Aliphatic esters as targets of esterase activity in the parsnip webworm (Depressaria pastinacella).

Abstract:

:As a specialist on the reproductive structures of Pastinaca sativa and species in the related genus Heracleum, the parsnip webworm (Depressaria pastinacella) routinely encounters a distinctive suite of phytochemicals in hostplant tissues. Little is known, however, about the detoxification mechanisms upon which this species relies to metabolize these compounds. In this study, larval guts containing hostplant tissues were homogenized, and metabolism was determined by incubating reactions with and without NADPH and analyzing for substrate disappearance and product appearance by gas chromatography-mass spectrometry. Using this approach, we found indications of carboxylesterase activity, in the form of appropriate alcohol metabolites for three aliphatic esters in hostplant tissues-octyl acetate, octyl butyrate, and hexyl butyrate. Involvement of webworm esterases in hostplant detoxification subsequently was confirmed with metabolism assays with pure compounds. This study is the first to implicate esterases in lepidopteran larval midgut metabolism of aliphatic esters, ubiquitous constituents of flowers and fruits. In addition, this method confirmed that webworms detoxify furanocoumarins and myristicin in their hostplants via cytochrome P450-mediated metabolism, and demonstrated that these enzymes also metabolize the coumarin osthol and the fatty acid derivative palmitolactone.

journal_name

J Chem Ecol

authors

Zangerl AR,Liao LH,Jogesh T,Berenbaum MR

doi

10.1007/s10886-012-0073-2

subject

Has Abstract

pub_date

2012-02-01 00:00:00

pages

188-94

issue

2

eissn

0098-0331

issn

1573-1561

journal_volume

38

pub_type

杂志文章
  • Fumigant toxicity of essential oils against four major stored-product insects.

    abstract::The fumigant toxicity of 28 essential oils extracted from various spice and herb plants and some of their major constituents were assessed for adult coleopteransRhyzopertha dominica, Oryzaephilus surinamensis, Tribolium castaneum, andSitophilus oryzae. Three groups of active materials were distinguished: (1) The compo...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00982120

    authors: Shaaya E,Ravid U,Paster N,Juven B,Zisman U,Pissarev V

    更新日期:1991-03-01 00:00:00

  • Biparental endowment of endogenous defensive alkaloids in Epilachna paenulata.

    abstract::Coccinellid beetles contain a variety of defensive alkaloids that render them unpalatable to predators. Epilachna paenulata (Coleoptera: Coccinellidae) is a South American ladybird beetle that feeds on plants of the Cucurbitaceae family. The defensive chemistry of E. paenulata has been characterized as a mixture of sy...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-008-9570-8

    authors: Camarano S,González A,Rossini C

    更新日期:2009-01-01 00:00:00

  • Protein-precipitating capacity of tannins inShorea (Dipterocarpaceae) seedling leaves.

    abstract::The protein-precipitating capacities of tanniferous extracts from immature and mature leaves of threeShorea spp. (Dipterocarpaceae) seedlings were measured by an adaptation of Goldstein and Swain's β-glucosidase precipitation assay. Protein precipitation by the extracts was not correlated with total phenolics (Folin-D...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01403099

    authors: Becker P,Martin JS

    更新日期:1982-11-01 00:00:00

  • Plant growth regulatory activities of artemisinin and its related compounds.

    abstract::Artemisinin, a sesquiterpene lactone produced in the leaves ofArtemisia annua, was evaluated for its phytotoxicity in mono- and dicotyledonous plants. Artemisinin inhibited seed germination, seedling growth, and root induction in all species tested. The concentration of artemisinin required for 50% inhibition ofLemna ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01020500

    authors: Chen PK,Leather GR

    更新日期:1990-06-01 00:00:00

  • The Origin and Ecological Function of an Ion Inducing Anti-Predator Behavior in Lithobates Tadpoles.

