Gloria Rosell

University of Barcelona, Barcino, Catalonia, Spain

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Publications (62)130.68 Total impact

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    ABSTRACT: We report the synthesis and pharmacological characterization of a new series of adenosine derivatives on the four adenosine receptors (AR). In radioligand binding assays, some of the compounds (1, 4, 6 and (R)-6) display a potent affinity for the A2AAR (Ki values <10 nM) with high A1/A2A and A2B/A2A selectivity, moderate for the A3AR and low for the A1AR. The affinity of the epimeric mixture 6 was similar to that of the corresponding (R)-6 stereoisomer and 10-fold higher than that of the (S)-6 stereoisomer. The phenylethylamino group appears to play a key role on the activity but introduction of groups of different size and electronegativity does not induce a substantial change in affinity for the A2AAR. In functional assays, most of the compounds produced similar amounts of cAMP compared to NECA, thus behaving as full A2AAR agonists. Also, compounds 1, 2, 3, 5, (S)-6 and 9 resulted good antagonists for A3AR with KB in 6-14 nM range. Docking studies on the A2AAR showed a conserved binding mode consistent with previous A2AAR agonist-bound crystal structures, allowing for a rational interpretation of the SAR of this compound series.
    Medicinal Chemistry Communication 05/2015; 6(6). DOI:10.1039/C5MD00086F · 2.63 Impact Factor
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    ABSTRACT: The flathead oak borer Coroebus undatus F. (Coleoptera: Buprestidae) is one of the primary pests of cork oak Quercus suber L. in the Mediterranean region causing great economic losses to the cork industry. Very little is known about its biology and behavior and, so far, no control measures have been established. We present the results of a pilot study aimed to develop an efficient trapping method for monitoring this harmful pest. In a 3-year field study, purple-colored prism traps baited with a mixture of green leaf volatiles (GLVs) from the host have been shown the most effective combination to catch C. undatus adults (solely females) compared to other trap and lure types tested. Wavelength and reflectance measurements revealed that purple traps exhibit reflectance peak values similar to those found in the abdominal and elytral cuticle of both sexes, suggesting the involvement of visual cues for mate location in this species. The data presented are the first to demonstrate captures of adults of the genus Coroebus by an attractant-based trapping method.This article is protected by copyright. All rights reserved.
    Insect Science 01/2015; 22:139-149. DOI:10.1111/1744-7917.12138 · 1.51 Impact Factor
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    ABSTRACT: Fatty acyl-CoA reductases (FARs), the enzymes that catalyse reduction of a fatty acyl-CoA to the corresponding alcohol in insect pheromone biosynthesis, are postulated to play an important role in determining the proportion of each component in the pheromone blend. For the first time, we have isolated and characterized from the Egyptian cotton leaf worm Spodoptera littoralis (Lepidoptera: Noctuidae) a FAR cDNA (Slit-FAR1), which appeared to be expressed only in the pheromone gland and was undetectable in other female tissues, such as fat body, ovaries, wings, legs or thorax. The encoded protein has been successfully expressed in a recombinant system, and the recombinant enzyme is able to produce the intermediate fatty acid alcohols of the pheromone biosynthesis of S. littoralis from the corresponding acyl-CoA precursors. The kinetic variables Km and Vmax, which have been calculated for each acyl-CoA pheromone precursor, suggest that in S. littoralis pheromone biosynthesis other biosynthetic enzymes (e.g. desaturases, acetyl transferase) should also contribute to the final ratio of components of the pheromone blend. In a phylogenetic analysis, Slit-FAR1 appeared grouped in a cluster of other FARs involved in the pheromone biosynthesis of other insects, with little or non-specificity for the natural pheromone precursors.
    Insect Molecular Biology 01/2015; 24(1):82-92. DOI:10.1111/imb.12138 · 2.98 Impact Factor
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    ABSTRACT: The tomato leafminer Tuta absoluta is a major pest of great economic importance throughout South America and Europe. Its primary host is tomato (Solanum lycopersicum), although potato (Solanum tuberosum), eggplant (Solanum melongena), and various wild solanaceous plants are also suitable hosts. As result of the high reproduction potential of T. absoluta (females may lay up to 300 eggs with 10-12 generations per year), and because of the mining behavior of the larvae, control of this species is extremely difficult. Therefore, development of environmentally-friendly control strategies is highly desirable. Previous studies on T. absoluta show the essential role of plant volatiles not only on attraction, but also in female egg-laying (Proffit et al. 2011). In the present study, we will present the activity of different compounds in tomato and potato plants, and the importance of the presence of tomato plants on female pheromone production. In addition, we will also report the activity in the field of dienic pheromone analogues as putative antagonists of the sex pheromone as a new approach to control the pest.
