Chemistry and functions of exocrine secretions of the antsTapinoma melanocephalum and T. erraticum

Volatile constituents produced by ant workers belonging to the speciesTapinoma melanocephalum andT. erraticum have been analyzed by gas chromatography-mass spectrometry. The pygidial (=anal) gland secretion ofT. melanocephalum is fortified with 6-methyl-5-hepten-2-one and actinidine (the mass spectrum of which is corrected in this paper). An unidentified compound was detected in cephalic extracts. The pygidial gland secretion ofT. erraticum was also dominated by 6-methyl-5-hepten-2-one, in addition to two isomers of iridodial, and iridomyrmecin. The sternal glands contained iridodial and C₁₅-C₂₀ hydrocarbons. Workers ofT. melanocephalum effectively utilize their pygidial gland secretions as an alarm-defense system during aggressive encounters with workers ofSolenopsis geminata. 6-Methyl-5-hepten-2-one is active as a releaser of alarm behavior, and actinidine is repellent to workers ofT. melanocephalum. Cephalic extracts possessed attractant and arrestant properties for workers of this species.     

Detoxification of cereal plant allelochemicals by aphids: Activity and molecular weights of glutathioneS-transferase in three species of cereal aphids

The activity and molecular weights of glutathioneS-transferase were studied in three species of cereal aphid:Metopolophium dirhodum, Sitobion avenae, andRhopalosiphum padi. The highest level of glutathioneS-transferase activity was recorded in extracts fromM. dirhodum and the lowest fromS. avenae, and extracts of larvae were more active than those from adults. The activity of this enzyme was higher in extracts ofS. avenae andR. padi previously fed on a moderately resistant wheat variety than on a susceptible variety. Gel filtration followed by SDS-PAGE revealed three protein bands in the active fractions. The first had a molecular weight of 28,500 and the second of 27,500 and were present in all three species of aphid. The third protein differed in the three species, having a molecular weight of 26,000 inS. avenae, 25,500 inM. dirhodum, and 24,000 inR. padi.     

Identification of major components of larviposition pheromone from larvae of tsetse fliesGlossina morsitans morsitans Westwood andGlossina morsitans centralis Machado

The presence of pheromones produced by larvae ofGlossina morsitans morsitans andG. m. centralis, respectively, which attract gravid females and result in aggregation of pupae, is confirmed. Behavioral experiments indicated that females preferred to larviposit over moist sand conditioned by previously allowing larvae to pupariate in it. Similar results were obtained with filter papers contaminated with the prepupariation excretions of larvae and with volatiles collected from larvae prior to pupariation.n-Pentadecane andn-dodecane were identified as the dominant electrophysiologically active components of the larviposition pheromones ofG. m. morsitans andG. m. centralis, respectively, by GC-EAD and GC-MS analysis of the trapped larval volatiles. Both identified compounds were shown to significantly attract gravid females to larviposition sites in laboratory behavioral assays.     

Chemical stimulants and deterrents regulating acceptance or rejection of crucifers by cabbage butterflies

GravidPieris rapae butterflies oviposit on many, but not all, crucifers. Rejection ofErysimum cheiranthoides andCapsella bursa-pastoris was initially explained by the presence of chemical deterrents in the plants. Analyses and bioassays of plant extracts indicated the absence of oviposition stimulants inC. bursa-pastoris, but similar chemical separation ofE. cheiranthoides extracts revealed the presence of stimulants as well as deterrents. Choice tests illustrate how acceptance or rejection of a plant by an insect may depend on the balance of positive and negative chemical stimuli within the plant.     

Phototoxicity ofCitrus jambhiri to fungi under enhanced UV-B radiation: Role of furanocoumarins

Extracts ofCitrus jambhiri foliage exposed to and shielded from UV-B radiation were assayed for phytochemical changes and phototoxicity against four fungal pathogens, two of which (Fusarium solani andF. oxysporum) are causative agents of root rots and two of which (Penicillium italicum andP. digitatum) are associated with fruit rots. Conidial pigment mutants of these four fungal species were assayed to determine whether pigments play a role in protecting fungi against plant photosensitizers. Exposure to 10.2 kJ/ day UV-B radiation for 95 days significantly reduced phototoxicity of leaf extracts to fungi. Although furanocoumarin levels were reduced by UV-B, analysis of covariance revealed that variation in phototoxicity of the extracts cannot be attributed entirely to variation in furanocoumarin content; thus, the possibility exists that nonfuranocoumarin phototoxic constituents, as yet unidentified, respond to UV-B exposure and contribute to overall phototoxic defense ofC. jambhiri against pathogens. Root rot fungi were substantially more sensitive to furanocoumarin phototoxicity than were fruit rot fungi, a pattern consistent with the amount of light exposure normally experienced by these fungi when associated with phototoxic plants. Although pigmented strains of all four species displayed greater resistance to phototoxicity of pure furanocoumarins, no strain differences were detected in assays of foliar extracts; this finding also suggests that nonfuranocoumarin constituents may be involved in the phototoxic defense ofC. jambhiri against pathogens.Deceased.     

