Chemical composition, in vitro antifungal activity, DFT, molecular docking and molecular dynamics simulation studies of the essential oil from Anvillea gracinii subsp. radiata (Coss. & Durieu) Anderb

References

• J.L. Slavin and B. Lloyd, Health benefits of fruits and vegetables. Advances in Nutrition, 3(4), 506–516 (2012). doi:10.3945/an.112.002154
   PubMed Web of Science ®Google Scholar
• P. Nartvaranant, Fruit growth, fruit carbohydrate concentration and fruit nutrient concentration in dropped Pummelo (Citrus grandis (L.) Osbeck) fruit cv. Thong Dee. International Journal of Fruit Science, 19(1), 91–103 (2019). doi:10.1080/15538362.2018.1528924
   Web of Science ®Google Scholar
• C. Ziv and E. Fallik, Postharvest storage techniques and quality evaluation of fruits and vegetables for reducing food loss. Agronomy, 11(6), 1133 (2021). doi:10.3390/agronomy11061133
   Google Scholar
• S. Rguez, I.B. Slimene, G. Abid, M. Hammemi, A. Kefi, S. Elkahoui, R. Ksouri, I.H. Sellami and N. Djébali, Tetraclinis articulata essential oil reduces Botrytis cinerea infections on tomato. Scientia Horticulturae, 266, 109291 (2020). doi:10.1016/j.scienta.2020.109291
   Web of Science ®Google Scholar
• A.T. Zatla, I. Mami, M.E. Dib and M.E.A. Sifi, Efficacy of essential oil and hydrosol extract of Marrubium vulgare on fungi responsible for apples rot. Anti-Infective Agents, 18, 285–293 (2020)
   Google Scholar
• M. Znini, Chemical composition, liquid and vapor-phase antifungal activities of essential oil of Teucrium luteum subsp. flavovirens against three postharvest phytopathogenic fungi. International Journal of Fruit Science, 21, 400–412 (2021)
   Web of Science ®Google Scholar
• S. Basak and P. Guha, A review on antifungal activity and mode of action of essential oils and their delivery as nano-sized oil droplets in food system. Journal of Food Science and Technology, 55(12), 4701–4710 (2018). doi:10.1007/s13197-018-3394-5
   PubMed Web of Science ®Google Scholar
• O.O. Fajinmi, M.G. Kulkarni, S. Benická, S.Ć. Zeljković, K. Doležal, P. Tarkowski, J.F. Finnie and J. Van Staden, Antifungal activity of the volatiles of Agathosma betulina and Coleonema album commercial essential oil and their effect on the morphology of fungal strains Trichophyton rubrum and T. mentagrophytes. South African Journal of Botany, 122, 492–497 (2019). doi:10.1016/j.sajb.2018.03.003
   Web of Science ®Google Scholar
• S.A. Kulkarni, P.S. Sellamuthu, S.K. Nagarajan, T. Madhavan and E.R. Sadiku, Antifungal activity of wild bergamot (Monarda fistulosa) essential oil against postharvest fungal pathogens of banana fruits. South African Journal of Botany, 144, 166–174 (2022). doi:10.1016/j.sajb.2021.08.019
   Web of Science ®Google Scholar
• F. Nazzaro, F. Fratianni, R. Coppola and V.D. Feo, Essential oils and antifungal activity. Pharmaceuticals, 10(4), 86 (2017). doi:10.3390/ph10040086
   Web of Science ®Google Scholar
• D. Wang, J. Zhang, X. Jia, L. Xin and H. Zhai, Antifungal effects and potential mechanism of essential oils on Collelotrichum gloeosporioides in vitro and in vivo. Molecules, 24(18), 3386 (2019). doi:10.3390/molecules24183386
   PubMed Web of Science ®Google Scholar
• ISO 9235, Aromatic Natural Raw Materials—vocabulary. International Organization for Standardization, Geneva, Switzerland (2013)
   Google Scholar
• A.C.G. Fiori, K.R.F. Schwan-Estrada, J.R. Stangarlin, J.B. Vida, C.A. Scapim, M.E.S. Cruz and S.F. Pascholati, Antifungal activity of leaf extracts and essential oils of some medicinal plants against Didymella bryoniae. Journal of Phytopathology, 148(7–8), 483–487 (2000). doi:10.1046/j.1439-0434.2000.00524.x
   Web of Science ®Google Scholar
• E. Haque, S. Irfan, M. Kamil, S. Sheikh, A. Hasan, A. Ahmad, V. Lakshmi, A. Nazir and S.S. Mir, Terpenoids with antifungal activity trigger mitochondrial dysfunction in Saccharomyces cerevisiae. Microbiology (Reading, England), 85, 436–443 (2016)
   PubMed Web of Science ®Google Scholar
• J.E.T. Do Nascimento, A.L.M. Rodrigues, D.S. de Lisboa, H.R. Liberato, M.J.C. Falcão, C.R. da Silva, H.V. Nobre Júnior, R. Braz Filho, V.F. de Paula Junior and D.R. Alves, Chemical composition and antifungal in vitro and in silico, antioxidant, and anticholinesterase activities of extracts and constituents of Ouratea fieldingiana (DC.) Baill. Evidence-Based Complementary and Alternative Medicine, 1–12 (2018). doi:10.1155/2018/1748487.
