Compounds isolated from botanical sources represent innovative and promising alternatives to conventional insecticides. Carlina oxide is a compound isolated from Carlina acaulis L. (Asteraceae) essential oil (EO) with great potential as bioinsecticide, being effective on various arthropod vectors and agricultural pests, with moderate toxicity on non-target species. Since the production from the wild source is limited, there is the need of exploring new synthetic routes for obtaining this compound and analogues with improved bioactivity and lower toxicity. Herein, the chemical synthesis of carlina oxide analogues was developed. Their insecticidal activity was assessed on the vectors Musca domestica L. and Culex quinquefasciatus Say, and their cytotoxicity was evaluated on a human keratinocyte cell line (HaCaT). The compounds' activity was compared with that of the natural counterparts EO and carlina oxide. In housefly tests, the analogues were comparably effective to purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantly higher efficacy (LC50 of 0.71 μg mL-1) than the EO and carlina oxide (LC50 1.21 and 1.31 μg mL-1, respectively) and a better safety profile than carlina oxide on keratinocytes. Overall, this study can open the way to an agrochemical production of carlina oxide analogues employable as nature-inspired insecticides.
- MeSH
- Asteraceae * chemie MeSH
- Culex * MeSH
- insekticidy * farmakologie MeSH
- komáří přenašeči MeSH
- larva MeSH
- lidé MeSH
- oleje prchavé * farmakologie chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Marsh rosemary (Ledum palustre, Ericaceae) has been widely used in the traditional medicine of various regions worldwide, and as insect repellent. Little is known on its essential oil insecticidal potential. This study explored the insecticidal effects of the essential oil obtained from L. palustre growing in Poland on selected insect pests and vectors. GC-MS analysis evidenced an uncommon chemotype characterized by ascaridole (35.3% as sum of cis-ascaridole and isoascaridole) and p-cymene (25.5%). The essential oil was effective against Culex quinquefasciatus, Spodoptera littoralis and Musca domestica, showing LC50/LD50 of 66.6 mg L-1, 117.2 μg larva-1 and 61.4 μg adult-1, respectively. It was not toxic to non-target Eisenia fetida earthworms and moderately toxic to Daphnia magna microcrustaceans, over the positive control α-cypermethrin. The essential oil cytotoxicity on human keratinocytes and fibroblasts showed high IC50 values (71.3 and 84.4 μg mL-1, respectively). Comet assay data highlighted no DNA damages. Based on our findings, this essential oil, characterized by the ascaridole/p-cymene chemotype, could be a candidate for the formulation of botanical insecticides; large-scale production of green insecticides by this rare species may be assured by ex situ cultivation and biotechnological techniques.
- MeSH
- buněčné linie MeSH
- Culex účinky léků MeSH
- Culicidae účinky léků MeSH
- cymeny analýza farmakologie MeSH
- Daphnia účinky léků MeSH
- insekticidy analýza farmakologie MeSH
- keratinocyty cytologie účinky léků MeSH
- komáří přenašeči účinky léků MeSH
- kometový test MeSH
- larva účinky léků MeSH
- lidé MeSH
- monoterpeny s cyklohexanovým kruhem analýza farmakologie MeSH
- moucha domácí účinky léků MeSH
- můry účinky léků MeSH
- oleje prchavé analýza farmakologie MeSH
- Oligochaeta účinky léků MeSH
- peroxidy analýza farmakologie MeSH
- pyrethriny analýza farmakologie MeSH
- repelenty proti hmyzu analýza farmakologie MeSH
- rozmarýn chemie MeSH
- Spodoptera účinky léků MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Polsko MeSH