    Joint Meeting ISCE-CSiV, Univ. Illinois Urbana-Champaign; 08/2014
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    ABSTRACT: Outbreaks of locusts cause enormous economic losses to agriculture in many countries. To develop environmentally friendly strategies for their control, much research has been focused on the factors that influence locust biology, particularly infochemical-mediated interactions. We present herein the identification and synthesis of both Z and E isomers of phytal (3,7,11,15-tetramethylhexadec-2-enal, 1), which are involved in chemical communication and behaviour of the Moroccan locust, Dociostaurus maroccanus, a serious agricultural pest. The compound was identified by comparison of its chromatographic and spectrometric features and microchemical reactions with those of a synthetic sample. The natural compound was shown to have the R,R configuration by chiral HPLC analysis, and its structure is unique as an insect pheromone component. Both isomers of phytal are produced by sexually mature adult males and elicit electroantennographic responses in antennae of both sexes. In two-choice olfactometer bioassays, males and females significantly preferred the stream enriched with racemic phytal to the control. In contrast, hydrogenated phytal was behaviourally inert. Both isomers of phytal are specific to D. maroccanus as they are absent in the closely related, habitat-sharing species Dociostaurus jagoi and Calliptamus wattenwylianus. Legs and wings are the main release sites of the compound: approximately 90 % of that emitted by living individuals. In biosynthetic studies, phytal appears to proceed from oxidation of phytol (2) after injection of deuterated phytol into the abdomen of the insect or after administration in the diet. Our results demonstrate that phytal is a candidate sex pheromone component of the Moroccan locust; it is produced by mature males, and might be eavesdropped upon by conspecific males.
    ChemBioChem 08/2013; 14(12). DOI:10.1002/cbic.201300247 · 3.06 Impact Factor
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    ABSTRACT: BACKGROUND: Pheromone antagonists are good disruptants of the pheromone communication in insects and, as such, have been used in mating disruption experiments. In this study, new non-fluorinated electrophilic keto derivatives structurally related to the pheromone of Cydia pomonella (codlemone) have been synthesised and tested as putative pheromone antagonists. RESULTS: Codlemone (1) was prepared in excellent stereoselectivity in a new, iterative approach involving two Horner-Wadsworth-Emmons reactions. Methyl ketone (2), keto ester (3) and diketone (4) were obtained from codlemone in straightforward approaches in good overall yields and excellent stereochemical purity (≥98% E,E). In electrophysiology, only compound 2 displayed inhibition of the antennal response to the pheromone after presaturation of the antennal receptors. Compounds 2 to 4 did not inhibit the pheromone-degrading enzyme responsible for codlemone metabolism, but mixtures of ketone 2 and diketone 4 with codlemone elicited erratic flights on males in a wind tunnel. In the field, blends of either compound (2 or 4) with the pheromone caught significantly fewer males than codlemone alone. CONCLUSION: Codlemone and the potential antagonists 2 to 4 have been synthesised in good yields and excellent stereoselectivity. These chemicals behave as pheromone antagonists of the codling moth both in the laboratory and in the field. © 2013 Society of Chemical Industry.
    Pest Management Science 01/2013; 69:1280-1290. DOI:10.1002/ps.3500 · 2.74 Impact Factor
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    ABSTRACT: The flathead oak borer (FOB) Coroebus undatus Fabricius (Coleoptera: Buprestidae) is one of the primary pests of the cork oak Quercus suber, endemic tree of the occidental Mediterranean and only producer of cork. FOB females lay their eggs individually or in small groups in bark flaps and fissures of the trunk. The larvae perforate successive layers of the cork, penetrate into the bark and construct large galleries around the trunk (up to 1.8 m long and 3-4 mm wide), downgrading the cork quality and causing important economic losses. Knowledge of the cues that FOB adults use to locate host trees or sex partners could enhance the current goal to control this pest. In this communication, we present studies directed to develop a suitable combination of trap type (visual cue) and lure (olfactory cue) to capture FOB adults. Among different types of purple colored traps, prism traps were the most effective in capturing FOB females, significantly more than single panel and Lindgren funnel traps. Single panel traps were superior to Lindgren traps indicating that this type, often used for trapping wood boring and bark beetles, is not appropriate to catch FOB. In addition, prism traps combined with host-plant green leaf volatiles (GLVs) caught more insects than traps baited with other lures tested, suggesting that GLVs play an important role in the host and/or mate finding behavior of FOB females. These data are the first to demonstrate attraction of the genus Coroebus to a semiochemical-based trapping method, and set the basis for future studies addressed to monitoring and control of this important species.
