Abstract
The essential oil (EO) was hydrodistilled from of Deverra tortuosa aerial parts. Fifty-six components amounting 99.3% were identified in EO through using gas chromatography–flame ionization detection (GC–FID) and (GC–MS). Phenylpropanoids, dillapiole (41.6%), elemicin (7.3%) and myristicin (5.1%), and the monoterpene, sabinene (4.2%) were identified as the major terpenes. An oil-in-water nanoemulsion (particle size 70.3 nm) was developed from EO adopting a low-energy method. The EO products showed insecticidal and biochemical effects against the cowpea weevil Callosobruchus maculatus. Based on a 48-h exposure period, the oil nanoemulsion exhibited a superior contact bioactivity (LC50 = 10.3 µg/cm2), followed by EO (LC50 = 23.1 µg/cm2), dillapiole (LC50 = 27.8 µg/cm2), and myristicin (LC50 = 37.1 µg/cm2). Upon fumigation, nanoemulsion and EO were superior as fumigants (LC50 after 48 h were 6.9 and 14.3 µl/l, respectively). Test materials showed a residual bioactivity against C. maculatus, where EO, dillapiole, and myristicin showed the strongest grain protecting activity. EO products significantly inhibited acetylcholinesterase (AChE) activity of C. maculatus adults. Test products were safe toward the non-target earthworms and did not alter the viability of cowpea seeds. There are evidences for the potential of using EO of D. tortuosa and its nanoemulsion and phenylpropanoids as natural grain protectants against C. maculatus.
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References
Abbott WS (1925) A method for computing the effectiveness of an insecticide. J Econ Entomol 18(2):265–267. https://doi.org/10.1093/jee/18.2.265a
Abdallah HM, Ezzat SM (2011) Effect of the method of preparation on the composition and cytotoxic activity of the essential oil of Pituranthos tortuosus. Z Naturforsch 66c:143–148. https://doi.org/10.1515/znc-2011-3-408
Adak T, Barik N, Patil NB, Govindharaj G-P-P, Gadratagi BG, Annamalai M, Mukherjee AK, Rath PC (2020) Nanoemulsion of eucalyptus oil: an alternative to synthetic pesticides against two major storage insects (Sitophilus oryzae (L.) and Tribolium castaneum (Herbst)) of rice. Ind Crop Prod 143:111849
Adams RP (2007) Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy, 4th edn. Allured Publishing Corporation, Carol Stream
Afshar F, Maggi F, Iannarelli R, Cianfaglione K, Isman MB (2017) Comparative toxicity of Helosciadium nodiflorum essential oils and combinations of their main constituents against the cabbage looper, Trichoplusia ni (Lepidoptera). Ind Crop Prod 98:46–52. https://doi.org/10.1016/j.indcrop.2017.01.004
Almadiy AA, Nenaah GE (2022) Bioactivity and safety evaluations of Cupressus sempervirens essential oil, its nanoemulsion and main terpenes against Culex quinquefasciatus Say. Environ Sci Pollut R 29(9):13417–13430
Athanassiou GC, Kavallieratos NG, Evergetis E, Katsoula A-M, Haroutounian SA (2013) Insecticidal efficacy of silica gel with Juniperus oxycedrus ssp. Oxycedrus (Pinales: Cupressaceae) essential oil against Sitophilus oryzae (Coleoptera: Curculionidae) and Tribolium confusum (Coleoptera: Tenebrionidae). J Econ Entomol 106(4):1902–1910. https://doi.org/10.1603/EC12474
Bandara K, Saxena R (1995) A technique for handling and sexing Callosobruchus maculatus (F.) adults (Coleoptera, Bruchidae). J Stored Prod Res 31:97–100. https://doi.org/10.1016/0022-474X(94)00030-W
Banga KS, Kumar S, Kotwaliwale N, Mohapatra D (2020) Major insects of stored food grains. Int J Chem Stud 8:2380–2384. https://doi.org/10.22271/chemi.2020.v8.i1aj.8624
