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1.
The chemical composition of the defensive secretions of 52 species from 15 genera of the tenebrionid subtribe Stizopina was
analyzed. The secretions of all species contained 1,4-benzoquinones, 1-alkenes, and monoterpene hydrocarbons, only one species
was lacking the latter. Methyl- and ethyl-1,4-benzoquinone were ubiquitous, mostly accompanied by smaller amounts of 1,4-benzoquinone
as well as isopropyl- and propyl-1,4-benzoquinone. 1-Alkenes were dominated by 1-undecene with varying admixtures of other
1-alkenes. The monoterpene hydrocarbons always consisted of a mixture of α-pinene, camphene, β-pinene and limonene, but also
p-cymene, α-terpinene or α-phellandrene were found in some species. Furthermore, some species synthesized additional compounds
such as phenols, ketones, 2,5-dihydroxy-6-methylbenzoate, 2-hydroxy-4-methoxyacetophenone and naphthoquinones. Bioassays showed
that the defensive secretion co-functioned as an aggregation pheromone in the subtribe Stizopina. All nine tested species
from six genera were attracted to defensive secretion of Stizopina species, but they did not distinguish between defensive
secretions of different Stizopina species. This lack of discrimination might be the initial step for the formation of interspecific
aggregations and the evolution of cleptoparasitism within the Stizopina. 相似文献
2.
Summary. The presence of considerable quantities of hydroquinones including hydroquinone, 2-methylhydroquinone, 2,3- dimethoxyhydroquinone,
2-methoxy-3-methylhydroquinone, and 2,3-dimethoxy-5-methylhydroquinone renders the defensive secretion of Acladocricus setigerus (Silvestri, 1897) significantly different from that of other quinone-producing millipedes. In addition, two hitherto undescribed
compounds, namely, 2,3-dimethoxy-5-methylhydroquinone and 2-methyl-3,4-methylenedioxyphenol, were characterized from the defensive
secretion. However, it is uncertain if the latter compound is formed after the release of the secretion. The two major compounds,
2-methyl-1,4-benzoquinone and 2-methoxy-3-methyl-1,4-benzoquinone, constitute about 75% of the defensive fluid. Furthermore,
hydrocarbons, which are typically present in the secretions of most other arthropods that use benzoquinones as repellents,
are notably absent in the secretion of A. setigerus. 相似文献
3.
Aphids have an extremely intimate relationship with their plant hosts. Although this might suggest that aphid infestation
would be largely cryptic, there are a wide range of changes that can be detected behaviourally, chemically and also at the
molecular genetic level. Colonisation by aphids can cause release of semiochemicals characteristic of the aphid species and
besides reducing acceptability to incoming aphids; these can enable recruitment of specific parasitoids. Some semiochemicals
involved in these processes can also influence the defence status of neighbouring intact plants through air or the rhizosphere.
Electrophysiological and behavioural studies on the aphids, their parasitoids and other organisms facilitate the identification
of compounds having direct effects on plant defence. New developments from work on semiochemicals such as (Z)-jasmone and 6-methyl-5-hepten-2-one, and allelobiotic agents such as 6-hydroxy-1,2,3,4-tetrahydro-β-carboline-3-carboxylic
acid and 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one, as well as new work on these compounds and others as potential phytopheromones
are discussed. 相似文献
4.
Floral scents are known as an olfactory signal for attracting pollinators, but why the flowers pollinated by highly specialised pollinators emit scents consisting of mixtures of many compounds and dominated by one or a few compounds is still poorly understood. We supposed that each (especially characteristic) chemical in floral scents may play a specific role in mediating pollinator behaviours and tested this supposition in a fig-fig wasp mutualism. Ficus curtipes is obligately pollinated by an undescribed Eupristina species. In the scent of F. curtipes receptive figs, over 50 compounds have been identified, and the scent is dominated by two compounds, 6-methyl-5-hepten-2-ol (OL) and 6-methyl-5-hepten-2-one (NE). We therefore tested the roles of the two major chemicals in mediating the pollinator behaviours. Our results show that OL and NE, respectively, act as a long-distance attractant and a fig-entry behaviour stimulant to the obligate pollinator wasp. Namely, OL attracts the wasps to the figs and NE guides the wasps into the figs. This finding on the work division of floral scent compounds partially explains the maintenance mechanism of the fig-fig wasp mutualism and the significance of the chemical diversity of floral scent in plant–pollinator interactions, especially in specialised pollination systems. 相似文献
5.
