ISSN: 2665-8488 JOURNAL OF ANALYTICAL SCIENCES AND APPLIED BIOTECHNOLOGY 2020, Vol. 2, Issue (2) An International Open Access, Peer Reviewed Research Journal Pages: 67-72

Biotechnology

Chemical characterization of essential oil of Artemisia herba-alba asso and his possible potential against covid-19

Ali ASDADI1*, Aicha HAMDOUCH1, Said GHARBY2, Lalla Mina IDRISSI HASSANI1

1Laboratory of Plant Biotechnology, Planta Sud team, Faculty of Sciences of , Ibn Zohr University, B.P 28 / S, Agadir, 2Laboratory Biotechnology, Materials and Environment (LBME), Faculty Polydisciplinary of , University Ibn Zohr, Morocco

ARTICLE INFO ABSTRACT Received June 5th, 2020 In this work, we studied the chemical composition of the essential oil obtained by Received in revised form June 25th, 2020 Accepted July 1st, 2020 hydrodistillation from the aerial parts of Artemisia herba-alba Asso growing wild in in Morocco. The oil yield was 0,71% based on dry weight. Chemical analysis by GC / MS identified twenty-five constituents representing 98.43% of Keywords: the essential oil. Chrysanthenone (39.67%) was the main component of A. Herba- Artemisia herba-alba Asso, alba Asso. Moreover, a high content of oxygenated monoterpenes characterizes Asteraceae, Essential oil composition, this essential oil. This suggests that it has biological activities, namely antiviral Chemotypes, activities of at least one of its constituents. Hence the idea of proposing the plant COVID-19. for scientific research as a potential source of antiviral molecules against COVID- 19.

© 2020 EST-Khenifra, University of Sultan Moulay Slimane. All rights reserved.

1. Introduction: COVID-19, launched in December 2019 in Wuhan in China. It is manifested by a severe acute respiratory syndrome caused by an emerging SARS-CoV-2 virus. Today the WHO declares it as a pandemic. SARS-CoV-2 is highly contagious, it has caused significant morbidity and mortality [1,2]. As of May 29, 2020, the number of people infected worldwide was 5,701,337 cases with 357,688 deaths [3]. To date, no approved vaccine or treatment are available for SARS-CoV-2. COVID- 19 is therefore a big challenge for scientists to find an antiviral agent to treat it. Researchers are working to find antiviral agents, some of which are natural products: ritonavir, chloroquine phosphate, arbidol, ribavirin and traditional Chinese medicines that have shown preliminary efficacy against SARS-CoV [4]. Essential oils have shown promising antiviral activity against several pathogenic viruses, including those from the flu and other viral respiratory infections [5]. Indeed, many recent plant species have been the subject of much research. Their secondary metabolites have been retained as natural antivirals for the management of COVID-19 [6].Thus a study carried out on several components of essential oils using molecular docking analysis with the main protease SARS-CoV-2 in order to find an alternative drug capable of blocking the activity of the converting enzyme angiotensin 2 (ACE2) as a receptor for SARS-COV-2, a potential therapeutic target for COVID-19. Moreover, he has shown that these secondary metabolites can act synergistically, essential oils can therefore potentiate other antiviral agents against COVID-19 [5,7]. Similarly, another study found that isothymol is a functional inhibitor of ACE2 activity, suggesting that the components of the essential oil can be used as potential inhibitors of the ACE2 of SARS-CoV-2 receptor [8]. Due to the activities of several essential oils and essential oil components against human pathogenic viruses, we hypothesized that the components of Artemisia herba alba Asso essential oils potential antiviral agents for SARS-CoV-2. The World Health Organization (WHO) welcomes innovations from traditional pharmacopeia and the development of new therapies in the search for potential treatments for coronavirus 2019 disease (COVID-19) [9].

