine, M., Allangba, A., Kadja, A., Guessennd, N., Kouadio, J., & Janat Akhanovna, M.-B. (2016). Etude phytochimique bio-guidée, activités antibactérienne et analgésique de décoctions éthanoliques d’une Mimosaceae de Côte d’Ivoire [ Bio-guided phytochemical survey, antibacterial and analgesic activities of ethanolic decoctions of a Mimosaceae from Côte d’Ivoire ]. 18, 2028‑9324.
4. Bensebia, B. (s. d.). Phytochemical analysis and assesment of antioxidant activity of Tetraclinis articulata (Vahl) Masters leaves. 1.
5. Boussaïd, M., Bekhechi, C., Atik-Bekkara, F., Paoli, M., Casanova, J., & Tomi, F. (2016). Composition and Chemical Variability of the Cone Oil from Algerian Tetraclinis articulata. Natural Product Communications, 11(8), 1934578X1601100834. https://doi.org/10.1177/1934578X1601100834
6. Buhagiar, J., Podestà, M. T. C., Cioni, P. L., Flamini, G., & Morelli, I. (2000). Essential Oil Composition of Different Parts of Tetraclinis articulata. Journal of Essential Oil Research, 12(1), 29‑32. https://doi.org/10.1080/10412905.2000.9712034
7. Calderón-Montaño, J. M., Martínez-Sánchez, S. M., Burgos-Morón, E., Guillén-Mancina, E., Jiménez-Alonso, J. J., García, F., Aparicio, A., & López-Lázaro, M. (2018). Screening for Selective Anticancer Activity of 65 Extracts of Plants Collected in Western Andalusia, Spain. https://doi.org/10.20944/preprints201806.0177.v1
8. Chikhoune, A., Hazzit, M., Kerbouche, L., Baaliouamer, A., & Aissat, K. (2013). Tetraclinis articulata (Vahl) Masters essential oils : Chemical composition and biological activities. Journal of Essential Oil Research, 25(4), 300‑307. https://doi.org/10.1080/10412905.2013.774625

9. Clevenger, J. F. (1928). Apparatus for the Determination of Volatile Oil*. The Journal of the American Pharmaceutical Association (1912), 17(4), 345‑349. https://doi.org/10.1002/jps.3080170407
10. Daoudi, A., Aarab, L., & Abdel-Sattar, E. (2013). Screening of immunomodulatory activity of total and protein extracts of some Moroccan medicinal plants. Toxicology and Industrial Health, 29(3), 245‑253. https://doi.org/10.1177/0748233711430972
11. Dassarma, B., Nandi, D. K., Gangopadhyay, S., & Samanta, S. (2018). Hepatoprotective effect of food preservatives (butylated hydroxyanisole, butylated hydroxytoluene) on carbon tetrachloride induced hepatotoxicity in rat. Toxicology Reports, 5, 31‑37.https://doi.org/10.1016/j.toxrep.2017.12.009
12. Djouahri, A., Saka, B., Boudarene, L., Benseradj, F., Aberrane, S., Aitmoussa, S., Chelghoum, C., Lamari, L., Sabaou, N., & Baaliouamer, A. (2014). In vitro synergistic/antagonistic antibacterial and anti-inflammatory effect of various extracts/essential oil from cones of Tetraclinis articulata (Vahl) Masters with antibiotic and anti-inflammatory agents. Industrial Crops and Products, 56, 60‑66. https://doi.org/10.1016/j.indcrop.2014.02.035
13. El-Shemy, H. (2020). Essential Oils : Oils of Nature. BoD – Books on Demand.
14. Fidah, A., Salhi, N., Janah, T., Rahouti, M., Kabouchi, B., El Alami, A., Ziani, M., & Famiri, A. (2016). Comparative natural durability of four Mediterranean softwoods against wood decay fungi. Journal of the Indian Academy of Wood Science, 13(2), 132‑137. https://doi.org/10.1007/s13196-016-0174-6
15. Hind, S.-J., Anas, F., & Lahcen, Z. (2017). Survey of Ethnomedicinal Plants Used for the Treatment of Gastrointestinal Disorders in Seksaoua Region (Western High Moroccan Atlas). Annual Research & Review in Biology, 1‑9. https://doi.org/10.9734/ARRB/2017/36112
16. Incalza, M. A., D’Oria, R., Natalicchio, A., Perrini, S., Laviola, L., & Giorgino, F. (2018). Oxidative stress and reactive oxygen species in endothelial dysfunction associated with cardiovascular and metabolic diseases. Vascular Pharmacology, 100, 1‑19. https://doi.org/10.1016/j.vph.2017.05.005
17. ISO 6799. (1991). Determination of the sterol fraction by gas chromatography.
18. Jamshidi-kia, F., Wibowo, J. P., Elachouri, M., Masumi, R., Salehifard-Jouneghani, A., Abolhasanzadeh, Z., & Lorigooini, Z. (2020). Battle between plants as antioxidants with free radicals in human body. Journal of Herbmed Pharmacology, 9(3), 191‑199.
