Defensive spiroketals from Asceles glaber (Phasmatodea): absolute configuration and effects on ants and mosquitoes.

Abstract:

:Insects are the largest and most diverse group of organisms on earth, with over 1,000,000 species identified to date. Stick insects ("walkingsticks" or "phasmids", Order Phasmatodea) are known for and name-derived from their camouflage that acts as a primary line of defense from predation. However, many species also possess a potent chemical defense spray. Recently we discovered that the spray of Asceles glaber contains spiroketals [a confirmed major component: (2S,6R)-(-)(E)-2-methyl-1,7-dioxaspiro[5.5]undecane, and a tentatively identified minor component: 2-ethyl-1,6-dioxaspiro[4.5]decane] and glucose. In this paper, we: 1) illustrate the identification of spiroketals and glucose in the defense spray of A. glaber by using Nuclear Magnetic Resonance (NMR), Gas Chromatography/Mass Spectrometry (GC/MS), and comparison with a synthetic reference sample; 2) provide the elucidation of the absolute configuration of the major spiroketal in that defense spray; and 3) demonstrate the effect of this compound and its enantiomer on both fire ants (Solenopsis invicta) and mosquitoes (Aedes aegypti).

journal_name

J Chem Ecol

authors

Dossey AT,Whitaker JM,Dancel MC,Vander Meer RK,Bernier UR,Gottardo M,Roush WR

doi

10.1007/s10886-012-0183-x

subject

Has Abstract

pub_date

2012-09-01 00:00:00

pages

1105-15

issue

9

eissn

0098-0331

issn

1573-1561

journal_volume

38

pub_type

临床试验,杂志文章
  • The Role of Diet in Shaping the Chemical Signal Design of Lacertid Lizards.

    abstract::Lizards communicate with others via chemical signals, the composition of which may vary among species. Although the selective pressures and constraints affecting chemical signal diversity at the species level remain poorly understood, the possible role of diet has been largely neglected. The chemical signals of many l...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-017-0884-2

    authors: Baeckens S,García-Roa R,Martín J,Van Damme R

    更新日期:2017-09-01 00:00:00

  • Widespread Chemical Detoxification of Alkaloid Venom by Formicine Ants.

    abstract::The ability to detoxify defensive compounds of competitors provides key ecological advantages that can influence community-level processes. Although common in plants and bacteria, this type of detoxification interaction is extremely rare in animals. Here, using laboratory behavioral assays and analyses of videotaped i...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-015-0625-3

    authors: LeBrun EG,Diebold PJ,Orr MR,Gilbert LE

    更新日期:2015-10-01 00:00:00

  • Identification of female-produced sex pheromone of the honey locust gall midge, Dasineura gleditchiae.

    abstract::The honey locust gall midge, Dasineura gleditchiae Osten Sacken 1866 (Diptera: Cecidomyiidae) is the main pest of ornamental varieties of the honey locust tree, Gleditsia triacanthos L., in North America, and is now becoming a pest of concern in Europe. Female midges were observed to emerge in the early morning with t...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9641-5

    authors: Molnár B,Kárpáti Z,Szocs G,Hall DR

    更新日期:2009-06-01 00:00:00

  • Volatile hydrocarbons in the dufour's gland of the parasiteNemeritis canescens (Grav.) (Hymenoptera; ichneumonidae).

    abstract::The Dufour's gland of the parasitic waspNemeritis (= Venturia) canescens (Grav.) was shown by gas chromatography and mass spectrometry to contain a mixture of C21, C23, and C25 saturated and monounsaturated hydrocarbons. The main component (62%) was (Z)-10-tricosene. The biological activity of the components is discus...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987884

    authors: Mudd A,Fisher RC,Smith MC

    更新日期:1982-07-01 00:00:00

  • Effectiveness of metal-metal and metal-organic compound combinations against Plutella xylostella: implications for plant elemental defense.

    abstract::Plants that contain elevated foliar metal concentrations can be categorized as accumulators or, if the accumulation is extreme, hyperaccumulators. The defense hypothesis suggests that these plants may be defended against folivore attack, and recent research has indicated that metal concentrations at or below the accum...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-005-9000-0

    authors: Jhee EM,Boyd RS,Eubanks MD

    更新日期:2006-02-01 00:00:00

  • Chemical communication during tandem running inPachycondyla obscuricornis (Hymenoptera: Formicidae).

    abstract::Communication during tandem running inPachycondyla obscuricornis is chemically mediated by a pheromone produced in the pygidial gland, which is composed of a cluster of gland cells and an associated reservoir located beween the 6th and 7th tergites of the gaster. The secretion of the gland appears to be transferred to...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00988543

    authors: Traniello JF,Hölldobler B

    更新日期:1984-05-01 00:00:00

  • Strategies to determine the molecular basis of chemical communication by trematodes.

    abstract::The identification of pheromones and chemicals that may inhibit or stimulate growth and reproduction necessarily leads to the consideration of biochemical methods to isolate and characterize these molecules. Analysis ofSchistosoma mansoni surface antigens by direct radioiodination, metabolic labeling with tritiated an...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01022388

    authors: Hayunga EG,Sumner MP

    更新日期:1986-08-01 00:00:00

  • Female sex pheromone polymorphism in adzuki bean borer, Ostrinia scapulalis, is similar to that in European corn borer, O. nubilalis.

    abstract::Individual analysis of the female sex pheromone of the adzuki bean borer, Ostrinia scapulalis, has shown that the sex pheromone of this species comprised (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc) at variable blend ratios. The pheromone blend could be tentatively categorized ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1014540011854

    authors: Huang Y,Takanashi T,Hoshizaki S,Tatsuki S,Ishikawa Y

    更新日期:2002-03-01 00:00:00

  • Oviposition stimulants for the tropical swallowtail butterfly, Papilio polytes, feeding on a rutaceous plant, Toddalia asiatica.

    abstract::In nature, Papilio polytes utilizes a limited range of rutaceous plants as hosts. We isolated and identified oviposition stimulants for the butterfly from the foliage of its primary host plant Toddalia asiatica. Females readily deposited eggs in response to a methanolic extract of the plant. Partition of the extract w...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1024274814402

    authors: Nakayama T,Honda K,Omura H,Hayashi N

    更新日期:2003-07-01 00:00:00

  • Prior exposure to carbaryl alters behavior ofTetranychus urticae Koch on acaricide-treated leaf surfaces.

    abstract::Preadult exposure to carbaryl affected the subsequent behavior of two-spotted spider mites (Tetranychus urticae Koch) on leaf surfaces with discontinuous acaricide residues. In dicofol bioassays, preexposure to carbaryl caused a loss of avoidance behavior (eliminating the tendency of mites to feed and stand longer off...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02065992

    authors: Dombrowski JA,Kolmes SA,Dennehy TJ

    更新日期:1994-01-01 00:00:00

  • Constituents of temporal gland secretion of the African elephant,Loxodonta africana.

    abstract::Temporal gland secretion (TGS), obtained from 15 different mature African elephants in Kruger National Park was analyzed for volatile constituents. Only five volatile components were present.p-Cresol was present in all samples, but phenol was found as an appreciable component of only one sample and as trace amounts in...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00994782

    authors: Wheeler JW,Rasmussen LE,Ayorinde F,Buss IO,Smuts GL

    更新日期:1982-05-01 00:00:00

  • Flavonoid pigments in marbled white butterfly (Melanargia galathea) are dependent on flavonoid content of larval diet.

    abstract::Analyses of two-dimensional chromatographic flavonoid patterns of butterflies reared on different grass species have shown that the flavonoid pattern ofMelanargia galathea is dependent on the flavonoid content of the larval diet. This confirms the dietary origin of flavonoid pigments inM. galathea. The flavonoid patte...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01024106

    authors: Wilson A

    更新日期:1985-09-01 00:00:00

  • An IDS-Type Sesquiterpene Synthase Produces the Pheromone Precursor (Z)-α-Bisabolene in Nezara viridula.

    abstract::Insects use a wide range of structurally diverse pheromones for intra-specific communication. Compounds in the class of terpenes are emitted as sex, aggregation, alarm, or trail pheromones. Despite the common occurrence of terpene pheromones in different insect lineages, their origin from dietary host plant precursors...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-018-1019-0

    authors: Lancaster J,Lehner B,Khrimian A,Muchlinski A,Luck K,Köllner TG,Weber DC,Gundersen-Rindal DE,Tholl D

    更新日期:2019-02-01 00:00:00

  • Lespedeza phenolics and Penstemon alkaloids: Effects on digestion efficiencies and growth of voles.