   Web of Science ®Google Scholar
• M. Erol, I. Celik and G. Kuyucuklu, Synthesis, molecular docking, molecular dynamics, DFT and antimicrobial activity studies of 5-substituted-2-(p-methylphenyl) benzoxazole derivatives. Journal of Molecular Structure, 1234, 130151 (2021). doi:10.1016/j.molstruc.2021.130151
   Web of Science ®Google Scholar
• M. Anza, M. Endale, L. Cardona, D. Cortes, R. Eswaramoorthy, N. Cabedo, B. Abarca, J. Zueco, H. Rico and I. Domingo-Ortí, Cytotoxicity, antimicrobial activity, molecular docking, drug likeness and DFT analysis of benzo [c] phenanthridine alkaloids from roots of Zanthoxylum chalybeum. Biointerface Research in Applied Chemistry, 12, 1569–1586 (2021)
   Web of Science ®Google Scholar
• A. Anderberg, The genus Anvillea (Compositae) Nord. Journal of Botany, 2, 297–305 (1982)
   Google Scholar
• M.A. Boukhris, É. Destandau, A. El Hakmaoui, L. El Rhaffari and C. Elfakir, A dereplication strategy for the identification of new phenolic compounds from Anvillea radiata (Coss. & Durieu). Comptes Rendus Chimie, 19(9), 1124–1132 (2016). doi:10.1016/j.crci.2016.05.019
   Web of Science ®Google Scholar
• A. Benabid, Flore Et Écosystèmes du Maroc: Evaluation Et Préservation de la Biodiversité. Ibis Press, Paris (2000)
   Google Scholar
• P. Ozenda, Flora and Vegetation of the Sahara, 3th. CNRS, Paris (1991)
   Google Scholar
• A.-C. Benchelah, H. Bouziane and M. Maka, Fleurs du Sahara, arbres et arbustes, voyage au coeur de leurs usages avec les Touaregs du Tassili. Phytothérapie, 2(6), 191–197 (2004). doi:10.1007/s10298-004-0052-z
   Google Scholar
• M. Bammou, E.D. Tariq Bouhlali, K. Sellam, M. Derouich, L. El-Rhaffari, J. Ibijbijen and L. Nassiri, Chemical profile and antimicrobial properties of liquid and vapor phases of the essential oil of Cladanthus eriolepis: An endemic Asteraceae growing in the Moroccan Oases. Journal of Essential Oil Bearing Plants, 23(5), 1042–1053 (2020). doi:10.1080/0972060X.2020.1822758
   Web of Science ®Google Scholar
• M. Hebi and M. Eddouks, Glucose lowering activity of Anvillea radiata coss & durieu in diabetic rats. Cardiovascular & Haematological Disorders-Drug Targets (Formerly Current Drug Targets-Cardiovascular & Hematological Disorders), 18, 71–80 (2018)
   PubMedGoogle Scholar
• B. El Hassany, F. El Hanbali, M. Akssira, F. Mellouki, A. Haidour and A.F. Barrero, Germacranolides from Anvillea radiate. Fitoterapia, 75(6), 573–576 (2004). doi:10.1016/j.fitote.2004.06.003
   PubMed Web of Science ®Google Scholar
• H. Dendougui, M. Jay, F. Benayache and S. Benayache, Flavonoids from Anvillea radiata Coss. & Dur.(asteraceae). Biochemical Systematics and Ecology, 34(9), 718–720 (2006). doi:10.1016/j.bse.2006.05.002
   Web of Science ®Google Scholar
• M. Moumou, A. El Bouakher, H. Allouchi, A. El Hakmaoui, A. Benharref, V. Mathieu, G. Guillaumet and M. Akssira, Synthesis and biological evaluation of 9α- and 9β-hydroxyamino-parthenolides as novel anticancer agents. Bioorganic & Medicinal Chemistry Letters, 24(16), 4014–4018 (2014). doi:10.1016/j.bmcl.2014.06.019
   PubMed Web of Science ®Google Scholar
• F. El Hanbali, A. El Hakmaoui, F. Mellouki, L. El Rhaffari and M. Akssira, Chemical composition and antibacterial activity of essential oil of Anvillea radiata Coss. & Dur. Natural Product Communications, 2, 595–597 (2007)
   Web of Science ®Google Scholar
• W. König, D. Hochmuth and D. Joulain, Terpenoids and Related Constituents of Essential Oils. Library of Mass Finder; Institute of Organic Chemistry, Hamburg, Germany (2001)
   Google Scholar
• R.P. Adams, Identification of Essential Oil Components by Gas Chromatography/mass Spectrometry, 4th ed. Allured Publishing, Carol Stream, IL (2007)
   Google Scholar
