A Chemical Approach to Obtaining α-copaene from Clove Oil and Its Application in the Control of the Medfly
Source abstract
Abstract
The Ceratitis capitata (Wiedemann) fruit fly pest has been widely ecologically controlled by means of using attractant substances. This study supports the idea that α-copaene, a naturally occurring substance found in numerous plants, might be used as a semiochemical to control this pest. The possibility of obtaining this natural compound in abundant quantities may reveal its potential use in integrated pest management. The main goal of this study was to demonstrate, on a small scale, how the extraction of clove oil by fractional distillation and other laboratory-assisted techniques can facilitate the obtaining of abundant amounts of α-copaene for its use in the control of the medfly. As a result, the male attraction of α-copaene isolated from clove oil was confirmed to be 5–6 times higher than commercial trimedlure. In its field projection, five distilled fractions with an α-copaene content of less than 10% were shown to have from a quarter to half of the attractive power exerted by trimedlure on males. It can be concluded that the use of selected distilled fractions of α-copaene can be enough to obtain large quantities of this compound to be applied successfully in ecological programs to lure medflies.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Insect behavior and control techniques · Insect Pest Control Strategies · Insect-Plant Interactions and Control
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Research Group in Forest Science and Technology (Re-ForeST), Research Institute of Water and Environmental Engineering (IIAMA), Universitat Politècnica de València, Camí de Vera s/n, E-46022 Valencia, Spain
Independent Researcher
Instituto de Tecnología Química, Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas, E-46022 Valencia, Spain
Funding
Consejería de Educación y Ciencia de la C. Valenciana
References (99)
Show source-provided references
1. EC (European Commission) (2023, March 01). EU Biodiversity Strategy for 2030. Bringing Nature Back into Our Lives, Available online: https://op.europa.eu/en/publication-detail/-/publication/31e4609f-b91e-11eb-8aca-01aa75ed71a1.
2. EC (European Commission) (2023, March 01). The European Green Deal, Available online: https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:52019DC0640&from=EN.
3. Enabling forecasts of environmental exposure to chemicals in European agriculture under global change10.1016/j.scitotenv.2022.156478 ↗
4. Sexual communication and related behaviours in Tephritidae: Current knowledge and potential applications for Integrated Pest Management10.1007/s10340-014-0577-3 ↗
5. From integrated pest management to integrated pest eradication: Technologies and future needs10.1002/ps.3670 ↗
6. Garcia, F.R.M., Ovruski, S.M., Suárez, L., Cancino, J., and Liburd, O.E. (2020). Biological control of tephritid fruit flies in the Americas and Hawaii: A review of the use of parasitoids and predators. Insects, 11.10.3390/insects11100662 ↗
7. Tephritidae bacterial symbionts: Potentials for pest management10.1017/S0007485319000403 ↗
8. Carlina acaulis L. (Asteraceae): Biology, phytochemistry, and application as a promising source of effective green insecticides and acaricides10.1016/j.indcrop.2022.116076 ↗
9. de Pedro, L., Beitia, F., and Tormos, J. (2023). Two Better Than One? Potential Effects of Intraguild Predation on the Biological Control of Ceratitis capitata (Diptera: Tephritidae) by the Parasitoid Aganaspis daci (Hymenoptera: Figitidae) and the Predator Pseudoophonus rufipes (Coleoptera: Carabidae). Agronomy, 13.10.3390/agronomy13010087 ↗
10. Predation potential of the earwig Euborellia annulipes on fruit fly larvae and trophic interactions with the parasitoid Diachasmimorpha longicaudata10.1111/jen.13091 ↗
11. Scolari, F., Valerio, F., Benelli, G., Papadopoulos, N.T., and Vaníčková, L. (2021). Tephritid fruit fly semiochemicals: Current knowledge and future perspectives. Insects, 12.10.3390/insects12050408 ↗
12. Advancements in management of major fruit flies (Diptera: Tephritidae) in North Africa and future challenges: A review10.1111/jen.12938 ↗
13. Host Suitability Index for Polyphagous Tephritid Fruit Flies10.1093/jee/toab035 ↗
14. Liquido, N.J., Barr, P.G., and Cunningham, R.T. (1997). Medhost: An Encyclopedic Bibliography of the Host Plants of the Mediterranean Fruit by, Ceratitis capitata (Wiedemann) (Electronic Database/Program).
