Antifeedant and toxic effects of sesquiterpenes fromSenecio palmensis to colorado potato beetle

A bioassay-guided fractionation of the aerial parts ofSenecio palmensis resulted in the isolation of two sesquiterpenes, 2,10-bisaboladien-1-one and 11-acetoxy-5-angeloyloxy-silphinen-3-one. The bisabolene and the silphinene represented 0.012% and 0.024% of the plant dry weight, respectively. Both compounds showed antifeedant activity againstLeptinotarsa decemlineata larvae and adults in short-term choice and no-choice bioassays. Both compounds were also tested against different species of phytopathogenic fungi. The beetles were more sensitive to these compounds in choice than in no-choice assays, with a gradient of increasing sensitivity from second instars to adults. Bisabolene was 45 times less active as an antifeedant than juglone, which was tested as a positive control. The silphinen was more active than the bisabolene, with a range of activity similar to juglone. Furthermore, exposure of fourth instars to these compounds over a 24-hr period resulted in reduced feeding and growth rates. To distinguish between antifeedant and toxic effects, growth efficiencies were calculated as the slope of the regression of relative growth rate on relative consumption rate. The comparison of these results with those of antifeedant simulation and contact toxicity bioassays indicates that feeding inhibition is the primary mode of action of the bisabolene, while the silphinene shows both antifeedant and toxic effects.     

Identification of a volatile attractant forDiabrotica andAcalymma spp. from blossoms ofCucurbita maxima duchesne

Fractionation of headspace volatiles fromCucurbita maxima blossoms by high-performance liquid chromatography resulted in the isolation of a single component which was highly active in an electroantennogram bioassay onDiabrotica undecimpunctata howardi antennae. This compound was identified as indole by gas chromatography-mass spectrometry. Field-trapping bioassays were conducted which indicated that indole is a potent attractant of the western corn rootworm,D. virgifera virgifera, and the striped cucumber beetle,Acalymma vittatum. The southern corn rootworm,D. u. howardi, did not respond, despite its strong EAG response. The sex ratio ofD. v. virgifera found in indole-baited traps varied seasonally. Males were trapped in abundance in late July and later September, 1983, while females were more abundant August and early September. The effectiveness of indole as aD. v. virgifera attractant also varied seasonally. A prolonged period of depressed trap catches occurred in early August 1983, during the silking and tasseling period of the corn in the field where trapping was carried out.Coleoptera: Chrysomelidae.     

Behavioral responses of western corn rootworm larvae to volatile semiochemicals from corn seedlings

Corn seedling volatiles collected cryogenically are highly attractive to western corn rootworm larvae,Diabrotica virgifera virgifera LeConte (Coleoptera: Chrysomelidae), in a laboratory bioassay. Carbon dioxide is known as an attractant for western corn rootworm larvae, and the amount of carbon dioxide in the cryogenic collections was measured with an infrared gas analyzer. In a choice test between a source containing carbon dioxide alone and a source containing corn seedling volatiles with an equal amount of carbon dioxide (verified by infrared gas analysis), western corn rootworm larvae chose the corn volatile source significantly more often than the side with carbon dioxide alone. This indicates that carbon dioxide is only one of the volatiles from corn seedlings that is behaviorally important and that other compounds of behavioral importance are present as well.     

Effects ofneo-clerodane diterpenes fromTeucrium on feeding behavior of colorado potato beetle larvae

Treatment of potato leaf disks with fourneo-clerodane diterpenes fromTeucrium (eriocephalin, teucrin-A, teucvin, and teuscorolide) significantly reduced feeding by larvae ofLeptinotarsa decemlineata (Colorado potato beetle). Choice and no-choice tests suggest that teuscorolide acts as a feeding deterrent, whereas the antifeedant activity of teucrin-A, teucvin, and eriocephalin is likely associated with a toxic mode of action. Nutritional tests, antifeedant simulation assays, and posttreatment studies confirmed that teucrin-A can be categorized by its mode of action as a toxin, rather than as a feeding deterrent.     

Identification of cantharidin in false blister beetles (Coleoptera,Oedemeridae) from florida

Cantharidin, a potent vesicant and antifeedant, is identified for the first time in two oedemerid beetles from the western hemisphere. Amounts of the substance per beetle were found to range from 2 to 7 g inHeliocis repanda and from 15 to 35 g inOxycopis thoracica. Females had two to three times more cantharidin than males of the same species. Cantharidin loads of these beetles are sufficient to irritate human skin.     