    28th Annual Meeting of the International Society of Chemical Ecology, Vilnius, Lithuania; 07/2012
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    ABSTRACT: Insects respond to the spatial and temporal dynamics of a pheromone plume, which implies not only a strong response to 'odor on', but also to 'odor off'. This requires mechanisms geared toward a fast signal termination. Several mechanisms may contribute to signal termination, among which odorant-degrading enzymes. These enzymes putatively play a role in signal dynamics by a rapid inactivation of odorants in the vicinity of the sensory receptors, although direct in vivo experimental evidences are lacking. Here we verified the role of an extracellular carboxylesterase, esterase-6 (Est-6), in the sensory physiological and behavioral dynamics of Drosophila melanogaster response to its pheromone, cis-vaccenyl acetate (cVA). Est-6 was previously linked to post-mating effects in the reproductive system of females. As Est-6 is also known to hydrolyze cVA in vitro and is expressed in the main olfactory organ, the antenna, we tested here its role in olfaction as a putative odorant-degrading enzyme. We first confirm that Est-6 is highly expressed in olfactory sensilla, including cVA-sensitive sensilla, and we show that expression is likely associated with non-neuronal cells. Our electrophysiological approaches show that the dynamics of olfactory receptor neuron (ORN) responses is strongly influenced by Est-6, as in Est-6° null mutants (lacking the Est-6 gene) cVA-sensitive ORN showed increased firing rate and prolonged activity in response to cVA. Est-6° mutant males had a lower threshold of behavioral response to cVA, as revealed by the analysis of two cVA-induced behaviors. In particular, mutant males exhibited a strong decrease of male-male courtship, in association with a delay in courtship initiation. Our study presents evidence that Est-6 plays a role in the physiological and behavioral dynamics of sex pheromone response in Drosophila males and supports a role of Est-6 as an odorant-degrading enzyme (ODE) in male antennae. Our results also expand the role of Est-6 in Drosophila biology, from reproduction to olfaction, and highlight the role of ODEs in insect olfaction.
    BMC Biology 06/2012; 10:56. DOI:10.1186/1741-7007-10-56 · 7.43 Impact Factor
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    ABSTRACT: Aspects of the chemical ecology of the black-banded oak borer, (BBOB) Coroebus florentinus (Coleoptera: Buprestidae), were studied. Odors produced by males and females were similar, both qualitatively and quantitatively. Nonanal, decanal, and geranylacetone, identified in the headspace of both sexes, elicited strong electroantennographic responses from male antennae, but not from female antennae. In dual-choice olfactometer experiments, a blend of these three compounds was attractive to both sexes; males responded to decanal alone, while females responded to geranylacetone alone, suggesting that these compounds are responsible for activity of the blend to the respective sexes. Antennae of both sexes responded electroantennographically to the green leaf volatiles (E)-2-hexenal, (E)-2-hexenol, 1-hexanol, (Z)-3-hexenyl acetate, and n-hexyl acetate, all identified from the host plant Quercus suber. In behavioral experiments, only females were attracted to host-plant odors, and in tests with synthetic compounds, females were attracted to (E)-2-hexenol, 1-hexanol, and (Z)-3-hexenyl acetate. It is likely that these compounds play a role in foraging and/or oviposition behavior of BBOB females.
    Journal of Chemical Ecology 04/2012; 38(4):378-88. DOI:10.1007/s10886-012-0110-1 · 2.24 Impact Factor
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    ABSTRACT: Butterflies and moths show different reproductive behaviours. Whereas butterflies rely on visual stimuli for mate location, moths use the 'female calling plus male seduction' system, where females release long-range sex pheromones to attract conspecific males. There are few exceptions from this pattern but in all known cases female moths possess sex pheromone glands which apparently have been lost in female butterflies. In the moth family Castniidae (“butterfly-moths”), which includes some important crop pests, no pheromones have been found so far. We present herein evidence for the first time that females of the castniid Paysandisia archon do not produce any pheromone to attract males and that mate location is achieved only visually by patrolling males, which release a pheromone at short distance. Several behavioural, morphological and physiological traits support this and are likely to be widespread in Castniidae. This implies a novel butterfly-like reproductive behaviour in moths.