    abstract::Lespedeza cuneata contains high levels of phenolics and is a common food plant of the meadow vole (Microtus pennsylvanicus);Penstemon digitalis contains substantial quantities of alkaloids and is a common food plant of meadow voles and prairie voles (M. ochrogaster). We investigated the palatability of these plants an...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012104

    authors: Lindroth RL,Batzli GO,Avildsen SI

    更新日期:1986-03-01 00:00:00

  • Biological activity and tentative identification of flavonoid components in velvetleaf (Abutilon theophrasti Medik.) seed coats.

    abstract::The biological activity of aqueous extracts of velvetleaf (Abutilon theophrasti Medik.) seed coats and their flavonoid components against three plant species and five soil fungi was investigated. Aqueous extracts slightly inhibited germination and significantly inhibited radicle growth of all plant species tested. Fun...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012523

    authors: Paszkowski WL,Kremer RJ

    更新日期:1988-07-01 00:00:00

  • Analysis and manipulation of the structure of odor plumes from a piezo-electric release system and measurements of upwind flight of male almond moths, Cadra cautella, to pheromone plumes.

    abstract::We investigated the plume structure of a piezo-electric sprayer system, set up to release ethanol in a wind tunnel, using a fast response mini-photoionizaton detector. We recorded the plume structure of four different piezo-sprayer configurations: the sprayer alone; with a 1.6-mm steel mesh shield; with a 3.2-mm steel...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-007-9349-3

    authors: Girling RD,Cardé RT

    更新日期:2007-10-01 00:00:00

  • Anointing chemicals and ectoparasites: effects of benzoquinones from millipedes on the lone star tick, Amblyomma americanum.

    abstract::Many mammals and birds roll on or rub themselves with millipedes that discharge benzoquinones. Chemicals transferred from millipedes onto the integument of anointing animals are thought to deter ectoparasites. We tested the lone star tick, Amblyomma americanum (L.), for responses to three widespread components of mill...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-005-0974-4

    authors: Carroll JF,Kramer M,Weldon PJ,Robbins RG

    更新日期:2005-01-01 00:00:00

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

    abstract::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, s...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00982109

    authors: Kuti JO,Jarvis BB,Mokhtari-Rejali N,Bean GA

    更新日期:1990-12-01 00:00:00

  • Biosynthesis, production site, and emission rates of aggregation-attachment pheromone in males of twoAmblyomma ticks.

    abstract::The aggregation-attachment pheromone componentso-nitrophenol (ONP) and methyl salicylate (MS) in maleAmblyomma variegatum ticks appeared after three days of feeding on the host and reached high values after about six days. Variable quantities of 1.3-7.3 μg ONP and about 0.6 μg MS were present within ticks. ONP and MS ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01395594

    authors: Diehl PA,Guerin P,Vlimant M,Steullet P

    更新日期:1991-05-01 00:00:00

  • Aggregation of larvae of the house cricket,Acheta domesticus (L.), by propionic acid present in the excreta.

    abstract::Acetic, propionic, butyric, isobutyric, valeric, and isovaleric acids have been identified in extracts of the excreta of the house cricket,Acheta domesticus (L.), by gas-liquid chromatography. Solutions of propionic acid applied to filter paper aggregated 1- to 2-week-old larvae, while solutions of acetic, butyric, va...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00994799

    authors: McFarlane IE,Steeves E,Alli I

    更新日期:1983-09-01 00:00:00

  • Prey and non-prey arthropods sharing a host plant: effects on induced volatile emission and predator attraction.

    abstract::It is well established that plants infested with a single herbivore species can attract specific natural enemies through the emission of herbivore-induced volatiles. However, it is less clear what happens when plants are simultaneously attacked by more than one species. We analyzed volatile emissions of lima bean and ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-007-9405-z

    authors: de Boer JG,Hordijk CA,Posthumus MA,Dicke M

    更新日期:2008-03-01 00:00:00

  • Disruption of male spruce budworm orientation to calling females in a wind tunnel by synthetic pheromone.

    abstract::Male spruce budworm [Chorisloneura fumiferana (Clem.)] moths were held for 3 hr in a wind tunnel and subjected to various concentrations of background synthetic pheromone. They were then exposed to calling females and their response was recorded. The background pheromone was presented either as discrete turbulent plum...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987797

    authors: Sanders CJ

    更新日期:1982-02-01 00:00:00

  • Zea mays: benzoxazolinone detoxification under sulfur deficiency conditions--a complex allelopathic alliance including endophytic Fusarium verticillioides.

