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1.
Molecules ; 26(16)2021 Aug 19.
Artículo en Inglés | MEDLINE | ID: mdl-34443611

RESUMEN

Pheromones are biologically important in fruit fly mating systems, and also have potential applications as attractants or mating disrupters for pest management. Bactrocera kraussi (Hardy) (Diptera: Tephritidae) is a polyphagous pest fruit fly for which the chemical profile of rectal glands is available for males but not for females. There have been no studies of the volatile emissions of either sex or of electrophysiological responses to these compounds. The present study (i) establishes the chemical profiles of rectal gland contents and volatiles emitted by both sexes of B. kraussi by gas chromatography-mass spectrometry (GC-MS) and (ii) evaluates the detection of the identified compounds by gas chromatography-electroantennogram detection (GC-EAD) and -electropalpogram detection (GC-EPD). Sixteen compounds are identified in the rectal glands of male B. kraussi and 29 compounds are identified in the rectal glands of females. Of these compounds, 5 were detected in the headspace of males and 13 were detected in the headspace of females. GC-EPD assays recorded strong signals in both sexes against (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, 2-ethyl-7-mehtyl-1,6-dioxaspiro[4.5]decane isomer 2, (E,Z)/(Z,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, and (Z,Z)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane. Male antennae responded to (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane, 2-methyl-6-pentyl-3,4-dihydro-2H-pyran, 6-hexyl-2-methyl-3,4-dihydro-2H-pyran, 6-oxononan-1-ol, ethyl dodecanoate, ethyl tetradecanoate and ethyl (Z)-hexadec-9-enoate, whereas female antennae responded to (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane and 2-methyl-6-pentyl-3,4-dihydro-2H-pyran only. These compounds are candidates as pheromones mediating sexual interactions in B. kraussi.


Asunto(s)
Fenómenos Electrofisiológicos , Recto/metabolismo , Tephritidae , Compuestos Orgánicos Volátiles/metabolismo , Animales , Femenino , Masculino
2.
J Agric Food Chem ; 68(36): 9654-9663, 2020 Sep 09.
Artículo en Inglés | MEDLINE | ID: mdl-32794749

RESUMEN

We report on the vapor pressures at ambient temperatures of seven attractants of Bactrocera, Dacus, and Zeugodacus fruit flies-raspberry ketone, cuelure, raspberry ketone trifluoroacetate, methyl eugenol, methyl isoeugenol, dihydroeugenol, and zingerone-by a vapor saturation method. Dry nitrogen was passed over each compound at well-controlled temperatures. Entrained vapor from the compounds was trapped on Tenax GR tubes and analyzed by thermal desorption-gas chromatography-mass spectrometry. The measured attractant amounts on the traps were converted to vapor pressures. Data were subsequently fitted by the Antoine equation. From the Antoine equation parameters, thermodynamic properties for each compound were calculated at 298 K. The calculated vapor pressures were used to compare the volatility of the fruit fly attractants and to infer implications for field applications. Using ambient temperature readings yields far better estimates of vapor pressure values at temperatures relevant for insect control than do Antoine equation parameters derived from high-temperature readings.


Asunto(s)
Ácidos Borónicos/química , Fenilpropionatos/química , Feromonas/química , Tephritidae/fisiología , Animales , Butanonas/química , Femenino , Control de Insectos , Masculino , Temperatura , Termodinámica , Presión de Vapor
3.
Molecules ; 25(12)2020 Jun 22.
Artículo en Inglés | MEDLINE | ID: mdl-32580521

RESUMEN

Passiflora maliformis is an introduced plant in Australia but its flowers are known to attract the native Jarvis's fruit fly, Bactrocera jarvisi (Tryon). The present study identifies and quantifies likely attractant(s) of male B. jarvisi in P. maliformis flowers. The chemical compositions of the inner and outer coronal filaments, anther, stigma, ovary, sepal, and petal of P. maliformis were separately extracted with ethanol and analyzed using gas chromatography-mass spectrometry (GC-MS). Polyisoprenoid lipid precursors, fatty acids and their derivatives, and phenylpropanoids were detected in P. maliformis flowers. Phenylpropanoids included raspberry ketone, cuelure, zingerone, and zingerol, although compositions varied markedly amongst the flower parts. P. maliformis flowers were open for less than one day, and the amounts of some of the compounds decreased throughout the day. The attraction of male B. jarvisi to P. maliformis flowers is most readily explained by the presence of zingerone in these flowers.


Asunto(s)
Flores/química , Guayacol/análogos & derivados , Passiflora/química , Tephritidae/fisiología , Animales , Australia , Conducta Animal/efectos de los fármacos , Femenino , Cromatografía de Gases y Espectrometría de Masas , Guayacol/química , Guayacol/aislamiento & purificación , Masculino , Feromonas/química
4.
Sci Rep ; 9(1): 19332, 2019 12 18.
Artículo en Inglés | MEDLINE | ID: mdl-31852933

RESUMEN

Tephritid fruit flies are amongst the most significant horticultural pests globally and male chemical lures are important for monitoring and control. Zingerone has emerged as a unique male fruit fly lure that can attract dacine fruit flies that are weakly or non-responsive to methyl eugenol and cuelure. However, the key features of zingerone that mediate this attraction are unknown. As Jarvis's fruit fly, Bactrocera jarvisi (Tryon), is strongly attracted to zingerone, we evaluated the response of B. jarvisi to 37 zingerone analogues in a series of field trials to elucidate the functional groups involved in attraction. The most attractive analogues were alkoxy derivatives, with isopropoxy being the most attractive, followed by ethoxy and trifluoromethoxy analogues. All of the phenolic esters tested were also attractive with the response typically decreasing with increasing size of the ester. Results indicate that the carbonyl group, methoxy group, and phenol of zingerone are key sites for the attraction of B. jarvisi and identify some constraints on the range of structural modifications that can be made to zingerone without compromising attraction. These findings are important for future work in developing and optimising novel male chemical lures for fruit flies.


Asunto(s)
Factores Quimiotácticos/farmacología , Guayacol/análogos & derivados , Tephritidae/fisiología , Animales , Guayacol/química , Guayacol/farmacología , Masculino , Tephritidae/efectos de los fármacos , Presión de Vapor , Volatilización
5.
PLoS One ; 11(5): e0155827, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-27196605

RESUMEN

The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.


Asunto(s)
Butanonas/química , Tephritidae/fisiología , Presión de Vapor , Animales , Australia , Calibración , Rastreo Diferencial de Calorimetría , Cromatografía de Gases , Femenino , Gases , Control de Insectos/métodos , Espectroscopía de Resonancia Magnética , Masculino , Feromonas , Temperatura
6.
J Chem Ecol ; 42(2): 156-62, 2016 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-26922349

RESUMEN

Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring raspberry ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis. Melolure is a more recently developed raspberry ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of raspberry ketone, raspberry ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.


Asunto(s)
Butanonas/metabolismo , Tephritidae/fisiología , Ácido Trifluoroacético/metabolismo , Animales , Conducta Animal , Femenino , Espectroscopía de Resonancia Magnética , Masculino , Espectrometría de Masa por Ionización de Electrospray , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción
7.
Plant Signal Behav ; 10(3): e990830, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-25734586

RESUMEN

The effect of drought on plant isoprene emission varies tremendously across species and environments. It was recently shown that an increased ratio of photosynthetic electron transport rate (ETR) to net carbon assimilation rate (NAR) consistently supported increased emission under drought. In this commentary, we highlight some of the physiological aspects of drought tolerance that are central to the observed variability. We briefly discuss some of the issues that must be addressed in order to refine our understanding of plant isoprene emission response to drought and increasing global temperature.


Asunto(s)
Aclimatación , Butadienos/metabolismo , Sequías , Hemiterpenos/metabolismo , Pentanos/metabolismo , Fotosíntesis/fisiología , Plantas/metabolismo , Estrés Fisiológico , Agua/metabolismo , Respiración de la Célula
8.
Opt Express ; 22(11): 13170-89, 2014 Jun 02.
Artículo en Inglés | MEDLINE | ID: mdl-24921513

RESUMEN

A continuous-wave, rapidly swept cavity-ringdown spectroscopic technique has been developed for localized atmospheric sensing of trace gases at remote sites. It uses one or more passive open-path optical sensor units, coupled by optical fiber over distances of >1 km to a single transmitter/receiver console incorporating a photodetector and a swept-frequency diode laser tuned to molecule-specific near-infrared wavelengths. Ways to avoid interference from stimulated Brillouin scattering in long optical fibers have been devised. This rugged open-path system, deployable in agricultural, industrial, and natural atmospheric environments, is used to monitor ammonia in air. A noise-limited minimum detectable mixing ratio of ~11 ppbv is attained for ammonia in nitrogen at atmospheric pressure.

9.
Trends Plant Sci ; 19(7): 439-46, 2014 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-24582468

RESUMEN

Light-dependent de novo volatile isoprene emission by terrestrial plants (approximately 2% of carbon fixed during photosynthesis) contributes as much as 0.5 PgC/year to the global carbon cycle. Although most plant taxa exhibit either constitutive or inducible monoterpene emissions, the evolution of isoprene emission capacity in multiple lineages has remained unexplained. Based on the predominant occurrence of isoprene emission capacity in long-lived, fast-growing woody plants; the relationship between 'metabolic scope' of tree genera and their species richness; and the proposed role of high growth rates and long generation times in accelerating molecular evolution, we hypothesise that long-lived plant genera with inherently high speciation rates have repeatedly acquired and lost the capacity to emit isoprene in their evolutionary history.


Asunto(s)
Butadienos/metabolismo , Hemiterpenos/metabolismo , Pentanos/metabolismo , Plantas/genética , Compuestos Orgánicos Volátiles/metabolismo , Dióxido de Carbono/metabolismo , Hemiterpenos/biosíntesis , Luz , Plantas/química , Plantas/efectos de la radiación , Temperatura
10.
Anal Biochem ; 349(1): 96-102, 2006 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-16321356

RESUMEN

A rapid and sensitive fluorescence-based bioassay for determination of indoleamine 2,3-dioxygenase (IDO) activity has been developed. This assay relies on the quantification of the amount of kynurenine produced in the assay medium by fluorescence and complements the standard absorbance and high-performance liquid chromatography (HPLC) assay methods. The fluorescence method has limits of detection similar to those of the standard assay methods. Measured activities of IDO, including in the presence of tryptophan-based inhibitors, were in statistical agreement with the absorbance and HPLC assay methods. The fluorescence-based assay was also suitable for assessment of IDO inhibition by compounds that are incompatible with the absorbance method.


Asunto(s)
Indolamina-Pirrol 2,3,-Dioxigenasa/análisis , Espectrometría de Fluorescencia , Indolamina-Pirrol 2,3,-Dioxigenasa/antagonistas & inhibidores , Indolamina-Pirrol 2,3,-Dioxigenasa/normas , Quinurenina , Estándares de Referencia , Hidróxido de Sodio , Espectrometría de Fluorescencia/métodos , Ácido Tricloroacético
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