    abstract::In aquatic environments, chemical cues are believed to be associated with prey response to predation risk, yet few basic cue compositions are known despite the pronounced ecological and evolutionary significance of such cues. Previous work indicated that negatively-charged ions of m/z 501 are possibly a kairomone that...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-018-0925-5

    authors: Austin CE,March RE,Stock NL,Murray DL

    更新日期:2018-02-01 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

  • 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

  • Genetic control of the enantiomeric composition of ipsdienol in the pine engraver, Ips pini.

    abstract::The genetic nature of pheromone variation within species has rarely been studied, and never for male-produced long-range pheromones. Males from western North American populations of Ips pini produce predominantly (R)-(-)-ipsdienol, whereas those from eastern North American populations produce higher proportions of (S)...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9042-y

    authors: Domingue MJ,Starmer WT,Teale SA

    更新日期:2006-05-01 00:00:00

  • Activity of volatile compounds in glandular trichomes ofLycopersicon species against two insect herbivores.

    abstract::Several major chemicals in the glandular heads of type VI trichomes ofLycopersicon species were identified and quantified by gas chromatography and mass spectrometry. Two normal odd-chained ketones, 2-undecanone (47 ng) and 2-tridecanone (146 ng), and one unknown sesquiterpene (5 ng), comprised approximately 95% of th...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01020164

    authors: Lin SY,Trumble JT,Kumamoto J

    更新日期:1987-04-01 00:00:00

  • Role of avian trigeminal sensory system in detecting coniferyl benzoate, a plant allelochemical.

    abstract::Coniferyl benzoate, a secondary metabolite found in quaking aspen (Populus tremuloides) and other plants, is an avian feeding deterrent of ecological and potential commercial importance. This study was conducted to determine if coniferyl benzoate is a trigeminal stimulant for birds and to ascertain if trigeminal chemo...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00988002

    authors: Jakubas WJ,Mason JR

    更新日期:1991-11-01 00:00:00

  • Effects of mixtures of phenolic acids on phosphorus uptake by cucumber seedlings.

    abstract::To determine how individual phenolic acids in a mixture might affect phosphorus (P) uptake, 15-day-old cucumber seedlings grown in solution culture were treated with ferulic, vanillic,p-coumaric, or equimolar mixtures of these phenolic acids. Phenolic acid and P uptake were determined by solution depletion. The joint ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01017478

    authors: Lyu SW,Blum U,Gerig TM,O'Brien TE

    更新日期:1990-08-01 00:00:00

  • Deterrence of repeated oviposition in sorghum shootflyAtherigona soccata.

    abstract::The sorghum shootfly,Atherigona soccata, under low population density conditions lays one egg per sorghum plant. Possible regulatory mechanisms of this oviposition behavior are reported. The presence of an egg thoroughly washed and reattached to a leaf does not deter further oviposition, indicating the absence of visu...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00992377

    authors: Raina AK

    更新日期:1981-09-01 00:00:00

  • Differences in Monoterpene Biosynthesis and Accumulation in Pistacia palaestina Leaves and Aphid-Induced Galls.

    abstract::Certain insect species can induce gall formation on numerous plants species. Although the mechanism of gall development is largely unknown, it is clear that insects manipulate their hosts' anatomy, physiology, and chemistry for their own benefit. It is well known that insect-induced galls often contain vast amounts of...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-016-0817-5

    authors: Rand K,Bar E,Ari MB,Davidovich-Rikanati R,Dudareva N,Inbar M,Lewinsohn E

    更新日期:2017-02-01 00:00:00

  • Cuticular hydrocarbons and aggression in the termite Macrotermes subhyalinus.

    abstract::Cuticular hydrocarbons are among the prime candidates for nestmate recognition in social insects. We analyzed the variation of cuticular hydrocarbons in the termite species M. subhyalinus in West Africa (Comoë National Park) on a small spatial scale (< 1 km). We found considerable variation in the composition of cutic...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/b:joec.0000017983.89279.c5

    authors: Kaib M,Jmhasly P,Wilfert L,Durka W,Franke S,Francke W,Leuthold RH,Brandl R

    更新日期:2004-02-01 00:00:00

  • Effects of tree phytochemistry on the interactions among endophloedic fungi associated with the southern pine beetle.

