Eugenol derivatives with potential insecticide activity
Abstract
In the present work, semisynthetic eugenol derivatives were obtained through epoxidation reaction followed by epoxide opening with nucleophiles, such as sodium azide and sodium cyanide. The optimization of the various reactions was performed using different experimental conditions. The main objective behind obtaining these eugenol derivatives was their evaluation as alternative insecticides, thus the biological activity of all compounds was compared to a commercial synthetic insecticide and tested against Sf9 (Spodoptera frugiperda) insect cell line.
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Organization Code Food and natural products Eugenol derivatives with potential insecticide activity José R. A. Coelho,a Maria José G. Fernandes,a David M. Pereira,b Elisabete M. S. Castanheira,c A. Gil Fortes,a M. Sameiro T. Gonçalvesa a) Centre of Chemistry (CQ/UM), University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal; b) REQUIMTE/LAQV, Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal; c) Centre of Physics (CFUM), University of Minho, Campus of Gualtar, 4710-057 Braga, Portugal. Email: [email protected] Eugenol, the generic name of 4-allyl-2-methoxyphenol, is the major component of clove’s essential oil, and displays antimicrobial, antioxidant and insecticide potential.1-3 Its structural simplicity, inexpensively and availability makes it a molecule widely used as a starting material in the preparation of derivatives of natural products and their analogs, as well as building block for obtaining complex functionalized bioactive compounds and co-drugs with improved physicochemical properties, macrocycles, heterocycles, and polymers.4-6 Eugenol is a phenylpropanoid, which has a double bond with capability for further functionalization, namely through epoxidation reaction. As it is well-known, the epoxide is a good and highly reactive synthetic intermediate, because of the associated ring tension, as its opening allows for numerous possibilities, depending on the nucleophiles chosen. Considering all the above facts, in the present work, semisynthetic eugenol derivatives were obtained through epoxidation reaction followed by epoxide opening with nucleophiles, such as sodium azide and sodium cyanide. The optimization of the various reactions was performed using different experimental conditions. The main objective behind obtaining these eugenol derivatives was their evaluation as alternative insecticides, thus the biological activity of all compounds was compared to a commercial synthetic insecticide and tested against Sf9 (Spodoptera frugiperda) insect cell line. Acknowledgements: We thank the financial support of project PTDC/ASP-AGR/30154/2017 (POCI-01-0145-FEDER-030154) of the COMPETE 2020 program, co-financed by the FEDER and the European Union. The authors acknowledge also to Foundation for Science and Technology (FCT, Portugal), and FEDER-COMPETE-QREN-EU for financial support to the research centres CQ-UM (UID/QUI/00686/2020), CF-UM-UP (UID/FIS/04650/2020) and REQUIMTE (UIDB/50006/2020). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. References: 1. Ju J.; Xie Y.; Yu H.; Guo Y.; Cheng Y.; Qian H.; Yao W. LWT Food Sci. Technol. 2020, 123, 109128. 2. Sohilait H. J.; Kainama H. Open Chem. 2019, 17, 422. 3. Raveau R.; Fontaine J.; Sahraoui A. L.-H. Foods, 2020, 9, 365. 4. Kaufman T. S. J. Braz. Chem. Soc. 2015, 26, 1055. 5. Fernandes M. J. G.; Pereira R. B.; Pereira D. M.; Fortes A. G.; Castanheira E. M. S.; Gonçalves M. S. T. Int. J. Mol. Sci. 2020, 21, 9257. 6. Potapov V. A.; Ishigeev R. S.; Shkurchenko I. V.; Zinchenko S. V.; Amosova S. V. Molecules 2020, 25, 376.