Diterpene composition of defense secretion of four west AfricanTrinervitermes soldiers

The diterpene composition of the defensive secretions of minor and major soldiers is described for four sympatricTrinervitermes from the Ivory Coast. The degree of intra- and interspecific similarity between the secretions is assessed and related to available information on soldier behavior. A significant chemical dimorphism is observed between minor and major soldiers ofT. geminatus andT. togoensis. Both species build extensive foraging trails in the open air. During these excursions, the workers are protected by numerous minor soldiers, but only a few major ones. Internest comparison inT. geminatus suggests that the differences between minor and major soldiers is as large within a nest as between different nests. By, contrast, inT. trinervius andT. oeconomus both types of soldiers produce very similar secretions. The foraging habits of those species are far more cryptic. The first species builds earthen tunnels, and the second one forages in close proximity to its nest under cover of vegetation.Maître de Recherche du Fonds National de la Recherche Scientifique de Belgique.     

Interspecific attractivity of female sex pheromone components ofPeriplaneta americana

Female sex pheromones ofPeriplaneta americana, P. australasiae, andBlatta orientalis elicit locomotion and upwind orientation in conspecific males. Interspecific attraction between these species was observed in a wind tunnel assay for most species combinations, with the exception ofP. australasiae males not being attracted toP americana females. The role of twoP. americana sex pheromone components, periplanone-A (PA) and periplanone-B (PB) in male attraction was analyzed. PA induced locomotion in males of all three species, with highest threshold concentration inP. americana. PB was effective inP. americana andB. orientalis, but not inP. australasiae. Experiments with mixtures of both components confirmed an inhibitory influence of PB onP. australasiae males when it was added to PA in a ratio of 31 or higher. SinceP. americana andP. australasiae have been found to be syntopous, and their daily mating periods overlap, the female sex pheromone ofP. americana is discussed as an isolating factor between both species.     

Host recognition and the study of a chemical basis for attraction by cuckoo bumble bees (Hymenoptera: Apidae)

Species ofPsithyrus (Hymenoptera; Apidae) are obligate bumble bee social parasites. In this study, females ofP. vestalis andP. ashtoni were presented with pentane extracts prepared from different body parts of queens of their respective host species,Bombus terrestris andB. terricola. Parasites of both species were capable of distinguishing host bees from other bumble bee species using chemical cues contained within extracts. Among extracts of several body parts presented to parasites, the abdomen produced the greatest behavioral response, with Dufour's gland and terminal tergal segments eliciting the greatest response among abdominal regions. Extracts of these two body parts obtained fromB. terrestris queens shared a number of compounds, identified by GC-MS. Among the identified compounds are a number that have been reported to be of importance in bee sociochemistry.     

Interspecific response to sex pheromones,and calling behavior of severalAttagenus species (Coleoptera: Dermestidae)

Females of severalAttagenus species demonstrated calling behaviors similar to those previously reported forA. elongatulus. Attagenus rufipennis females did not call until they were 12–14 days old. OtherAttagenus species called at approx. 4 days of age. All species exhibited diurnal periods of calling activity. Interspecific pheromone responses were tested, withA. megatoma megatoma, A. megatoma canadensis, A. megatoma japonicus, andA. schaefferi spurcus showing equal cross-responses. Male response to females was demonstrated inA. rufipennis andA. bicolor. Attagenus rufipennis, bicolor, andelongatulus males responded only to female extracts of their own species.Mention of a proprietary product does not constitute an endorsement by the USDA.     

Allelopathic and autotoxic effects ofAnastatica hierochuntica L.