(* )Corresponding author. Tel.: +212 6 61 093 000 E-mail address: [email protected]

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Artemisia herba-alba Asso is used as an infusion in tea and in traditional medicine to treat colds, coughs, intestinal disorders and diabetes [10]. Scientific research on the medicinal properties of extracts of A. Herba alba have revealed anti-diabetic, leishmanicidal, anti-bacterial, anti-fungal, mutagenic, anti-mutagenic and antioxidant properties [11-20]. The white wormwood (Artemisia herba-alba) "Chih" is part of Artemisia genus containing over 450 species [21,22], spread over five continents. This seems to be of great economic interest in Morocco, which holds 90% of the world market for essential oil extracted from the plant [23]. This plant is one of the species that is widely used in classical medicine. In Morocco, it is represented by 19 species [24], the most important of which are: Artemisia alba sub sp. chitachensis, A. atlantica var. maroccana, A. flahauti, A. mesatlantica, A. negrei, A. ifranensis, A. herba-alba, A. arborescens and A. absinthium. This agent is inexpensive and readily available and will be of great value if it is effective against SARS-CoV-2, so scientific efforts are needed to try to find a treatment for COVID-19.

2. Materials and methods: 2.1. Plant materials: The sample of A. herba-alba Asso was collected in June 2015 near the Tafingoult village (30°46'44.0"N 8°23'50.0"W) in the Province of Taroudant (Morocco).The plant material consisted in the whole aerial parts formed by stems and flowers. Taxonomic identification of the species was confirmed and deposited in the Biotechnology Laboratory and Natural Resource Valuation of University Ibn Zohr, Planta Sud unity at Faculty of Sciences in Ibn Zohr University, Agadir, Morocco. 2.2. Oil isolation: Air-dried plant material was ground and hydrodistilled for 3 h using a Clevenger-type apparatus according to the European Pharmacopoeia [25-27]. The obtained essential oil was weighed, filtrated on anhydrous sodium sulfate, and kept in an amber vial at 4°C until used. 2.3. Gas chromatography/mass spectrometry (GC/MS) analysis of essential oils: The chemical compositions of essentials oils were analyzed using a gas chromatograph (TRACE GC Ultra) fitted to a mass spectrometer (Polaris Q-Ion Trap MS). Operating in electron impact EI (70 eV) mode. VB-5 (Methylpolysiloxane 5% phenyl) and a column (30m x 0.25mm x 0.25µm thickness) were used (National Center for Scientific research and Technology (CNRST), Rabat, Morocco). The chromatographic conditions were as follows: Injector and detector temperatures at 220 and 300°C, respectively; carrier gas, helium at flow rate of 1.4 ml/min; temperature program ramp from 40 to 300°C with gradient of 4°C/min (holding the initial and final temperature for 4 min). The relative amount of individual components of the total essential oil was expressed as a percentage of peak area relative to the total peak area. Library search was carried out using the combination of data already available in the NIST 2005 and Mass Spectral Library in the literature [28].

3. Results and discussion: Table 1 shows the qualitative and quantitative compositions of the oil analysed. Namely, it shows percentage compositions as well as the identities of compounds present in the essential oils of Artemisia herba-alba Asso. The yield of the essential oils (EOs) was 0,71% (v/w), calculated on a dry weight basis. Chemical composition of the EOs of Artemisia herba-alba Asso., was determined by GC/MS analyzes. The average yield obtained from essential oils extracted from the Artemisia herba-alba Asso plant studied is around 0.71%. This rate is relatively lower than that of the HE extracted from the same species collected in the region of Amskroud in Morocco (1.8%) [29], of Biskra (0.95%) [30], of M'sila ( 1.02%) [31] ] in Algeria and that of Jordan (1.3%) [32]. On the other hand, the essential oil yield of the species Artemisia herba-alba varies according to the harvest period in the Guerçif region in Morocco; it is between 0.56% and 1.23% [33]. in Spain, it varies according to source, from 0.41% to 2.30% [34]. The components of the essential oil were identified by GC-MS analyzes. This study identified 25 constituents (representing 98.43% of essential oil). Furthermore, among the 300 volatile compounds reported in the literature [35], a large number of them have not been detected in the present work. The chromatographic analyzes of essential oils extracted (Tab. 1) have highlighted the predominance of the two oxygenated monoterpenes: chrysanthenone (39.67%) and camphor (13.34%). Some monoterpenes are present with relatively large percentages as α-thujone (12,87%), β-thujone (11.5%) and 1,8-cineol (4.3%). Other constituents are minor: tricyclene (0.11%), Sabinene (0.13%) and α-terpinene (0.37%). Similar observations have been made by Paolini et al. [36] with 16 samples from Eastern Morocco, of which chrysanthenone, camphor, L’α- and β-thujone are the main compounds. In addition, other authors have highlighted camphor (49.3%) in essential oils from the north of Algerian ’s, while chrysanthenone (3.2%) remaining minor in these extracts [37]. However, some secondary chemical elements in this study have been described by other researchers as the majority of A. herba-alba essential oil’s. This is case for α-thujone, the main constituent of HE extracted by Paolini et al. (2010) [36] and those obtained by Sbayou et al. [38] in Taroudant in Morocco.