Effect of trichome B exudate ofSolanum berthaultii Hawkes on consumption by the colorado potato beetle,Leptinotarsa decemlineata (Say)

The leaf extract fromS. berthaultii Hawkes (PI 473340) contains exudate from trichomes (type B). Consumption ofS. tuberosum var. Norchip foliage by the Colorado potato beetleLeptinotarsa decemlineata (Say) was reduced when treated with the leaf extract. The leaf extract from a resistantS. berthaultii clone without type B trichome had no antifeedant activity. It suggests that more than one mechanism of resistance to the Colorado potato beetle exists inS. berthaultii.     

Responses of northern and western corn rootworms to semiochemical attractants in corn fields

Small plots (18 × 18 m) were treated with grids of cotton wicks that contained semiochemicals for adultDiabrotica barberi Smith and Lawrence, the northern corn rootworm (NCR). In plots treated with eugenol (350 g/hectare), NCR were attracted to point sources of the compound, but there were no significant changes in numbers of either NCR orD. virgifera virgifera LeConte, the western corn rootworm (WCR), found on plants in the plots. In plots treated with 12.5 mg/hectare of 8R-methyl-2R-decyl propanoate (2R,8R-MDP, the apparent female-produced sex pheromone of NCR and WCR), males of both species were attracted to point sources, but beetles did not congregate within treated plots. With racemic 2,8-MDP at 1.0 g/hectare, male WCR were attracted into plots, but NCR of both sexes were strongly repelled. In a separate study, capture of beetles at pheromone-baited traps declined when the surrounding area contained wicks that emitted racemic 2,8-MDP. In treated plots, male WCR were relatively inefficient at finding pheromone sources. With NCR, emigration from plots could account totally for the observed 3- to 10-fold reduction in catch at 0.01–1.0 g/hectare.Coleoptera: Chrysomelidae.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

Effects ofSolanum glycoalkaloids on chemosensilla in the Colorado potato beetle

Steroidal glycoalkaloids, found in species of the Solanaceae, elicit bursting activity in galeal and tarsal chemosensilla of adult Colorado potato beetles. The effect has an average latency of 6–12 sec, depending on the sensillum/alkaloid combination. A 20-sec alkaloid treatment is often suffficient to render galeal sensilla unresponsive to gamma-aminobutyric acid, normally an effective stimulant. The alkaloids have similar effects on galeal sensilla of larval Colorado potato beetles and on labellar chemosensilla of the blowfly. It is concluded that these compounds act independently of any specialized chemoreceptor in the Colorado potato beetle, and that association of the Colorado potato beetle with solanaceous plants has not led to evolution of a specific receptor forSolanum glycoalkaloids.     

Response of Colorado potato beetles,Leptinotarsa decemlineata (Say), to volatile components of tansy,Tanacetum vulgare

The responses of Colorado potato beetle,Leptinotarsa decemlineata (Say), to volatile components of tansy,Tanacetum vulgare L., were investigated in order to establish a chemical basis for observed reduction in beetle populations when potatoes,Solanum tuberosum L., were interplanted with tansy. Colorado potato beetles exhibited avoidance behavior to tansy oil, volatiles from intact tansy plants, a hydrocarbon fraction of tansy oil, obtained by fractionation on alumina, and five of the 13 known components of tansy oil that were tested. One constituent of tansy oil, -pinene, attracted beetles.     

The influence of dietaryβ-carboline alkaloids on growth rate,food consumption,and food utilization of larvae ofSpodoptera exigua (Hubner)

-Carboline alkaloids are found worldwide in many plant families. Harman, harmine, and other simple -carboline alkaloids were tested for activity against a generalist phytophagous insect, the beet army worm [Spodoptera exigua (Hubner)]. Chronic dietary exposure tests (neonate to pupa) reveal potent antifeedant and possible toxic effects. Acute dietary exposure tests on fifth-instar larvae also demonstrate antifeedant activity.     

