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Documentos generados por los docentes e investigadores de la Universidad en su labor de investigación científica producida o editada por los departamentos y centros de la Universitat Politècnica de València.
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Browsing Investigación by UPV Entity "Centro de Ecología Química Agrícola"
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- PublicationCircundatin H, a new inhibitor of mitochondrial NADH oxidase from Aspergillus ochraceus(Nature Publishing Group, 2005) López Gresa, María Pilar; Gonzalez Más, Mª Carmen; Primo Millo, Jaime; Moya Sanz, Mª del Pilar; Romero, V.; Estornell, E.; Instituto Universitario Mixto de Biología Molecular y Celular de Plantas; Dpto. de Biotecnología; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural[EN] Circumdatin H (1), a new alkaloid from the culture broth of Aspergillus ochraceus, has been isolated, together with a known circumdatin, circumdatin E (2) and other known compounds: flavacol (3) and stephacidin A (4). The structure of 1 was established on the basis of chemical and spectral evidence. All of these alkaloids showed biological activity as inhibitors of the mammalian mitochondrial respiratory chain.
- PublicationField Efficacy of a Metarhizium anisopliae-Based Attractant Contaminant Device to Control Ceratitis capitata (Diptera: Tephritidae)(Oxford University Press, 2015) Navarro Llopis, Vicente; Ayala Mingol, Ildefonso; Sanchis Cabanes, Juan; Primo Millo, Jaime; Moya Sanz, Mª del Pilar; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Ministerio de Educación y Ciencia; Instituto Nacional de Investigación y Tecnología Agraria y Alimentaria[EN] Biological control of Ceratitis capitata (Wiedemann) (Diptera: Tephritidae) using entomopathogenic fungi is being studied as a viable control strategy. The efficacy of a Metarhizium anisopliae (Metschnikoff) Sorokin (Hypocreales: Clavicipitaceae)-based attractant contaminant device (ACD) to control C. capitata was evaluated in a medium-scale (40 ha) 2-yr field trial using a density of 24 ACD per ha. Results showed that this density was adequate to efficiently reduce fruitfly populations and that the inoculation dishes (IDs) needed replacing mid-season to provide protection for the entire season. In this study, fungal treatment was even more effective than conventional chemical treatment. Population dynamics in fungus-treated fields along with the infectivity study of field-aged IDs in the laboratory found that the ACD remained effective for at least 3 mo. The results suggest M. anisopliae-based ACD can be used to control C. capitata in the field. The implications of its use, especially as a tool in an integrated pest management program, are discussed.
- PublicationIsolation and synthesis of N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo(2,1-b)-3-oxazine, two new fungal metabolites with in vivo antijuvenile hormone and insecticidal activity(John Wiley & Sons, 1999) Cantin Sanz, Angel; Moya Sanz, Mª del Pilar; Castillo López, María Ángeles; Primo Millo, Jaime; Miranda Alonso, Miguel Ángel; Primo Yufera, Eduardo; Instituto Universitario Mixto de Tecnología Química; Dpto. de Biotecnología; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Centro Avanzado de Microbiología de Alimentos; Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural[EN] Two new natural products, N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2) and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), have been isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the preparation of 6-octenoic acid and its transformation into the corresponding acid chloride, in order to acylate Meldrum's acid. Subsequent aminolysis with pyrrolidine, followed by methylation at the activated position of the ß-oxo amide with iodomethane, introduction of a methoxy group at the pyrrolidine ring by anodic oxidation and final elimination of methanol on SiO2 led to 2 and 3. The fact that both metabolites can be prepared by the same sequence indicates that they must be biogenetically related. Based on structural similarities, compounds 2 and 3 are also closely related to the recently discovered brevioxime
- PublicationLaboratory evaluation of the compatibility of a new attractant contaminant device ciontaining Metarhizium anisopliae with Ceratitis capitata sterile males(Elsevier, 2014-05) San Andrés Aura, Victoria; Ayala Mingol, Ildefonso; Abad Payá, María del Carmen; Primo Millo, Jaime; Casteñera, P.; Moya Sanz, Mª del Pilar; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Ministerio de Educación y Ciencia[EN] Laboratory experiments were conducted to evaluate the compatibility of using the entomopathogenic fungus Metarhizium anisopliae, to be dispensed in a new attractant contaminant device (ACD), jointly with sterilized Ceratitis capitata males, as an integrated approach to control this major pest. The exposure of sterile Vienna 8 (V8) strain and wild type (WT) males to the contaminating part (infective dish) of the ACD showed similar susceptibility levels to the fungal strain (LT50 value of 4.52 and 4.72 days, respectively). Sterile V8 males were significantly less attracted to the infective dish (18.4%) than WT males (28.5%). As the success of Sterile Insect Technique (SIT) heavily relies on the mating success of sterile males in the field, mating performance of infected males was assessed. Around 85% of the females were mated, independently of the male strain and treatment (fungus-treated or untreated males) indicating that mating performance was unaffected by the fungus under laboratory conditions. Females showed a greater tendency to remate if previously mated to fungus-treated males, either V8 or WT. Our data suggest that this M. anisopliae based-ACD does not impair the performance of C. capitata sterile males and, therefore, it could be used combined with area wide SIT-based programs, providing that these results are validated in field conditions. The implications of this combined strategy to control C. capitata are discussed. (C) 2014 Elsevier Inc. All rights reserved.
