Moya Sanz, Mª del Pilar
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- PublicaciónSynthesis 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.
- PublicaciónLaboratory 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.
- PublicaciónNovel 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.
- PublicaciónCircundatin 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.
- PublicaciónSynthesis 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.
- PublicaciónIsolation 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
- PublicaciónField 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.