Extractives of seeds of the meliaceae: Effects onSpodoptera frugiperda (J.E. Smith),Acalymma vittatum (F.), andArtemia salina Leach

Hexane and ethanol extracts of seeds from 22 species of plants of the family Meliaceae from a number of countries were prepared. The extracts were submitted to antifeedant and toxicity bioassays utilizing fall armyworm [Spodoptera frugiperda (J.E. Smith)] (Lepidoptera: Noctuidae) larvae and striped cucumber beetle [Acalymma vittatum (F.)] (Coleoptera: Chrysomelidae) adults. Toxicity tests were also performed with brine shrimp,Anemia salina Leach. Feeding inhibition and mortality produced by some of these extracts were comparable to and, in certain cases, slightly greater than the effects produced by comparable neem (Azadiracta indica A. Juss.) seed preparations. Brine shrimp toxicity data do not extrapolate to insect activity, and vice versa.Presented at the national meeting of the Entomological Society of America in Hollywood, Florida, December 8–12, 1985.Mention of firm or product names does not imply recommendation or endorsement by USDA over others not mentioned.     

Antifeedant effects of proteinase inhibitors on feeding behaviors of adult western corn rootworm (Diabrotica virgifera virgifera)

Low-molecular-weight peptidyl proteinase inhibitors (PIs) including leupeptin, calpain inhibitor I, and calpeptin were found to be potent antifeedants for adult western corn rootworm (WCR) against the phagostimulation of cucurbitacin B (Cuc B) or a corn pollen extract (CPE). Leupeptin was the strongest (ED₅₀ = 0.36 and 0.55 nmol/disk for Cuc B and CPE, respectively) among PIs tested with an antifeedant potency much stronger than the steroid progesterone (ED₅₀ = 2.29 and 5.05 nmol/disk for Cuc B and CPE, respectively), but slightly less than the reference alkaloid, strychnine (ED₅₀ = 0.17 and 0.37 nmol/disk for Cuc B and CPE, respectively). All active PIs contain a di- or tripeptidyl aldehyde moiety, indicating that PIs exert their antifeedant effects by covalent interaction with putative sulfhydryl (SH) groups on taste receptors as do these PIs with cysteine proteinases. However, opposite inhibition potency against Cuc B versus CPE by two thiol-group reducing agents, DTT and L-cysteine, and the results with other cysteine-modifying reagents obscure the net functional role of SH groups at WCR taste chemoreceptors. Surprisingly, the model phagostimulant for diabroticites, Cuc B, was more easily counteracted by these feeding deterrents than the stimulants present in CPE. Three-dimensional structure–antifeedant relationships for the PIs suggest that a novel taste chemoreception mechanism exists for these peptidyl aldehydes or that they fit partially into a strychnine binding pocket on protein chemoreceptors. Favorable economic benefit may be achieved if PIs are discovered to be useful in adult WCR control, since both pre- and postingestive sites would be targeted.     

Comparative Analysis of Headspace Volatiles from Different Caterpillar-Infested or Uninfested Food Plants of Pieris Species

Plants that are infested by herbivores emit volatile cues that can be used by the natural enemies of the herbivores in their search for hosts. Based on results from behavioral studies, we investigated to what extent intact and herbivore-infested plant species and varieties from the food plant range of Pieris herbivore species differ in the composition of the volatile blends. Parasitoids of Pieris species, Cotesia glomerata and C. rubecula, show differential responses towards various herbivore-infested food plants, whereas differences in responses to plants infested by other herbivore species were less clear. Chemical analysis of the headspace samples of red cabbage, white cabbage, and nasturtium plants that were infested by P. brassicae or P. rapae larvae, or that were intact, yielded 88 compounds including alcohols, ketones, aldehydes, esters, nitriles, terpenoids, sulfides, (iso)thiocyanates, carboxylic acids, and others. The analysis revealed that herbivore-infested plants emit the largest number of compounds in the highest amounts. The plant species affected the volatile blend more than did the herbivore species, and differences between plant varieties were less pronounced than differences between plant species. Differences in headspace composition between plants infested by P. brassicae or P. rapae were mainly of a quantitative nature. Herbivore-infested nasturtium differed considerably from the cabbage varieties in a qualitative way. Headspace compositions of red and white cabbage varieties were comparable to that of the food plant Brussels sprouts (Brassica oleracea gemmifera cv. Titurel) as determined in earlier studies in our laboratory. With respect to plant response to herbivory, nasturtium differed considerably from the cabbage varieties analyzed so far and shows resemblance with Lima bean, cucumber, and corn. These plant species produce a greater quantity and variety of volatiles under herbivore attack than intact plants. The results of this study are discussed in relation to behavioral observations on C. glomerata and C. rubecula.     