    abstract::We examined the interaction between host trees and fungi associated with a tree-killing bark beetle, Dendroctonus frontalis. We evaluated (1) the response of four Pinus species to fungal invasion and (2) the effects of plant secondary metabolites on primary growth of and secondary colonization of three consistent fung...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-005-2035-4

    authors: Hofstetter RW,Mahfouz JB,Klepzig KD,Ayres MP

    更新日期:2005-03-01 00:00:00

  • Iridoid glycoside sequestration by two aposematicPenstemon-feeding geometrid larvae.

    abstract::The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mulle...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01013895

    authors: Stermitz FR,Gardner DR,McFarland N

    更新日期:1988-02-01 00:00:00

  • To fix or not to fix: the role of 2-phenoxyethanol in rabbit, Oryctolagus cuniculus, chin gland secretion.

    abstract::The European rabbit (Oryctolagus cuniculus) uses the secretion of the chin gland to maintain dominance hierarchies in the wild. Recent work has investigated changes in the secretion when social status is manipulated in the rabbit. When a rabbit becomes dominant, a new compound appears in his secretion, 2-phenoxyethano...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1023836319677

    authors: Hayes RA,Richardson BJ,Wyllie SG

    更新日期:2003-05-01 00:00:00

  • Brook charr alevins alter timing of nest emergence in response to chemical cues from fish predators.

    abstract::Brook charr (Salvelinus fontinalis) lay their eggs in gravel nests called redds. The nests are not defended for extended periods and the eggs and young may be subject to predation from predators that travel through the substrate into the redd. In this study we tested whether long-term exposure of brook charr eggs to c...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1010404624556

    authors: Mirza RS,Chivers DP,Godin JG

    更新日期:2001-09-01 00:00:00

  • An interactive video-computer tracking system for quantification of locomotor behavior.

    abstract::We have developed a flexible, moderately priced, behavioral analysis system which has been used to determine the response of salmonids to certain olfactory stimulants. The system, which we call ITS for interactive computer-video tracking system, consists of a 128K Apple IIe computer with software, a video camera and v...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01020536

    authors: Royce-Malmgren CH,Watson WH 3rd

    更新日期:1987-05-01 00:00:00

  • Plant growth inhibiting flavonoids in exudate of Cistus ladanifer and in associated soils.

    abstract::Of the aglycone flavonoids identified in the exudate of cistus ladanifer, two, the flavone apigenin-4'-(O)-methyl and the flavonol kaempferol-3,7-di(O)-methyl inhibit development of the seedlings of Rumex crispus at 0.5 and 1 mM. Additive effects were observed between the major flavonols of the exudate kaempferol-3-(O...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1010388905923

    authors: Chaves N,Sosa T,Escudero JC

    更新日期:2001-03-01 00:00:00

  • Different Responses of an Invasive Clonal Plant Wedelia trilobata and its Native Congener to Gibberellin: Implications for Biological Invasion.

    abstract::The invasive clonal plant Wedelia trilobata contains higher levels of ent-kaurane diterpenes, which are precursors of gibberellins (GAs), and higher rates of clonal growth than its native congener W. chinensis in invaded habitats. We hypothesized that the higher levels of endogenous GAs facilitate greater ramet growth...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-016-0670-6

    authors: Dai ZC,Fu W,Qi SS,Zhai DL,Chen SC,Wan LY,Huang P,Du DL

    更新日期:2016-02-01 00:00:00

  • Evolution of behavioral responses to sex pheromone in mutant laboratory colonies ofTrichoplusia ni.

    abstract::Male cabbage looper moths,Trichoplusia ni, from two colonies in which all females express an abnormal sex pheromone production phenotype were evaluated in a laboratory wind tunnel for upwind flight responses to the normal and abnormal sex pheromones. The abnormal sex pheromone blend consisted of 20 times as much (Z)-9...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02064433

    authors: Liu YB,Haynes KF

    更新日期:1994-02-01 00:00:00

  • Chemistry of fruit flies: Nature of glandular secretion and volatile emission ofBactrocera (bactrocera) cacuminatus (Héring).

