Moya Sanz, Mª del Pilar
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- 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; Departamento 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.
- 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; Departamento de Biotecnología; Instituto Agroforestal Mediterráneo; Departamento 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.
- 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; Departamento de Ingeniería Textil y Papelera; Instituto Agroforestal Mediterráneo; Departamento 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.
- 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; Departamento de Biotecnología; Instituto Agroforestal Mediterráneo; Departamento de Química; Centro de Ecología Química Agrícola; Escuela Técnica Superior de Ingeniería Industrial; Centro Avanzado de Microbiología Aplicada; 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; Departamento 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.
- 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; Departamento 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.
- 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; Departamento 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.
- 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; Departamento de Biotecnología; Instituto Agroforestal Mediterráneo; Centro de Ecología Química Agrícola; Centro Avanzado de Microbiología Aplicada; 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
- 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; Departamento de Biotecnología; Instituto Agroforestal Mediterráneo; Departamento 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.
- 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; Departamento 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.