In Silico Study of Eugenol and trans-Caryophyllene also Clove Oil Fumigant Toxicity on Tribolium castaneum

In Silico Study and Fumigant Toxicity of Clove Oil

Authors

  • Silvi Ikawati Department of plant protection, Faculty of Agriculture, University of Brawijaya http://orcid.org/0000-0001-8731-2055
  • Toto Himawan Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia
  • Abdul Latief Abadi Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia
  • Hagus Tarno Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia
  • Alvan Fajarudin Department of plant protection, Faculty of Agriculture, University of Brawijaya

DOI:

https://doi.org/10.11594/jtls.12.03.07

Keywords:

Docking, a botanical insecticide, Syzygium aromaticum, fumigant, eugenol, caryophyllene

Abstract

Alternative storage pest control that is more environmentally friendly than the use of synthetic chemical pesticides is to use botanical pesticides from plant essential oils, including clove (Syzygium aromaticum) which contains the main compounds eugenol and trans-caryophyllene. To study the various mechanisms of action of essential oils as botanical insecticides could use in silico approach through molecular docking. This study aims to predict the dominant binding mode(s) of a ligand with a protein of a known three-dimensional structure through docking. Then tested its fumigant activity on Tribolium castaneum. The docking results showed that the trans-caryophyllene and eugenol compounds had a more stable bond strength in the acetylcholinesterase enzyme T. castaneum than the control compound linalool. In addition, there is a synergy between eugenol and trans-caryophyllene when the two compounds interact with acetylcholinesterase. These results can be used as prediction material that trans-caryophyllene and eugenol have potential as protein acetylcholinesterase inhibitors of T. castaneum. After being tested in the laboratory, clove oil which contains two main compounds namely eugenol and trans-caryophylene has the potential to control T. castaneum with an LC50 value of 5,227 μL/L air.

Keywords: Botanical insecticide, Caryophyllene, Docking, Eugenol, Fumigant,
Syzygium aromaticum

Author Biographies

  • Silvi Ikawati, Department of plant protection, Faculty of Agriculture, University of Brawijaya
    Department of plant protection, Faculty of Agriculture, University of Brawijaya
  • Toto Himawan, Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia

    Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145,
    Indonesia

  • Abdul Latief Abadi, Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia

    Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145,
    Indonesia

  • Hagus Tarno, Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145, Indonesia

    Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Brawijaya, Malang 65145,
    Indonesia

  • Alvan Fajarudin, Department of plant protection, Faculty of Agriculture, University of Brawijaya
    Department of plant protection, Faculty of Agriculture, University of Brawijaya

References

Good NE (1936) The flour beetles of the genus Tribolium. USDA Technical Bulletin 5 27–28.

Ajayi FA, Rahman SA (2006) Susceptibility of some staple processed meals to red flour beetle, Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Pakistan J Biol Sci. doi: 10.3923/pjbs.2006.1744.1748.

Lo PK (1986) Recognition and control of insect pests in stored grains. Post-harvest prevention of paddy/rice loss Taiwan Council of Agriculture, Asian Productivity Organization,Taipei 171–186.

Gasch T (2014) The use of semiochemicals for stored product protection. Berichte aus dem Julius Kühn-Institut (177): 32.

Rajendran S, Sriranjini V (2008) Plant products as fumigants for stored-product insect control. Journal of Stored Products Research 44 (2): 126–135. doi: 10.1016/j.jspr.2007.08.003.

Devi MA, Sahoo D, Singh TB, Rajashekar Y (2019) Toxicity, repellency and chemical composition of essential oils from Cymbopogon species against red flour beetle Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). J Consum Prot Food Saf. doi: 10.1007/s00003-019-01264-y

Ebadollahi A, Safaralizadeh M, Pourmirza A (2010) Fumigant Toxicity of Lavandula Stoechas L. Oil Against Three Insect Pests Attacking Stored Products. Journal of Plant Protection Research 50 (1): 56–60. doi: 10.2478/v10045-010-0010-8.

Lashgari A, Mashayekhi S, Javadzadeh M, Marzban R (2014) Effect of Mentha piperita and Cuminum cyminum essential oil on Tribolium castaneum and Sitophilus oryzae. Archives Of Phytopathology And Plant Protection 47 (3): 324–329. doi: 10.1080/03235408.2013.809230.

Hummelbrunner LA, Isman MB (2001) Acute, Sublethal, Antifeedant, and Synergistic Effects of Monoterpenoid Essential Oil Compounds on the Tobacco Cutworm, Spodoptera litura (Lep., Noctuidae). Journal of Agricultural and Food Chemistry 49 (2): 715–720. doi: 10.1021/jf000749t.

Isman MB (2016) Pesticides based on plant essential oils: Phytochemical and practical considerations. ACS Symp Ser. doi: 10.1021/bk-2016-1218.ch002.

Bernards MA (2010) Plant natural products: a primer The present review is one in the special series of reviews on animal–plant interactions. Canadian Journal of Zoology 88 (7): 601–614. doi: 10.1139/Z10-035.

Tripathi AK, Upadhyay S, Bhuiyan M, Bhattacharya PR (2009) A review on prospects of essential oils as biopesticide in insect-pest management. Kyōtoshi Maizō Bunkazai Kenkyūjo.