- PublicationNovel inhibitors of the mitochondrial respiratory chain: Oximes and pyrrolines isolated from Penicillium brevicompactum and synthetic analogues(American Chemical Society, 2005) Cantin Sanz, Angel; López Gresa, María Pilar; Gonzalez Más, Mª Carmen; Moya Sanz, Mª del Pilar; Miranda Alonso, Miguel Ángel; Primo Millo, Jaime; Romero, Vanessa; Peris, Eva; Estornell, Ernesto; Instituto Universitario Mixto de Tecnología Química; Instituto Universitario Mixto de Biología Molecular y Celular de Plantas; Dpto. de Biotecnología; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural; Generalitat Valenciana[EN] The capacity of inhibition of the mammalian mitochondrial respiratory chain of brevioxime 5a, a natural insecticide compound isolated from Penicillium brevicompactum culture broth, and another 15 analogue compounds, other oximes 5b and 5c; two diastereomeric pyrrolidines 1c' and 1c"; five pyrrolines 3c', 3c" (diastereomers between them), 3a, 3b, and 6; two oxazines 4c' and 4c" (also diastereomers between them); and four pyrrol derivatives 7-10, are analyzed in this paper. Compounds 3b, 3c', 3c", 4c', 4c", 5b, 5c, 6, and 10 were found to be inhibitors of the integrated electron transfer chain (NADH oxidase activity) in beef heart submitochondrial particles (SMP), establishing that all of them except compound 3b and 6 only affected to complex I of the mitochondrial respiratory chain. The most potent product was 5b, with an IC50 of 0.27 mu M, similar to the IC50 values of other known complex I inhibitors. The diastereomeric pairs 1 c'/1c", 3c'/3c", 4c'/4c", and 5c have not been previously described. Chemical characterization, on the basis of spectral data, is also shown.
- PublicationPhotoreactivity of new rose bengal-SiO2 heterogeneous photocatalysts with and without a magnetite core for drug degradation and disinfection(Elsevier, 2023-03-15) Flores, Jenny; Moya Sanz, Mª del Pilar; Bosca Mayans, Francisco; Marín García, María Luisa; Instituto Universitario Mixto de Tecnología Química; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; European Commission; AGENCIA ESTATAL DE INVESTIGACION; Universitat Politècnica de València[EN] The main drawback of homogeneous photocatalysis is the difficult separation of the photocatalysts from the reaction media after treatment completion; thus, heterogeneous photocatalysis represents a step forward in this technology. Moreover, heterogeneous catalysts incorporating magnetic properties further facilitate their separation and recovery. In this context, some photocatalyst of Rose Bengal (RB) on heterogeneous supports have been synthesized but how derivatization influences its mechanism of action against organic pollutants degradation and water disinfection still deserves a deeper investigation. In this context, new heterogeneous nanosized photocatalysts incorporating Rose Bengal (RB) have been prepared. The first one was based on the covalent anchoring to SiO2 nanoparticles and the second one incorporates a magnetite core. They have demonstrated to efficiently achieve photodegradation of ACF, DCF, and OFX under visible-light irradiation, with greater efficiency in the case of DCF. Interestingly, the photostability of RB is higher in heterogeneous than in homogeneous media. The presence of magnetite core in the heterogeneous photocatalyst facilitates its recovery from the medium but the photophysical properties of RB remain unchanged. These new photocatalysts also show a great efficiency in the photoinactivation of Enterococcus faecalis Gram-positive bacteria but not for the Gram-negative Escherichia coli and Pseudomonas aeruginosa. Analysis of all constants involving the photosensitized degradations of ACF, DCF, and OFX has evidenced that electron transfer process between RB, in homogeneous solutions and as a heterogeneous photocatalyst, and the three drugs is the initial step of their oxidations. In view of the results achieved, we believe that they could be used as a starting point for the development of new RB heterogeneous photocatalyst with adjustable oxidizing properties.
- PublicationSíntesis y caracterización de nuevos fotocatalizadores heterogéneos para degradación de contaminantes y/o desinfección en medio acuoso(Universitat Politècnica de València, 2024-02-23) Flores Garcia, Jenny; Bosca Mayans, Francisco; Marín García, María Luisa; Moya Sanz, Mª del Pilar; Instituto Universitario Mixto de Tecnología Química; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial[ES] En los últimos años, la detección de un número creciente de contaminantes xenobióticos en los sistemas acuáticos ha traído como consecuencia efectos nocivos en los ecosistemas, así como en la salud humana. Los procesos de oxidación avanzada como la fotocatálisis heterogénea están recibiendo una gran atención debido a su eficiencia, bajo costo, fácil recuperación de los catalizadores. En este contexto, el objetivo de esta tesis fue sintetizar nuevos fotocatalizadores sólidos basados en la heterogeneización del Rosa de Bengala (RB) con el propósito de obtener materiales con propiedades fotocatalíticas mejoradas respecto a las del colorante orgánico en medio homogéneo, lo cual, además permitía poder recuperar y reutilizar con facilidad el fotocatalizador. Para ello, el RB como sustancia fotoactiva se unió mediante diferentes procesos sintéticos a varios soportes sólidos. Los nuevos materiales fotocatalíticos, se caracterizaron y estudiaron sus propiedades fotocatalíticas de cada material en procesos de descontaminación y/o desinfección, así como las propiedades fotofísicas y fotoquímicas que presentaba el colorante asociado a cada uno los diferentes materiales. Para los estudios de fotodescontaminacion se usaron compuestos tóxicos y persistentes en el agua como el diclofenaco y el acetaminofeno, así como el ofloxacino. La capacidad fotocatalítica de los materiales para desinfección de aguas se evaluó usando cepas bacterianas Gram positivas y negativas. En cuanto a los estudios fotofísicos y fotoquímicos se realizaron estudiando la reactividad del estado excitado singlete y triplete del RB en estos catalizadores frente a los contaminantes y al oxígeno molecular. A continuación, se resumen los Capítulos que conforman esta tesis doctoral: En el Capítulo I de esta tesis, se sintetizaron dos nuevos fotocatalizadores heterogéneos nanoestructurados de sílice con y sin núcleo de magnetita que incorporan covalentemente RB en su superficie. Ambos mostraron ser capaces de producir la fotodegradación de fármacos, bajo irradiación con luz visible. Adicionalmente, estos fotocatalizadores también mostraron tener una gran eficacia en la fotoinactivación de bacterias Gram positivas. El efecto que se observó en estos materiales por la presencia del núcleo de magnetita fue principalmente físico ya que ayudaba a su recuperación mediante campos magnéticos y producía un aumento de la concentración de RB en la superficie. En el Capítulo II, se sintetizaron dos fotocatalizadores heterogéneos con RB unido covalentemente a la superficie de micropartículas de sílice con y sin núcleo de magnetita. Las micropartículas de sílice con RB demostraron una gran eficiencia en la eliminación de DCF en medio acuoso bajo irradiación de luz visible. En el Capítulo III, se determinó la influencia del porcentaje de RB al 0.5, 1 y 3% soportado sobre tejidos de poliamida, para la inactivación de bacterias Gram positivas. Así se vio que el tejido teñido al 1% de RB tenía la capacidad de fotoinactivación bacteriana más alta, siendo esta de 6 log10 unidades de reducción en ufc/mL bajo luz visible en 15 min. Con ello se vio que la cantidad de RB sobre los tejidos de poliamida tiene una gran importancia. Así, una cantidad menor de RB en el tejido no era capaz de generar suficiente oxígeno singlete, mientras que en una cantidad mayor al 1% debe generar una agregación del fotosensibilizador. Finalmente, en el Capítulo IV se sintetizó un fotocatalizador de lana de vidrio con RB en su superficie para evaluar su capacidad de fotoinactivación de bacterias Gram positivas y negativas. Para ello, primero se caracterizó el material y se evaluaron las propiedades fotofísicas por espectroscopía de fluorescencia y experimentos de fotólisis de destello láser. Posteriormente, se evaluó la fotoinactivación de bacterias Gram negativas y positivas a una concentración inicial de 106 ufc/mL, pero solo se observó, una significativa inactivación sobre las bacterias Gram positivas.
- PublicationSusceptibility of Ceratitis capitata Wiedeman (Diptera:Tephritidae) to entomopathogenic fungi and their extracts(Elsevier, 2000) Castillo López, María Ángeles; Moya Sanz, Mª del Pilar; Hernández Giménez, Enrique; Primo Yufera, Eduardo; Dpto. de Biotecnología; Instituto Agroforestal Mediterráneo; Centro de Ecología Química Agrícola; Centro Avanzado de Microbiología de Alimentos; Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural; Comisión Interministerial de Ciencia y Tecnología; Generalitat Valenciana[EN] The effectiveness of seven strains of entomopathogenic fungi against Ceratitis capitata adults was evaluated in the laboratory. Adults were susceptible to five of seven aqueous suspensions of conidia. Metarhizium anisopliae and strain CG-260 of Paecilomyces fumosoroseus were the most pathogenic fungi, with 10- day LD50 values of 5.1 and 6.1 3 103 conidia/fly, respectively, when applied topically. Sublethal effects on fecundity and fertility of the fungal-exposed females were also studied. The most effective fungus in reducing fecundity was P. fumosoroseus CECT 2705, with reductions on the order of 65% at 1 3 106 conidia/fly. M. anisopliae and Aspergillus ochraceus also showed significant reductions of fecundity (40–50% for most of the assayed concentrations). Fertility was moderately affected by the fungi. M. anisopliae at 1 3 106 conidia/fly was the most effective fungus, showing egg eclosion reduction of over 50% compared with the control. In addition, culture broth dichloromethane extracts from the entomopathogenic fungi were tested for insecticide activity against C. capitata, including effects on fecundity and fertility. The extract from M. anisopliae was the most toxic, resulting in about 90% mortality at a concentration of 25 mg/g of diet; under these conditions, fecundity and fertility of treated females were reduced by 94 and 53%, respectively, compared with untreated controls. © 2000 Academic Press
- PublicationSynthesis and biological evaluation of new analogs of the active fungal metabolites N-(2-methyl-3-oxodecanoyl)-2-pyrroline and N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (II)(ACS, 2000) Cantin Sanz, Angel; Moya Sanz, Mª del Pilar; Miranda Alonso, Miguel Ángel; Primo Millo, Jaime; Primo Yufera, Eduardo; Instituto Universitario Mixto de Tecnología Química; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial[EN] New analogues of the bioactive enamides isolated from P. brevicompactum (2 and 3) have been synthesized to improve the biological activities. Two different structural modifications have been introduced: substitution of the aliphatic side chain present in the natural products (1-4) by other groups frequently found in other active compounds and use of other nitrogen-containing five-membered rings with different degrees of oxidation. In this way, the insecticidal and fungicidal activities have been improved. Thus, compound 9, which posseses a 3-pyrroline ring, exhibited important insecticidal activity against third-instar nymphs of Oncopeltus fasciatus Dallas (100% mortality at 7.5 mu g/cm(2)). Remarkable fungicidal activity was also found, and preliminary structure-activity relationships could be established.
- PublicationSynthesis and biological evaluation of new analogues of the active fungal metabolites N-(2-methyl-3-oxodecanoyl)-2-pyrroline and N-(2-methyl-3-oxodec-enoyl)-2-pyrroline(ACS, 1999) Moya Sanz, Mª del Pilar; Cantin Sanz, Angel; Miranda Alonso, Miguel Ángel; Primo Millo, Jaime; Primo Yufera, Eduardo; Instituto Universitario Mixto de Tecnología Química; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial[EN] To evaluate the effect of simplifying the ß-ketoamide system present in active isolated metabolites from Penicillium brevicompactum (2 and 3) on the activity, new analogues with a monocarbonylic amide functionality have been obtained. In this way, the insecticidal and fungicidal activities have been improved in relation to the natural products taken as lead molecules. Thus, two of the synthetic analogues (5a and 5b) showed very important insecticidal activities against third-instar nymphs of Oncopeltus fasciatus Dallas, with acute LD50 values of 3.0 and 1.5 ¿g/cm2, respectively. Moreover, some analogues showed good levels of fungicidal activity against a wide range of commercially important and taxonomically diverse fungi; remarkably, compound 7c has proved to be highly active against Colletotrichum gloesporoides and Colletotrichum coccodes, with ED50 values of 2.04 and 11.7 ¿g/mL, respectively.