Zhizhuo Liu Zhemin Shen Shouyan Xiang Yang sun Jiahua Cui Jinping Jia 《Frontiers of Environmental Science & Engineering》2023,17(3):31
6.
3,4-Annelated coumarin-pyrimido-pyrimidine systems (7-imino-8-mercapto-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 2 and 8-hydroxy-7-imino-10-methyl-7H-5-oxa-7a,9,12-triaza-benzo[a]anthracen-6-one 3) were synthesized by the action of 4-amino-2-mercapto-pyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine, respectively, on 4-chlorocoumarin-3-carbonitrile 1. The synthesized compounds were examined for in vitro antibacterial activity against 4 bacterial cultures: Staphylococcus aureus, Streptococcus pneumonia, Escherichia coli, and Aeromonas Salmonicida. The antibacterial activity of synthesized compounds 2 and 3 was compared to antibacterial activity of novobiocin as a standard drug. 相似文献
7.
Audrey Copp��e Tifany Mathy Marie-Claire Cammaerts Fran?ois J. Verheggen Michael Terzo St��phanie Iserbyt Irena Valterov�� Pierre Rasmont 《Chemoecology》2011,21(2):75-82
Males of Bombus terrestris (L.) adopt a patrolling behaviour during their nuptial parade using cephalic labial gland (CLG) secretions containing sexual pheromones to attract conspecific virgin queens. The changes in chemical composition of their CLG secretions with age are quite well known. In this study, we investigate the evolution of CLG secretions with age in greater detail and compare behavioural reactions of conspecific virgin queens to the secretions. We show that compounds of CLG secretions follow two profiles. Most of the compounds increase from the first day after emergence until the bees are 15-days-old and then decrease. Others are less abundant in 1 to 15-day-old males and then increase (e.g. tricosane, tricosene, henicosane, tetradecanoic acid, pentacosene, pentacosane, heptacosene, heptacosane, nonacosene and geranylcitronellyl tetradecanoate). Differences in secretion composition lead to preferences of virgin queens for males according to the male??s age. Virgin queens prefer the pheromonal gland secretions of bees of the following ages in decreasing order; 1?day?=?3?days?<?7?days?=?30?days?<?15?days?<?10?days. The virgin queens are strongly attracted by secretions containing high amounts of 2,3-dihydrofarnesol, 2,3-dihydrofarnesal, ethyl dodecanoate and hexadecanol. On the contrary, geranylcitronellol is more abundant in 30-day-old males. 相似文献
8.
Summary. Worker ants of Camponotus socius employ multicomponent signals during group recruitment to food sources and nest emigrations. The chemical signals consist of trail orientation pheromones that originate from the hindgut. Two components that elicit trail orientation behavior were identified: (2S,4R,5S)-2,4-dimethyl-5-hexanolide and 2,3-dihydro-3,5-dihydroxy-6-methylpyran-4-one. Although both compounds release trail following behavior, in choice tests the former compound is preferred significantly. The major recruitment signal appears to be formic acid discharged from the poison gland. Compounds identified in the Dufour gland secretions do not seem to be involved in the recruitment process. 相似文献
9.
1,3-Oxazines have a wide variety of biological activities. Naphthoquinone scaffolds also exhibit several biological responses such as antithrombotic, apoptosis and lipoxygenase inhibitors. There is, therefore, a need to develop efficient green methodologies for hybridizing the two scaffolds in a single entity. Herein, we report a novel protocol for the synthesis of 3-aryl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones by one-pot three-component condensation of 2-hydroxy-1,4-naphthoquinone, aromatic amines and formaldehyde in glycerol at 50 °C. After separation of products, the glycerol–water layer was extracted using ethyl acetate and the dried glycerol layer was successfully reused several times. The products were obtained in 85–95 % yields in 5–10 min. This environmentally benign protocol holds advantages of high yields, operational simplicity and easy workup over our earlier report. 相似文献
10.
