{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,6]],"date-time":"2026-05-06T19:47:45Z","timestamp":1778096865955,"version":"3.51.4"},"reference-count":39,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2020,12,4]],"date-time":"2020-12-04T00:00:00Z","timestamp":1607040000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["CQ\/UM (UIDB\/00686\/2020),"],"award-info":[{"award-number":["CQ\/UM (UIDB\/00686\/2020),"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["REDE\/1517\/RMN\/2005"],"award-info":[{"award-number":["REDE\/1517\/RMN\/2005"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","award":["PTDC\/ASP-AGR\/30154\/2017 (POCI-01-0145-FEDER-030154)."],"award-info":[{"award-number":["PTDC\/ASP-AGR\/30154\/2017 (POCI-01-0145-FEDER-030154)."]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia Portugal","award":["CF-UM-UP (UIDB\/04650\/2020)"],"award-info":[{"award-number":["CF-UM-UP (UIDB\/04650\/2020)"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia Portugal","award":["REQUIMTE (UIDB\/50006\/2020)"],"award-info":[{"award-number":["REQUIMTE (UIDB\/50006\/2020)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Eugenol, the generic name of 4-allyl-2-methoxyphenol, is the major component of clove essential oil, and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant actions. New O-alkylated eugenol derivatives, bearing a propyl chain with terminals like hydrogen, hydroxyl, ester, chlorine, and carboxylic acid, were synthesized in the present work. These compounds were later subjected to epoxidation conditions to give the corresponding oxiranes. All derivatives were evaluated against their effect upon the viability of insect cell line Sf9 (Spodoptera frugiperda), demonstrating that structural changes elicit marked effects in terms of potency. In addition, the most promising molecules were evaluated for their impact in cell morphology, caspase-like activity, and potential toxicity towards human cells. Some molecules stood out in terms of toxicity towards insect cells, with morphological assessment of treated cells showing chromatin condensation and fragmentation, which are compatible with the occurrence of programmed cell death, later confirmed by evaluation of caspase-like activity. These findings point out the potential use of eugenol derivatives as semisynthetic insecticides from plant natural products.<\/jats:p>","DOI":"10.3390\/ijms21239257","type":"journal-article","created":{"date-parts":[[2020,12,4]],"date-time":"2020-12-04T11:59:00Z","timestamp":1607083140000},"page":"9257","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":51,"title":["New Eugenol Derivatives with Enhanced Insecticidal Activity"],"prefix":"10.3390","volume":"21","author":[{"given":"Maria Jos\u00e9 G.","family":"Fernandes","sequence":"first","affiliation":[{"name":"Centre of Chemistry, Department of Chemistry, Campus of Gualtar, University of Minho, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8500-7364","authenticated-orcid":false,"given":"Renato B.","family":"Pereira","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0384-7592","authenticated-orcid":false,"given":"David M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"REQUIMTE\/LAQV, Laboratory of Pharmacognosy, Department of Chemistry, Faculty of Pharmacy, University of Porto, R. Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8754-2472","authenticated-orcid":false,"given":"A. Gil","family":"Fortes","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, Department of Chemistry, Campus of Gualtar, University of Minho, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5829-6081","authenticated-orcid":false,"given":"Elisabete M. S.","family":"Castanheira","sequence":"additional","affiliation":[{"name":"Centre of Physics, Department of Physics, Campus of Gualtar, University of Minho, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2048-1190","authenticated-orcid":false,"given":"M. Sameiro T.","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, Department of Chemistry, Campus of Gualtar, University of Minho, 4710-057 Braga, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2020,12,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/j.chemosphere.2018.09.071","article-title":"Ecotoxicity of a novel biopesticide from Artemisia absinthium on non-target aquatic organisms","volume":"216","author":"Ballestero","year":"2019","journal-title":"Chemosphere"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"105043","DOI":"10.1016\/j.cropro.2019.105043","article-title":"Chemical characterization and insecticidal effect against Sitophilus zeamais (maize weevil) of essential oil from Croton rudolphianus leaves","volume":"129","author":"Ribeiro","year":"2020","journal-title":"Crop Prot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"110812","DOI":"10.1016\/j.ecoenv.2020.110812","article-title":"Global trends in pesticides: A looming threat and viable alternatives","volume":"201","author":"Sharma","year":"2020","journal-title":"Ecotoxicol. 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