Toxic effect and genotoxicity of carvacrol ethers in Drosophila melanogaster

Nesterkina, Mariia; Bilokon, Svitlana; Алєксєєва, Т. Г.; Chebotar, S. V.; Kravchenko, Iryna

doi:10.1016/j.mrfmmm.2020.111713

Cited by 7 publications

(2 citation statements)

References 18 publications

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“…Carvacrol propyl, butyl, octyl and benzyl ethers demonstrated the ability to reduce fertility and viability of the fruit fly Drosophila melanogaster after oral administration or inhalation exposure [ 109 ]. Moreover, different alkyl 4-oxobutanoate p -substituted carvacryl ethyl ethers have been synthesized ( Scheme 7 ) and screened as tyrosinase inhibitors, which are valuable molecules in medicine, agriculture and cosmetics because of their ability to control melanin overproduction [ 110 ].…”

Section: Monophenolsmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored.

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Section: Monophenolsmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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“…Drosophila melanogaster is an insect model that has been used traditionally in genetic and developmental biology studies; however, nowadays is also used in biomedical (Pasini et al 2010, Martín-Bermudo et al 2017, Wang et al 2018) and toxicological research (Rand 2010, Vecchio et al 2013, Ong et al 2015, Chifiriuc et al 2016, Affleck and Walker 2019. In diverse studies, Drosophila has been used, with excellent results, to analyze the effect of metals (Soares et al 2017, Sundararajan et al 2019, Li et al 2020, nanoparticles (Vela et al 2020, Sarkar et al 2021, antioxidants (Yi et al 2021), chemical products (Soares et al 2017, Nesterkina et al 2020, Senthilkumar et al 2020, and drugs (Kruger and Denton 2020, Matinyan Karkhanis et al 2021. In this study, we use Drosophila melanogaster features to observe the transference and accumulation of metals through oral exposure under controlled conditions.…”

Section: Introductionmentioning

confidence: 99%

Dietary intake and trophic transfer of cadmium and lead from three daily consumption vegetables in Quito, Ecuador

Vela,

Simbaña-Farinango,

Navarrete

et al. 2023

Rev. Int. Contam. Ambie.

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The presence of toxic metals in vegetables of daily consumption is a concern for human health. Little is known about the concentration of toxic metals in vegetables sold in markets in Quito, Ecuador, and the corresponding risk to the population. This study aimed to measure the concentration of cadmium (Cd), and lead (Pb) in tomatoes, carrots, and lettuce, to estimate the risk for human health, and to determine the trophic transfer factor using Drosophila melanogaster flies. Vegetable samples were obtained from four local markets in Quito to measure the concentration of Cd and Pb (expressed in mg/kg of dry weight) in the vegetables by microwave-assisted acid digestion and atomic absorption spectrophotometry. Drosophila melanogaster flies were fed with contaminated vegetables to determine de trophic transfer factor of metals in the trophic chain. Our results showed the highest accumulation of Pb and Cd occurred in lettuce. In all cases, the Pb and Cd concentrations exceeded the maximum levels established by the Food and Agriculture Organization. However, the daily intake of metals and the health risk index showed no risk from daily consumption. Pb’s trophic transfer factor was excessively high in the tomato-fed flies, showing transference and accumulation in the flies. Cadmium concentration in tomato-fed flies was also the highest among the three vegetables. The trophic chain transfer of toxic metals from vegetables to Drosophila has been observed through a high accumulation of these metals in flies, and this suggests a negative impact on both human health and ecosystems.

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Behavioral and electrophysiological responses of the male medfly, Ceratitis capitata, to thymol and carvacrol ethers

Tabanca,

Cloonan,

Nesterkina

et al. 2024

Pest Management Science

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BACKGROUNDThe Mediterranean fruit fly, Ceratitis capitata, is one of the most economically important insect pests attacking fruits and vegetables in tropical and subtropical areas of the world. Semiochemical‐based pest management programs are being used to provide environmentally friendly control methods for medflies. The goals of the current study were to discover potential new, attractive, kairomones by designing, synthesizing, and testing simplified ethers of thymol and carvacrol along with their ether derivatives in short‐range attraction assays and electroantennogram (EAG) assays with male C. capitata. To the best of our knowledge, this study represents the first investigation of thymol and carvacrol, and their respective ethers for attractancy to C. capitata, a major agricultural pest worldwide.RESULTSIn short‐range attraction bioassays, parent compounds, thymol and carvacrol, along with their propyl, butyl, benzyl, and octyl ethers captured the most male C. capitata. The attraction patterns changed over time and captures were only significant if they were greater than the positive control tea tree oil (TTO) at 90 min. In EAG assays, thymol benzyl, octyl ethers, and carvacrol benzyl ether evoked significantly greater antennal responses than their parent compounds. The EAG responses did not correlate with short‐range male attraction. The aliphatic side chains of thymol and carvacrol had a small effect on the activity. Future studies will investigate the long‐range attraction of the ethers that elicited large EAG responses.CONCLUSIONThis report provides new information for discovering potential kairomones through synthesis and structure–activity studies for sterile male medflies. Thymol, carvacrol, and several of their ether derivatives displayed improved longevity of attraction compared with TTO (a strong medfly attractant), with significantly higher captures than TTO observed at 90 min in laboratory bioassays. Further chemical synthesis of thymol and carvacrol ethers within this series may lead to the development of ethers that are more attractive or persistent than their parent compounds, thymol and carvacrol. © 2024 Society of Chemical Industry. This article has been contributed to by U.S. Government employees and their work is in the public domain in the USA.

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Toxic effect and genotoxicity of carvacrol ethers in Drosophila melanogaster

Cited by 7 publications

References 18 publications

Tailored Functionalization of Natural Phenols to Improve Biological Activity

Tailored Functionalization of Natural Phenols to Improve Biological Activity

Dietary intake and trophic transfer of cadmium and lead from three daily consumption vegetables in Quito, Ecuador

Behavioral and electrophysiological responses of the male medfly, Ceratitis capitata, to thymol and carvacrol ethers

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