15. Solid phase microextraction of volatile emissions of Ceratitis capitata (Wiedemann) (Diptera: Tephritidae): Influence of fly sex, age, and mating status10.1021/jf104183c ↗
16. Minor and intermediate components enhance attraction of female mediterranean fruit flies to natural male odor pheromone and its synthetic major components10.1023/A:1020855625244 ↗
17. Efficacy of attract-and-kill devices for the control of Ceratitis capitata10.1002/ps.3393 ↗
18. Sterile insect technique (SIT) effectiveness to control Ceratitis capitata (Diptera: Tephritidae) and medfly catches in two mass trapping layouts10.1080/09670874.2022.2130468 ↗
19. Evaluation of the effectiveness of two types of traps for Ceratitis capitata (Wiedemann, 1824) (Diptera; Tephritidae)10.5958/0974-4576.2022.00042.1 ↗
20. Effects of male lure dispensers and trap types for monitoring of Ceratitis capitata and Bactrocera dorsalis (Diptera: Tephritidae)10.1002/ps.6246 ↗
21. Bali, E.M.D., Moraiti, C.A., Ioannou, C.S., Mavraganis, V., and Papadopoulos, N.T. (2021). Evaluation of mass trapping devices for early seasonal management of Ceratitis capitata (Diptera: Tephritidae) populations. Agronomy, 11.10.3390/agronomy11061101 ↗
22. Evaluation of type, color of traps and different attractants in attracting and capturing of mediterranean fruit fly Ceratitis capitata (Wied.)
23. Laboratory evaluation of the compatibility of a new attractant contaminant device containing Metarhizium anisopliae with Ceratitis capitata sterile males10.1016/j.biocontrol.2014.02.007 ↗
24. Field evaluation of Mediterranean fruit fly (Diptera: Tephritidae) female selective attractants for use in monitoring programs10.1093/jee/92.3.583 ↗
25. Field evaluation of female-targeted trapping systems for Ceratitis capitata (Diptera: Tephritidae) in seven countries10.1093/jee/92.1.156 ↗
26. Attraction of Ceratitis capitata (Diptera: Tephritidae) and endemic and introduced nontarget insects to BioLure bait and its individual components in Hawaii10.1603/EN09287 ↗
27. Evaluation of traps and lures for mass trapping of Mediterranean fruit fly in citrus groves10.1093/jee/101.1.126 ↗
28. Identification of pheromone components and their binding affinity to the odorant binding protein CcapOBP83a-2 of the Mediterranean fruit fly, Ceratitis capitata10.1016/j.ibmb.2014.02.005 ↗
29. Effect of Aging on Three Lures Used for Monitoring Ceratitis capitata (Diptera: Tephritidae): Release Rate, Volatile Composition, and Fly Recaptures10.1093/jee/toab246 ↗
30. Evaluation of lures and traps for male and female monitoring of Mediterranean fruit fly in pome and stone fruit10.1111/jen.12360 ↗
31. Comparison between trimedlure and capilure®–attractants for male Ceratitis capitata (Wiedemann) (Diptera: Tephritidae)10.1111/j.1440-6055.1987.tb00254.x ↗
32. A new long-life trimedlure dispenser for mediterranean fruit fly10.1603/0022-0493(2008)101[1325:ANLTDF]2.0.CO;2 ↗
33. Kouloussis, N.A., Mavraganis, V.G., Damos, P., Ioannou, C.A., Bempelou, E., Koveos, D.S., and Papadopoulos, N.T. (2022). Trapping of Ceratitis capitata using the low-cost and non-toxic attractant Biodelear. Agronomy, 12.10.3390/agronomy12020525 ↗
34. Sexual competitiveness of sterile Ceratitis capitata males exposed to essential oils from non-host plant species native to Argentina10.1111/eea.13255 ↗
35. Attraction of Ceratitis capitata (Diptera: Tephritidae) sterile males to essential oils: The importance of linalool10.1093/ee/nvy096 ↗
36. Improving sterile male performance in support of programmes integrating the sterile insect technique against fruit flies10.1111/j.1439-0418.2011.01664.x ↗
37. Enhanced mating competitiveness of Ceratitis capitata males following exposure to citrus compounds10.1111/j.1439-0418.2010.01535.x ↗
38. Exposure to α-copaene and α-copaene-containing oils enhances mating success of male Mediterranean fruit flies (Diptera: Tephritidae)10.1603/0013-8746(2001)094[0497:ETCACC]2.0.CO;2 ↗
39. Isolation and identification of male medfly attractive components in Litchi chinensis stems and Ficus spp. stem exudates10.1007/BF01012277 ↗
40. Parapheromones
41. Angelica oils as Mediterranean fruit fly lures10.1093/jee/50.4.505 ↗
42. The role of attractants in the recent Mediterranean fruit fly eradication program in Florida10.1093/jee/54.1.30 ↗
43. Identificazione della sostanza attrattiva per i maschi della Ceratitis capitata, contenunuta nell’olio essenziale dei semi di Angelica archangelica
44. Duke, J.A. (2001). Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants: Herbal Reference Library, Routledge. [2nd ed.].
45. Blythe, E.K., Tabanca, N., Demirci, B., and Kendra, P.E. (2020). Chemical Composition of Essential Oil From Tetradenia riparia and Its Attractant Activity for Mediterranean Fruit Fly, Ceratitis capitata. Nat. Prod. Commun., 15.10.1177/1934578X20953955 ↗
46. Haro-González, J.N., Castillo-Herrera, G.A., Martínez-Velázquez, M., and Espinosa-Andrews, H. (2021). Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health. Molecules, 26.10.20944/preprints202108.0386.v1 ↗
47. Bauer, K., Garbe, D., and Surburg, H. (2001). Common Fragrance and Flavor Materials: Preparation, Properties and Uses, Wiley-VCH. [2nd ed.].10.1002/3527600205 ↗
48. EC (European Commission) (2023, March 01). Authorising Certain Products and Substances for Use in Organic Production and Establishing Their Lists. C(2021) 5149 Final, Available online: https://ec.europa.eu/info/law/better-regulation/have-your-say/initiatives/12377-Organic-farming-list-ofproducts-&-substances-authorised-in-organic-production-update-_en.
49. A comprehensive review on clove (Caryophyllus aromaticus L.) essential oil and its significance in the formulation of edible coatings for potential food applications10.3389/fnut.2022.987674 ↗
50. The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): A short review10.1002/ptr.2124 ↗
51. Adams, R.P. (1989). Identification of Essential Oils by Ion-Trap Mass Spectroscopy, Academic Press Inc.10.1016/B978-0-12-044230-0.50005-8 ↗
52. α-Copaene, a potential rendezvous cue for the Mediterranean fruit fly, Ceratitis capitata?10.1023/A:1005489411397 ↗
53. Additional male Mediterranean fruitfly (Ceratitis capitata Wied.) attractants from angelica seed oil (Angelica archangelica L.)10.1007/BF02066237 ↗
54. Optical isomers of α-copaene derived from several plant sources10.1021/jf00077a038 ↗
55. Capture of mass-reared vs. wild-like males of Ceratitis capitata (Dipt., Tephritidae) in trimedlure-baited traps10.1111/j.1439-0418.2009.01414.x ↗
56. Mass trapping of the Mediterranean fruit fly, Ceratitis capitata (Wiedemann) on pomegranate in southern Portugal (Algarve)
57. Howse, P.E., Stevens, I.D., and Jones, C.O. (1998). Insect Pheromones and Their Use in Pest Management, Springer.10.1007/978-94-011-5344-7 ↗
58. Evaluation of dispensers containing trimedlure, the attractant for the Mediterranean fruit fly (Diptera: Tephritidae)10.1093/jee/77.3.744 ↗
59. Field capture of male Mediterranean fruit flies (Diptera: Tephritidae) in traps baited with varying amounts of trimedlure10.1653/024.103.0403 ↗
60. Improving the lifetime efficiency of trimedlure-dispensing system in trapping the fruit fly Ceratitis capitata using polyethylene matrix
61. Field longevity and attractiveness of trimedlure plugs to male ceratitis capitata in Florida and Hawaii10.1653/024.101.0322 ↗
62. Performance of controlled release formulations of trimedlure to attract the Mediterranean fruit fly (Ceratitis capitata)10.1111/j.1570-7458.1987.tb02238.x ↗
63. Relative attractiveness of enriched ginger root oil and trimedlure to male Mediterranean fruit flies (Diptera: Tephritidae)10.1653/0015-4040(2002)085[0545:RAOEGR]2.0.CO;2 ↗
64. A review of effective essential oils and their biologically active compounds to protect the safety of food stored against insect pests10.1080/10412905.2022.2032420 ↗
65. Emulsions containing essential oils, their components or volatile semiochemicals as promising tools for insect pest and pathogen management10.1016/j.cis.2020.102330 ↗
66. Essential oils and their bioactive compounds as eco-friendly novel green pesticides for management of storage insect pests: Prospects and retrospects10.1007/s11356-021-12841-w ↗
67. Total synthesis of (±)-copaene and (±)-ylangene. A General Method for the Synthesis of Tricyclo[4.4.0.02,7]decanes10.1021/ja00992a032 ↗
68. A Total Synthesis of (±)-α- and (±)-β-Copaenes and Ylangenes10.1021/ja00788a034 ↗
69. The Total Synthesis of (±)-Copaene and (±)-8-Isocopaene10.1021/ja00969a051 ↗
70. Studies on a new route to (±)-copaene and (±)-ylangene10.1039/P19880003223 ↗
71. Total Syntheses of (±)-α-and (±)-β-Copaene and Formal Total Syntheses of (±)-Sativene, (±)-cis-Sativenediol, and (±)-Helminthosporalt10.1021/ja00028a034 ↗
72. Utilisation of the MVA pathway to produce elevated levels of the sesquiterpene α-copaene in potato tubers10.1016/j.phytochem.2011.08.023 ↗
73. Metabolic engineering of Escherichia coli for the biosynthesis of α-copaene from glucose10.1016/j.bej.2022.108561 ↗
74. Investigation of methods for fuel desulfurization wastewater treatment10.1016/j.cherd.2022.12.021 ↗
75. Pyrolytic conversion of waste plastics to energy products: A review on yields, properties, and production costs10.1016/j.scitotenv.2022.160721 ↗
76. Recent advances and future prospects in direct solar desalination systems using membrane distillation technology10.1016/j.jclepro.2022.135737 ↗
77. Alves-Ferreira, J., Duarte, L.C., Fernandes, M.C., Pereira, H., and Carvalheiro, F. (2023). Cistus ladanifer as a potential feedstock for biorefineries: A review. Energies, 16.10.3390/en16010391 ↗
78. Roni, K.A., and Martini, S. (2022). The effectiveness of octane booster as additive for fuel quality improvement. Asia-Pac. J. Sci. Technol., 27.