    PLoS ONE 01/2012; 7(1):e29282, 1-11, 2012. · 3.53 Impact Factor
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    ABSTRACT: In the course of evolution butterflies and moths developed two different reproductive behaviors. Whereas butterflies rely on visual stimuli for mate location, moths use the 'female calling plus male seduction' system, in which females release long-range sex pheromones to attract conspecific males. There are few exceptions from this pattern but in all cases known female moths possess sex pheromone glands which apparently have been lost in female butterflies. In the day-flying moth family Castniidae ("butterfly-moths"), which includes some important crop pests, no pheromones have been found so far. Using a multidisciplinary approach we described the steps involved in the courtship of P. archon, showing that visual cues are the only ones used for mate location; showed that the morphology and fine structure of the antennae of this moth are strikingly similar to those of butterflies, with male sensilla apparently not suited to detect female-released long range pheromones; showed that its females lack pheromone-producing glands, and identified three compounds as putative male sex pheromone (MSP) components of P. archon, released from the proximal halves of male forewings and hindwings. This study provides evidence for the first time in Lepidoptera that females of a moth do not produce any pheromone to attract males, and that mate location is achieved only visually by patrolling males, which may release a pheromone at short distance, putatively a mixture of Z,E-farnesal, E,E-farnesal, and (E,Z)-2,13-octadecadienol. The outlined behavior, long thought to be unique to butterflies, is likely to be widespread in Castniidae implying a novel, unparalleled butterfly-like reproductive behavior in moths. This will also have practical implications in applied entomology since it signifies that the monitoring/control of castniid pests should not be based on the use of female-produced pheromones, as it is usually done in many moths.
    PLoS ONE 01/2012; 7(1):e29282. DOI:10.1371/journal.pone.0029282 · 3.53 Impact Factor
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    ABSTRACT: Odorant-Degrading Enzymes (ODEs) are supposed to be involved in the signal inactivation step within the olfactory sensilla of insects by quickly removing odorant molecules from the vicinity of the olfactory receptors. Only three ODEs have been both identified at the molecular level and functionally characterized: two were specialized in the degradation of pheromone compounds and the last one was shown to degrade a plant odorant. Previous work has shown that the antennae of the cotton leafworm Spodoptera littoralis, a worldwide pest of agricultural crops, express numerous candidate ODEs. We focused on an esterase overexpressed in males antennae, namely SlCXE7. We studied its expression patterns and tested its catalytic properties towards three odorants, i.e. the two female sex pheromone components and a green leaf volatile emitted by host plants. SlCXE7 expression was concomitant during development with male responsiveness to odorants and during adult scotophase with the period of male most active sexual behaviour. Furthermore, SlCXE7 transcription could be induced by male exposure to the main pheromone component, suggesting a role of Pheromone-Degrading Enzyme. Interestingly, recombinant SlCXE7 was able to efficiently hydrolyze the pheromone compounds but also the plant volatile, with a higher affinity for the pheromone than for the plant compound. In male antennae, SlCXE7 expression was associated with both long and short sensilla, tuned to sex pheromones or plant odours, respectively. Our results thus suggested that a same ODE could have a dual function depending of it sensillar localisation. Within the pheromone-sensitive sensilla, SlCXE7 may play a role in pheromone signal termination and in reduction of odorant background noise, whereas it could be involved in plant odorant inactivation within the short sensilla.
    PLoS ONE 12/2011; 6(12):e29147. DOI:10.1371/journal.pone.0029147 · 3.53 Impact Factor
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    ABSTRACT: Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used.
    Organic & Biomolecular Chemistry 12/2011; 9(23):8171-7. DOI:10.1039/c1ob06251d · 3.49 Impact Factor
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    ABSTRACT: Trifluoromethyl ketones (TFMKs), structurally related to the pheromones, are good inhibitors of pheromone communication in insects. To determine their activity on Zeuzera pyrina L. (Lepidoptera: Cossidae), a polyphagous pest, the authors have prepared two diunsaturated TFMK analogues of the major (3) and the minor (4) pheromone components, and two monounsaturated ones (5, 6). Their biological activity in electroantennogram (EAG), wind tunnel and field tests is presented. The synthetic strategy to obtain the allylic TFMKs 3 and 5 is based on the reactions of diene 10 and 1-octadecene with trifluoroacetaldehyde ethyl hemiacetal, followed by Dess-Martin oxidation of the resulting homoallylic trifluoromethyl alcohols. In EAG, topical application of analogues 3 and 4 on male antennae significantly reduced the pheromone response. In the wind tunnel, compound 4 reduced the number of contacts with the pheromone source. In the field, traps baited with mixtures of pheromone and inhibitors captured significantly fewer males than the pheromone alone. An efficient synthesis of allylic TFMKs is reported, with good overall yield, regiospecificity and diastereoselectivity. These compounds are good inhibitors of the pheromone in electrophysiology, wind tunnel and field tests. The results show the importance of two unsaturations at positions 2 and 13 of the trifluoroacyl group in the structure of the analogues, the latter being critical for inhibitory activity.