    abstract::The major component of the rectal glandular extract and volatile emission of maleBactrocera cacuminatus is racemic 1,7-dioxaspiro[5.5]undecane. l-Hydroxy-5-nonanone as its open chain form, together with 6-n-butyl-3,4-dihydro-2H-pyran are minor components. 1,7-Dioxaspiro[5.5]undecan-4-ol is present at a low level and i...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00994347

    authors: Krohn S,Fletcher MT,Kitching W,Drew RA,Moore CJ,Francke W

    更新日期:1991-02-01 00:00:00

  • Aggregation pheromones of the flat grain beetle,Cryptolestes pusillus (Coleoptera: Cucujidae).

    abstract::Aggregation pheromones were isolated fromCryptolestes pusillus (Schönherr), a coleopteran pest of stored products. Porapak Q-captured beetle and frass volatiles were fractionated by preparative gas-liquid chromatography. The fractions were bioassayed with an arena olfactometer and/or with a two-choice, pitfall olfacto...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01020675

    authors: Millar JG,Pierce HD Jr,Pierce AM,Oehlschlager AC,Borden JH,Barak AV

    更新日期:1985-08-01 00:00:00

  • Necrodols: Anti-insectan terpenes from defensive secretion of carrion beetle (Necrodes surinamensis).

    abstract::Two compounds recently isolated from the defensive gland ofNecrodes surinamensis, α-and β-necrodol, first representatives of a new category of monoterpenes (the necrodanes), are shown to be repellent to ants and other insects and irritating to cockroaches and flies. The compounds doubtless play a defensive role inNecr...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012360

    authors: Eisner T,Deyrup M,Jacobs R,Meinwald J

    更新日期:1986-06-01 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

  • Mating stimulant of the pine weevilHylobius abietis (L.).

    abstract::Factors eliciting copulatory behavior in mature maleHylobius abietis were studied in the laboratory. Dead female weevils were sexually attractive, while dead mature males and pentane-extracted female weevils were not. The sexual attractiveness of dead females declined with time after death. Pentane extracts of whole f...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012421

    authors: Tilles DA,Eidmann HH,Solbreck B

    更新日期:1988-06-01 00:00:00

  • Sex pheromone components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia.

    abstract::In field experiments in the Okanagan Valley, British Columbia, the pheromone blend of (11Z)-tetradecen-1-ol acetate (Z11-14:OAc), (11E)-tetradecen-1-ol acetate (E 11-14:OAc), (9Z)-tetradecen-1-ol acetate (Z9-14:OAc) and dodecan-1-ol acetate (12: OAc) at a 100∶64∶2∶1 ratio (western FTLR blend) attracted significantly m...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00980587

    authors: Deland JP,Gries R,Gries G,Judd GJ,Roitberg BD

    更新日期:1993-12-01 00:00:00

  • Phenol contents, oxidase activities, and the resistance of coffee to the leaf miner Leucoptera coffeella.

    abstract::We examined the role of phenolic compounds, and the enzymes peroxidase and polyphenol oxidase, in the expression of resistance of coffee plants to Leucoptera coffeella (Lepidoptera: Lyonetiidae). The concentrations of total soluble phenols and chlorogenic acid (5-caffeoylquinic acid), and the activities of the oxidati...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9122-z

    authors: Ramiro DA,Guerreiro-Filho O,Mazzafera P

    更新日期:2006-09-01 00:00:00

  • Hybrid Sex Pheromones of the Hibiscus Flower-bud Borer, Rehimena surusalis.

    abstract::The sex pheromone of the hibiscus flower borer Rehimena surusalis (Walker) (Lepidoptera: Crambidae) was analyzed by gas chromatography with electroantennographic detection (GC-EAD) and GC-mass spectrometry (GC/MS). Three EAD-active components were found in crude pheromone gland extracts of calling females. GC/MS and G...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-015-0638-y

    authors: Honda H,Yamasaki R,Sumiuchi Y,Uehara T,Matsuyama S,Ando T,Naka H

    更新日期:2015-11-01 00:00:00