79. Experiences in the development of a container system for the distillation of essential oils at the agrargenossenschaft hedersleben e.G
80. Valorization of essential oils from citrus peel powder using hydro-distillation10.1016/j.scp.2023.101036 ↗
81. Evaluation of biological activities of two essential oils as a safe environmental bioinsecticides: Case of Eucalyptus globulus and Rosmarinus officinalis
82. Essential oils: Extraction techniques, pharmaceutical and therapeutic potential-A review10.2174/1389200219666180723144850 ↗
83. Supercritical fluid extraction assisted by cold pressing from clove buds: Extraction performance, volatile oil composition, and economic evaluation10.1016/j.supflu.2018.10.003 ↗
84. Eugenol enrichment of clove bud essential oil using different microwave-assisted distillation methods10.3136/fstr.23.385 ↗
85. Ayub, M.A., Goksen, G., Fatima, A., Zubair, M., Abid, M.A., and Starowicz, M. (2023). Comparison of conventional extraction techniques with superheated steam distillation on chemical characterization and biological activities of Syzygium aromaticum L. essential oil. Separations, 10.10.3390/separations10010027 ↗
86. Challenges and perspectives on innovative technologies for biofuel production and sustainable environmental management10.1016/j.fuel.2022.124845 ↗
87. Ramadan, M.F. (2022). Clove (Syzygium aromaticum): Chemistry, Functionality and Applications, Academic Press (Elsevier).
88. Clove oil as a source of attractant pheromones to the fruit flies, Ceratits capitata (Wiedemann) and Bactrocera zonata (saunders) (Diptera: Tephritidae)10.21608/jppp.2012.84423 ↗
89. Hu, Z.J., Yang, J.W., Chen, Z.H., Chang, C., Ma, Y.P., Li, N., Deng, M., Mao, G.L., Bao, Q., and Deng, S.Z. (2022). Exploration of clove bud (Syzygium aromaticum) essential oil as a novel attractant against Bactrocera dorsalis (Hendel) and its safety evaluation. Insects, 13.10.3390/insects13100918 ↗
90. Development of clove oil based nanoencapsulated biopesticide employing mesoporous nanosilica synthesized from paddy straw via bioinspired sol-gel route10.1016/j.envres.2022.115208 ↗
91. Milićević, Z., Krnjajić, S., Stević, M., Ćirković, J., Jelušić, A., Pucarević, M., and Popović, T. (2022). Encapsulated clove bud essential oil: A new perspective as an eco-friendly biopesticide. Agriculture, 12.10.3390/agriculture12030338 ↗
92. Coetzee, D., Militky, J., and Venkataraman, M. (2022). Functional coatings by natural and synthetic agents for insect control and their applications. Coatings, 12.10.3390/coatings12040476 ↗
93. Implication of SAR of male medfly attractants in insect olfaction10.1080/1062936021000043382 ↗
94. Male lures for mediterranean fruitfly (Ceratitis capitata Wied.): Structural analogs of α-copaene10.1007/BF02036194 ↗
95. Field observations on attraction of Ceratitis capitata Wiedemann to alphacopaene
96. Mating success of male Mediterranean fruit flies following exposure to two sources of α-copaene, manuka oil and mango10.1653/0015-4040(2008)091[0009:MSOMMF]2.0.CO;2 ↗
97. Role of α-copaene in the susceptibility of olive fruits to Bactrocera oleae (Rossi)10.1021/jf504821a ↗
98. Quantitative analysis of contents and volatile emissions from α-copaene and quercivorol lures, and longevity for attraction of Euwallacea nr. fornicatus in Florida10.1007/s10340-018-0960-6 ↗
99. Efficacy of α-copaene, cubeb, and eucalyptol lures for detection of redbay ambrosia beetle (Coleoptera: Curculionidae: Scolytinae)10.1093/jee/tow214 ↗