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Table 1: Chemical composition of the essential oil of Artemisia herba-alba Asso. By GC/MS analyses: Compounds Percentage tricyclène 0,11 α-thujène 0,21 α-pinène * 1,92 camphène 2,83 β-pinène 0,71 Sabinene 0,13 p-Cymene* 1,04 1,8-Cineole* 4,3 myrcène 0,11 α-terpinène * 0,37 limonène 0,93 γ-terpinène * 0,39 α-thujone 12,87 β-thujone 11,5 Nopol 0,5 chrysanthenone 39,67 camphre 13,34 terpinen-4-ol * 1,3 α-terpinéol * 0,22 α -terpin-7-al 0,38 β-elemène 1,96 β-germacrène 1,37 α-munrolène 0,41 germacrène D-4-ol 1,07 davanone 0,79 Total identified 98,43 Yield of essential oils (%) 0,71%

In addition, cis-chrysanthenyl acetate, which is considered to be the majority constituent of Biskra's HE in Algeria, is absent, for example, in our samples [30]. It seems that the species A. herba-alba is characterized by significant intra-specific variability in the chemical profile of its essential oils. Thus, the chrysanthenone-camphor (present work), α-thujone-camphor [39], camphor, thujone [36,39,40], chrysanthenone [36], davanone [40,41] chemotypes cis-chrysanthenyl acetate [40] are described in Morocco; those with 1,8- cineole and cis-chrysanthenol in Egypt; chrysanthenone [35] in Algeria; camphor is found in sagebrushes of the four countries: Morocco, Egypt, Algeria and Spain. The davanone, 1,8-cineole, chrysanthenone, cis-chrysanthenol and cis- chrysanthenyl acetate chemotypes are found in other Mediterranean areas [40,42]. The intra-specific variability existing within the species A. herba-alba can be of geographic, genetic [43], seasonal [33] or even ecological (soil, humidity, etc.) origin [36,43,44]. One of the most popular plants in traditional Chinese preparations is the Artemisia species, which are widespread around the world and are frequently used for the treatment of diseases such as malaria, hepatitis, cancer, inflammation and fungal, bacterial and viral infections. Extensive studies of the chemical components and essential oils of Artemisia have led to the identification of many very interesting compounds [45]. Indeed, bioactive compounds present in Artemisia annua are active against, the hepatitis B virus, the bovine viral diarrhea virus and the Epstein-Barr virus [46]. Also, A. annua has shown significant activity against the SARS coronavirus which appeared in 2002 [47]. Since these components extracted from A.annua are not expensive and readily available, they will be of great value if they are effective against SARS-CoV-2. Scientific attention is therefore needed towards Artemisia species to find an effective treatment for COVID-19. So far, there are no effective vaccines or antiviral agents against coronavirus infections, so it is a challenge for scientists to find an antiviral agent to treat this disease. Hence, our proposal for Artemeisia herba-alba as a source of active ingredients that may have activity against SARS-COV- 2. Indeed, some authors have demonstrated that the antiviral activity of essential oils is attributed to their majority components [48]. In other words, the components of our essential oil extracted from Artemisia herba_alba Asso. Namely: α-pinene, p-Cymene, 1,8-Cineole, α-terpinene, γ-terpinene, terpinen-4-ol and α-terpineol have shown anti-viral action against herpes simplex virus type 1 which is dose dependent as components alone or as part of essential oils [49]. In fact, oils rich in components such as α-terpineol and camphene have shown antiviral activities in vitro on various viruses [5,49-55]. Other studies based on molecular docking analysis performed on several components of essential oils to look for possible drugs 69