19. Jensen, W. B. (2007, décembre 1). The Origin of the Soxhlet Extractor (world) [Research-article]. ACS Publications; Division of Chemical Education. https://doi.org/10.1021/ed084p1913
20. Jlizi, S., Zardi-Bergaoui, A., Znati, M., Flamini, G., Ascrizzi, R., & Ben Jannet, H. (2018). Chemical composition and biological evaluation of the resin from Tetraclinis articulata (Vahl.) Masters : A promising source of bioactive secondary metabolites. Industrial Crops and Products, 124, 74‑83. https://doi.org/10.1016/j.indcrop.2018.07.055
21. Kapoor, D., Singh, S., Kumar, V., Romero, R., Prasad, R., & Singh, J. (2019). Antioxidant enzymes regulation in plants in reference to reactive oxygen species (ROS) and reactive nitrogen species (RNS). Plant Gene, 19, 100182. https://doi.org/10.1016/j.plgene.2019.100182
22. Karumi, Y., Onyeyili, P.A., & Ogugbuaja, V.O, (2004). Identification of Active Principles of M. balsamina (Balsam Apple) Leaf Extract. Journal of Medical Sciences, 4. https://doi.org/10.3923/jms.2004.179.182
23. Koczurkiewicz, P., Czyż, J., Podolak, I., Wójcik, K., Galanty, A., Janeczko, Z., & Michalik, M. (2015). Multidirectional effects of triterpene saponins on cancer cells-Mini-review of in vitro studies. Acta Biochimica Polonica, 62(3), Article 3. https://ojs.ptbioch.edu.pl/index.php/abp/article/view/1740
24. Kouider, H., & Assia, L. (2017). Synthèse bibliographique sur le thuya de berbérie [Tetraclinis articulata (Vahl) Mast.]. Geo-Eco-Trop, 41, 13‑27.
25. Liu, R., & Mabury, S. A. (2020). Synthetic Phenolic Antioxidants : A Review of Environmental Occurrence, Fate, Human Exposure, and Toxicity. Environmental Science & Technology, 54(19), 11706‑11719. https://doi.org/10.1021/acs.est.0c05077
26. Lopes-Lutz, D., Alviano, D. S., Alviano, C. S., & Kolodziejczyk, P. P. (2008). Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils. Phytochemistry, 69(8), 1732‑1738. https://doi.org/10.1016/j.phytochem.2008.02.014
27. Madkour, L. H. (2020). RETRACTED CHAPTER : Sources of Oxidants and Function of ROS Inside the Macromolecule Cells. In L. H. Madkour (Éd.), RETRACTED BOOK Nanoparticles Induce Oxidative and Endoplasmic Reticulum Stresses : Antioxidant Therapeutic Defenses (p. 99‑138). Springer International Publishing. https://doi.org/10.1007/978-3-030-37297-2_3
28. Massy, Z. A., & Nguyen-Khoa, T. (2002). Oxidative stress and chronic renal failure : Markers and management. Journal of Nephrology, 15(4), 336‑341.