Belhamel C, Boulekbachee-Makhlouf L, Bedini S, Tani C, Lombardi T, Giannotti P, Madani K, Belhamel K, Conti B (2020) Nanostructured alumina as seed protectant against three stored product insect pests. J Stored Prod Res 87:101607. https://doi.org/10.1016/j.jspr.2020.101607
Benelli G (2021) Green synthesis of nanomaterials and their biological applications. Nanomaterials 11:2842. https://doi.org/10.3390/nano11112842
Benelli G, Ceccarelli C, Zeni V, Rizzo R, Verde GL, Sinacori M, Boukouvala MC, Kavallieratos NG, Ubaldi M, Tomassoni D, Benvenuti F, Roy P, Petrelli R, Cappellacci L, Spinozzi E, Maggi F, Canale A (2022) Lethal and behavioural effects of a green insecticide against an invasive polyphagous fruit fly pest and its safety to mammals. Chemosphere 287:132089. https://doi.org/10.1016/j.chemosphere.2021.132089
Benelli G, Pavela R, Drenaggi E, Desneux N, Maggi F (2020) Phytol, (E)-nerolidol and spathulenol from Stevia rebaudiana leaf essential oil as effective and eco-friendly botanical insecticides against Metopolophium dirhodum. Ind Crop Prod 155:112844. https://doi.org/10.1016/j.indcrop.2020.112844
Benelli G, Pavela R, Iannarelli R, Petrelli R, Cappellacci L, Cianfaglione K, Afshar FH, Nicoletti M, Canale A, Maggi F (2017) Synergized mixtures of Apiaceae essential oils and related plant-borne compounds: larvicidal effectiveness on the filariasis vector Culex quinquefasciatus say. Ind Crop Prod 96:186–195
Benelli G, Pavela R, Maggi F, Wandjou JGN, Fofie NGB, Kone Bambae D, Sagratini G, Vittori S, Caprioli G (2019) Insecticidal activity of the essential oil and polar extracts from Ocimum gratissimum grown in Ivory Coast: efficacy on insect pests and vectors and impact on non-target species. Ind Crop Prod 132:377–385
Benelli G, Pavela R, Petrelli R, Cappellacci L, Santini G, Fiorini D, Sut S, Dall’Acqua S, Canale A, Maggi F, (2018a) The essential oil from industrial hemp (Cannabis sativa L.) by-products as an effective tool for insect pest management in organic crops. Ind Crop Prod 122:308–315
Benelli G, Rajeswary M, Govindarajan M (2018b) Towards green oviposition deterrents? Effectiveness of Syzygium lanceolatum (Myrtaceae) essential oil against six mosquito vectors and impact on four aquatic biological control agents. Environ Sci Pollut R 25:10218–10227. https://doi.org/10.1007/s11356-016-8146-3
Boulos L (2000) Flora of Egypt, vol 2. AL-Hadara Publishing, Cairo
Bughio FM, Wilkins RM (2021) Fitness in a malathion resistant Tribolium castaneum strain; feeding, growth and digestion. J Stored Prod Res 92:101814. https://doi.org/10.1016/j.jspr.2021.101814
Cicció-Alberti JF, Ballestero CM (1997) Constituyentes volátiles de las hojas y espigas de Piper aduncum (Piperaceae) de Costa Rica. Rev Biol Trop 45:783–790
Dorla E, Gauvin-Bialecki A, Deuscher Z et al (2017) Insecticidal activity of the leaf essential oil of Peperomia borbonensis Miq. (Piperaceae) and its major components against the Melon Fly Bactrocera cucurbitae (Diptera: Tephritidae). Chem. Biodivers. 14(6):e1600493. https://doi.org/10.1002/cbdv.201600493
Figueiredo AC, Barroso JG, Pedro LG, Scheffer JJC (2008) Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavor Frag J 23:213–226
Finney DJ (1971) Probit Analysis, 3rd edn. Cambridge University Press, London
Gad HA, Abo Laban GF, Metwaly KH, Al-Anany FS, Abdelgaleil SAM (2021) Efficacy of ozone for Callosobruchus maculatus and Callosobruchus chinensis control in cowpea seeds and its impact on seed quality. J Stored Prod Res 92:101786. https://doi.org/10.1016/j.jspr.2021.101786