• National Institute of Standards and Technology, PC Version of the NIST/EPA/NIH Mass Spectra Library. NIST, Gaithersburg, MD (2008)
   Google Scholar
• A. Ansari, O. Ou-Ani, L. Oucheikh, Y. Youssefi, D. Chebabe, A. Oubair and M. Znini, Experimental, theoretical modeling and optimization of inhibitive action of Ocimum basilicum essential oil as green corrosion inhibitor for C38 steel in 0.5 M H2SO4 medium. Chemistry Africa, 5(1), 37–55 (2021). doi:10.1007/s42250-021-00289-x
   Google Scholar
• V. Yele, D.K. Sigalapalli, S. Jupudi and A.A. Mohammed, DFT calculation, molecular docking, and molecular dynamics simulation study on substituted phenylacetamide and benzohydrazide derivatives. Journal of Molecular Modeling, 27(12), 1–12 (2021). doi:10.1007/s00894-021-04987-8
   Web of Science ®Google Scholar
• G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell and A.J. Olson, AutoDock4 and AutoDocktools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791 (2009). doi:10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• K.J. Bowers, D.E. Chow, H. Xu, R.O. Dror, M.P. Eastwood, B.A. Gregersen, J.L. Klepeis, I. Kolossvary, M.A. Moraes and F.D. Sacerdoti, Scalable algorithms for molecular dynamics simulations on commodity clusters, In SC06 Proc. ACMIEEE Conf. Supercomput. New York, USA: IEEE. 43–43 (2006). doi:10.1109/SC.2006.54.
   Google Scholar
• D. Shivakumar, J. Williams, Y. Wu, W. Damm, J. Shelley and W. Sherman, Prediction of absolute solvation free energies using molecular dynamics free energy perturbation and the OPLS force field. Journal of Chemical Theory and Computation, 6(5), 1509–1519 (2010). doi:10.1021/ct900587b
   PubMed Web of Science ®Google Scholar
• G. Cristofari, M. Znini, L. Majidi, H. Mazouz, P. Tomi, J. Costa and J. Paolini, Chemical diversity of essential oils from Asteriscus graveolens (Forssk.) Less.: Identification of cis-8-Acetoxychrysanthenyl Acetate as a new natural component. Chemistry & Biodiversity, 9(4), 727–738 (2012). doi:10.1002/cbdv.201100118
   PubMed Web of Science ®Google Scholar
• V.I. Babushok, P.J. Linstrom and I.G. Zenkevich, Retention indices for frequently reported compounds of plant essential oils. Journal of Physical and Chemical Reference Data, 40(4), 043101-01–043101-47 (2011). doi:10.1063/1.3653552
   Web of Science ®Google Scholar
• P. Avato, F. Raffo, N.A. Aldouri and S.T. Vartanian, Essential oils of varthemia iphionoides from Jordan. Flavour and Fragrance Journal, 19(6), 559–561 (2004)
   Web of Science ®Google Scholar
• D. Vokou, S. Kokkini and J.-M. Bessiere, Geographic variation of Greek oregano (Origanum vulgare ssp. hirtum) essential oils hirtum) essential oils. Biochemical Systematics and Ecology, 21(2), 287–295 (1993). doi:10.1016/0305-1978(93)90047-U
   Web of Science ®Google Scholar
• J. Niu, X. Hou, C. Fang, J. An, D. Ha, L. Qiu, Y. Ju, H. Zhao, W. Du and J. Qi, Transcriptome analysis of distinct Lindera glauca tissues revealed the differences in the unigenes related to terpenoid biosynthesis. Gene, 559(1), 22–30 (2015). doi:10.1016/j.gene.2015.01.002
   PubMed Web of Science ®Google Scholar
• M. Znini, G. Cristofari, L. Majidi, H. Mazouz, P. Tomi, J. Paolini and J. Costa, Antifungal activity of essential oil from Asteriscus graveolens against postharvest phytopathogenic fungi in apples. Natural Product Communications, 6, 1793–1968 (2011)
   Web of Science ®Google Scholar
• H. Alilou, A. Asdadi, L.I. Hassani, C. González-Mas, M.A. Blázquez and M. Akssira, Antifungal and antioxidant activity of Asteriscus graveolens subsp. odorus essential oil. Journal of Natural Sciences Research, 1, 1–10 (2014)
   Google Scholar