- PublicationSynthesis of novel heterogeneous photocatalysts based on Rose Bengal for effective wastewater disisnfection and decontamination(Elsevier, 2023-03) Blázquez Moraleja, Alberto; Moya Sanz, Mª del Pilar; Marín García, María Luisa; Bosca Mayans, Francisco; Instituto Universitario Mixto de Tecnología Química; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; European Commission; AGENCIA ESTATAL DE INVESTIGACION; Universidad Complutense de Madrid; Universitat Politècnica de València[EN] Anionic photosensitizers such as rose Bengal (RB) exhibit low efficiency in the photoinactivation of Gram-negative bacteria. Different strategies have been developed to improve their efficiency being the most effec-tive the addition of the photosensitizer to organic cationic materials. In this context, we have designed the synthesis of a novel heterogeneous photocatalyst based on silica in which the oxidizing properties of singlet oxygen photogenerated by RB have been combined with the chemoattraction of the bacteria to the cationic chains and their biocidal action. Thus, RB and cationic chains have been covalently linked to glass wool to obtain a photocatalyst that showed a highly efficient photodynamic activity against the Gram-positive (Enterococcus faecalis) and Gram-negative (Escherichia coli) bacteria. In addition, the new heterogeneous photocatalyst also resulted to be efficient in the decontamination of drugs such as diclofenac under visible light irradiation.
- PublicationWhat is the most effective percentage of Rose Bengal on polyamide fabrics for the visible-light photoinactivation of Gram-positive bacteria?(Elsevier, 2023-10) Flores, Jenny; Blázquez Moraleja, Alberto; Bonet Aracil, María Angeles; Moya Sanz, Mª del Pilar; Bosca Mayans, Francisco; Marín García, María Luisa; Instituto Universitario Mixto de Tecnología Química; Dpto. de Ingeniería Textil y Papelera; Instituto Agroforestal Mediterráneo; Dpto. de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Escuela Politécnica Superior de Alcoy; Grupo de Investigación Gestión Integral en la Industria Textil; European Commission; AGENCIA ESTATAL DE INVESTIGACION; Universidad Complutense de Madrid; Agència Valenciana de la Innovació; Universitat Politècnica de València[EN] Heterogeneous photocatalysts based on fabric materials have achieved great relevance for water disinfection. However, studies have yet to be performed looking for the best percentage of a photosensitizer on fabric, considering the 1O2 generation efficiency as well as the charge distribution of the dye fabrics surface for bacterial inactivation. Therefore, polyamide fabrics (PAF) dyed at different Rose Bengal (RB) percentages (RB-PAF) as an anionic photosensitizer were prepared to determine the best value for photodynamic inactivation of Gram-positive bacteria (Enterococcus faecalis). Time-resolved and steady-state emission measurements, as well as laser flash photolysis experiments, were also performed. RB-PAF at a percentage of 1% (on-weigth-of-fiber, o.w. f.) showed 100% inactivation efficiency against E. faecalis (reduction of more than 6 log10 units in the viable count) in only 15 min. Contrarily, fabrics with RB values of 0.5 or 3% (o.w.f.) showed no bacterial inactivation or only a small activity (1 log10 unit reduction), respectively. Results revealed that the effects observed by RB-PAF are mediated by 3RF* and the subsequent generation of 1O2. The insignificant photooxygenation of 9,10-dimethyl anthracene observed for RB-PAF at 0.5% explains the lack of bacterial inactivation, while the low effect observed for RB-PAF at 3% is produced by electrostatic repulsions between the anionic RB and the bacteria surface. These results reveal that in order to design newly dyed fabrics for disinfection, it is important to optimize the percentage of dye to avoid aggregation of photosensitizers and to obtain an adequate net negative charge distribution in the antimicrobial fabrics.