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

Carlina acaulis (Compositae) is traditionally used for food and medicinal purposes in central and southern Europe. Its root essential oil (EO), mainly composed by carlina oxide, is included in the BELFRIT botanical list of food supplements. It is also recognized as a potent mosquito larvicide. It is matter of concern whether this EO could be endowed with intrinsic toxicity to limit its use on a food level. Focusing on the insecticidal activity of this EO, we investigated the acute toxicity and sublethal effects on Musca domestica. In topical assays, the EO was extremely effective (LD50 = 2.74 and 5.96 μg fly-1, on males and females, respectively). The exposure to a sublethal dose (LD30) led to significant reductions of female longevity (LT50 = 6.7-9.0 days vs. control LT50 = 12.9-13.7 days). Treated females laid 2.5 times fewer eggs over control ones. F1 vitality decreased: F1 larvae and pupae showed high mortality, 2-4-fold higher over the control. The EO also showed high cytotoxicity on normal human fibroblasts (NHF-A12, IC50 = 9.4-14.2 μg mL-1 after 6-48 h). Overall, our findings support the employ of this EO for developing botanical insecticides. At the same time, they encourage food safety authorities to perform a full toxicological assessment for possible restrictions at food level.

• MeSH
• buněčné linie MeSH
• insekticidy toxicita   MeSH
• kořeny rostlin chemie   MeSH
• kukla účinky léků   MeSH
• larva účinky léků   MeSH
• lidé MeSH
• Magnoliopsida chemie   MeSH
• moucha domácí účinky léků   MeSH
• oleje prchavé toxicita   MeSH
• oleje rostlin toxicita   MeSH
• zvířata MeSH
• Check Tag
• lidé MeSH
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH