Alkyl ether and enol ether analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum: probing a proposed bioactive conformation for chain-elongated analogs.

Abstract:

:In order to test a previous conclusion that chain-elongated analogs of (Z)-5-decenyl acetate(1), a pheromone component of the turnip moth,Agrotis segetum, adopt a loop conformation of the terminal alkyl chain in the bioactive conformation, a series of alkyl ether and enol ether analogs of1 and (Z)-5-dodecenyl acetate(2) have been synthesized and tested using singlecell electrophysiology. In these analogs a methylene group in positions 7 and 9 of1 and in positions 7 and 11 in2 have been replaced by an oxygen atom in order to energetically facilitate the formation of a loop conformation in the chain-elongated analogs. The electrophysiological results in combination with molecular mechanics (MM2 and MM3) calculated conformational energies show that the activity decreases of the chain-elongated ether analogs are significantly smaller than that for2 and that these activity decreases parallel the conformational energies for a loop formation of the terminal chains in the analogs. The results support our previous conclusion that the terminal chain of chain-elongated analogs of1 adopts a loop conformation in their bioactive conformations.

journal_name

J Chem Ecol

authors

Gustavsson AL,Liljefors T,Hansson BS

doi

10.1007/BF02033463

subject

Has Abstract

pub_date

1995-06-01 00:00:00

pages

815-32

issue

6

eissn

0098-0331

issn

1573-1561

journal_volume

21

pub_type

杂志文章
  • 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

  • Dufour gland contents of ants of the Cataglyphis bicolor group.

    abstract::The species of desert-dwelling ants of the Cataglyphis bicolor (Hymenoptera: Formicidae) group are difficult to distinguish by morphological features. Analysis of the secretion from the Dufour glands of workers of a number of colonies was undertaken to see if it provided a clear test of species. Linked 6c-ms showed in...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1013521123356

    authors: Gökçen OA,Morgan ED,Dani FR,Agosti D,Wehner R

    更新日期:2002-01-01 00:00:00

  • Antennal olfactory response of boll weevil to grandlure and vicinal dimethyl analogs.

    abstract::Electroantennogram techniques were used to elucidate antennal olfactory response of male and female boll weevils to a dilution series of grandlure, its components, and some vicinal dimethyl analogs. At higher concentrations, response to the mixture of the two aldehyde components of grandlure was significantly higher t...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987617

    authors: Gutmann A,Payne TL,Roberts EA,Schulte-Elte KH,Giersch W,Ohloff G

    更新日期:1981-11-01 00:00:00

  • 1,8-cineole inhibits both proliferation and elongation of BY-2 cultured tobacco cells.

    abstract::Volatile monoterpenes such as 1,8-cineole inhibit the growth of Brassica campestris seedlings in a dose-dependent manner, and the growth-inhibitory effects are more severe for roots than hypocotyls. The preferential inhibition of root growth may be explained if the compounds inhibit cell proliferation more severely th...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-011-9919-2

    authors: Yoshimura H,Sawai Y,Tamotsu S,Sakai A

    更新日期:2011-03-01 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

  • 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

  • Alkadienes mediating courtship in the parasitoidCardiochiles nigriceps (Hymenoptera: Braconidae).

    abstract::Courtship inCardiochiles nigriceps (Viereck) (Hymenoptera: Braconidae) involves male attraction to females and male antennation of females followed by mounting and copulation. Once the female is located, antennation and mounting of the female are mediated by the hydrocarbon fraction of female's Dufour's gland and cuti...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02033856

    authors: Syvertsen TC,Jackson LL,Blomquist GJ,Vinson SB

    更新日期:1995-12-01 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

  • Transfer of pyrrolizidine and quinolizidine alkaloids toCastilleja (Scrophulariaceae) hemiparasites from composite and legume host plants.

    abstract::Castilleja (Scrophulariaceae) species of the western United States contain pyrrolizidine and quinolizidine alkaloids. TheCastilleja obtain the alkaloids by root parasitism on host plants, withSenecio atratus andS. triangularis (Asteraceae) furnishing the pyrrolizidines, and quinolizidines being obtained fromLupinus sp...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01013240

    authors: Stermitz FR,Harris GH

    更新日期:1987-08-01 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

  • De novo synthesis vs. sequestration: negatively correlated metabolic traits and the evolution of host plant specialization in cyanogenic butterflies.

    abstract::Larvae of Heliconius butterflies (Nymphalidae: Heliconiinae) feed exclusively on cyanogenic leaves of Passiflora (passion vine). Most Heliconius manufacture cyanogenic glycosides (cyanogens) and some species sequester cyanogens from host plants. We compare ability to sequester simple monoglycoside cyclopentenyl (SMC) ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9207-8

    authors: Engler-Chaouat HS,Gilbert LE

    更新日期:2007-01-01 00:00:00

  • Effects of 1,4-benzoxazin-3-one derivatives from maize on survival and fecundity of Metopolophium dirhodum (Walker) on artificial diet.

    abstract::Effects of 2-beta-D-glucopyranosyloxy-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA-Glc) and DIMBOA-Glc N-O-methylated (HDMBOA-Glc), two compounds present in high concentration in maize, were tested on the aphid Metopolophium dirhodum reared on artificial diet. HDMBOA-Glc and DIMBOA-Glc decrease survival of adults ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1005636607138

    authors: Cambier V,Hance T,De Hoffmann E

    更新日期:2001-02-01 00:00:00

  • Olfactory sensitivity of two sympatric species of rice leaf folders (Lepidoptera: Pyralidae) to plant volatiles.

    abstract::Electroantennograms (EAGs) were recorded from male and female moths of two sympatric leaf folder species,Cnaphalocrocis medinalis (Gue-née) andMarasmia patnalis Bradley (Lepidoptera: Pyralidae) to 91 volatile chemicals of plant origin. Responses of both leaf folder species were similar to all compounds except to three...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00988076

    authors: Ramachandran R,Khan ZR,Caballero P,Juliano BO

    更新日期:1990-09-01 00:00:00

  • Responses by king snakes (Lampropeltis getulus) to chemicals from colubrid and crotaline snakes.

    abstract::Four litters of king snakes (Lampropeltis getulus), a snake-eating species, were tested for responses to chemicals from colubrid and crotaline snakes. King snakes presented with swabs rubbed against the dorsal skin of living snakes and with swabs treated with methylene chloride extracts of shed snake skins tongue-flic...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00990320

    authors: Weldon PJ,Schell FM

    更新日期:1984-10-01 00:00:00

  • Molasses Grass Induces Direct and Indirect Defense Responses in Neighbouring Maize Plants.

    abstract::Plants have evolved intricate defence strategies against herbivore attack which can include activation of defence in response to stress-related volatile organic compounds (VOCs) emitted by neighbouring plants. VOCs released by intact molasses grass (Melinis minutiflora), have been shown to repel stemborer, Chilo parte...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-019-01122-z

    authors: Tolosa TA,Tamiru A,Midega CAO,Van Den Berg J,Birkett MA,Woodcock CM,Bruce TJA,Kelemu S,Pickett JA,Khan ZR

    更新日期:2019-12-01 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

  • Effect of birch (Betula pendula) bark and food protein level on root voles (Microtus oeconomus): II. detoxification capacity.

    abstract::The effect of protein and birch bark powder (BBP) content of forage on detoxification capacity of root voles (Microtus oeconomus) was studied. Young voles were fed with eight different diets for two weeks. Individuals on low (3%) protein diets had significantly lighter livers and kidneys than those on moderate (6%) or...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02033581

    authors: Harju A

    更新日期:1996-04-01 00:00:00

  • Host finding and oviposition behavior in a chrysomelid specialist--the importance of host plant surface waxes.

    abstract::Although several studies have elucidated the role of plant epicuticular waxes in host recognition and oviposition by herbivorous insects, there is little known about this subject in Chrysomelidae. In the present study, chemical cues for host recognition behavior and oviposition by the monophagous chrysomelid species C...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1010343205114

    authors: Müller C,Hilker M

    更新日期:2001-05-01 00:00:00

  • Allelopathic potential ofPiqueria trinervia (Compositae) and piquerols A and B.

    abstract::Bioassays were carried out to test extracts of roots and leaves ofPiqueria trinervia and solutions of piquerol A and B, in order to appraise their allelopathic potential. Leaves seem to have greater concentrations of inhibitory compounds than roots. Both piquerol compounds show strong biological activity, but piquerol...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987699

    authors: De La Parra MG,Anaya AL,Espinosa F,Jiménez M,Castillo R

    更新日期:1981-05-01 00:00:00

  • Hyperaccumulators and herbivores-a Bayesian meta-analysis of feeding choice trials.

    abstract::The leading hypothesis for the evolution of the metal hyperaccumulation trait in plants is as a defense against herbivores. A central piece of evidence expected for this hypothesis is that plants benefit from herbivores being deterred from eating high metal tissues. While many studies have investigated whether or not ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章,meta分析

    doi:10.1007/s10886-009-9607-7

    authors: Vesk PA,Reichman SM

    更新日期:2009-03-01 00:00:00

  • Differential performance of a specialist and two generalist herbivores and their parasitoids on Plantago lanceolata.

    abstract::The ability to cope with plant defense chemicals differs between specialist and generalist species. In this study, we examined the effects of the concentration of the two main iridoid glycosides (IGs) in Plantago lanceolata, aucubin and catalpol, on the performance of a specialist and two generalist herbivores and the...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-011-9983-7

    authors: Reudler JH,Biere A,Harvey JA,van Nouhuys S

    更新日期:2011-07-01 00:00:00

  • Sexual dimorphism in territorial scent marking by adult Eurasian beavers (Castor fiber).

    abstract::Mammalian scent marking is often associated with territorial defense. However, males and females may demonstrate different activity patterns and play different roles. Female mammals nurture the young during lactation, while males purportedly perform other tasks more frequently, such as territorial maintenance and defe...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9087-y

    authors: Rosell F,Thomsen LR

    更新日期:2006-06-01 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

  • 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

  • Spodoptera frugiperda Caterpillars Suppress Herbivore-Induced Volatile Emissions in Maize.

    abstract::The vast spectrum of inducible plant defenses can have direct negative effects on herbivores, or indirect effects, for instance in the form of herbivore-induced plant volatiles (HIPVs) that attract natural enemies. Various arthropods have evolved ways to suppress plant defenses. To test whether this is the case for ca...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-020-01153-x

    authors: De Lange ES,Laplanche D,Guo H,Xu W,Vlimant M,Erb M,Ton J,Turlings TCJ

    更新日期:2020-03-01 00:00:00

  • "This is not an apple"-yeast mutualism in codling moth.

    abstract::The larva of codling moth Cydia pomonella (Tortricidae, Lepidoptera) is known as the worm in the apple, mining the fruit for food. We here show that codling moth larvae are closely associated with yeasts of the genus Metschnikowia. Yeast is an essential part of the larval diet and further promotes larval survival by r...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-012-0158-y

    authors: Witzgall P,Proffit M,Rozpedowska E,Becher PG,Andreadis S,Coracini M,Lindblom TU,Ream LJ,Hagman A,Bengtsson M,Kurtzman CP,Piskur J,Knight A

    更新日期:2012-08-01 00:00:00

  • The auxin-like activity of humic substances is related to membrane interactions in carrot cell cultures.

    abstract::A detailed characterization of two humic fractions was performed: One with low relative molecular mass (LMr<3,500 Da) and one with high relative molecular mass (HMr>3,500 Da). Distinct (1)H NMR spectroscopic patterns were observed for the two fractions. HMr showed an aromatic proton region, an intense and broad region...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-006-9206-9

    authors: Muscolo A,Sidari M,Francioso O,Tugnoli V,Nardi S

    更新日期:2007-01-01 00:00:00

  • Toxicity of Milkweed Leaves and Latex: Chromatographic Quantification Versus Biological Activity of Cardenolides in 16 Asclepias Species.

    abstract::Cardenolides are classically studied steroidal defenses in chemical ecology and plant-herbivore coevolution. Although milkweed plants (Asclepias spp.) produce up to 200 structurally different cardenolides, all compounds seemingly share the same well-characterized mode of action, inhibition of the ubiquitous Na+/K+ ATP...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-018-1040-3

    authors: Züst T,Petschenka G,Hastings AP,Agrawal AA

    更新日期:2019-01-01 00:00:00

  • Attractive and inhibitory pheromones produced in the bark beetle,Dendroctonus brevicomis, during host colonization: Regulation of inter- and intraspecific competition.

    abstract::Quantities of attractive (exo-brevicomin and frontalin) and inhibitory (trans-verbenol, verbenone, and ipsdienol) pheromones were monitored in both sexes ofDendroctonus brevicomis during their colonization of a ponderosa pine. Verbenone was found in males in the greatest amounts at the time of landing, and it declined...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987969

    authors: Byers JA,Wood DL,Craig J,Hendry LB

    更新日期:1984-06-01 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