Plata-Rueda A, Campos JM, da Silva Rolim G et al. (2018) Terpenoid constituents of cinnamon and clove essential oils cause toxic effects and behavior repellency response on granary weevil, Sitophilus granarius. Ecotoxicology and Environmental Safety 156 263–270. doi: 10.1016/j.ecoenv.2018.03.033.

Jirovetz L, Buchbauer G, Stoilova I et al. (2006) Chemical Composition and Antioxidant Properties of Clove Leaf Essential Oil. Journal of Agricultural and Food Chemistry 54 (17): 6303–6307. doi: 10.1021/jf060608c.

Park I-K, Shin S-C (2005) Fumigant Activity of Plant Essential Oils and Components from Garlic ( Allium sativum ) and Clove Bud ( Eugenia caryophyllata ) Oils against the Japanese Termite ( Reticulitermes speratus Kolbe). Journal of Agricultural and Food Chemistry 53 (11): 4388–4392. doi: 10.1021/jf050393r.

Koul O, Walia S, Dhaliwal GS (2008) Essential Oils as Green Pesticides: Potential and Constraints. Biopestic Int 4 (1): 63–84.

Liao M, Xiao J-J, Zhou L-J et al. (2016) Insecticidal Activity of Melaleuca alternifolia Essential Oil and RNA-Seq Analysis of Sitophilus zeamais Transcriptome in Response to Oil Fumigation. PLOS ONE 11 (12): e0167748. doi: 10.1371/journal.pone.0167748.

Regnault-Roger C, Vincent C, Arnason JT (2012) Essential Oils in Insect Control: Low-Risk Products in a High-Stakes World. Annual Review of Entomology 57 (1): 405–424. doi: 10.1146/annurev-ento-120710-100554.

Yung-Chi C, Prusoff WH (1973) Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol. doi: 10.1016/0006-2952(73)90196-2.

Campolo O, Verdone M, Laudani F et al. (2013) Response of four stored products insects to a structural heat treatment in a flour mill. Journal of Stored Products Research 54 54–58. doi: 10.1016/J.JSPR.2013.05.001.

Abbott WS (1925) A method for computing the effectiveness of an insecticide. J. Econ. Entomol.

Pavela R, Benelli G (2016) Essential Oils as Ecofriendly Biopesticides? Challenges and Constraints. Trends Plant Sci. doi: 10.1016/j.tplants.2016.10.005

Motiejunas D, Wade RC (2006) Structural, energetic, and dynamic aspects of ligand-receptor interactions. Compr Med Chem II. doi: 10.1016/b0-08-045044-x/00250-9

Sugita M, Hamano M, Kasahara K et al. (2020) New Protocol for Predicting the Ligand-Binding Site and Mode Based on the 3D-RISM/KH Theory. Journal of Chemical Theory and Computation 16 (4): 2864–2876. doi: 10.1021/ACS.JCTC.9B01069.

Foloppe N, Chen I-J (2009) Conformational Sampling and Energetics of Drug-Like Molecules. Curr Med Chem. doi: 10.2174/092986709789057680

Richards S, Gibbs RA, Weinstock GM et al. (2008) The genome of the model beetle and pest Tribolium castaneum. Nature 452 (7190): 949–955. doi: 10.1038/nature06784.

Vangone A, Bonvin AMJJ (2015) Contacts-based prediction of binding affinity in protein–protein complexes. Elife. doi: 10.7554/eLife.07454

Ikawati S, Himawan T, Abadi AL, Tarno H (2020) Thermostability, photostability, and toxicity of clove oil nanoparticles against Cryptolestes ferrugineus (Stephens) (Coleoptera: Laemophloeidae). Biodiversitas Journal of Biological Diversity 21 (10): 4764–4771. doi: 10.13057/BIODIV/D211041.

Hu Q, Zhou M, wei S (2018) Progress on the Antimicrobial Activity Research of Clove Oil and Eugenol in the Food Antisepsis Field. Journal of Food Science 83 (6): 1476–1483. doi: 10.1111/1750-3841.14180.

Ikawati S, Himawan T, Abadi AL, Tarno H (2021) Toxicity nanoinsecticide based on clove essential oil against Tribolium castaneum (Herbst). Journal of Pesticide Science 46 (2): 222–228. doi: 10.1584/JPESTICS.D20-059.

Ikawati S, Himawan T, Abadi AL, Tarno H (2021) Characterization of clove oil nanoparticles and their insecticidal activity against cryptolestes ferrugineus (Stephens) (coleoptera: Laemophloeidae). Agrivita 43 (1): 43–55. doi: 10.17503/AGRIVITA.V1I1.2532.

Ikawati S, Dhuha MS, Himawan T (2017) Bioactivity of Citrus Hystrix D.C. Leaf Extract Against Cigarette Beetle Lasioderma Serricorne (F.). Journal of Tropical Life Science 7 (3): 189–196.

Pinheiro PF, Queiroz VT de, Rondelli VM et al. (2013) Insecticidal activity of citronella grass essential oil on Frankliniella schultzei and Myzus persicae. Ciência e Agrotecnologia. doi: 10.1590/s1413-70542013000200004.

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Published

2022-10-14

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