Glucosinolate-related glucosides in Alliaria petiolata: sources of variation in the plant and different metabolism in an adapted specialist herbivore, Pieris rapae.

Abstract:

:Specialized metabolites in plants influence their interactions with other species, including herbivorous insects, which may adapt to tolerate defensive phytochemicals. The chemical arsenal of Alliaria petiolata (garlic mustard, Brassicaceae) includes the glucosinolate sinigrin and alliarinoside, a hydroxynitrile glucoside with defensive properties to glucosinolate-adapted specialists. To further our understanding of the chemical ecology of A. petiolata, which is spreading invasively in North America, we investigated the metabolite profile and here report a novel natural product, petiolatamide, which is structurally related to sinigrin. In an extensive study of North American populations of A. petiolata, we demonstrate that genetic population differences as well as developmental regulation contribute to variation in the leaf content of petiolatamide, alliarinoside, sinigrin, and a related glycoside. We furthermore demonstrate widely different metabolic fates of these metabolites after ingestion in the glucosinolate-adapted herbivore Pieris rapae, ranging from simple passage over metabolic conversion to sequestration. The differences in metabolic fate were influenced by plant β-glucosidases, insect-mediated degradation, and the specificity of the larval gut transport system mediating sequestration.

journal_name

J Chem Ecol

authors

Frisch T,Agerbirk N,Davis S,Cipollini D,Olsen CE,Motawia MS,Bjarnholt N,Møller BL

doi

10.1007/s10886-014-0509-y

subject

Has Abstract

pub_date

2014-10-01 00:00:00

pages

1063-79

issue

10

eissn

0098-0331

issn

1573-1561

journal_volume

40

pub_type

杂志文章
  • 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

  • Evidence that ribonuclease activity present in beetle regurgitant is found to stimulate virus resistance in plants.

    abstract::Phaseolus vulgaris L. cv. 'Pinto' bean is a local lesion host for the plant pathogen Southern bean mosaic virus (SBMV) and its vector is the Mexican bean beetle, Epilachna varivestis Mulsant. The objective of this study was to determine if prior feeding by the beetle would affect 'Pinto' bean's resistance to SBMV and ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1019985417720

    authors: Musser RO,Hum-Musser SM,Slaten-Bickford SE,Felton GW,Gergerich RC

    更新日期:2002-08-01 00:00:00

  • Using generic pheromone lures to expedite identification of aggregation pheromones for the cerambycid beetles Xylotrechus nauticus, Phymatodes lecontei, and Neoclytus modestus modestus.

    abstract::Males of several species of longhorned beetles in the subfamily Cerambycinae produce sex or aggregation pheromones consisting of 2,3-hexanediols and/or hydroxyhexanones. We tested the hypothesis that this diol/hydroxyketone pheromone motif is highly conserved within the subfamily, and the resulting prediction that mul...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-007-9275-4

    authors: Hanks LM,Millar JG,Moreira JA,Barbour JD,Lacey ES,McElfresh JS,Reuter FR,Ray AM

    更新日期:2007-05-01 00:00:00

  • Altered glucosinolate hydrolysis in genetically engineered Arabidopsis thaliana and its influence on the larval development of Spodoptera littoralis.

    abstract::The antiherbivore potential of the glucosinolate-myrosinase defense system found in plants of the order Capparales is heavily influenced by the types of hydrolysis products (e.g. isothiocyanates, nitriles) formed from the parent glucosinolates upon plant damage. However, comparison of the effects of glucosinolate hydr...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9149-1

    authors: Burow M,Müller R,Gershenzon J,Wittstock U

    更新日期:2006-11-01 00:00:00

  • Separation and identification of phenolic acids and related compounds by gas chromatography and fourier transform infrared spectroscopy.

    abstract::Phenolic acids and related compounds were separated by gas chromatography using three separate columns. One of these columns was coupled to a Fourier transform infrared spectrometer. The trimethylsilyl derivatives could be separated and identified by comparing the relative retention times of the three different column...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01025891

    authors: Melhuish JH Jr,Willis RB,Wright CS

    更新日期:1987-02-01 00:00:00

  • Potential of synthetic sex pheromone blend for mating disruption of the swede midge, Contarinia nasturtii.