Ganji S, Svensson FG, Unelius CR (2020) Asymmetric synthesis of oxygenated monoterpenoids of importance for bark beetle ecology. J Nat Prod 83(11):3332–3337
Giunti G, Campolo O, Laudani F, Palermo D, Zappalà L, Palmeri V (2021) Bioactivity of essential oil-based nano-biopesticides toward Rhyzopertha dominica (Coleoptera: Bostrichidae). Ind Crop Prod 162:113257. https://doi.org/10.1016/j.indcrop.2021.113257
Giunti G, Palermo D, Laudani F, Algeri GM, Campolo O, Palmeri V (2019) Repellence and acute toxicity of a nano-emulsion of sweet orange essential oil toward two major stored grain insect pests. Ind Crop Prod 142:111869. https://doi.org/10.1016/j.indcrop.2019.111869
Guetat A, Boulila A, Boussaid M (2019) Phytochemical profile and biological activities of Deverra tortuosa (Desf.) DC.: a desert aromatic shrub widespread in Northern Region of Saudi Arabia. Nat Prod Res 33(18):2708–2713. https://doi.org/10.1080/14786419.2018.1460842
Hano C, Abbasi BH (2022) Plant-based green synthesis of nanoparticles: Production, characterization and applications. Biomolecules 12:31. https://doi.org/10.3390/biom12010031
Hillocks RJ (2012) Farming with fewer pesticides: EU pesticide review and resulting challenges for UK agriculture. Crop Prot 31:85–93. https://doi.org/10.1016/j.cropro.2011.08.008
Hubert J, Stejskal V, Athanassiou CG, Throne JE (2018) Health hazards associated with arthropod infestation of stored products. Annu Rev Entomol 63:553–573. https://doi.org/10.1146/annurev-ento-020117-043218
Ihekoronye AI, Ngoddy PO (1995) Integrated food science and technology for tropics. Macmillan Publishers Ltd, London
Isman MB (2004) Plant essential oils as green pesticides for pest and disease management. ACS Symp Ser 887:41–51
Kang JK, Pittendrigh BR, Onstad DW (2013) Insect resistance management for stored product pests: a case study of cowpea weevil (Coleoptera: Bruchidae). J Econ Entomol 106(6):2473–2490. https://doi.org/10.1603/EC13340
Kavallieratos NG, Boukouvala MC, Ntalaka CT, Skourti A, Nika EP, Maggi F, Spinozzi E, Mazzara E, Petrelli R, Lupidi G, Giordani C, Benelli G (2021a) Efficacy of 12 commercial essential oils as wheat protectants against stored-product beetles, and their acetylcholinesterase inhibitory activity. Entomol Gen. https://doi.org/10.1127/entomologia/2021/1255
Kavallieratos NG, Skourti A, Nika EP, Ntalaka CT, Boukouvala MC, Bonacucina G, Cespi M, Petrelli R, Cappellacci L, Maggi F, Benelli G, Canale A (2021b) Isofuranodiene-based nanoemulsion: larvicidal and adulticidal activity against tenebrionid beetles attacking stored wheat. J Stored Prod Res 93:101859. https://doi.org/10.1016/j.jspr.2021.101859
Krifa M, Gharad T, Haouala R (2011) Biological activities of essential oil, aqueous and organic extracts of Pituranthos tortuosus (Coss.) Maire. Sci Hortic 128(1):61–67. https://doi.org/10.1016/j.scienta.2010.12.016
Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko K-H, Ryu J-H (2005) Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. Toxicol Lett 157:49–56. https://doi.org/10.1016/j.toxlet.2005.01.012
Lima LA, Ferreira-Sá PS, Garcia MDN Jr, Pereira VLP, Carvalho JCT, Rocha L, Fernandes CP, Souto RNP, Araújo RS, Botas G, Cruz RAS (2021) Nano-emulsions of the essential oil of Baccharis reticularia and its constituents as eco-friendly repellents against Tribolium castaneum. Ind Crop Prod 162:113282. https://doi.org/10.1016/j.indcrop.2021.113282
Liu SQ, Scott IM, Pelletier Y, Kramp K, Durst T, Sims SR, Arnason JT (2014) Dillapiol: a pyrethrum synergist for control of the Colorado potato beetle. J Econ Entomol 107(2):797–805. https://doi.org/10.1603/ec13440
