Insecticidal and synergistic components isolated from dill plants

Lichtenstein, E. P.; Liang, Tan; Schulz, K. R.; Schnoes, Heinrich K.; Carter, G T

doi:10.1021/jf60194a037

Cited by 86 publications

(55 citation statements)

References 4 publications

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“…Isomeric isodillapiole showed no significant activity. The pure active metabolite proved a natural insecticide compound with LC50 = 11ppm against A. aegypti (Lichtenstein et al 1974). Literature sources reported that dillapiole, usually isolated from essential oils from the leaves of P. aduncum, has insecticidal, fungicidal and antimicrobial activities.…”

Section: The Use Of Larvicidal Essential Oils From the Piper Species mentioning

confidence: 99%

“…Another natural occurring compound, dillapiole, a phenylpropanoid isolated from essential oil from leaves of Piper aduncum, was assayed in vivo against larvae and pupae of A. aegypti. The pure active metabolite was reported as a natural insecticide compound with LC50 = 11ppm (Lichtenstein et al 1974) and LC50 of 0.381μg/cm 2 (Pinto et al 2012) against A. aegypti. The mortality, oviposition, chromosome breakage, and anaphase bridges were significantly greater in the extract treatments in concentrations of 200 and 400 µg/mL than in the controls.…”

Section: Larvicidal Potential Of Isolated Metabolites From Piper Speciesmentioning

confidence: 99%

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Active metabolites of the genus Piper against Aedes aegypti: natural alternative sources for dengue vector control

Marques

Kaplan²

2014

Univ. Sci.

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The mosquito, Aedes aegypti, is the principal vector of the viruses responsible for dengue and dengue hemorrhagic fevers. The mosquito is widespread throughout tropical and sub-tropical regions; its prevalence makes dengue one of the most important mosquito-borne viral diseases in the world occurring annually in more than 100 endemic countries. Because blood is essential to their development cycle, the Aedes species maintains a close association with humans and their dwellings. Fittingly, the most widely adopted strategy to decrease the incidence of these diseases is the control of the mosquito larvae population. The emergence of insecticide-resistant mosquitoes has amplified the interest in finding natural products effective against Aedes aegypti adults, as well as larvae. Plantderived compounds have played an important role in the discovery of new active entities for vector management as they are safer and have lower toxicity to humans in comparison to conventional insecticides. This review assesses a naturally occurring plant matrix and pure compounds of the Piper species, which have been shown to be active against Aedes aegypti.

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Section: The Use Of Larvicidal Essential Oils From the Piper Species mentioning

confidence: 99%

Section: Larvicidal Potential Of Isolated Metabolites From Piper Speciesmentioning

confidence: 99%

Active metabolites of the genus Piper against Aedes aegypti: natural alternative sources for dengue vector control

Marques

Kaplan²

2014

Univ. Sci.

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“…For d-carvone, the oral LD 50 was 1,640 mg/kg bw in rats (unspecified strain) and 766 mg/kg bw for guinea pigs (Jenner et al, 1964 The intravenous LD 50 value for d-carvone in mice was 1,500 mg/kg (Lichtenstein et al, 1974). Stoner et al (1973) reported that no adverse effects were observed in mice given six intraperitoneal injections of 250 mg/kg bw d-carvone over a 2-week period.…”

Section: Acute Toxicitymentioning

confidence: 99%

Scientific Opinion on the safety assessment of carvone, considering all sources of exposure