    abstract::The potential for pheromone-based mating disruption of the Brassica pest Contarinia nasturtii was tested, both in small-scale plots with Brussels sprouts and in commercial-scale fields with either broccoli or cauliflower. Experiments in the small-scale plots used laboratory-reared insects released into a previously un...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-012-0180-0

    authors: Samietz J,Baur R,Hillbur Y

    更新日期:2012-09-01 00:00:00

  • Non-volatile intact indole glucosinolates are host recognition cues for ovipositing Plutella xylostella.

    abstract::The diamondback moth (Plutella xylostella), a crucifer-specialist pest, has been documented to employ glucosinolates as host recognition cues for oviposition. Through the use of mutant Arabidopsis thaliana plants, we investigated the role of specific classes of glucosinolates in the signaling of oviposition by P. xylo...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9723-4

    authors: Sun JY,Sønderby IE,Halkier BA,Jander G,de Vos M

    更新日期:2009-12-01 00:00:00

  • Secondary metabolites released by the burying beetle Nicrophorus vespilloides: chemical analyses and possible ecological functions.

    abstract::Burying beetles of the genus Nicrophorus localize small vertebrate carcasses by emitted volatiles. The carcass that serves as reproduction and breeding site is buried in the soil by the beetles. Biparental care for offspring includes both preservation of the carrion and its preparation as diet and nursery. Buried carc...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-011-9978-4

    authors: Degenkolb T,Düring RA,Vilcinskas A

    更新日期:2011-07-01 00:00:00

  • Statistical problems encountered in trapping studies of scolytids and associated insects.

    abstract::Traps baited with semiochemicals are often used to investigate the chemical ecology of scolytids and associated insects. One statistical problem frequently encountered in these studies are treatments that catch no insects and, thus, have zero mean and variance, such as blank or control traps. A second problem is the u...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/b:joec.0000042069.17533.3c

    authors: Reeve JD,Strom BL

    更新日期:2004-08-01 00:00:00

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

    abstract::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 ch...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00988575

    authors: Moore LV,Scudder GG

    更新日期:1985-05-01 00:00:00

  • Relative importance of infochemicals from first and second trophic level in long-range host location by the larval parasitoidCotesia glomerata.

    abstract::Recently parasitoids were hypothesized to encounter a reliability-detectability problem relating to chemical stimuli from the first and second trophic level, when searching for hosts. The relative role of infochemicals originating from the host,Pieris brassicae (second trophic level), and its food plant, cabbage (firs...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987470

    authors: Steinberg S,Dicke M,Vet LE

    更新日期:1993-01-01 00:00:00

  • Intraspecific variation in plant defense alters effects of root herbivores on leaf chemistry and aboveground herbivore damage.

    abstract::Root herbivores can indirectly affect aboveground herbivores by altering the food quality of the plant. However, it is largely unknown whether plant genotypes differ in their response to root herbivores, leading to variable defensive phenotypes. In this study, we investigated whether root-feeding insect larvae (Agriot...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-008-9537-9

    authors: Wurst S,Van Dam NM,Monroy F,Biere A,Van der Putten WH

    更新日期:2008-10-01 00:00:00

  • Inactivation of baculovirus by isoflavonoids on chickpea (Cicer arietinum) leaf surfaces reduces the efficacy of nucleopolyhedrovirus against Helicoverpa armigera.

    abstract::Biological pesticides based on nucleopolyhedroviruses (NPVs) can provide an effective and environmentally benign alternative to synthetic chemicals. On some crops, however, the efficacy and persistence of NPVs is known to be reduced by plant specific factors. The present study investigated the efficacy of Helicoverpa ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-010-9748-8

    authors: Stevenson PC,D'Cunha RF,Grzywacz D

    更新日期:2010-02-01 00:00:00

  • Courtship pheromone production and body size as correlates of larval diet in males of the arctiid moth,Utetheisa ornatrix.