Isolation of corn semiochemicals attractive and repellent to western corn rootworm larvae

Dichloromethane extracts of germinating corn are significantly attractive to western corn rootworm larvae in choice tests with equal levels of carbon dioxide present on both sides of the choice. Two fractions that are significantly attractive and two fractions that are significantly repellent to larvae were isolated from these extracts of germinating corn by gas chromatography and silica gel chromatography. In a separate set of experiments, Porapak N was used to collect headspace volatiles from germinating corn; significantly more larvae were attracted to aliquots of these extracts in singlechoice tests without added carbon dioxide present than to solvent controls.Coleoptera: Chrysomelidae.     

Distribution and antifeedant associations of sesquiterpene lactones in cultivated sunflower (Helianthus annuus L.) on western corn rootworm (Diabrotica virgifera virgifera LeConte)

Seven antifeedant sesquiterpene lactones (STLs), 4,5-dihydroniveusin A, argophyllin B, argophyllin A, 15-hydroxy-3-dehydrodesoxytifruticin, niveusin B, 1,2-anhydridoniveusin A, and an unidentified epoxide, in cultivated sunflower (Helianthus annuus L.) have been quantified by a highperformance thin-layer chromatography and UV-reflectance scanning densitometry analysis. Age-related expression of STL content in sunflower reveals a heretofore undescribed pattern in which nonpolar STLs such as 15-hydroxy-3-dehydrodesoxytifruticin predominate up to an age of three weeks, but are subsequently displaced by polar STLs, especially argophyllin A, through later foliar stages and anthesis. This leaf pattern of STL ontogeny is maintained in three widely differentH. annuus cultivars (Giant Gray Stripe, Royal Hybrid 2141, Hybrid 7111), which in turn had similar total contents of STLs. Antifeedant activity for western corn rootworm was positively correlated with STL content, particularly with argophyllin A and its isomer argophyllin B, in respective tissue extracts. Enhanced amounts of highly antifeedant argophyllins, especially in newly grown leaf and floral tissues yielding sunflower progeny, strongly suggest that these epoxy-STLs are a chemical defense against insect herbivory.     

Response ofDiabrotica virgifera virgifera,D. v. Zeae,andD. porracea to stereoisomers of 8-methyl-2-decyl propanoate

The four stereoisomers of 8-methyl-2-decyl propanoate were tested in the United States and Mexico for attractiveness toDiabrotica virgifera virgifera LeConte, the western corn rootworm,D. v. zeae Krysan and Smith, the Mexican corn rootworm, andD. porracea Harold. Males ofD. v. virgifera andD. v. zeae responded strongly to the (2R,8R)-isomer and secondarily to (2S,8R), whileD. ponacea responded exclusively to the (2S,8R)-isomer. The (2S,8S)- and (2R,8S)-isomers were inactive in all tests. Synergism or inhibition was not detected when various mixtures of the isomers were tested withD. v. virgifera. These phenomena were not tested withD. v. zeae andD. ponacea.Coleoptera: Chrysomelidae.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

Transfer of pyrrolizidine and quinolizidine alkaloids toCastilleja (Scrophulariaceae) hemiparasites from composite and legume host plants

Castilleja (Scrophulariaceae) species of the western United States contain pyrrolizidine and quinolizidine alkaloids. TheCastilleja obtain the alkaloids by root parasitism on host plants, withSenecio atratus andS. triangularis (Asteraceae) furnishing the pyrrolizidines, and quinolizidines being obtained fromLupinus species andThermopsis montana (Leguminosae). Individual plants within a givenCastilleja species population may be devoid of alkaloids while others have high alkaloid content. No populations have been found which are made up of both pyrrolizidine- and quinolizidine-containing individuals. These results have important implications forCastilleja ecology, for the study of insect herbivores which areCastilleja specialists, and in the development of systems for the investigation of the role of alkaloids as plant defenses.Paper 10 in the series Chemistry of the Scrophulariaceae. Paper 9: D.R. Gardner, J. Narum, D. Zook, and F.R. Stermitz.J. Nat. Prod. 50: In press.     

