Molluscicidal and anti‐feedant activities of diterpenes from <i>Euphorbia paralias</i> L

Abdelgaleil, Samir A. M.; El-Aswad, Ahmed F.; Nakatani, Munehiro

doi:10.1002/ps.487

Cited by 25 publications

(16 citation statements)

References 14 publications

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“…Therefore, it could be concluded that compounds 1 – 3 exhibited antifeeding activity against S littoralis in a concentration‐dependant manner. The antifeedant activities of the isolated limonoids ( 1 – 4 ) were stronger than the activities of a limonid toosendanin isolated from Melia toosendan Seib ex Zucc,16 diterpenes from Salvia spp17 and Euphorbia paralias L18 but weaker than the well‐known antifeedant azadirachtin from Azadirachta indica A Juss 19. This finding agreed with our previous study15 in which the compounds 1 – 4 showed a minimum antifeedant inhibition concentration at 300 µg ml −1 when evaluated by conventional leaf‐choice‐disk method, while azadirachtin showed the minimum antifeedant inhibition concentration at 50 µg ml −1 .…”

Section: Resultsmentioning

confidence: 90%

Feeding deterrent and growth inhibitory properties of limonoids from Khaya senegalensis against the cotton leafworm, Spodoptera littoralis

El-Aswad

Abdelgaleil

Nakatani

2003

Pest Management Science

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Three rearranged phragmalin-type limonoids, khayanolide A, khayanolide B and 1-O-acetylkhayanolide B, and a mexicanolide-type limonoid, khayalactol, have been isolated from the stem bark of Khaya senegalensis (Desr) A Juss (Meliaceae). The antifeedant and growth-inhibitory activities of the isolated compounds were evaluated on Spodoptera littoralis (Boisduval). When added to an artificial diet, khayanolide A, khayanolide B and 1-O-acetylkhayanolide B showed antifeedant activity in a concentration-dependent manner. Khayalactol exhibited strong antifeedant activity without significant differences at all of the tested concentrations (7.5-100 mg kg(-1)). Khayanolide B was the most potent antifeedant with an ECso of 2.19 mg kg(-1). The results also revealed that the isolated compounds caused marked larval growth inhibition on S littoralis after 7 days of feeding on treated diet; this effect was concentration-dependent. Khayanolide B was the most active growth inhibitor among the isolated compounds, with an EC50 of 6.96 mg kg(-1).

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Section: Resultsmentioning

confidence: 90%

Feeding deterrent and growth inhibitory properties of limonoids from Khaya senegalensis against the cotton leafworm, Spodoptera littoralis

El-Aswad

Abdelgaleil

Nakatani

2003

Pest Management Science

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“…Natural molluscicidal organic compounds include a variety Preliminary investigation of the disposition of the molluscicidal saponin deltonin from Balanites aegyptiaca in a snail species (Biomphalaria glabrata) and in mice of substance classes such as coumarins, 6) diterpenes, 7) alkaloids 8) and saponins. 9,10) Several saponins were investigated as pesticides for the control of snails, which are vectors for Schistosomiasis.…”

Section: Introductionmentioning

confidence: 99%

Preliminary investigation of the disposition of the molluscicidal saponin deltonin from Balanites aegyptiaca in a snail species (Biomphalaria glabrata) and in mice

Brimer

El-Sheikh

Furu³

2007

J. Pestic. Sci.

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A mixture of deltonin and 25-isodeltonin (approx. 1 : 1) was found to be the molluscicidal principle in seeds of Balanites aegyptiaca (L.) Del. The disposition in the schistosomiasis vector Biomphalaria glabrata and in mice was studied. Snails were exposed to 3 H-labelled saponin in water. Administration to mice was oral (O) and intravenous (IV). Snails absorbed the compounds rapidly and showed a high degree of bioaccumulation. The highest concentration was found in the foot followed by the intestines. Snails could excrete the compounds from all organs investigated. Saponin given orally to mice was partly hydrolysed in the intestine, a fraction of genuine and hydrolysed compound being absorbed. Genuine saponin given IV was rapidly distributed to the liver, kidney (medulla), lung and spleen. Compounds did not pass the placenta nor enter the CNS. Excretion was mainly biliary, a minor fraction being excreted in the urine all as genuine compound. About 80% was excreted within 72 hr. While only two (more lipophilic) metabolites were formed in significant amounts by the mice, three such metabolites were seen in extracts of snails. The final toxic agent and the mode of action to target snails remains to be further investigated.

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“…In order to enable a clear 262 A. K. Hundsdoerfer et al CHEMOECOLOGY identification of the experimentally administered TPA in the larval tissues, E. myrsinites was thus chosen as food plant for the caterpillars in our experiments. The diterpene esters from E. paralias have been shown to exhibit molluscicidal and anti-feedant properties (Abdelgaleil et al 2002) and those of Jatropha curcas (Euphorbiaceae) to exhibit insecticidal activities against several species of e.g. moths, butterflies, aphids, bugs, bettles, flies and cockroaches (Wink et al 1997).…”

Section: Introductionmentioning

confidence: 99%

Sequestration of phorbol esters by aposematic larvae of Hyles euphorbiae (Lepidoptera: Sphingidae)?

2005

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The larvae of the hawkmoth species Hyles euphorbiae have a conspicuous aposematic colouration and show gregarious behaviour. It has thus been suggested that they sequester phorbol esters from their food plants which include different species of the genus Euphorbia (Euphorbiaceae) for chemical protection against predators. To test this hypothesis in more detail, we fed larvae an artificial diet with three doses of 12-tetradecanoyl-phorbol-13-acetate (TPA), then examined the faeces and the larval tissues, such as integument, haemolymph and gut of the caterpillars for the presence of TPA. In order to determine the ability of the larvae to detoxify phorbol esters, other larvae were directly injected with a TPA solution and analysed in the same manner. Our study indicates that the larvae of Hyles euphorbiae do not sequester phorbol esters. Upon oral application TPA was not found in the larval integument or the haemolymph. Instead, it was mostly metabolised (about 70-90 %). Nevertheless, about 10-30 % were retained and recovered in the faeces. The larvae were also able to metabolise and thus detoxify the phorbol ester when TPA was injected directly into the body. These hawkmoth caterpillars are relatively large and have a gut full of plant material, which they regurgitate into the direction of the predator when attacked in nature. Since phorbol esters are very potent toxins and irritants, we postulate that the gut content (and especially the plant slurry disgorged as regurgitant from the anterior gut) alone could be aversive for a potential predator, even if some metabolism has taken place. Thus, although H. euphorbiae caterpillars do not actively sequester phorbol esters, their aposematic colouration appears to be based on chemical defence through phorbol esters retained in the gut.

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Molluscicidal and anti‐feedant activities of diterpenes from Euphorbia paralias L

Cited by 25 publications

References 14 publications

Feeding deterrent and growth inhibitory properties of limonoids from Khaya senegalensis against the cotton leafworm, Spodoptera littoralis

Feeding deterrent and growth inhibitory properties of limonoids from Khaya senegalensis against the cotton leafworm, Spodoptera littoralis

Preliminary investigation of the disposition of the molluscicidal saponin deltonin from Balanites aegyptiaca in a snail species (Biomphalaria glabrata) and in mice

Sequestration of phorbol esters by aposematic larvae of Hyles euphorbiae (Lepidoptera: Sphingidae)?

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