In-silico ADMET Pharmacoinformatics of Geraniol (3,7-dimethylocta-trans-2,6-dien-1-ol) - acyclic monoterpene alcohol drug from Leaf Essential Oil of Cymbopogon martinii from Sirumalai Hills (Eastern Ghats), INDIA
Abstract
Cymbopogon martinii is a grass from genus Cymbopogon (lemongrasses) native to India, but widely cultivated in other places for its aromatic essential oil. C. martinii known as Palmarosa smells sweet with rose-like odor. Geraniol, a terpene alcohol present in Cymbopogon martinii essential oil (CMEO) is much valued for its typical aroma and medicinal uses. In addition to the pleasant odor, Geraniol is known for fungicidal, nematicidal, acaricidal, insecticidal, repellent properties hence, used as Natural Pest Control Agent (NPCA) exhibiting low toxicity. Furthermore, geraniol has been suggested to exemplify a new class of chemoprevention agents in the treatment of cancer. Biological activities such as antimicrobial, anti-oxidant, anti-inflammatory and vascular effects have been investigated. In the present study, GCMS based in-silico ADMET pharmacoinformatics aspects (Physicochemical, Lipophilicity, Medicinal Chemistry, Druglikeness, Absorption, Water Solubility, Distribution, Metabolism, Pharmacokinetics, Excretion, Environmental Toxicity, Tox21 Pathway and Toxicophore Rules) with PASS prediction of geraniol from CMEO has been bioprospected from human health perspective point of view.
Keywords: GCMS; ADMET; Pharmacoinformatics; Geraniol; Essential Oil; Cymbopogon martinii; Palmarosa; CMEO; PBNPs; Sirumalai Hills; Eastern Ghats
Keywords:
GCMS, ADMET, Pharmacoinformatics, Geraniol, Essential Oil, Cymbopogon martinii, Palmarosa, CMEO, PBNPs, Sirumalai Hills, Eastern GhatsDOI
https://doi.org/10.22270/jddt.v11i4-S.4965References
Bedoukian PZ. Geraniol and nerol. Perfumery and Flavoring Synthetics. 1986.
Clark GS. Geraniol. Perfumer & flavorist. 1998; 23(3):19-25.
Simon DZ, Beliveau J, Aube C. Extraction by hydrodiffusion of the essential oil of Monarda fistulosa grown in the province of Quebec: Assay of geraniol in the hydro-diffused oil. International Journal of Crude Drug Research. 1986; 24(3):120-2. https://doi.org/10.3109/13880208609060888
Baser KH, Kürkçüoglu M, Demirci B. Ninde oil (Aeollanthus myrianthus Taylor) revisited: analysis of historical oil. Journal of essential oil research. 2005; 17(2):137-8. https://doi.org/10.1080/10412905.2005.9698856
Baydar H, Baydar NG. The effects of harvest date, fermentation duration and Tween 20 treatment on essential oil content and composition of industrial oil rose (Rosa damascena Mill.). Industrial crops and products. 2005; 21(2):251-5. https://doi.org/10.1016/j.indcrop.2004.04.004
Dubey VS, Luthra R. Biotransformation of geranyl acetate to geraniol during palmarosa (Cymbopogon martinii, Roxb. wats. var. motia) inflorescence development. Phytochemistry. 2001; 57(5):675-80. https://doi.org/10.1016/S0031-9422(01)00122-4
Rajeswara Rao BR, Bhattacharya AK, Mallavarapu GR, Ramesh S. Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.). Flavour and fragrance journal. 2004; 19(4):344-50. https://doi.org/10.1002/ffj.1313
Chen W, Viljoen AM. Geraniol-a review of a commercially important fragrance material. South African Journal of Botany. 2010; 76(4):643-51. https://doi.org/10.1016/j.sajb.2010.05.008
Regev S, Cone WW. Analyses of pharate female two spotted spider mites for nerolidol and geraniol: evaluation for sex attraction of males. Environmental Entomology. 1976; 5(1):133-8. https://doi.org/10.1093/ee/5.1.133
Burdock Geranio Fenaroli's Handbook of Flavor Ingredients (6th ed), CRC Press (2010), pp. 733-734
Barnard DR, Xue RD. Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae). Journal of medical entomology. 2004; 41(4):726-30. https://doi.org/10.1603/0022-2585-41.4.726
Jeon JH, Lee CH, Lee HS. Food protective effect of geraniol and its congeners against stored food mites. Journal of food protection. 2009; 72(7):1468-71. https://doi.org/10.4315/0362-028X-72.7.1468
Khallaayoune K, Biron JM, Chaoui A, Duvallet G. Efficacy of 1% geraniol (Fulltec®) as a tick repellent. Parasite. 2009; 16(3):223-6. https://doi.org/10.1051/parasite/2009163223
Traina O, Cafarchia C, Capelli G, Iacobellis NS, Otranto D. In vitro acaricidal activity of four monoterpenes and solvents against Otodectes cynotis (Acari: Psoroptidae). Experimental & applied acarology. 2005; 37(1-2):141.