Lu X, Feng Y, Du Y, Zheng Y, Borjigidai A, Zhang X, Du SS (2021) Insecticidal and repellent activity of Thymus quinquecostatus Celak. essential oil and major compositions against three stored-product insects. Chem Biodivers. https://doi.org/10.1002/cbdv.202100374
Matysik E, Wofniak A, Paduch R, Rejdak R, Polak B, Donica H (2016) The new TLC method for separation and determination of multicomponent mixtures of plant extracts. J Anal Methods Chem 1813581:6. https://doi.org/10.1155/2016/1813581
Miura PT, Jonsson CM, Queiroz SCN, Chagas EC, Chaves FCM, Reyes FGR (2021) Ecological risk assessment of Piper aduncum essential oil in non-target organisms. Acta Amazon 51(1):71–78. https://doi.org/10.1590/1809-4392202002691
Mossa AH, Mohafrash SM, Chandrasekaran N (2018). Safety of natural insecticides: Toxic effects on experimental animals. BioMed Res Int 4308054.https://doi.org/10.1155/2018/4308054
Nenaah GE (2014) Chemical composition, toxicity and growth inhibitory activities of essential oils of three Achillea species and their nano-emulsions against Tribolium castaneum (Herbst). Ind Crop Prod 53:252–260. https://doi.org/10.1016/j.indcrop.2013.12.042
Nenaah GE, Almadiy AA, Al-Assiuty BA, Mahnashi MH (2022) The essential oil of Schinus terebinthifolius and its nanoemulsion and isolated monoterpenes: investigation of their activity against Culex pipiens with insights into the adverse effects on non-target organisms. Pest Manag Sci 78(3):1035–1047
Nenaah GE, Ibrahim S, Al-Assiuty B (2015) Chemical composition, insecticidal activity and persistence of three Asteraceae essential oils and their nanoemulsions against Callosobruchus maculatus (F.). J Stored Prod Res 61:9–16. https://doi.org/10.1016/j.jspr.2014.12.007
Nisar MS, Haq IU, Ramzan H, Aljedani D, Qasim M, Islam W, Khan K (2021) Screening of different legumes for the developmental preference of Callosobruchus maculatus (Bruchidae: Coleoptera). Int J Trop Insect Sci. https://doi.org/10.1007/s42690-021-00507-6
NIST (2017) NIST Chemistry WebBook: NIST Standard Reference Database Number 69. Available: http://webbook.nist.gov/chemistry/. Accessed 12 Sept 2021
Papanikolaou NE, Kavallieratos NG, Iliopoulos V et al (2022) Essential oil coating: mediterranean culinary plants as grain protectants against larvae and adults of Tribolium castaneum and Trogoderma granarium. Insects 13(2):165. https://doi.org/10.3390/insects13020165
Parra-Arroyo L, González-González RB, Castillo-Zacarías C, Martínez EMM, Sosa-Hernández JE, Bilal M, Iqbal HMN, Barceló D, Parra-Saldívar R (2022) Highly hazardous pesticides and related pollutants: toxicological, regulatory, and analytical aspects. Sci Total Environ 807(3):151879. https://doi.org/10.1016/j.scitotenv.2021.151879
Pavela R (2018) Essential oils from Foeniculum vulgare Miller as a safe environmental insecticide against the aphid Myzus persicae Sulzer. Environ Sci Pollut R 25:10904–10910. https://doi.org/10.1007/s11356-018-1398-3
Pavela R, Benelli G (2016) Essential oils as eco-friendly biopesticides? Challenges and constraints. Trends Plant Sci 21:1000–1007. https://doi.org/10.1016/j.tplants.2016.10.005
Pavela R, Maggi F, Cianfaglione K, Bruno M, Benelli G (2018) Larvicidal activity of essential oils of five Apiaceae taxa and some of their main constituents against Culex quinquefasciatus. Chem Biodivers 15(1). https://doi.org/10.1002/cbdv.201700382
Pavela R, Maggi F, Mazzara E, Torresi J, Cianfaglione K, Benelli G, Canale A (2021) Prolonged sublethal effects of essential oils from non-wood parts of nine conifers on key insect pests and vectors. Ind Crop Prod 168:113590. https://doi.org/10.1016/j.indcrop.2021.113590