Laboratory experiments were undertaken to investigate the autotoxic effects ofAnastatica hierochuntica and possible effects on five other desert plants:Rumex cyprius, Trigonella stellata, Diplotaxis harra, Cleome droserifolia, andFarsetia aegyptia. Seed germination, seedling growth, and cell division of all species tested were inhibited by the shoot aqueous extract ofA. hierochuntica. A gradual increase in the percentage of prophase and decrease in the other mitotic stages as well as the mitotic index were observed with increasing extract concentration. At an extract concentration of 8% the mitotic index was reduced from the control by 55% inC. droserifolia, 54% inT. stellata, 45% inF. aegyptia, 43% inA. hierochuntica, and 35% inR. cyprius. The inhibitory substances are apparently released onto soil by repeated washing of the standing plants by rain and dew interception.     

Effects of pine-produced chemicals on selected understory species in aPinus ponderosa community

Pinus ponderosa accounted for more than 98% of all tree and shrub stratum stems in a climax community with low herb coverage and aboveground biomass, 35% and 60 g/m², respectively. Because of our previous report that nitrification and nitrifying bacteria in the same community were allelopathically inhibited, we speculated that the pine-produced allelochemics might also directly influence the development and growth of the herb stratum. In most cases decaying needles, needle leachate, and field soils significantly reduced germination and radicle growth ofAndropogon gerardii andA. scoparius, pine-associated herbaceous species. Additionally, growth ofAndropogon scoparius seedling radicles was reduced 28–56% by pine needle extracts, 33% by pine bark extracts, and 67% by soil hydrolysate extracts.Andropogon seed germination was reduced 20–25% by pine needles and soil. Phytotoxins identified in various plant parts and associated soils were caffeic acid, chlorogenic acid, quercetin, and condensed tannins. Pine needle water and soil hydrolysate extracts were most inhibitory to the radicle growth of the test species. Thus it appears that the limited growth of the herbaceous stratum in the pine community may be accounted for, in part, by allelopathy. Such allelopathic interactions may have an adaptive ecological significance in various forest and other plant communities.     

Multivariate discrimination of host use by dwarf mistletoeArceuthobium vaginatum subsp.cryptopodum: Inter- and intraspecific comparisons

The parasitic dwarf mistletoeArceuthobium vaginatum attacksPinus ponderosa as its primary host andP. contorta as an occasional host. Within ponderosa pine stands there is also differential parasitism among individual trees. We compared biochemical features of phloem and xylem oleoresin between infected individuals of the two pine species (N=15 for each species) and also between infected (N=30) and nearby uninfected (N=30) ponderosa pine conspecifics. There were significant differences in chemical features, both at the interspecific (P. ponderosa vs.P. contorta) and intraspecific (P. ponderosa) levels. Discriminant function analysis based on chemical features of phloem correctly classified all trees used in the analysis as eitherP. ponderosa orP. contorta, and 95% of all ponderosa pine trees as either parasitized or nonparasitized. Monoterpene composition of oleoresin was distinct between species, and differences between parasitized and nonparasitizedP. ponderosa were also significant. Many of the observed chemical differences are probably constitutive, although levels of nonstructural carbohydrates and -pinene may change in response to dwarf mistletoe infection. Biochemical differences at the intraspecific level were distinct from interspecific differences. Patterns of differential attack can have genetic consequences upon both the parasite and its hosts, and, in the process, may contribute to the evolution of host races of the parasite and to the evolution of host resistance within ponderosa pine.     

Selective sequestration of milkweed (Asclepias sp.) cardenolides inOncopeltus fasciatus (Dallas) (Hemiptera: Lygaeidae)

The cardenolide content of the gut, wings, and fat body ofOncopeltus fasciatus was examined. The female fat body contained 4–5% of the total cardenolide content of the insect. The cardenolide content of male fat body, and gut and wings of both sexes was below the detection limit of the cardenolide assay. Thin-layer chromatography was used to determine the cardenolide array of various tissues and secretions ofO. fasciatus reared on seeds of a single species of milkweed (A. Speciosa) and adult extracts and dorsolateral space fluid ofO. fasciatus reared on seeds of two species of milkweed with different cardenolide arrays (A. speciosa andA. syriaca). Our results indicate that cardenolides are not sequestered in the insect simply on the basis of polarity and that metabolism and differential excretion of cardenolides are involved in the sequestration of cardenolides inO. fasciatus. The similarities in the cardenolide profiles ofO. fasciatus reared on different food sources, and tissues ofO. fasciatus reared on a single food source indicates that there is regulation of the cardenolide array inO. Fasciatus.     