Qualls WA, Xue RD. Field evaluation of three botanical repellents against Psorophora ferox, Aedes atlanticus, and Aedes mitchellae. Journal of the American Mosquito Control Association. 2009; 25(3):379-81. https://doi.org/10.2987/09-5850.1
Müller GC, Junnila A, Butler J, Kravchenko VD, Revay EE, Weiss RW, Schlein Y. Efficacy of the botanical repellents geraniol, linalool, and citronella against mosquitoes. Journal of Vector Ecology. 2009; 34(1):2-8. https://doi.org/10.1111/j.1948-7134.2009.00002.x
Burke YD, Stark MJ, Roach SL, Sen SE, Crowell PL. Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol. Lipids. 1997; 32(2):151-6. https://doi.org/10.1007/s11745-997-0019-y
ChO MI, So I, Chun JN, Jeon JH. The antitumor effects of geraniol: Modulation of cancer hallmark pathways. International journal of oncology. 2016; 48(5):1772-82. https://doi.org/10.3892/ijo.2016.3427
Dalleau S, Cateau E, Bergès T, Berjeaud JM, Imbert C. In vitro activity of terpenes against Candida biofilms. International journal of antimicrobial agents. 2008; 31(6):572-6. https://doi.org/10.1016/j.ijantimicag.2008.01.028
Andrade BM, Barbosa LN, Alves FB, Albano M, Fernandes RK, Gorgulho CM, Júnior AF, Brüggemann H. Cymbopogon martinii essential oil: chemical characterization, effects on Propionibacterium acnes and immune response in lymphocytes. Planta Medica. 2016; 82(S 01):P185.
Jeon JH, Kim HW, Kim MG, Lee HS. Mite-control activities of active constituents isolated from Pelargonium graveolens against house dust mites. Journal of microbiology and biotechnology. 2008; 18(10):1666-71.
Kumaran AM, D'Souza P, Agarwal A, Bokkolla RM, Balasubramaniam M. Geraniol, the putative anthelmintic principle of Cymbopogon martinii. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives. 2003; 17(8):957-. https://doi.org/10.1002/ptr.1267
Burt S. Essential oils: their antibacterial properties and potential applications in foods-a review. International journal of food microbiology. 2004; 94(3):223-53. https://doi.org/10.1016/j.ijfoodmicro.2004.03.022
Fang HJ, Su XL, Liu HY, Chen YH, Ni JH. Studies on the chemical components and anti-tumour action of the volatile oils from Pelargonium graveoleus. Yao xue xue bao= Acta pharmaceutica Sinica. 1989; 24(5):366-71.
Tabari MA, Youssefi MR, Esfandiari A, Benelli G. Toxicity of β-citronellol, geraniol and linalool from Pelargonium roseum essential oil against the West Nile and filariasis vector Culex pipiens (Diptera: Culicidae). Research in veterinary science. 2017; 114:36-40. https://doi.org/10.1016/j.rvsc.2017.03.001
González-Marrugo LB, Granados-Llamas EA, Granados-Conde C, Tejada-Tovar CN, Ortega-Toro R. Extraction and evaluation of the antioxidant properties of coriander (Coriandrum sativum) seed essential oil. Contemporary Engineering Sciences. 2018; 77:3841-8. https://doi.org/10.12988/ces.2018.87356
Kellogg E, Abbott JR, Bawa K, Gandhi K, Kailash BR, Ganeshaiah KN, Shrestha UB, Raven P. Checklist of the grasses of India. PhytoKeys. 2020; 163:1. https://doi.org/10.3897/phytokeys.163.38393
Gebashe F, Moyo M, Aremu AO, Finnie JF, Van Staden J. Ethnobotanical survey and antibacterial screening of medicinal grasses in KwaZulu-Natal Province, South Africa. South African Journal of Botany. 2019; 122:467-74. https://doi.org/10.1016/j.sajb.2018.07.027
Avoseh O, Oyedeji O, Rungqu P, Nkeh-Chungag B, Oyedeji A. Cymbopogon species; ethnopharmacology, phytochemistry and the pharmacological importance. Molecules. 2015 May; 20(5):7438-53.