29. Mitra, A. K. (2020). Antioxidants : A Masterpiece of Mother Nature to Prevent Illness. Journal of Chemical Reviews, 2(4), 243‑256. https://doi.org/10.22034/jcr.2020.112730
30. Mojab, F., Kamalinejad, M., Ghaderi, N., & Vahidipour, H. R. (2010). Phytochemical Screening of Some Species of Iranian Plants. Iranian Journal of Pharmaceutical Research, 0(Number 2), 77‑82. https://doi.org/10.22037/ijpr.2010.16
31. N’Guessan, K., Kadja, B., Zirihi, G., Traoré, D., & Aké-Assi, L. (2009). Screening phytochimique de quelques plantes médicinales ivoiriennes utilisées en pays Krobou (Agboville, Côte d’Ivoire). Sciences & Nature, 6(1), Article 1. https://doi.org/10.4314/scinat.v6i1.48575
32. Park, H. S., Chun, J. N., Jung, H. Y., Choi, C., & Bae, Y. S. (2006). Role of NADPH oxidase 4 in lipopolysaccharide-induced proinflammatory responses by human aortic endothelial cells. Cardiovascular Research, 72(3), 447‑455. https://doi.org/10.1016/j.cardiores.2006.09.012
33. Quettier-Deleu, C., Gressier, B., Vasseur, J., Dine, T., Brunet, C., Luyckx, M., Cazin, M., Cazin, J.-C., Bailleul, F., & Trotin, F. (2000). Phenolic compounds and antioxidant activities of buckwheat (Fagopyrum esculentum Moench) hulls and flour. Journal of Ethnopharmacology, 72(1), 35‑42. https://doi.org/10.1016/S0378-8741(00)00196-3
34. Rabib, H., Elagdi, C., Hsaine, M., Fougrach, H., Koussa, T., & Badri, W. (2020). Antioxidant and Antibacterial Activities of the Essential Oil of Moroccan Tetraclinis articulata (Vahl) Masters. Biochemistry Research International, 2020, e9638548. https://doi.org/10.1155/2020/9638548
35. Rached, W., Zeghada, F. Z., Bennaceur, M., Barros, L., Calhelha, R. C., Heleno, S., Alves, M. J., Carvalho, A. M., Marouf, A., & Ferreira, I. C. F. R. (2018). Phytochemical analysis and assessment of antioxidant, antimicrobial, anti-inflammatory and cytotoxic properties of Tetraclinis articulata (Vahl) Masters leaves. Industrial Crops and Products, 112, 460‑466. https://doi.org/10.1016/j.indcrop.2017.12.037
36. Račková, L., Májeková, M., Košt’álová, D., & Štefek, M. (2004). Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorganic & Medicinal Chemistry, 12(17), 4709‑4715. https://doi.org/10.1016/j.bmc.2004.06.035
37. Saber, M., Hicham, H., Bouyahya, A., Ouchbani, T., & Tabyaoui, M. (2021). Chemical Composition and Antioxidant Activity of Essential Oil of Sawdust from Moroccan Thuya (Tetraclinis articulata (Vahl) Masters. Biointerface Research in Applied Chemistry, 11, 7912‑7920. https://doi.org/10.33263/BRIAC111.79127920
38. Sadiki, F. Z., Idrissi, M. E., Cioanca, O., Trifan, A., Hancianu, M., Hritcu, L., & Postu, P. A. (2019). Tetraclinis articulata essential oil mitigates cognitive deficits and brain oxidative stress in an Alzheimer’s disease amyloidosis model. Phytomedicine, 56, 57‑63. https://doi.org/10.1016/j.phymed.2018.10.032
39. Singleton, V. L., Orthofer, R., & Lamuela-Raventós, R. M. (1999). [14] Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent. In Methods in Enzymology (Vol. 299, p. 152‑178). Academic Press. https://doi.org/10.1016/S0076-6879(99)99017-1
40. Soleimanian, Y., Goli, S. A. H., Varshosaz, J., Di Cesare Mannelli, L., Ghelardini, C., Cirri, M., & Maestrelli, F. (2020). β-Sitosterol Loaded Nanostructured Lipid Carrier : Physical and Oxidative Stability, In Vitro Simulated Digestion and Hypocholesterolemic Activity. Pharmaceutics, 12(4), 386. https://doi.org/10.3390/pharmaceutics12040386
41. Sosa, V., Moliné, T., Somoza, R., Paciucci, R., Kondoh, H., & LLeonart, M. E. (2013). Oxidative stress and cancer : An overview. Ageing Research Reviews, 12(1), 376‑390. https://doi.org/10.1016/j.arr.2012.10.004
42. Teixidor-Toneu, I., Martin, G. J., Puri, R. K., Ouhammou, A., & Hawkins, J. A. (2017). Treating infants with frigg : Linking disease aetiologies, medicinal plant use and care-seeking behaviour in southern Morocco. Journal of Ethnobiology and Ethnomedicine, 13(1), 4. https://doi.org/10.1186/s13002-016-0129-4
43. Tsouli Faroukh, A., Tellal, R., & Qarro, M. (2017). Analysis of socio-economic mutations in the Benslimane forest Lever for sustainable development (Province of Benslimane, Morocco. Journal of Materials and Environmental Sciences, 8(12), 4415‑4425. https://doi.org/10.26872/jmes.2017.8.12.466
44. Uttara, B., Singh, A. V., Zamboni, P., & Mahajan, R. T. (2009). Oxidative Stress and Neurodegenerative Diseases : A Review of Upstream and Downstream Antioxidant Therapeutic Options. Current Neuropharmacology, 7(1), 65‑74.
45. Yang, X., Song, W., Liu, N., Sun, Z., Liu, R., Liu, Q. S., Zhou, Q., & Jiang, G. (2018). Synthetic Phenolic Antioxidants Cause Perturbation in Steroidogenesis in Vitro and in Vivo. Environmental Science & Technology, 52(2), 850‑858. https://doi.org/10.1021/acs.est.7b05057