Electrophysiologically and Behaviorally Active Volatiles of Buffalo Gourd Root Powder for Corn Rootworm Beetles

The dried, powdered roots of buffalo gourd, Cucurbita foetidissima, were tested in a cornfield and shown to attract adult northern and southern corn rootworm beetles. Coupled gas chromatography–electroantennography (GC-EAG) analyses of headspace samples of the root powder showed several GC-EAG-active compounds on the antennae of female northern, southern, and western corn rootworms. Among other techniques, solid-phase microextraction and GC-mass spectrometry identified the following GC-EAG-active compounds: hexanol, nonanal, 1-octen-3-ol, benzaldehyde, benzyl alcohol, (E)-3-octen-2-one, (E,E)-3,5-octadien-2-one, and (E,Z)-3,5-octadien-2-one. EAG dose–response studies of several of the identified root powder volatiles also were performed and compared with results from known attractants. Field tests of synthetic root powder volatiles in commercial cornfields showed that northern corn rootworm adults were attracted to (E,E)-3,5-octadien-2-one. The antennae of the Diabrotica species and the field tests showed specificity for different geometrical isomers of 3,5-octadien-2-one, with a behavioral preference for (E,E)-3,5-octadien-2-one. In addition, we have shown that the efficacy of buffalo gourd root powder as a feeding stimulant and arrestant can be enhanced for northern and western corn rootworm adults by augmenting buffalo gourd root powder with additional (E,E)-3,5-octadien-2-one.     

Avoidance of antinutritive plant defense: Role of midgut pH in Colorado potato beetle

The fate of the tomato foliar phenolic, chlorogenic acid, in the digestive systems of Colorado potato beetleLeptinotarsa decemlineata (Coleoptera: Chrysomelidae) andHelicoverpa tea (Lepidoptera: Noctuidae) is compared. In larvalH. zea and other lepidopteran species previously examined, approximately 35–50% of the ingested chlorogenic acid was oxidized in the digestive system by foliar phenolic oxidases (i.e., polyphenol oxidase and peroxidase) from the tomato plant. The oxidized form of chlorogenic acid, chlorogenoquinone, is a potent alkylator of dietary protein and can exert a strong antinutritive effect upon larvae through chemical degradation of essential amino acids. In contrast, inL. decemlineata less than 4% of the ingested dose of chlorogenic acid was bound to protein. In vitro experiments to determine the influence of pH on covalent binding of chlorogenic acid to protein showed that 30–45% less chlorogenic acid bound to protein at pHs representative of the beetle midgut (pH 5.5–6.5) than at a pH representing the lepidopteran midgut (pH 8.5). At an acidic pH, considerably more of the alkylatable functional groups of amino acids (–NH₂, –SH) are in the nonreactive, protonated state. Hence, polyphenol oxidases are unlikely to have significant antinutritive effects against the Colorado potato beetle and may not be a useful biochemical source of resistance against this insect. The influence of feeding by larval Colorado potato beetle on foliar polyphenol oxidase activity in tomato foliage and its possible significance to interspecific competition is also considered.Approved by the Director of the Arkansas Agricultural Experiment Station.     

Disruption of Secondary Attraction of the Spruce Beetle, Dendroctonus rufipennis, by Pheromones of Two Sympatric Species

Capture of spruce beetles, Dendroctonus rufipennis, in multiple-funnel traps baited with frontalin and -pinene was reduced by up to 42% in the presence of synthetic (+)-exo- and (+)-endo-brevicomin, aggregation pheromones of the sympatric species Dryocoeles affaber. (±)-endo-Brevicomin was inhibitory to spruce beetles in two experiments and (±)-exo-brevicomin was inhibitory in one experiment, reducing spruce beetle trap catches by up to 87% and 75%, respectively. Spruce beetle trap catches were also reduced by 85% by (±)- or (+)-ipsdienol, but not by (–)-ipsdienol. Ips tridens, a second sympatric species, produces both enantiomers of ipsdienol in its pheromone blend. Responses by D. affaber to its own pheromone were significantly enhanced by addition of the spruce beetle lure. Enantiospecific pheromones of secondary competing species, or less costly racemic substitutes, may be useful for managing spruce beetles using competitive displacement or exclusion. Baiting susceptible hosts with pheromones of secondary species may enhance attack by secondary species, while partially repelling spruce beetles.