    Pest Management Science 08/2011; 67(8):956-64. DOI:10.1002/ps.2139 · 2.74 Impact Factor
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    Synthesis 01/2011; 2010(18):3117-3120. DOI:10.1002/chin.201103054 · 2.44 Impact Factor
  • 20th Congress of European Chemoreception Research Organization; 01/2011
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    ABSTRACT: Carboxyl/cholinesterases (CCEs) are highly diversified in insects. These enzymes have a broad range of proposed functions, in neuro/developmental processes, dietary detoxification, insecticide resistance or hormone/pheromone degradation. As few functional data are available on purified or recombinant CCEs, the physiological role of most of these enzymes is unknown. Concerning their role in olfaction, only two CCEs able to metabolize sex pheromones have been functionally characterized in insects. These enzymes are only expressed in the male antennae, and secreted into the lumen of the pheromone-sensitive sensilla. CCEs able to hydrolyze other odorants than sex pheromones, such as plant volatiles, have not been identified. In Spodoptera littoralis, a major crop pest, a diversity of antennal CCEs has been previously identified. We have employed here a combination of molecular biology, biochemistry and electrophysiology approaches to functionally characterize an intracellular CCE, SlCXE10, whose predominant expression in the olfactory sensilla suggested a role in olfaction. A recombinant protein was produced using the baculovirus system and we tested its catabolic properties towards a plant volatile and the sex pheromone components. We showed that SlCXE10 could efficiently hydrolyze a green leaf volatile and to a lesser extent the sex pheromone components. The transcript level in male antennae was also strongly induced by exposure to this plant odorant. In antennae, SlCXE10 expression was associated with sensilla responding to the sex pheromones and to plant odours. These results suggest that a CCE-based intracellular metabolism of odorants could occur in insect antennae, in addition to the extracellular metabolism occurring within the sensillar lumen. This is the first functional characterization of an Odorant-Degrading Enzyme active towards a host plant volatile.
    PLoS ONE 11/2010; 5(11):e15026. DOI:10.1371/journal.pone.0015026 · 3.53 Impact Factor
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    ABSTRACT: Carboxylesterases (CEs) are a family of ubiquitous enzymes with broad substrate specificity, and their inhibition may have important implications in pharmaceutical and agrochemical fields. One of the most potent inhibitors both for mammalian and insect CEs are trifluoromethyl ketones (TFMKs), but the mechanism of action of these chemicals is not completely understood. This study examines the balance between reactivity versus steric effects in modulating the activity against human carboxylesterase 1. The intrinsic reactivity of the ketone moiety is determined from quantum mechanical computations, which combine gas phase B3LYP calculations with hydration free energies estimated with the IEF/MST model. In addition, docking and molecular dynamics simulations are used to explore the binding mode of the inhibitors along the deep gorge that delineates the binding site. The results point out that the activity largely depends on the nature of the fluorinated ketone, since the activity is modulated by the balance between the intrinsic electrophilicity of the carbonyl carbon atom and the ratio between keto and hydrate forms. However, the results also suggest that the correct alignment of the alkyl chain in the binding site can exert a large influence on the inhibitory activity, as this effect seems to override the intrinsic reactivity features of the fluorinated ketone. Overall, the results sustain a subtle balance between reactivity and steric effects in modulating the inhibitory activity of TFMK inhibitors.
    Journal of Molecular Modeling 11/2010; 16(11):1753-64. DOI:10.1007/s00894-010-0807-4 · 1.87 Impact Factor
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 10/2010; 28(43). DOI:10.1002/chin.199743163

Publication Stats

450 Citations
130.68 Total Impact Points

Institutions

  • 1988–2015
    • University of Barcelona
      • • Department of Pharmacology and Therapeutic Chemistry
      • • Faculty of Pharmacy
      Barcino, Catalonia, Spain
  • 2005–2013
    • Universitat de Lleida
      • Department of Chemistry
      Lérida, Catalonia, Spain
  • 2010
    • Institut Marqués, Spain, Barcelona
      Barcino, Catalonia, Spain
  • 2004–2005
    • Spanish National Research Council
      Madrid, Madrid, Spain
    • University of Santiago de Compostela
      • Faculty of Pharmacy
      Santiago, Galicia, Spain