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.
- 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.
- 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