Effects of lignoids on a hematophagous bug, Rhodnius prolixus: feeding, ecdysis and diuresis

Garcia, Elói S.; Cabral, Marise M. O.; Schaub, Günter A.; Gottlieb, Otto R.; Azambuja, Patrı́cia

doi:10.1016/s0031-9422(00)00228-4

Cited by 29 publications

(22 citation statements)

References 26 publications

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“…These were compared with only one aryltetraline (B type, form V) lignan, podophyllotoxin (4), as a representative of more than 200 natural and semisynthetic derivatives (Ward, 1999). 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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“…Pinoresinol was found at high levels in dormant stems of Manchurian ash (Eyles et al, 2007), but found only in North American ashes in this study. Lignans have wide biological activities, and effects on insects have been well documented for some of them (Cabral et al, 1999;Garcia et al, 2000;Rios et al, 2002;Schroeder et al, 2006). Other compounds found either exclusively or at higher levels in Manchurian ash, such as homovanillic Table 2 alcohol, fraxin, fraxidin hexoside, mandshurin, and calceolariosides A and B have not been examined for their bioactivity against insects, but several of them have shown anti-oxidant, anti-cancer, and other medically relevant biological activities (e.g., Deiana et al, 2008).…”

Section: Discussionmentioning

confidence: 99%

Distinguishing Defensive Characteristics in the Phloem of Ash Species Resistant and Susceptible to Emerald Ash Borer

et al. 2011

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We examined the extent to which three Fraxinus cultivars and a wild population that vary in their resistance to Emerald Ash Borer (EAB) could be differentiated on the basis of a suite of constitutive chemical defense traits in phloem extracts. The EAB-resistant Manchurian ash (F. mandshurica, cv. Mancana) was characterized by having a rapid rate of wound browning, a high soluble protein concentration, low trypsin inhibitor activities, and intermediate levels of peroxidase activity and total soluble phenolic concentration. The EAB-susceptible white ash (F. americana, cv. Autumn Purple) was characterized by a slow wound browning rate and low levels of peroxidase activity and total soluble phenolic concentrations. An EAB-susceptible green ash cultivar (F. pennsylvanica, cv. Patmore) and a wild accession were similar to each other on the basis of several chemical defense traits, and were characterized by high activities of peroxidase and trypsin inhibitor, a high total soluble phenolic concentration, and an intermediate rate of wound browning. Lignin concentration and polyphenol oxidase activities did not differentiate resistant and susceptible species. Of 33 phenolic compounds separated by HPLC and meeting a minimum criterion for analysis, nine were unique to Manchurian ash, five were shared among all species, and four were found in North American ashes and not in the Manchurian ash. Principal components analysis revealed clear separations between Manchurian, white, and green ashes on the basis of all phenolics, as well as clear separations on the basis of quantities of phenolics that all species shared. Variation in some of these constitutive chemical defense traits may contribute to variation in resistance to EAB in these species.

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“…The sample of larval secretion obtained through rinsing of whole larvae was redissolved in 0.55 ml of benzene-d 6 and analyzed by NMR spectroscopy, which included acquisition of phase-sensitive ( 1 H, 1 H)-dqf-COSY spectra, ( 1 H, 1 H)-nuclear Overhauser spectroscopy spectra, ( 1 H, 13 C)-heteronuclear multiple-quantum correlation spectra, and magnitude-mode nongradient ( 1 H, 13 C)-heteronuclear multiple-bond correlation spectra optimized for long-range 13 C-1 H-coupling constants of 4 Hz and 8 Hz. In addition, small samples of the residue were analyzed by using combinations of gas chromatography and electron-impact ionization MS as well as HPLC and electrospray-ionization MS. For additional NMR spectroscopic and MS analyses, the extract was subjected to column chromatography on silica with a 1:1 mixture of ethyl acetate and hexane as solvent, which produced 0.05 mg of pure pinoresinol.…”