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capable of blocking the activity of the receptor for the angiotensin converting enzyme 2 (ACE2) of SARS -COV-2 have shown that the constituents of some essential oils can potentiate conventional antiviral agents and thus relieve the symptoms of COVID-19 as is the case for limonene, p-cymene and γ -terpinene [5,7], while other constituents even inhibited the ACE2 receptor for SARS-COV -2 [8]. Hence the idea that our essential oil extracted from A.herba-alba Asso. may have antiviral activity on SARS COV-2. If essential oils and their constituents had activities against human pathogenic viruses. So necessarily, the total essential oil of A.herba-alba Asso., One or all of its constituents could be potential antiviral agents against SARS-COV-2. In addition, it could then be used as an antiviral drug alone, as a potentiator of another conventional antiviral drug or at least as a dietary supplement to relieve symptoms or strengthen the immune system of affected patients, or even its use as an adjuvant in solutions hydro-alcoholic or hydro-alcoholic gels to increase their effectiveness in the external fight against COVID-19. Clinical studies are needed to assess the efficacy and safety and to provide clinical evidence for traditional medicine. Integrating traditional medicine into conventional treatment could be an alternative approach for the treatment of COVID- 19 in the future.

4. CONCLUSION This study revealed the chemical composition of the essential oils of A. Herba-alba Asso from the Tafengoult locality of Taroudant in Morocco. The sample had a chemical composition similar to that published for A. herba-alba oils from different countries but had an original chemical composition. Indeed, the composition of the essential oil of wild A. Herba-alba indicates that the oil belongs to the chrysanthenone / camphor / thujones / 1,8-cineole chemotype, so rich in oxygenated monoterpenes which have demonstrated in previous studies their antifungal, antibacterial and antiviral properties. However, toxicological and clinical studies are needed to prove the safety of the oil as a drug. Hence the idea of proposing the plant for scientific purposes as a potential source of antiviral molecules against COVID-19.

References: 1. Lai, C. C., Shih, T. P., Ko, W. C., Tang, H. J., & Hsueh, P. R. (2020). Severe acute respiratory syndrome coronavirus 2 (SARS- CoV-2) and corona virus disease-2019 (COVID-19): the epidemic and the challenges. International journal of antimicrobial agents, 105924. 2. Yang, X., Yu, Y., Xu, J., Shu, H., Liu, H., Wu, Y., ... & Wang, Y. (2020). Clinical course and outcomes of critically ill patients with SARS-CoV-2 pneumonia in Wuhan, China: a single-centered, retrospective, observational study. The Lancet Respiratory Medicine. 3. WHO. Coronavirus disease 2019 (COVID-19) Situation Report-131. Available online: https://www.who.int/docs/default- source/coronaviruse/situation-reports/ ( accessed on 30 Mai 2020). 2020. 4. Alami, A. E., Fattah, A., Chait, A. (2020) Medicinal plants used for the prevention purposes during the covid-19 pandemic in Morocco. Journal of Analytical Sciences and Applied Biotechnology, 2(1), 4-11. 5. da Silva, J. K. R., Figueiredo, P. L. B., Byler, K. G., & Setzer, W. N. (2020). Essential Oils as Antiviral Agents, Potential of Essential Oils to Treat SARS-CoV-2 Infection: An In-Silico Investigation. International Journal of Molecular Sciences, 21(10), 3426. 6. Yang, Y., Islam, M. S., Wang, J., Li, Y., & Chen, X. (2020). Traditional Chinese medicine in the treatment of patients infected with 2019-new coronavirus (SARS-CoV-2): a review and perspective. International journal of biological sciences, 16(10), 1708. 7. Ang, L., Lee, H. W., Choi, J. Y., Zhang, J., & Lee, M. S. (2020). Herbal medicine and pattern identification for treating COVID- 19: a rapid review of guidelines. Integrative Medicine Research, 100407. 8. In silico study the inhibition of Angiotensin converting enzyme 2 receptor of COVID-19 by Ammoides verticillata components harvested from western Algeria, Journal of Biomolecular Structure and Dynamics, 2020(just-accepted): p. 1-17. 9. Ainane, T. (2020). Moroccan traditional treatment for fever and influenza, similar to symptoms of coronavirus COVID-19 disease: Mini Review. Journal of Analytical Sciences and Applied Biotechnology, 2(1), 1-3. 10. Aydın, T., Yurtvermez, B., Şentürk, M., Kazaz, C., & Çakır, A. (2019). Inhibitory effects of metabolites isolated from Artemisia dracunculus L. against the human carbonic anhydrase I (hCA I) and II (hCA II). Records of Natural Products, 13(3), 225. 11. Yashphe, J., Segal, R., Breuer, A., & Erdreich‐Naftali, G. (1979). Antibacterial activity of Artemisia herba‐alba. Journal of pharmaceutical sciences, 68(7), 924-925. 12. Al-Shamaony, L., Al-Khazraji, S. M., & Twaij, H. A. (1994). Hypoglycaemic effect of Artemisia herba alba. II. Effect of a valuable extract on some blood parameters in diabetic animals. Journal of ethnopharmacology, 43(3), 167-171. 13. Al-Khazraji, S. M., Al-Shamaony, L. A., & Twaij, H. A. (1993). Hypoglycaemic effect of Artemisia herba alba. I. Effect of different parts and influence of the solvent on hypoglycaemic activity. Journal of ethnopharmacology, 40(3), 163-166. 14. Hatimi, S., Boudouma, M., Bichichi, M., Chaib, N., & Idrissi, N. G. (2001). Evaluation in vitro de l’activité antileishmanienne d’Artemisia herba-alba Asso. Bull Soc Pathol Exot, 94, 29-31. 15. Tahraoui, A., El-Hilaly, J., Israili, Z. H., & Lyoussi, B. (2007). Ethnopharmacological survey of plants used in the traditional treatment of hypertension and diabetes in south-eastern Morocco (Errachidia province). Journal of ethnopharmacology, 110(1), 105-117.

70

Journal of Analytical Sciences and Applied Biotechnology Asdadi et al.

16. Djeridane, A., Yousfi, M., Nadjemi, B., Boutassouna, D., Stocker, P., & Vidal, N. (2006). Antioxidant activity of some Algerian medicinal plants extracts containing phenolic compounds. Food chemistry, 97(4), 654-660. 17. Saleh, M. A., Belal, M. H., & El-Baroty, G. (2006). Fungicidal activity of Artemisia herba alba Asso (Asteraceae). Journal of Environmental Science and Health Part B, 41(3), 237-244. 18. Megdiche-Ksouri, W., Trabelsi, N., Mkadmini, K., Bourgou, S., Noumi, A., Snoussi, M., ... & Ksouri, R. (2015). Artemisia campestris phenolic compounds have antioxidant and antimicrobial activity. Industrial Crops and Products, 63, 104-113. 19. Kordali, S., Kotan, R., Mavi, A., Cakir, A., Ala, A., & Yildirim, A. (2005). Determination of the chemical composition and antioxidant activity of the essential oil of Artemisia dracunculus and of the antifungal and antibacterial activities of Turkish Artemisia absinthium, A. dracunculus, Artemisia santonicum, and Artemisia spicigera essential oils. Journal of agricultural and food chemistry, 53(24), 9452-9458. 20. Talbi, M., Saadali, B., Boriky, D., Bennani, L., Elkouali, M. H., & Ainane, T. (2016). Two natural compounds–a benzofuran and a phenylpropane–from Artemisia dracunculus. Journal of Asian natural products research, 18(8), 724-729. 21. Jung, U. J., Baek, N. I., Chung, H. G., Bang, M. H., Yoo, J. S., Jeong, T. S., ... & Yeo, J. Y. (2007). The anti-diabetic effects of ethanol extract from two variants of Artemisia princeps Pampanini in C57BL/KsJ-db/db mice. Food and Chemical Toxicology, 45(10), 2022-2029. 22. Yin, Y., Gong, F. Y., Wu, X. X., Sun, Y., Li, Y. H., Chen, T., & Xu, Q. (2008). Anti-inflammatory and immunosuppressive effect of flavones isolated from Artemisia vestita. Journal of Ethnopharmacology, 120(1), 1-6. 23. Saadali, B., Boriky, D., Blaghen, M., Vanhaelen, M., & Talbi, M. (2001). Alkamides from Artemisia dracunculus. Phytochemistry, 58(7), 1083-1086. 24. Boriky, D., Berrada, M., Talbi, M., Keravis, G., & Rouessac, F. (1996). Eudesmanolides from Artemisia herba- alba. Phytochemistry, 43(1), 309-311. 25. 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. 26. Council of Europe, European Pharmacopoeia, D. 3rd ed, Editor. 1997. 27. Ainane, T., Askaoui, Z., Elkouali, M., Talbi, M., Lahsasni, S., Warad, I., & Hadda, T. B. (2014). Chemical composition and antibacterial activity of essential oil of Nigella sativa seeds from Beni Mellal (Morocco): What is the most important part, Essential Oil or the rest of seeds. Journal of Materials and Environmental Science, 5(6), 2017-2020. 28. Ainane, T., Elkouali, M., Ainane, A., & Talbi, M. (2014). Moroccan traditional fragrance based essential oils: Preparation, composition and chemical identification. Der Pharma Chemica, 6(6), 84-89. 29. Aljaiyash, A., Kasrati, A., Jamali, C. A., & Chaouch, A. (2018). Effect of cultivation on chemical composition and bioactivities of essential oils from Artemisia herba-alba Asso grown in Morocco. Biochemical Systematics and Ecology, 81, 74-79. 