Soorya C, Balamurugan S, Basha AN, Kandeepan C, Ramya S, Jayakumararaj R. Profile of Bioactive Phyto-compounds in Essential Oil of Cymbopogon martinii from Palani Hills, Western Ghats, INDIA. Journal of Drug Delivery and Therapeutics. 2021; 11(4):60-5. https://doi.org/10.22270/jddt.v11i4.4887
Matthew KM. Flora of the Tamilnadu Carnatic. The Rapinat Herbarium, St. Joseph's College, Tiruchirapalli, India; 1981
Gamble JS, & Fischer CE. Flora of the Presidency of Madras. London, UK: West, Newman and Adlard; 1915. https://doi.org/10.5962/bhl.title.21628 https://doi.org/10.5962/bhl.title.21628
Soorya C, Balamurugan S, Ramya S, Neethirajan K, Kandeepan C, & Jayakumararaj R. Physicochemical, ADMET and Druggable properties of Myricetin: A Key Flavonoid in Syzygium cumini that regulates metabolic inflammations. Journal of Drug Delivery and Therapeutics, 2021; 11(4):66-3. https://doi.org/10.22270/jddt.v11i4.4890
Gleeson M P. Generation of a set of simple, interpretable ADMET rules of thumb J Med Chem, 2008, 51(4): 817-34.
Xiong G, Wu Z, Yi J, Fu L, Yang Z, Hsieh C, Yin M, Zeng X, Wu C, Lu A, Chen X. ADMETlab 2.0: an integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Research. 2021 Apr 24.
Ramya S, & Jayakumararaj R. Antifeedant activity of selected ethno-botanicals used by tribals of Vattal Hills on Helicoverpa armigera (Hübner). Journal of Pharmacy Research. 2009; 2(8):1414-1418.
Ramya S, Neethirajan K & Jayakumararaj R. Profile of bioactive compounds in Syzygium cumini-a review. J. Pharm. Res 2012; 5(8):4548-4553.
Sundari A & Jayakumararaj R, Herbal remedies used to treat skin disorders in Arasankulam region of Thoothukudi District in Tamil Nadu, India. Journal of Drug Delivery and Therapeutics, 2020; 10(5):33-38. https://doi.org/10.22270/jddt.v10i5.4277
Sundari A & Jayakumararaj R. Medicinal plants used to cure cuts and wounds in Athur region of Thoothukudi district in Tamil Nadu, India. Journal of Drug Delivery and Therapeutics, 2020; 10(6-s):26-30.
Zehetner P, Höferl M, Buchbauer G. Essential oil components and cytochrome P450 enzymes: a review. Flavour and Fragrance Journal. 2019 Jul; 34(4):223-40.
Ekins S, Wrighton SA. The role of CYP2B6 in human xenobiotic metabolism. Drug metabolism reviews. 1999; 31(3):719-54. https://doi.org/10.1081/DMR-100101942
Pavan B, Dalpiaz A, Marani L, Beggiato S, Ferraro L, Canistro D, Paolini M, Vivarelli F, Valerii MC, Comparone A, De Fazio L. Geraniol pharmacokinetics, bioavailability and its multiple effects on the liver antioxidant and xenobiotic-metabolizing enzymes. Frontiers in pharmacology. 2018; 9:18. https://doi.org/10.3389/fphar.2018.00018
Ertl P, Schuffenhauer A. Estimation of synthetic accessibility score of drug-like molecules based on molecular complexity and fragment contributions J Cheminform, 2009; 1(1): 8.
Zhang YF, Huang Y, Ni YH, Xu ZM. Systematic elucidation of the mechanism of geraniol via network pharmacology. Drug design, development and therapy. 2019; 13:1069. https://doi.org/10.2147/DDDT.S189088
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced drug delivery reviews. 1997; 23(1-3):3-25.
Muegge I. Selection criteria for drug‐like compounds. Medicinal research reviews. 2003; 23(3):302-21. https://doi.org/10.1002/med.10041
Panikar S, Shoba G, Arun M, Sahayarayan JJ, Nanthini AU, Chinnathambi A, Alharbi SA, Nasif O, Kim HJ. Essential oils as an effective alternative for the treatment of COVID-19: Molecular interaction analysis of protease (Mpro) with pharmacokinetics and toxicological properties. Journal of Infection and Public Health. 2021; 14(5):601-10. https://doi.org/10.1016/j.jiph.2020.12.037
Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific reports. 2017; 7(1):1-3. https://doi.org/10.1038/srep42717
Leeson PD. Molecular inflation, attrition and the rule of five. Adv Drug Deliv Rev. 2016; 101:22-33. https://doi.org/10.1016/j.addr.2016.01.018
Schenone M, Dančík V, Wagner BK, Clemons PA. Target identification and mechanism of action in chemical biology and drug discovery. Nat Chem Biol. 2013; 9(4):232-240 https://doi.org/10.1038/nchembio.1199
Published
Abstract Display: 1084 
PDF Downloads: 852 PDF Downloads: 166 How to Cite
Issue
Section
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0). that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
How to Cite
.