2014

EFSA Journal

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Carvone occurs naturally as dextrorotatory (d-) and levorotatory (l-) enantiomers in several food items; these may also be used as a pesticide, food flavouring, feed flavouring, in feed additive, in personal care products and as (veterinary) medicine. In order to improve coherence regarding the risk assessment of carvone in the different food and feed sector areas, EFSA asked its Scientific Committee to establish a single ADI for carvone, estimate the overall exposure of European consumers, and quantify the contribution for each source of exposure to the overall exposure of carvone. Having reviewed the information available the Scientific Committee decided to address dcarvone and l-carvone separately and limit its assessment to the oral intake of d-and l-carvone. The Scientific Committee established an ADI of 0.6 mg/kg bw/day for d-carvone, based on the BMDL10 of 60 mg/kg bw/day for an increase in relative liver weight in the rat 90-day studies and an uncertainty factor of 100. The Scientific Committee could not establish an ADI for l-carvone because of a lack of toxicological data for this enantiomer. The highest level of aggregated exposure to d-carvone is estimated to be 0.60 mg/kg bw/day, i.e. is at the level of the ADI established for d-carvone. The highest level of aggregated exposure to l-carvone is three-fold that of d-carvone. In view of key uncertainties 1) on the toxicity of l-carvone, 2) on the biological relevance of the endpoint selected to establish the ADI for d-carvone and its use as a surrogate for the observed lethality in tested animals, 3) whether d-and l-carvone should be considered together for possible combined effects and 4) in the aggregated exposure assessments to d-and to l-carvone, the Scientific Committee recommended generating additional data to refine the current risk assessment. In order to improve coherence regarding the risk assessment of carvone in the different food and feed sector areas of the European Food Safety Authority, EFSA asked its Scientific Committee to 1) establish a single ADI for carvone to be used at European level, regardless of the food sector area, and considering all previous evaluations, 2) estimate the overall exposure of European consumers to the carvone resulting from its various uses, and 3) quantify the contribution for each source of exposure to the overall exposure of carvone. Having reviewed the data available and the previous assessments done, the Scientific Committee decided to address d-carvone and l-carvone separately and limit its assessment to the oral intake of d-and l-carvone. In view of an expected request for extending the application of d-carvone as an anti-sprouting agent to ware and starch potatoes; the Scientific Committee decided to include also this use in its assessment.The Scientific Committee considered the data available for d-carvone and selected the liver effects as the most likely relevant endpoint to be used as the basis for risk assessment. The Scientific Committee established an ADI of 0.6 mg/kg bw/day for d-carvo...

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“…Dillapiol (1) is the major component of the EO obtained from the leaves of Piper aduncum L. (Cicció and Ballestero, 1997). It has insecticidal activity against Drosophila melanogaster (LD 50 0.27 mg/jar) and A. aegypti larvae (LD 50 11.0 ppm, Lichtenstein et al, 1974). 1 is also known as an effective in vitro inhibitor of the epoxidase activity in larvae of the mosquito Ostrinia nubilalis (92% inhibition).…”

Section: Introductionmentioning

confidence: 99%

Adulticidal Activity of Dillapiol and Semi-synthetic Derivatives of Dillapiol against <i>Aedes aegypti</i> (L.) (Culicidae)

Pinto¹,

Nogueira²,

Chaves³

et al. 2012

jmr

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Phenylpropanoid dillapiol (1) isolated from the essential oil in leaves of Piper aduncum L. and thirteen semi-synthetic, C 3 side-chain modified dillapiol derivatives 2-14 were evaluated for lethality against hemorrhagic dengue fever mosquito vector Aedes aegypti L.. First, adult female mosquitoes were exposed to these substances in a contact bioassay carried out in glass bottles at a single surface density (0.57 μg/cm 2 ). Then, median lethal concentrations (LC 50 ) and LC 90 were determined for active compounds. It was found that the structure of the C 3 side chain was important for the toxic effects of these substances against A. aegypti adult females. Isodillapiol (2) and methyl, propyl and butyl 1-(2´,3´-dimethoxy-4´,5´-methylenedioxyphenyl)propan-2-yl ethers (3, 5 and 6, respectively) all exhibited greater mosquitocidal activity than dillapiol (1). The order of molar per surface area of mosquitocidal activities was isodillapiol (2) > butyl ether 6 > methyl ether 3 > propyl ether 5 > dillapiol (1). The potential of dillapiol and derivatives as A. aegypti mosquitocides was discussed.

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Insecticidal and synergistic components isolated from dill plants

Cited by 86 publications

References 4 publications

Active metabolites of the genus Piper against Aedes aegypti: natural alternative sources for dengue vector control

Active metabolites of the genus Piper against Aedes aegypti: natural alternative sources for dengue vector control

Scientific Opinion on the safety assessment of carvone, considering all sources of exposure

Adulticidal Activity of Dillapiol and Semi-synthetic Derivatives of Dillapiol against <i>Aedes aegypti</i> (L.) (Culicidae)

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