30. Bezza, L., Mannarino, A., Fattarsi, K., Mikail, C., Abou, L., Hadji-Minaglou, F., & Kaloustian, J. (2010). Composition chimique de l’huile essentielle d’Artemisia herba-alba provenant de la région de Biskra (Algérie). Phytothérapie, 8(5), 277-281. 31. Dob, T., & Benabdelkader, T. (2006). Chemical composition of the essential oil of Artemisia herba-alba Asso grown in Algeria. Journal of Essential Oil Research, 18(6), 685-690. 32. Hudaib, M. M., & Aburjai, T. A. (2006). Composition of the essential oil from Artemisia herba-alba grown in Jordan. Journal of Essential Oil Research, 18(3), 301-304. 33. Ghanmi, M., Satrani, B., Aafi, A., Isamili, M. R., Houti, H., El Monfalouti, H., ... & Chaouch, A. (2010). Effet de la date de récolte sur le rendement, la composition chimique et la bioactivité des huiles essentielles de l’armoise blanche (Artemisia herba- alba) de la région de Guerçif (Maroc oriental). Phytothérapie, 8(5), 295-301. 34. Salido, S., Altarejos, J., Nogueras, M., & Sánchez, A. (2001). Chemical composition of the essential oil of Artemisia herba-alba Asso ssp. valentina (Lam.) Marcl. Journal of Essential Oil Research, 13(4), 221-224. 35. Vernin, G., & Merad, L. O. (1994). Mass spectra and Kovats indices of some new cis-chrysanthenyl esters found in the essential oil of Artemisia herba alba from Algeria. Journal of Essential Oil Research, 6(4), 437-448. 36. Paolini, J., Bouyanzer, A., Hammouti, B., Desjobert, J. M., Costa, J., & Muselli, A. (2010). Chemical variability of Artemisia herba-alba Asso essential oils from East Morocco. Chemical papers, 64(5), 550-556. 37. Dahmani-Hamzaoui, N., & Baaliouamer, A. (2010). Chemical composition of Algerian Artemisia herba-alba essential oils isolated by microwave and hydrodistillation. Journal of Essential Oil Research, 22(6), 514-517. 38. Sbayou, H., Ababou, B., Boukachabine, K., Manresa, A., Zerouali, K., & Amghar, S. (2014). Chemical composition and antibacterial activity of artemisia herba-alba and mentha pulegium essential oils. Journal of Life Sciences, 8(1), 35-41. 39. Benjilali, B., & Richard, H. (1980). Study of some populations of Artemisia herba alba from Morocco. Riv. ltal. Essen, 62, 69- 74. 40. Salido, S., Valenzuela, L. R., Altarejos, J., Nogueras, M., Sánchez, A., & Cano, E. (2004). Composition and infraspecific variability of Artemisia herba-alba from southern Spain. Biochemical systematics and ecology, 32(3), 265-277. 41. Talbi, M., Ainane, T., Boriky, D., Bennani, L., Blaghen, M., & Elkouali, M. (2015) Antibacterial activity of Eudesmanolide compounds isolated from medicinal plant Artemisia herba-alba J. Mater. Environ. Sci., 6 (8), 2125-2128. 42. Boukhennoufa, A., Meddah, A. T. T., Meddah, B., Gabaldón, J. A., & Sonnet, P. (2018). Comparative study of Artemisia herba alba asso and citrus aurantium essential oils. The Journal of Microbiology, Biotechnology and Food Sciences, 9(3), 622. 43. Asdadi, A., Moutaj, R., Hadek, M. E., & Idrissi, L. M. (2014). Chemical polymorphism of populations of Thymus Leptobotrys L. harvested from the Argan Tree , assessed by analysis of their essential oils, and its impact on their anticandidal and antioxidant activity. Int J Pharm Sci Invent, 3, 60-70. 71

Journal of Analytical Sciences and Applied Biotechnology Asdadi et al.