Summary The exocrine glandular secretions of larvae of the subfamily Chrysomelinae are known to repel conspecific adults, other competitive phytophagous insects and natural enemies. InPhaedon cochleariae, the intraspecific activity of tlc fractions of the larval secretion was tested in order to examine the ecological significance of two fractions containing minor components and a fraction containing the major compound, the cyclopentanoid monoterpene (epi)chrysomelidial. InChrysomela lapponica, the defensive activity of the larval secretion against ants is known from specimens feeding upon willow or birch. The feeding preferences of larvae and adults ofC. lapponica from a Finnish and a Czech population were tested. The Finnish individuals significantly preferred feeding uponSalix borealis, whereas they hardly fed upon birch. The Czech specimens clearly preferred birch (Betula pubescens) to willow species. Application of salicin onto leaves of a willow species free of this phenolglycoside revealed that the Finnish individuals preferred feeding upon leaves with salicin. On the other hand, the Czech individuals avoided feeding upon leaves ofB. pubescens treated with salicin. The chemical composition of the glandular secretion of the Finnish larvae differed from the one of the Czech larvae. GC-MS-analyses of the secretions revealed that salicylaldehyde was the only major component of the secretion of Finnish larvae feeding upon the salicin-containing willowS. borealis. The glandular secretion of the Czech larvae feeding upon birch contained numerous esters of isobutyric acid and 2-methylbutyric acid. When Czech larvae had fed upon a salicin-containing willow (S. fragilis), the major compounds of their secretion were benzoic acid, salicylalcohol and benzoic acid esters; salicylaldehyde was only detected in traces. Thus,C. lapponica individuals from the Finland population adapted so closely to a salicincontaining willow that they clearly prefer this plant for food and that they obviously derive their main larval defensive compound (salicylaldehyde) from their host-plant. 相似文献
11.
Summary. The defensive chemistry of the ladybird beetle Epilachna paenulata (Coleoptera: Coccinellidae) was characterized as a mixture of piperidine, homotropane and pyrrolidine alkaloids. Whole body
extracts of adult beetles contain four major alkaloids: 1-(6-Methyl-2,3,4,5-tetrahydro-pyridin-2-yl)-propan-2-one; 1-(6-methyl-2-piperidyl)-propan-2-one;
9-aza-1-methyl-bicyclo[3.3.1]nonan-3-one and 1- (2′′- hydroxyethyl)-2-(12′-aminotridecyl)-pyrrolidine. Comparative studies
of the defensive chemistry of eggs, larvae, pupae and adults showed both qualitative and quantitative differences in alkaloid
composition among the four life stages, and also within adult age. Laboratory predation bioassays with wolf spiders showed
that the adults are better protected than the larvae and pupae. Field tests showed the adult alkaloid extract to be deterrent
to ants. 相似文献
12.
Summary Males ofCarpophilus freemani Dobson (Coleoptera: Nitidulidae) produce an aggregation pheromone to which both sexes fly in a wind-tunnel bioassay. The major pheromone component (ca. 30 ng per male per day in volatile collections) was identified as (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene. A minor component, (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene, was 3–10% as abundant as the major triene and was 5–20% as active when compared at relative doses ranging from natural proportions to 1:1. These compounds act synergistically: a mixture of major and minor components in natural proportions attracted more than twice as many beetles as the major component alone, and the mixture fully accounted for the activity of male-derived volatile collections. Six other male-derived conjugated hydrocarbons, ranging from 2% down to 0.04% as abundant as the major component, were also identified. These are (in order of decreasing bioassay activity when compared on an equal-weight basis): (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene, (2E,4E,6E)-5-ethyl-3-me-thyl-2,4,6-octatriene, (3E,5E,7E,9E)-8-ethyl-4,6-dimethyl-3, 5,7,9-dodecatetraene, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6, 8-undecatetraene, (3E,5E,7E)-5-ethyl-7-methyl-3,5,7-undecatriene, and (2E,4E,6E)-3,5-dimethyl-2,4,6-nonatriene. All structure identifications were confirmed by synthesis. In the wind tunnel, the pheromone acted synergistically with host-type volatiles such as propyl acetate, valeric acid, and ethanol. This concept was verified by fields tests in California, in which there was dramatic synergism between the pheromone and fermenting host materials. Pheromone biosynthesis is discussed. 相似文献
13.