Section: Methodsmentioning

confidence: 99%

“…Particularly high concentrations of pinoresinol have been found in young foliage, for example of Forsythia spp., as well as in the reproductive organs and seeds of many plants (5). The compound is therefore generally presumed to be a defensive agent, as is suggested also by its antihelminthic and antifungal activity (6)(7)(8)(9). Animals are not known to produce pinoresinol or other dimeric lignols, nor have they been shown to acquire such compounds from plants.…”

mentioning

confidence: 99%

Pinoresinol: A lignol of plant origin serving for defense in a caterpillar

Schroeder

Campo

Grant

et al. 2006

Proc. Natl. Acad. Sci. U.S.A.

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Pinoresinol, a lignan of wide distribution in plants, is found to occur as a minor component in the defensive secretion produced by glandular hairs of caterpillars of the cabbage butterfly, Pieris rapae. The compound or a derivative is appropriated by the larva from its normal food plant (the cabbage, Brassica oleracea). Pinoresinol was shown to be absent from the secretion if the larva was given a cabbage-free diet but present in the effluent if that diet was supplemented with pinoresinol. Pinoresinol is shown to be a feeding deterrent to ants (Formica exsectoides), indicating that it can complement the defensive action of the primary components of the secretion, a set of previously reported lipids called mayolenes. In the test with F. exsectoides, pinoresinol proved to be more potent than concomitantly tested mayolene-16.ignans comprise a large class of secondary metabolites in vascular plants. Derived from the three phenyl-propanoid precursors, p-coumaryl alcohol (1 in Fig. 1), coniferyl alcohol (2 in Fig. 1) and sinapyl alcohol (3 in Fig. 1), they fulfill important physiological functions in plants (1) and are of considerable pharmaceutical interest (2). For example, podophyllotoxin (4 in Fig. 1) derivatives are used extensively in anticancer treatments and have been shown recently to possess antiviral properties as well (3). Pinoresinol (5 in Fig. 1) is one of the structurally simplest lignans, being a dimer of coniferyl alcohol, and its frequent presence in woody or fibrous plants should come as no surprise [the Beilstein database (MDL Information Systems, San Leandro, CA) revealed 46 and 8 references, respectively, for the isolation of (ϩ)-pinoresinol and (Ϫ)-pinoresinol from plants] (4). Virtually any plant capable of producing lignin can be presumed to have the enzymes necessary to link two units of coniferyl alcohol (2 in Fig. 1) in a fashion leading to the bicyclic ring core of pinoresinol (5 in Fig. 1).The amount of pinoresinol produced by plants varies widely. Particularly high concentrations of pinoresinol have been found in young foliage, for example of Forsythia spp., as well as in the reproductive organs and seeds of many plants (5). The compound is therefore generally presumed to be a defensive agent, as is suggested also by its antihelminthic and antifungal activity (6-9). Animals are not known to produce pinoresinol or other dimeric lignols, nor have they been shown to acquire such compounds from plants. We here report the presence of pinoresinol in the defensive secretion of a caterpillar, the larva of Pieris rapae, the cabbage butterfly, one of the world's most familiar lepidopterans (10). We had earlier reported on the composition of this secretion, produced as droplets by glandular hairs on the back and flanks of the larva (11) (Fig. 2). We had noted the fluid to contain a series of structurally labile linolenic acid derivatives, the mayolenes (6 in Fig. 3), which we demonstrated to be protective against ants (Crematogaster lineolata) (11). We have found pinoresinol itself to also be dete...

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Effects of lignoids on a hematophagous bug, Rhodnius prolixus: feeding, ecdysis and diuresis

Cited by 29 publications

References 26 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

Distinguishing Defensive Characteristics in the Phloem of Ash Species Resistant and Susceptible to Emerald Ash Borer

Pinoresinol: A lignol of plant origin serving for defense in a caterpillar

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