Allelochemical regulation of reproduction and seed germination of two BrazilianBaccharis species by phytotoxic trichothecenes

The potent phytotoxic trichothecene roridins and baccharinoids occur naturally in the Brazilian plants,Baccharis coridifolia andB. megapotamica. Biosynthesis of roridins inB. coridifolia appears to be linked to pollination, and the phytotoxins then accumulate in the seed. The roles of the phytotoxins in pollination, seed maturation, and germination of theBaccharis species were investigated. The high production of roridins occurred only in seeds resulting from intraspecific pollination, and the concentration of the toxins in the seeds generally increased with seed maturity. Removal of seed coats from trichothecene-producing BrazilianBaccharis species (B. coridifolia andB. megapotamica) and non-trichothecene-producing AmericanBaccharis species (B. halimifolia andB. glutinosa) resulted in improved seed germination ofB. halimifolia andB. glutinosa but complete inhibition of seed germination ofB. coridifolia andB. megapotamica. Addition of seed coat extracts of the BrazilianBaccharis species of dilute solutions (10^–6g/ml) of roridins or baccharinoids to the decoated seeds ofB. coridifolia andB. megapotamica resulted in germination, while seeds ofB. halimifolia andB. glutinosa were killed by the phytotoxins. Roridins interacted with gibberellic acid, a germination promoter, but not with abscisic acid, a germination inhibitor. The results from this study suggest that macrocyclic trichothecenes have a regulatory role(s) on reproduction and germination of BrazilianBaccharis species in their natural habitat.     

Chemistry of metapleural gland secretions of three attine ants,Atta sexdens rubropilosa,Atta cephalotes,andAcromyrmex octospinosus (Hymenoptera: Formicidae)

The chemical composition of the secretions of the metapleural glands of workers and soldiers of twoAtta species,Atta sexdens rubropilosa andA. cephalotes, and workers ofAcromyrmex octospinosus, has been studied. As indicated by infrared spectrometry and confirmed by the ninhydrin test, the secretions contain chiefly proteins. Of the volatile acidic portion, which is present as ionized salts, phenylacetic acid is the major component in workers and soldiers ofA. s. rubropilosa andA. cephalotes. BothAtta species also contain 3-hydroxydecanoic acid and its homolog as minor components together with indoleacetic acid. While there are qualitative similarities in the acidic composition in the secretions ofA. s. rubropilosa andA. cephalotes, they differ quantitatively. The secretion ofAcromyrmex octospinosus contains 3-hydroxydecanoic and indoleacetic acids, but lacks phenylacetic acid. The bactericidal and fungicidal actions of the three major substances have been confirmed.     

Cross-attraction between two species ofMatsucoccus

In laboratory bioassays, males ofMatsucoccus resinosae fromPinus resinosa in New York andMatsucoccus n. sp. fromPinus thunbergiana in Korea were strongly attracted to crude hexane extracts ofM. resinosae females, andM. resinosae males responded strongly to extracts ofMatsucoccus n. sp. females. Males of the two species responded similarly to gas chromatographic fractions and subfractions of a pentane extract ofM. resinosae females. Sex pheromones of these two species appear to be the same or very similar.Homoptera: Coccoidea: Margarodidae.     

Pheromonal secretions from glands on the 5th abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera)

Extracts of different body parts of adult Trichoptera were tested for electrophysiological activity. Extracts of the IVth and Vth abdominal sternites of femaleHydropsyche angustipennis, Rhyacophila nubila, andR. fasciata, containing a paired exocrine gland, elicited significant electroan-tennographic responses when tested on conspecific male antennae. The paired gland occurs also in males of all the species, and inH. angustipennis, extracts from males were more active than female extracts when tested on male antennae. Female and male extracts from all species were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). EAD-active peaks in female extracts, stimulating male antennae, were identified inH. angustipennis as nonan-2-one; and inR. nubila andR. fasciata as heptan-2-one, heptan-2-ol, nonan-2-one, and nonan-2-ol. EAD-active components from maleH. angustipennis stimulating male antennae were octan-2-one, nonan-2-one (major peak), (Z)-6-nonen-2-one, decan-2-one, and a methylbranched decan-2-one. Female extracts and synthetic mixtures of compounds identified from femaleH. angustipennis andR. fasciata were tested for attractivity in the field. High catches with control traps obscured the results, but a synthetic mixture of the four identified compounds was significantly attractive and not different from female extracts for attracting maleR. fasciata. InH. angustipennis, a synthetic six-component male blend, in which nonan-2-one was the major component, attracted significant numbers of male and femaleH. angustipennis. Extracts of maleR. nubila andR. fasciata contained acetophenone and hexanoic and octanoic acids but did not have any electrophysiological or behavioral activity on either male or female antennae of conspecifics. The occurrence of a female sex pheromone inRhyacophila and an aggregation pheromone inHydropsyche corresponds to earlier described differences in mating behaviors in the Rhyacophilidae and Hydropsychidae.     