Reddy SR, Fogler HS (1981) Emulsion stability: determination from turbidity. J Colloid Interf Sci 79:101–104. https://doi.org/10.1016/0021-9797(81)90052-7
Rees D (2004) Insects of stored products. CSIRO publishing, Canberra, Australia
Rojas-Martínez R, Arrieta J, Cruz-Antonio L, Arrieta-Baez D, Velázquez-Méndez AM, Sánchez-Mendoza ME (2013) Dillapiole, isolated from Peperomia pellucida, shows gastroprotector activity against ethanol-induced gastric lesions in Wistar rats. Molecules 18(9):11327–11337
Silva-Aguayo G, Aguilar-Marcelino L, Cuevas-Padilla E, Loyola-Zapata P, Rodríguez-Maciel JC, Castañeda-Ramírez G, Figueroa-Cares I (2021) Essential oil of Peumus boldus Molina against the nematode Haemonchus contortus (L3) and three stored cereal insect pests. Chil J Agr Res 81(3):390–397
Song SY, Chang HJ, Kim SD, Kwag EB, Park SJ, Yoo HS (2021) Acute and sub-chronic toxicological evaluation of the herbal product HAD-B1 in Beagle dogs. Toxicol Rep 8:1819–1829. https://doi.org/10.1016/j.toxrep.2021.11.002
Spinozzi E, Pavela R, Bonacucina G, Perinelli DR, Cespi M, Petrelli R, Cappellacci L, Fiorini D, Scortichini S, Garzoli S, Angeloni C, Freschi M, Hrelia S, Quassinti L, Bramucci M, Lupidi G, Sut S, Dall’Acqua S, Benelli G, Canale A, Ttore Drenaggi E, Maggi F (2021) Spilanthol-rich essential oil obtained by microwave-assisted extraction from Acmella oleracea (L.) R.K. Jansen and its nanoemulsion: Insecticidal, cytotoxic and anti-inflammatory activities. Ind Crop Prod 172:114027. https://doi.org/10.1016/j.indcrop.2021.114027
Srivastava S, Bhargava A (2022) Applications of biosynthesized nanoparticles. In: Green nanoparticles: the future of nanobiotechnology. Springer, Singapore. https://doi.org/10.1007/978-981-16-7106-7_14
Tilman D, Balzer C, Hill J, Befort BL (2011) Global food demand and the sustainable intensification of agriculture. Proc Natl Acad Sci U S A 108(50):20260–20264. https://doi.org/10.1073/pnas.1116437108
Viana Cruz DL, Sumita TC, Silva Leão Ferreira M, Soares da Silva J, Pinto A, Marques Barcellos JF, Rafael MS (2020) Histopathological, cytotoxicological, and genotoxic effects of the semi-synthetic compound dillapiole n-butyl ether in Balb/C mice. J Toxicol Env Heal A 83(17–18):604–615. https://doi.org/10.1080/15287394.2020.1804026
Wang YK, Yang XN, Zhu X, Xiao XR, Yang XW, Qin HB, Gonzalez FJ, Li F (2019) Role of metabolic activation in elemicin-induced cellular toxicity. J Agric Food Chem 67(29):8243–8252
Wu X-f, Chen M-n, Wang Y-j, Yu S-q, Xia Y-l, Dong C-z, Hou Z-m, Cao Y (2021) Chemical composition and fumigant activities of essential oils from Piper hancei Maxim against Tribolium castaneum (Herbst). J Essent Oil Bear Pl 24(1):86–93. https://doi.org/10.1080/0972060X.2021.1886997
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This research is supported by the Deputy for Research and Innovation, Ministry of Education, Saudi Arabia (Grant no. NU/IFC/ENT/01/003), under the institutional Funding Committee at Najran University.
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Almadiy, A.A., Nenaah, G.E. & Albogami, B.Z. Bioactivity of Deverra tortuosa essential oil, its nanoemulsion, and phenylpropanoids against the cowpea weevil, a stored grain pest with eco-toxicological evaluations. Environ Sci Pollut Res 29, 65112–65127 (2022). https://doi.org/10.1007/s11356-022-20404-w
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DOI: https://doi.org/10.1007/s11356-022-20404-w