    abstract::Hydroxydanaidal, the corematal courtship pheromone of maleUtetheisa ornatrix, shows pronounced quantitative variation in natural populations of the moth. Males that, as larvae, fed on seed-bearing rather than immature food plants (Crotalaria spectabilis orC. mucronata) produce higher levels of hydroxydanaidal. Such ma...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01021785

    authors: Conner WE,Roach B,Benedict E,Meinwald J,Eisner T

    更新日期:1990-02-01 00:00:00

  • 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 p...

    journal_title:Journal of chemical ecology

    pub_type: 临床试验,杂志文章

    doi:10.1007/s10886-012-0183-x

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

    更新日期:2012-09-01 00:00:00

  • Hairpencil pheromone components of male oriental fruit moths,Grapholitha molesta.

    abstract::MaleGrapholitha molesta hairpencil components are ethyltrans-cinnamate, mellein, methyl jasmonate, and methyl 2-epijasmonate. The natural behavioral effect elicited by hairpencil-displaying males during courtship in attracting sex-pheromone-releasing females from several centimeters away can be duplicated by mixtures ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987661

    authors: Nishida R,Baker TC,Roelofs WL

    更新日期:1982-06-01 00:00:00

  • 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

  • Role of steroidal glycoalkaloid α-tomatine in host-plant resistance of tomato to colorado potato beetle.

    abstract::The role of the steroidal glycoalkaloid α-tomatine in the hostplant resistance of tomato to the Colorado potato beetle,Leptinotarsa decemlineata (Say) was examined in short- (24 hr; using first- and fourth-instar larvae) and long-term (first-instar larvae reared through the prepupal stage) feeding experiments. Consump...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01395604

    authors: Barbour JD,Kennedy GG

    更新日期:1991-05-01 00:00:00

  • The involvement of volatile infochemicals from spider mites and from food-plants in prey location of the generalist predatory mite Neoseiulus californicus.

    abstract::We investigated volatile infochemicals possibly involved in location of the generalist predatory mite Neoseiulus californicus to plants infested with spider mites in a Y-tube olfactometer. The predators significantly preferred volatiles from lima bean leaves infested with Tetranychus urticae to uninfested lima bean le...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-005-6075-6

    authors: Shimoda T,Ozawa R,Sano K,Yano E,Takabayashi J

    更新日期:2005-09-01 00:00:00

  • State-Dependent Plasticity in Response to Host-Plant Volatiles in a Long-Lived Moth, Caloptilia fraxinella (Lepidoptera: Gracillariidae).

    abstract::Volatile chemicals produced by plants mediate host location, mate-finding and oviposition behavior in insects. State-dependent response to plant cues allows for timing of foraging, mating and oviposition on ephemeral host plants or plant parts. Caloptilia fraxinella is a herbivorous specialist on the foliage of ash tr...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-018-0927-3

    authors: Lemmen-Lechelt JK,Wist TJ,Evenden ML

    更新日期:2018-03-01 00:00:00

  • Technique for injecting intact glands for analysis of sex pheromones of Lepidoptera by capillary gas chromatography : Reinvestigation of pheromone complex ofMamestra brassicae.

    abstract::The structure elucidation of sex pheromones of Lepidoptera by a solid-sample injection technique in conjunction with capillary gas chromatography is described. The applicability of this method in GC and GC-MS modes was demonstrated by reanalyzing the sex attractants of females ofOstrinia nubilalis andBombyx mori. The ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01020556

    authors: Attygalle AB,Herrig M,Vostrowsky O,Bestmann HJ

    更新日期:1987-05-01 00:00:00

  • Author Correction: Temporal Variation of White Rhino Dung Odours.

    abstract::The original version of this article unfortunately contained some mistakes. ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章,已发布勘误

    doi:10.1007/s10886-019-01057-5

    authors: Marneweck C,Jürgens A,Shrader AM

    更新日期:2019-04-01 00:00:00

  • Theophylline induces diapause-like state in social wasps.