C10-polyacetylenes as allelopathic substances in dominants in early stages of secondary succession

cis-Dehydromatricaria ester (cis-DME) inSolidago altissima, andcis-matricaria ester (cis-ME),trans-matricaria ester (trans-ME), andcis-lachnophyllum ester (cis-LE) inErigeron spp. show strong growth inhibitory effects on other plants. Thecis- andtrans-DMEs were found in soil at the border ofS. altissima communities in concentrations that were inhibitory to test plants. Among four species ofErigeron, the most dominant plant,E floribundus, showed the highest concentrations of the esters. From the results of our experiments, we conclude that these polyacetylenes are probably allelopathic substances with ecological importance.     

Oviposition stimulants inBarbarea vulgaris forPieris rapae andP. napi oleracea: isolation,identification and differential activity

The closely related butterflies,Pieris rapae andP. napi oleracea, readily laid eggs onBarbarea vulgaris in greenhouse cages. When offered a choice between cabbage andB. vulgaris, P. rapae showed no preference, butP. napi oleracea preferredB. vulgaris. Bioassays of extracts ofB. vulgaris foliage revealed the presence of oviposition deterrent(s) in l-butanol extracts as well as stimulants in the postbutanol water extracts. However, the deterrent effect was apparently outweighed by the strong stimulatory effect in the whole plants. The postbutanol water extract was preferred over an equivalent cabbage extract by both species, but more significantly in the case ofP. napi oleracea. The stimulants were isolated by open column chromatography and HPLC, and the activity was associated with three glucosinolates.P. napi oleracea was more sensitive thanP. rapae to the natural concentration of compounds1 and3, whereas both species were strongly stimulated to oviposit by natural concentrations of compound2. Compounds1 and2 were identified as (2R)-glucobarbarin and (2S)-glucobarbarin, respectively, and3 was identified as glucobrassicin, on the basis of their UV, mass, and NMR spectra. When the pure compounds were tested at the same concentrations applied to bean plants, the (2R)-glucobarbarin at 0.2 mg/plant was preferred over a standard cabbage extract by both butterfly species. However, at a dose of 0.02 mg/plant,P. rapae preferred the cabbage extract whereasP. napi oleracea still preferred the (2R)-glucobarbarin. No such difference in response of the two species to the same two concentrations of (2S)-glucobarbarin was obtained. The results indicate a distinct difference in sensitivity of these butterflies to the epimers of glucobarbarin, and the differences in behavioral responses of the two butterfly species depend to a large extent on the concentration of stimulant present.     

Recognition of aphid parasitoids by honeydew-collecting ants: The role of cuticular lipids in a chemical mimicry system

The aphidiid waspLysiphlebus cardui parasitizes in ant-attendedAphis fabae cirsiiacanthoidis colonies without causing aggressive behavior in the antLasius niger. By contrast,Trioxys angelicae, another aphidiid parasitoid of aphids, is rapidly recognized and vigorously attacked by the ants.L. niger workers also responded differently to dead individuals ofL. cardui andT. angelicae. DeadL. cardui parasitoids were often ignored when encountered byL. niger, whereas deadT. angelicae individuals were immediately grasped by ants that discovered them. However, hexane-washed parasitoids caused a similar reaction pattern in the ants, in that both aphidiid species were tolerated in the aphid colony. Lure experiments demonstrated that chemical stimuli on the cuticle are major cues for the ants to distinguish between the parasitoids. The hexane extract ofL. cardui transferred to washed individuals ofT. angelicae resulted in ant responses characteristic towardsL. cardui, andL. niger workers displayed the typical removal pattern they normally showed towardsT. angelicae whenT. angelicae extract was applied toL. cardui individuals. Both parasitoid species treated with the hexane extract ofA. fabae cirsiiacanthoidis were similarily treated by the ants as were aphid control individuals. The suggestion that the aphidiid waspL. cardui uses chemical mimicry is discussed.