In vitro Antioxidant and Anticholinesterase Activities of Senecio massaicus Essential Oil and Its Molecular Docking Studies as a Potential Inhibitor of Covid-19 and Alzheimer’s Diseases

Abstract The composition of the essential oil obtained from the dried aerial parts of Senecio massaicus was analyzed by GC/MS. Twenty-two components have been identified and represented 97.41 % of the total oil composition. The major constituents of the essential oil were m-cymene (30.58 %), n-hexadecanoic acid (14.88 %) and docosane-11-decyl (10.43 %). Four methods were used to determine the antioxidant activity: DPPH, ABTS, CUPRAC and reducing power assay. The results indicate that the essential oil extract has moderate to low activity compared to the reference antioxidant compounds. In vitro anticholinesterase activity of the essential oil has also been studied. It exhibited higher inhibitory activity against butyrylcholinesterase (BChE) than against acetylcholinesterase (AChE). Docking studies conducted for Alzheimer's disease-related enzymes have displayed that compounds docosane-11-decyl and octaethyleneglycol monododecyl ether have strong potency, and compounds 15,15’Bi1,4,7,10,13-pentaoxacyclohexadecane and n-Hexadecanoic acid have moderate inhibitory potential. In addition, these three compounds (Docosane-11-decyl, octaethyleneglycol monododecyl ether and 15,15’Bi1,4,7,10,13-pentaoxacyclohexadecane) of the essential oil displayed strong interaction against SARS-CoV-2 main protease and Nsp15 endoribonuclease. Therefore, it could be useful to provide anticholinesterase agent and anti-coronavirus candidate drugs.

[1]  O. Sytar,et al.  COVID-19 Prophylaxis Efforts Based on Natural Antiviral Plant Extracts and Their Compounds , 2021, Molecules.

[2]  M. Aarabi,et al.  Pathophysiological Clues to How the Emergent SARS-CoV-2 Can Potentially Increase the Susceptibility to Neurodegeneration , 2021, Molecular Neurobiology.

[3]  A. Nadhman,et al.  Therapeutic potential of medicinal plants against COVID-19: The role of antiviral medicinal metabolites , 2020, Biocatalysis and Agricultural Biotechnology.

[4]  Zaw Ali Khan,et al.  In-silico Study to Identify Dietary Molecules as Potential SARS-CoV-2 Agents , 2020, Letters in Drug Design & Discovery.

[5]  L. Martins,et al.  Alzheimer’s and Parkinson’s Diseases Predict Different COVID-19 Outcomes: A UK Biobank Study , 2020, medRxiv.

[6]  O. Sytar,et al.  A caryophyllene oxide and other potential anticholinesterase and anticancer agent in Salvia verticillata subsp. amasiaca (Freyn & Bornm.) Bornm. (Lamiaceae) , 2020 .

[7]  G. Pasinetti,et al.  Potential Novel Role of COVID-19 in Alzheimer's Disease and Preventative Mitigation Strategies. , 2020, Journal of Alzheimer's disease : JAD.

[8]  Hualiang Jiang,et al.  Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors , 2020, Nature.

[9]  Weiliang Zhu,et al.  Nelfinavir Is Active Against SARS-CoV-2 in Vero E6 Cells , 2020 .

[10]  I. Gulcin,et al.  Identification of non-alkaloid natural compounds of Angelica purpurascens (Avé-Lall.) Gilli. (Apiaceae) with cholinesterase and carbonic anhydrase inhibition potential , 2019, Saudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society.

[11]  O. Sytar,et al.  Antioxidant and anticholinesterase potential of Ferulago cassia with farther bio-guided isolation of active coumarin constituents , 2019, South African Journal of Botany.

[12]  O. Sytar,et al.  Molecular Docking Studies of Coumarins Isolated from Extracts and Essential Oils of Zosima absinthifolia Link as Potential Inhibitors for Alzheimer’s Disease , 2019, Molecules.

[13]  Xiaoxin Zhu,et al.  Artemisinin B Improves Learning and Memory Impairment in AD Dementia Mice by Suppressing Neuroinflammation , 2018, Neuroscience.

[14]  V. Virjamo,et al.  Climate Change Effects on Secondary Compounds of Forest Trees in the Northern Hemisphere , 2018, Front. Plant Sci..

[15]  A. Boligon,et al.  In vitro antioxidant activities and inhibitory effects of phenolic extract of Senecio biafrae (Oliv and Hiern) against key enzymes linked with type II diabetes mellitus and Alzheimer's disease , 2018, Food science & nutrition.

[16]  G. Oboh,et al.  Anticholinesterase activity and phenolic profile of two medicinal plants (Quassia undulata and Senecio abyssinicus) used in managing cognitive dysfunction in Nigeria , 2018 .

[17]  I. Demirtaş,et al.  PHYTOCHEMICAL CONSTITUENTS AND ANTIOXIDANT EFFECT OF SOLANUM ROSTRATUM SPECIES FROM ALGERIA T , 2018, Asian Journal of Pharmaceutical and Clinical Research.

[18]  Wen-Xing Li,et al.  A strategy to find novel candidate anti-Alzheimer’s disease drugs by constructing interaction networks between drug targets and natural compounds in medical plants , 2018, PeerJ.