    abstract::Feeding of theophylline to hornet workers from their moment of eclosion during the summer results in the following effects on the hornets: loss of appetite for proteins, inhibited ovarial development, no cell-building activity, negative phototaxis, gradual slow-down of spontaneous motor activity, difficulty in flight ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00984011

    authors: Ishay JS,Afek AB,Shimony TB

    更新日期:1982-01-01 00:00:00

  • Odor learning and foraging success in the parasitoid,Leptopilina heterotoma.

    abstract::A brief 2-hr experience with hostDrosophila larvae in artificial apple-yeast or mushroom microhabitats had three effects on the foraging behavior of femaleLeptopilina heterotoma (Hymenoptera: Eucoilidae) parasitoids under field conditions. First, experienced females released at the center of circular arrays of apple-y...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00979616

    authors: Papaj DR,Vet LE

    更新日期:1990-11-01 00:00:00

  • Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.

    abstract::The antifungal activity of essential oil (EO) from the Brazilian epazote (Chenopodium ambrosioides L.) was evaluated by the poison food assay at concentrations of 0.3%, 0.1%, and 0.05% with eight postharvest deteriorating fungi (Aspergillus flavus, Aspergillus glaucus, Aspergillus niger, Aspergillus ochraceous, Collet...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-008-9526-z

    authors: Jardim CM,Jham GN,Dhingra OD,Freire MM

    更新日期:2008-09-01 00:00:00

  • Responses of free-ranging coyotes to lures and their modifications.

    abstract::Several chemical modifications of a synthetic fermented egg (SFE) lure were field tested on free-ranging coyotes (Canis latrans) to determine the effects of odor intensity and quality on their behavioral responses. SFE was modified for testing by (1) enhancing one of the four basic odor components (fruity, sulfurous, ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987812

    authors: Bullard RW,Turkowski FJ,Kilburn SR

    更新日期:1983-07-01 00:00:00

  • Adaptive relationships of epoxide hydrolase in herbivorous arthropods.

    abstract::Epoxide hydrolase catalyzes a simple hydrolysis of reactive cyclic ethers that may otherwise alkylate and impair critical proteins and nucleic acids required for life. Although much less studied than the cytochrome P-450 monooxygenases that produce epoxides, differences in subcellular, tissue, pH, substrate, and inhib...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01013483

    authors: Mullin CA

    更新日期:1988-10-01 00:00:00

  • Plant-to-plant communication mediating in-flight orientation of Aphidius ervi.

    abstract::Broad bean plants (Viciafaba) infested by the pea aphid, Acyrthosiphonpisum, play akey role in the in-flightorientation of the parasitoidAphidius ervi, by producing host-induced synomones (HIS). These volatiles are herbivore-specific and are systemically released from insect-free parts of an infested plant, suggesting...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1020553531658

    authors: Guerrieri E,Poppy GM,Powell W,Rao R,Pennacchio F

    更新日期:2002-09-01 00:00:00

  • 2-Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroachNauphoeta cinerea (dictyoptera, blaberidae): A reinvestigation.

    abstract::InNauphoeta cinerea, male calling behavior is associated with sex pheromone release by the sternal glands. The male pheromone that attracts females from a distance is a mixture of 2-methylthiazolidine and 4-ethylguaiacol. It is active at very low concentrations, 0.05 and 0.01 ng, respectively. Two other compounds, 3-h...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00984949

    authors: Sirugue D,Bonnard O,Le Quere JL,Farine JP,Brossut R

    更新日期:1992-12-01 00:00:00

  • Male confusion of the nun moth with disparlure at high and low population densities.

    abstract::The feasibility of using the synthetic sex pheromone, disparlure, as a mating confusant of the nun moth (Lymantria monacha L.) was investigated on wild populations occurring in outbreak proportions in Poland and in low density in Czechoslovakia. The size of experimental plots ranged from 1 to 12 hectares. The amounts ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01013905

    authors: Zďárek J,Vrkoč J,Hochmut R,Kolk A

    更新日期:1988-02-01 00:00:00