    abstract::Benzoxazolinone detoxification is similar in plants grown under sulfur deficiency conditions and in control plants grown with an optimal S supply. However, when S-deficient plants were treated with metolachlor before benzoxazolin-2(3H)-one (BOA) incubation, detoxification was reduced, as indicated by a lower accumulat...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9226-5

    authors: Knop M,Pacyna S,Voloshchuk N,Kant S,Müllenborn C,Steiner U,Kirchmair M,Scherer HW,Schulz M

    更新日期:2007-02-01 00:00:00

  • Male-produced aggregation pheromone of the cerambycid beetle Rosalia funebris.

    abstract::We report the identification, synthesis, and field bioassays of a volatile, male-produced aggregation pheromone of a long-horned beetle, the banded alder borer, Rosalia funebris Mots. Headspace collections from males contained a major male-specific compound, (Z)-3-decenyl (E)-2-hexenoate, and several minor components,...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-008-9576-2

    authors: Ray AM,Millar JG,McElfresh JS,Swift IP,Barbour JD,Hanks LM

    更新日期:2009-01-01 00:00:00

  • Do elevated temperature and CO2 generally have counteracting effects on phenolic phytochemistry of boreal trees?

    abstract::Global climate change includes concomitant changes in many components of the abiotic flux necessary for plant life. In this paper, we investigate the combined effects of elevated CO2 (720 ppm) and temperature (+2 K) on the phytochemistry of three deciduous tree species. The analysis revealed that elevated CO(2) genera...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9235-4

    authors: Veteli TO,Mattson WJ,Niemelä P,Julkunen-Tiitto R,Kellomäki S,Kuokkanen K,Lavola A

    更新日期:2007-02-01 00:00:00

  • Uptake and sequestration of ouabain and other cardiac glycosides inDanaus plexippus (Lepidoptera: Danaidae): Evidence for a carrier-mediated process.

    abstract::Larvae ofDanaus plexippus feed almost exclusively on milkweed species of the genusAsclepias, whose characteristic secondary metabolites are cardiac glycosides (CGs). Aposematic last-instar larvae were fed with ouabain and other cardiac glycosides of differing polarities. Time course experiments show that ouabain is se...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02033701

    authors: Frick C,Wink M

    更新日期:1995-05-01 00:00:00

  • Identification of (-)-beta-caryophyllene as a gender-specific terpene produced by the multicolored Asian lady beetle.

    abstract::This work reports the development and use of techniques for characterizing volatile chemicals emitted by the multicolored Asian lady beetle, Harmonia axyridis (Pallas) (Coleoptera: Coccinellidae), in an effort to identify the semiochemicals involved in establishment and persistence of overwintering beetle aggregations...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9158-0

    authors: Brown AE,Riddick EW,Aldrich JR,Holmes WE

    更新日期:2006-11-01 00:00:00

  • Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone.

    abstract::Male pink bollworm,Pectinophora gossypiella, were tested in a sustained flight tunnel to 119 blend-dosage combinations of the sex pheromone components, (Z,Z)- and (Z,E)-7,11-hexadecadienyl acetates, which are released by conspecific females in a 61∶39 ratio. Hierarchical cluster analysis was used to define an area of ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012203

    authors: Linn CE Jr,Roelofs WL

    更新日期:1985-11-01 00:00:00

  • Novel Set-Up for Low-Disturbance Sampling of Volatile and Non-volatile Compounds from Plant Roots.

    abstract::Most studies on rhizosphere chemicals are carried out in substrate-free set-ups or in artificial substrates using sampling methods that require an air flow and may thus cause disturbance to the rhizosphere. Our study aimed to develop a simplified and inexpensive system that allows analysis of rhizosphere chemicals at ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-015-0559-9

    authors: Eilers EJ,Pauls G,Rillig MC,Hansson BS,Hilker M,Reinecke A

    更新日期:2015-03-01 00:00:00

  • Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species.

    abstract::Glutathione transferase activity towards various plant isothiocyanates was studied in larvae of the two generalists, fall armyworm [Spodoptera frugiperda (J.E. Smith)], and cabbage looper [Trichoplusia ni (Hübner)], and the specialist, velvetbean caterpillar (Anticarsia gemmatalis Hübner) using the midgut soluble frac...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01019352

    authors: Wadleigh RW,Yu SJ

    更新日期:1988-04-01 00:00:00