[19]  Vinod Kumar,et al.  Chemical constituents of essential oils of Himalayan Nepeta ciliaris Benth. and Senecio nudicaulis Buch-Ham. Ex D. Don , 2018 .

[20]  B. Ahmed,et al.  Medicinal plants: a repository of antiviral metabolites , 2017 .

[21]  Rajendra Singh,et al.  Antifungal and phytotoxic activity of essential oil from root of Senecio amplexicaulis Kunth. (Asteraceae) growing wild in high altitude-Himalayan region , 2016, Natural product research.

[22]  A. Chukwuka,et al.  In-vitro anti-cholinesterase activity of essential oil from four tropical medicinal plants , 2015, Toxicology reports.

[23]  Pankaj Sharma,et al.  Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh, India , 2015, Natural product research.

[24]  A. Aksoy,et al.  A comparative study on phenolic components and biological activity of some Senecio species in Turkey , 2014, The Journal of pharmacy and pharmacology.

[25]  Kaijun Xiao,et al.  Anti-inflammatory activity and chemical composition of the essential oils from Senecio flammeus , 2014, EXCLI journal.

[26]  Huan Wang,et al.  Acetylcholineestarase-Inhibiting Alkaloids from Lycoris radiata Delay Paralysis of Amyloid Beta-Expressing Transgenic C. elegans CL4176 , 2013, PloS one.

[27]  T. Aburjai,et al.  GC-MS Analysis of Senecio giganteus Desf. from Algeria , 2013 .

[28]  V. Rana,et al.  Chemical variability in the essential oil of Cinnamomum tamala L. leaves from India , 2012, Natural product research.

[29]  M. Faleiro,et al.  Acetylcholinesterase Inhibition Activity of Portuguese Thymus Species Essential Oils , 2011 .

[30]  O. A. Lawal,et al.  Chemical Composition of the Essential Oils of Cyperus rotundus L. from South Africa , 2009, Molecules.

[31]  Lawal A. Oladipupo,et al.  Chemical Composition of the Essential Oils of the Flowers, Leaves and Stems of Two Senecio polyanthemoides Sch. Bip. Samples from South Africa , 2009, Molecules.

[32]  D. Nori-Shargh,et al.  Analysis of the essential oil of Senecio vernalis Waldst. & Kit. from Iran , 2008 .

[33]  S. Terzioğlu,et al.  Chemical Composition of the Essential Oils from Flower, Leaf, and Stem of Senecio Trapezuntinus Boiss. Grown in Turkey , 2008 .

[34]  M. Mirza,et al.  Chemical Composition of the Essential Oil of Senecio leucostachys Baker , 2008 .

[35]  René Thomsen,et al.  MolDock: a new technique for high-accuracy molecular docking. , 2006, Journal of medicinal chemistry.

[36]  P. Houghton,et al.  Biological properties of different extracts of two Senecio species , 2006, International journal of food sciences and nutrition.

[37]  Hua Peng,et al.  In vitro antiviral activity of three enantiomeric sesquiterpene lactones from Senecio species against hepatitis B virus , 2005, Antiviral chemistry & chemotherapy.

[38]  P. Xiao,et al.  Identification of natural compounds with antiviral activities against SARS-associated coronavirus , 2005, Antiviral Research.

[39]  E. Oktayoglu,et al.  Traditional medicine in Sakarya province (Turkey) and antimicrobial activities of selected species. , 2004, Journal of ethnopharmacology.

[40]  R. Apak,et al.  Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. , 2004, Journal of agricultural and food chemistry.

[41]  A. Marchiaro,et al.  SENECIO FILAGINOIDES VAR. LOBULATUS ESSENTIAL OIL , 1999 .

[42]  J. Cabrera,et al.  The essential oil of Senecio graveolens (Compositae): chemical composition and antimicrobial activity tests. , 1999, Journal of ethnopharmacology.

[43]  C. Rice-Evans,et al.  Antioxidant activity applying an improved ABTS radical cation decolorization assay. , 1999, Free radical biology & medicine.

[44]  G. Hammond,et al.  A survey of traditional medicinal plants from the Callejón de Huaylas, Department of Ancash, Perú. , 1998, Journal of ethnopharmacology.

[45]  N. Schamp,et al.  The volatile fraction of Senecio glaucus subsp. Coronopifolius , 1986 .

[46]  Qin Lu,et al.  Preface , 1976, Brain Research Bulletin.

[47]  K. Courtney,et al.  A new and rapid colorimetric determination of acetylcholinesterase activity. , 1961, Biochemical pharmacology.

[48]  M. S. Blois,et al.  Antioxidant Determinations by the Use of a Stable Free Radical , 1958, Nature.

[49]  J. Chalchat,et al.  Essential oil and antibacterial activity of Senecio perralderianus , 2012 .

[50]  S. Terzioğlu,et al.  Chemical composition of the essential oils from flowers of Senecio vernalis and Senecio platyphyllus var. platyphyllus. , 2009 .

[51]  M. Oyaizu.  Studies on products of browning reaction--antioxidative activities of products of browning reaction prepared from glucosamine , 1986 .

[52]  P. Quézel,et al.  Nouvelle flore de l'Algerie et des regions desertiques meridionales - v. 1-2 , 1962 .