Summary Gyrinid beetles are common in freshwater habitats. They have paired pygidial glands with a secretion that contains high molecular weight substances rendering them toxic for predatory fish. In this paper we report on a laboratory study on volatile components released by three different gyrinid species when irritated. The volatile pattern had a clear difference between the different species.Gyrinus substriatus andG. aeratus, both produced 3-methyl-1-butanal and 3-methyl-1-butanol when irritated, but in quite different amounts. The third tested species,G. minutus, did not produce any substances above the detection level. It is suggested that the volatile compounds may be part of the beetles' communication and/or defence system. 相似文献
14.
Summary When the larvae of the caddis flyApatania fimbriata (Pictet) are threatened, drops of fluid appear on their head capsules. The secretions are produced in a gland in the dorsal part of the prothorax. The neck region contains an eversible sac with numerous single setae, groups of 3 setae, or rows of setae on the surface. The secretion is released through two paris of orifices on the lateral sides of the sac. For the most part the secretion is composed of some 30 fatty acids, with the major components having 12–14 carbon atoms and up to 4 double bonds (approx. 1–2 µg secretion per specimen). Biotests with synthetic saturated acids (C6–C12) in a stream and in the laboratory demonstrated a paralysing effect on small invertebrate predators (Rhyacophila sp.,Plectrocnemia conspersa, Hydropsyche sp., larvae, all Trichoptera). In choice experiments,Rhyacophila sp. larvae preferred larvae ofAgapetus fuscipes andDrusus annulatus (Trichoptera) as food as compared withApatania fimbriata larvae. Larger predators, such asDinocras cephalotes (Insecta, Plecoptera) and the fishCottus gobio, did not discriminate betweenApatania fimbriata and other prey species. The use of fatty acids in defensive secretions is interpreted as an adaptation to the running water environment. They are effective repellents againstRhyacophila sp. larvae, the most important predator in the natural environment ofApatania larvae. 相似文献
15.
Settling larvae of the bryozoans Flustrellida hispida, Flustra foliacea, Alcyonidium polycum, and Bugula neritina exhibit a common behavioral pattern. A settlement site is selected after initial exploration, and temporary attachment is accomplished with a sticky acid mucopolysaccharide secretion exuded from the pyriform organ. Permanent attachment is accomplished by acid mucopolysaccharide and protein secretions of the everted internal sac. 相似文献
16.
Summary 2-methyl-1,4-benzoquinone as a target compound of the tergal gland secretion of the rove beetle,Aleochara curtula, was quantified from the reservoirs of individual beetles. Males store less secretion than females, and they evaporate more of the secretion as measured by adsorption from the air (closed-loop-stripping-analysis). The amount of emitted quinone is increased during aggressive interactions of rival males. The pulsed emission of the secretion during aggression is demonstrated by a novel technique combining observation of behavior with the on-line measurement of target fragment ions by mass-spectrometry (tandem bioassay — mass fragmentography). The emission of the secretion is used as a weapon in combats between males and may result in the repulsion of subordinate males from the mating site, but may also serve to mimic females chemically in order to avoid aggressive encounters. 相似文献
17.
Dietrich Mebs Georg Petschenka Werner Pogoda Stefan W. Toennes Jens Amendt Barbara K. Zajac Susanne Dobler 《Chemoecology》2014,24(4):159-164
The blowfly Lucilia bufonivora shows high host specificity for toads despite the host’s toxic skin secretion, which consists mainly of bufadienolides. These toxins are effective blockers of the Na+, K+-ATPase, an enzyme that is essential for many physiological processes in animals. Whereas common toad (Bufo bufo) toxins were identified in the larvae of the fly, few toxins were found in the pupae and empty puparia as trace amounts, while adult flies were entirely free of these toxic compounds. Similar results were obtained when larvae of generalist necrophagous blowflies (L. sericata, Calliphora vicina) fed on toad carcasses. Analysis of the Na+, K+-ATPase gene revealed no amino acid substitution at positions known to mediate resistance to bufadienolides in other systems. Alternative mechanisms of resistance such as efficient excretion of the compounds may enable the flies to use this poisonous food source. 相似文献
18.
