Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities

Dinan, Laurence; Bourne, Pauline; Meng, Yanhui; Sarker, Satyajit D.; Tolentino, R. B.; Whiting, Pensri

doi:10.1007/pl00000859

Cited by 55 publications

(32 citation statements)

References 32 publications

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“…The biological effects of podophillotoxin on other unrelated insect species can be more complex, interfering not only with feeding, but also with ecdysis or diuresis (Garcia et al, 2000). However, in the Drosophila melanogaster B II cell bioassay for ecdysteroid agonist and antagonist activities, podophillotoxin was inactive and cytotoxic (> 10 −5 M), equally as azadirachtin (Dinan et al, 2001).…”

Section: Resultsmentioning

confidence: 99%

Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety

Harmatha

Nawrot

2002

Entomologia Exp Applicata

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The antifeedant activity of a series of lignan lactones, hemiacetals, ethers, and alcohols derived from yatein and cubebin, together with structurally related phenylpropanoids and phenolics possessing a methylenedioxyphenyl (piperonyl) moiety, was tested against selected stored products pests: Sitophilus granarius L. (Coleoptera: Curculionidae), Tribolium confusum Duv. (Coleoptera: Tenebrionideae), and Trogoderma granarium Ev. (Coleoptera: Dermestridae). The relation between molecular structure and antifeedant activity was examined and implication of the piperonyl moiety is assessed. The compounds represent either natural substances isolated from plants (Libocedrus yateensis Guillaumin and Piper cubeba L.) or their structural analogues prepared by simple chemical transformations as well as compounds selected from commercially available sources. Natural lignan lactones with methoxy and/or methylenedioxy substituents showed significant activity that is strong enough to affect plantinsect interactions. Presence of polar substituents, especially hydroxy or glycosyl groups, often reduce the activity. Non-polar substituents, such as methoxy or methylenedioxy groups, enhance the activity not only in lignans but also in simple phenylpropanoids. The most active compound was synthetic piperonylbutoxide.

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Section: Resultsmentioning

confidence: 99%

Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety

Harmatha

Nawrot

2002

Entomologia Exp Applicata

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“…Demethylzeylasterone (78) showed weak ecdysteroid antagonist activity in a Drosophila cell-based assay (Dinan et al, 2001). (Figs.…”

Section: Insecticidal Activitymentioning

confidence: 99%

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

et al. 2007

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Plants in the genus Tripterygium, such as Tripterygium wilfordii Hook. f., have a long history of use in traditional Chinese medicine. In recent years there has been considerable interest in the use of Tripterygium extracts and of the main bioactive constituent, the diterpene triepoxide triptolide (1), to treat a variety of autoimmune and inflammation-related conditions. The main mode of action of the Tripterygium extracts and triptolide (1) is the inhibition of expression of proinflammatory genes such as those for interleukin-2 (IL-2), inducible nitric oxide synthase (iNOS), tumor necrosis factor-α (TNF-α), cyclooxygenase-2 (COX-2) and interferon-gamma (IFN-γ). The efficacy and safety of certain types of Tripterygium extracts were confirmed in human clinical trials in the US and abroad. Over 300 compounds have been identified in the genus Tripterygium, and many of these have been evaluated for biological activity. The overall activity of the extract is based on the interaction between its components. Therefore, the safety and efficacy of the extract cannot be fully mimicked by any individual constituent. This review discusses the biochemical composition and biological and pharmacological activities of Tripterygium extracts, and their main bioactive components.

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“…enzymes remains a distinct possibility (e. g. [17]). When the activity of natural and synthetic brassinosteroid analogues was determined in a simpler in vitro cell-based ecdysteroid-responsive system which does not appear to metabolise ecdysteroids [18,19], they were found to be essentially inactive [20]. Ecdysteroids possess very weak or no activity in brassinosteroid-responsive plant bioassays [21,22].…”

Section: Cmls Cellular and Molecular Life Sciencesmentioning

confidence: 99%

The ecdysteroid agonist/antagonist and brassinosteroid-like activities of synthetic brassinosteroid/ecdysteroid hybrid molecules

Voigt

Whiting

Dinan

2001

CMLS, Cell. Mol. Life Sci.

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A series of synthetic hybrid brassinosteroid/ecdysteroid structures has been assessed for their ecdysteroid agonist/antagonist activities in the Drosophila melanogaster B(II) cell bioassay and for brassinosteroid-like activity in the rice lamina inclination test. Most of the compounds proved inactive for ecdysteroid agonist activity, demonstrating the specificity of the ecdysteroid receptor for compounds closely structurally related to 20-hydroxyecdysone. However, compound 18, with 14alpha-hydroxy-7-en-6-one and 22S-hydroxy functionalities (as in most active ecdysteroids), possessed distinct agonist activity (median effective concentration = 1.4 x 10(-5) M), although this is still almost 2000-fold less active than 20-hydroxyecdysone (25). Compounds 13 and 15 possessed weak agonist activity. Compounds 5, 11 and 14 weakly antagonised the action of 20-hydroxyecdysone (at 5 x 10(-8) M) on B(II) cells. In the brassinosteroid bioassay, most of the tested compounds showed activity. This may reflect the metabolic capability of plant tissue to convert test compounds to more active analogues. However, it is clear that biological activity declines as the structure of the test compound deviates further from that of castasterone (16). Three ecdysteroids (25, 26 and 27) are completely inactive in the rice lamina inclination test. These studies demonstrate the high specificities of the insect ecdysteroid receptor and the plant brassinosteroid receptor and indicate that phytoecdysteroids, even in high concentrations, would not interfere with brassinosteroid signalling pathways in plants where the two classes of compounds co-occur. Equally, brassinosteroids would not interfere with ecdysteroid signalling in insects, especially if one takes into account the low concentrations of brassinosteroids in the diet of phytophagous insects.

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Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities

Cited by 55 publications

References 32 publications

Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety

Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

The ecdysteroid agonist/antagonist and brassinosteroid-like activities of synthetic brassinosteroid/ecdysteroid hybrid molecules

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