• E. Chibane, A. Essarioui, M. Ouknin, A. Boumezzourh, A. Bouyanzer and L. Majidi, Antifungal activity of Asteriscus graveolens (Forssk.) Less essential oil against Fusarium oxysporum sp.albedinis, the causal agent of “Bayoud” disease on date palm. Moroccan Journal of Chemistry, 8, 456–465 (2020)
   Web of Science ®Google Scholar
• R. Parthasarathi, V. Subramanian, D.R. Roy and P.K. Chattaraj, Electrophilicity index as a possible descriptor of biological activity. Bioorganic & Medicinal Chemistry, 12(21), 5533–5543 (2004). doi:10.1016/j.bmc.2004.08.013
   PubMed Web of Science ®Google Scholar
• M.D.L.Á. Zermeño-Macías, M.M. González-Chávez, F. Méndez, R. González-Chávez and A. Richaud, Theoretical reactivity study of indol-4-ones and their correlation with antifungal activity. Molecules, 22(3), 427 (2017). doi:10.3390/molecules22030427
   PubMed Web of Science ®Google Scholar
• X.-H. Liu, P.-Q. Chen, B.-L. Wang, Y.-H. Li, S.-H. Wang and Z.-M. Li, Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor, Bioorg. Bioorganic & Medicinal Chemistry Letters, 17(13), 3784–3788 (2007). doi:10.1016/j.bmcl.2007.04.003
   PubMed Web of Science ®Google Scholar
• Y. Liu, K. Lv, Y. Li, Q. Nan and J. Xu, Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings. Scientific Reports, 8, 1–14 (2018). doi:10.1038/s41598-017-17765-5
   PubMed Web of Science ®Google Scholar
• E. Scrocco and J. Tomasi, Electronic molecular structure, reactivity and intermolecular forces: An euristic interpretation by means of electrostatic molecular potentials. Advances in Quantum Chemistry, 11, 115–193 (1978)
   Google Scholar
• P. Politzer and J.S. Murray, The fundamental nature and role of the electrostatic potential in atoms and molecules. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), 108(3), 134–142 (2002). doi:10.1007/s00214-002-0363-9
   Web of Science ®Google Scholar
• Y.N. Mabkhot, F.D. Aldawsari, S.S. Al-Showiman, A. Barakat, S.M. Soliman, M.I. Choudhary, S. Yousuf, M.S. Mubarak and T.B. Hadda, Novel enaminone derived from thieno [2, 3-b] thiene: Synthesis, x-ray crystal structure, HOMO, LUMO, NBO analyses and biological activity. Chemistry Central Journal, 9(1), 1–11 (2015). doi:10.1186/s13065-015-0100-9
   PubMedGoogle Scholar
• S. Kumar, V. Saini, I.K. Maurya, J. Sindhu, M. Kumari, R. Kataria and V. Kumar, Design, synthesis, DFT, docking studies and ADME prediction of some new coumarinyl linked pyrazolylthiazoles: Potential standalone or adjuvant antimicrobial agents. PLoS One, 13, 1–23 (2018)
   Web of Science ®Google Scholar
• G.S. Mol, D. Aruldhas, I.H. Joe, S. Balachandran, A.R. Anuf, J. George and A.G. Nadh, Structural activity, fungicidal activity and molecular dynamics simulation of certain triphenyl methyl imidazole derivatives by experimental and computational spectroscopic techniques. Spectrochimica Acta: Part A, Molecular and Biomolecular Spectroscopy, 212, 105–120 (2019). doi:10.1016/j.saa.2018.12.047
   PubMed Web of Science ®Google Scholar
• S. Chinnasamy, G. Selvaraj, A.C. Kaushik, S. Kaliamurthi, S. Chandrabose, S.K. Singh, R. Thirugnanasambandam, K. Gu and D.-Q. Wei, Molecular docking and molecular dynamics simulation studies to identify potent AURKA inhibitors: Assessing the performance of density functional theory, MM-GBSA and mass action kinetics calculations. Journal of Biomolecular Structure & Dynamics, 38(14), 4325–4335 (2020). doi:10.1080/07391102.2019.1674695
   PubMed Web of Science ®Google Scholar
• Z. Hafidi, M. El Achouri, F.F.O. Sousa and L. Pérez, Antifungal activity of amino-alcohols based cationic surfactants and in silico, homology modeling, docking and molecular dynamics studies against lanosterol 14-α-demethylase enzyme. Journal of Biomolecular Structure & Dynamics, 1–17 (2021). doi:10.1080/07391102.2021.1902396
   Web of Science ®Google Scholar