44. Asdadi, A., Alilou, H., Akssira, M., Hassani, L. M. I., Chebli, B., Moutaj, R., Blặzquez, M. A. (2014) Chemical Composition and Anticandidal Effect of Three Thymus Species Essential Oils from Southwest of Morocco against the Emerging Nosocomial Fluconazole-Resistant Strains. Journal of Biology, Agriculture and Healthcare, 4(11),16-26. 45. Abad, M. J., Bedoya, L. M., Apaza, L., & Bermejo, P. (2012). The Artemisia L. genus: a review of bioactive essential oils. Molecules, 17(3), 2542-2566. 46. Haq, F. U., Roman, M., Ahmad, K., Rahman, S. U., Shah, S. M. A., Suleman, N., Ullah, W. (2020). Artemisia annua: trials are needed for COVID‐19. Phytotherapy Research, 1-2. 47. Lin, L., Han, Y., & Yang, Z. M. (2003). Clinical observation on 103 patients of severe acute respiratory syndrome treated by integrative traditional Chinese and Western Medicine. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi= Chinese journal of integrated traditional and Western medicine, 23(6), 409. 48. Bian, Y. J., Qi, W. S., & Song, Q. Q. (2003). Evaluation on effect of integrative medical treatment on quality of life of rehabilitation stage in 85 patients with SARS. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi= Chinese journal of integrated traditional and Western medicine, 23(9), 658-660. 49. Elabboubi, M., Bennani, L., Ainane, A., Charaf, S., Bouhadi, M., Elkouali, M., Talbi, M., Ainane, T. Treatment of mycoses by essential oils: Mini Review. Journal of Analytical Sciences and Applied Biotechnology, 1(2), 35-40. 50. Astani, A., Reichling, J., & Schnitzler, P. (2010). Comparative study on the antiviral activity of selected monoterpenes derived from essential oils. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives, 24(5), 673-679. 51. Gavanji, S., Sayedipour, S. S., Larki, B., & Bakhtari, A. (2015). Antiviral activity of some plant oils against herpes simplex virus type 1 in Vero cell culture. Journal of Acute Medicine, 5(3), 62-68. 52. Ainane, A., Khammour, F., El Kouali, M., Talbi, M., Oussaid, A., Lemhidi, A., Ainane, T. (2019). Evaluation of the toxicity of the essential oils of certain mints grown in the region of Settat (Morocco): Mentha piperita, Mentha pulegium and Mentha spicata against, Sitophilus Granarius, Sitophilus Oryzae and Sitophilus Zeamais. Journal of Analytical Sciences and Applied Biotechnology, 1(1), 1-10. 53. Sokolova, A. S., Yarovaya, O. I., Semenova, M. D., Shtro, A. A., Orshanskaya, I. R., Zarubaev, V. V., & Salakhutdinov, N. F. (2017). Synthesis and in vitro study of novel borneol derivatives as potent inhibitors of the influenza A virus. MedChemComm, 8(5), 960-963. 54. Tariq, S., Wani, S., Rasool, W., Shafi, K., Bhat, M. A., Prabhakar, A., ... & Rather, M. A. (2019). A comprehensive review of the antibacterial, antifungal and antiviral potential of essential oils and their chemical constituents against drug-resistant microbial pathogens. Microbial pathogenesis, 134, 103580. 55. Aanouz, I., Belhassan, A., El-Khatabi, K., Lakhlifi, T., El-Ldrissi, M., & Bouachrine, M. (2020). Moroccan Medicinal plants as inhibitors against SARS-CoV-2 main protease: Computational investigations. Journal of Biomolecular Structure and Dynamics, 1-9.

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