Stephen T. Deyrup Laura E. Eckman Eleanor E. Lucadamo Patrick H. McCarthy Jacqueline C. Knapp Scott R. Smedley 《Chemoecology》2014,24(4):145-157
Delphastus catalinae (Horn) is a predatory ladybird beetle (Coccinellidae) commonly used as a biocontrol agent against greenhouse infestation by whiteflies. It belongs to the basal subfamily Microweisinae, a group for which chemical defenses have not been previously investigated. The larval and pupal stages of D. catalinae possess minute secretory hairs that produce droplets containing compounds of both isoprenoid and polyketide origin. Bioassays with the predatory ant Crematogaster lineolata showed both the larval and pupal secretions to be deterrent. Moreover, isolated secretion components, from both classes of compounds, displayed antipredator activity against the ant. Experiments with D. catalinae larvae fed isotopically labeled glucose showed 13C-incorporation into both categories of compounds within the pupal secretion, demonstrating that these antipredator compounds, which differ from the typical nitrogenous defensive molecules of coccinellids, are biosynthesized endogenously. This suggests that the wide use of alkaloids by more derived coccinellids may have arisen after their divergence from the more basal Microweisinae. 相似文献
19.
Summary. Larvae of Chrysomela leaf beetles release for defence volatile compounds belonging to various chemical families. This study focuses on the defensive
strategy based on the esterification of isobutyric acid and 2-methylbutyric acid with a wide variety of alcohols taken up
from the host plant. To date, only two species are known to produce these repellents C. interrupta, which is associated with Betulaceae and C. lapponica which occurs either on Betulaceae or Salicaceae.? In order to know if other species have developed this chemical defence
and how the food plant influences the secretion of these toxins, we targeted by mass spectrometry the presence of iso- and
2-methylbutyric acids and esters of them in the defensive secretions of Chrysomela larvae exclusively associated with Betulaceae or Salicaceae. ?Screening analyses reveal that the synthesis of these compounds
is a common character restricted to all the members belonging to the C. interrupta group sensu Brown (1956) regardless of the host-plant family. These results suggest that the biochemical mechanism leading
to the synthesis of these compounds could be considered as a synapomorphy meaning that the group is probably monophyletic.
?Defensive secretions of the members of the interrupta group are quantitatively assayed for iso- and 2-methylbutyric acids
and their (Z)-3-hexenyl esters. Results reveal a chemical plasticity developed by Chrysomela species associated with Salicaceae. The amounts of iso- and 2-methylbutyric acids derivatives and of salicylaldehyde in their
larval secretions depend on the food plant and on its content in phenolglucosides.
Received 5 October 1998; accepted 25 November 1998. 相似文献
20.
We present data indicating that three species of cerambycid beetles (subfamily Cerambycinae) produce the common cerambycine pheromone component (R)-3-hydroxyhexan-2-one as well as an alkan-2-one component, a possible new motif for cerambycid pheromone components. GC/MS analyses of headspace volatiles produced by male beetles indicated that Cyrtophorus verrucosus (Olivier) produced (R)-3-hydroxyhexan-2-one but also nonan-2-one at ~18 % of the hydroxyketone component, whereas Orwellion gibbulum arizonense (Casey) and Parelaphidion aspersum (Haldeman) produced decan-2-one at ~40 and 7 % of the amount of the hydroxyketone, respectively. In field bioassays, adult C. verrucosus were attracted by (R)-3-hydroxyhexan-2-one alone, but attraction was significantly enhanced by nonan-2-one. This effect was lost if the quantity of nonan-2-one exceeded 100 % of the hydroxyketone, suggesting that beetles could discern ratios of the two chemicals and were most strongly attracted to those approximating the blend produced by males. We suggest that nonan-2-one plays a role in the species specificity of the pheromone signal of C. verrucosus, and that decan-2-one plays a similar role in the semiochemical communication of O. g. arizonense and P. aspersum. 相似文献