Pilar Moya

Circumdatin H, a new inhibitor of mitochondrial NADH oxidase, from Aspergillus ochraceus

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.

Screening for metabolites from Penicillium novae-zeelandiae displaying radical-scavenging activity and oxidative mutagenicity: isolation of gentisyl alcohol

In the search for new natural products with anti-oxidant activity, we have combined the cell-free assay based on the scavenging of the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH), with a bioassay that detects oxidative mutagens. This bioassay uses a new Escherichia coli tester strain, IC203, specifically sensitive to oxidative stress due to a deficiency in the OxyR function. OxyR is a redox-sensitive transcriptional activator of genes encoding anti-oxidant enzymes such as catalase and peroxiredoxin alkyl hydroperoxide reductase. The positive response observed in E. coli IC203 with several known anti-oxidants, including cysteine, catechol and ascorbic acid, suggested to us the usefulness of the mutagenicity assay for a rapid screening of anti-oxidant compounds. The extract from Penicillium novae-zeelandiae was found to scavenge the DPPH radical. Subsequently, guided by the DPPH-scavenging assay and the oxidative mutagenesis assay, we isolated and identified three compounds in fractions from that active extract: patulin (1). 3-hydroxybenzyl alcohol (2). and gentisyl alcohol (2,5-dihydroxybenzyl alcohol) (3). Of these, gentisyl alcohol showed both DPPH-scavenging activity and oxidative mutagenicity. This compound also gave rise to intracellular formation of superoxide, evaluated by monitoring the oxidation of dihydroethidium, and was able to inhibit mutagenesis induced by the model oxidant t-butyl hydroperoxide (t-BuOOH).

Isolation 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]1,3-oxazine – Two New Fungal Metabolites with in vivo Anti-Juvenile-Hormone and Insecticidal Activity

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 Meldrums acid. Subsequent aminolysis with pyrrolidine, followed by methylation at the activated position of the β-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 (1).

Evaluation of lufenuron as a chemosterilant against fruit flies of the genus Anastrepha (Diptera: Tephritidae)

BACKGROUND Chemosterilisation with lufenuron bait stations is a recently developed technique that is being implemented for Ceratitis capitata Wiedemann control. The aim of this work was to evaluate the chemosterilising effect of lufenuron against four economically important Latin American fruit flies species: Anastrepha ludens (Loew.), A. obliqua Macquart, A. serpentina Wiedemann and A. striata Schiner (Diptera: Tephritidae) in order to design a similar strategy for their control. RESULTS Sexually mature adults were treated by ingestion with concentrations ranging from 0.1 to 30.0 mg g(-1) of lufenuron in the diet. In addition, conspecific crosses with only one of the sexes being treated (30.0 mg g(-1)) were performed in order to appraise the contribution of each sex to the sterilising effect. In all cases, fecundity was not affected by the treatments, as opposed to fertility where all Anastrepha species studied were significantly affected, although to different extents. The conspecific crosses showed that treated males of A. ludens, A. obliqua and A. serpentina were not able to transmit the sterility to their respective untreated females. Only in the case of A. striata did crossing treated males with untreated females significantly reduced egg hatch. CONCLUSION Although further investigations are required, the present results demonstrate that the use of lufenuron for controlling A. striata could be potentially viable.

A heterocyclic oxime from a fungus with anti-juvenile hormone activity

Two fractions obtained after chromatography of dichloromethane extract of Penicillium brevicompactum culture medium showed anti-juvenile hormone activity. One was active when assayed in vivo against Oncopeltus fasciatus third-instar nymphs, whereas the other showed a strong in vitro inhibition of JH III biosynthesis on Locusta migratoria corpora allata. A subfraction of the latter, constituting 97% of this fraction, is a main component that possessed the juvenile hormone biosynthesis inhibitory activity. Chemical characterization of this compound shows a sesquiterpene-like structure, molecular mass of 278.16185 daltons, corresponding to an empirical formula of C15H22N2O3 named brevioxime. Evidence suggests that the final steps of JH III biosynthesis are the target of the active compound. Its effects may be compared with those of a known inhibitor of P-450-linked epoxidase, KK-42 (1-benzyl-5-[(E)-2,6-dimethyl-1,5-heptadienyl]imidazole), whose effects on L. Migratoria corpora allata are also reported here for the first time. Arch. Insect Biochem. Physiol. 37:287–294, 1998.

Field Efficacy of a Metarhizium anisopliae-Based Attractant-Contaminant Device to Control Ceratitis capitata (Diptera: Tephritidae)

ABSTRACT 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.

Inmunoferon (Am3) Enhances the Activities of Early–Type Interferon Inducers and Natural Killer Cells.

AbstractThe “in vivo” effect of Inmunoferon (AM3) on the production of interferon (IFN) and natural killer (NK) activity in young and old mice was studied. Although AM3 is not an IFN inducer by itself, enhancements in the serum IFN levels were produced when drug was associated to Newcastle disease virus or bacterial lipopo-lysaccharides as IFN inducers. This effect appeared to be dependent on the time lapsed between the inducer agent and drug. In addition, a significant stimulating effect on NK cell activity was also produced by AM3 treatments. This effect could be a consequence of a marked IFN induction and/or a modifying effect in prostaglandin synthesis.

Immunomodulatory activity of isoprinosine on experimental viral infections in avian models

The immunomodulatory activity of Isoprinosine treatments have been experimentally verified on chicken infected by three different viruses: Newcastle disease, fowl plague and avian infectious bronchitis. In protection tests, positive variations in the mean day of death rather than in the mortality rate were found depending on the modality of treatment. A stimulatory influence on primary anti-Newcastle disease virus antibody response was observed. In the avian model the Isoprinosine antiviral effect appears as due mainly to the enhancement of interferon production and to a synergistic interferon-isoprinosine interaction.

Modeling Pheromone Dispensers Using Genetic Programming

Mating disruption is an agricultural technique that intends to substitute the use of insecticides for pest control. This technique consists of the diffusion of large amounts of sexual pheromone, so that the males are confused and mating is disrupted. Pheromones are released using devices called dispensers. The speed of release is, generally, a function of time and atmospheric conditions such as temperature and humidity. One of the objectives in the design of the dispensers is to minimise the effect of atmospheric conditions in the performance of the dispenser. With this objective, the Centro de Ecologia Quimica Agricola (CEQA) has designed an experimental dispenser that aims to compete with the dispensers already in the market. The hypothesis we want to validate (and which is based on experimental results) is that the performance of the CEQA dispenser is independent of the atmospheric conditions, as opposed to the most widely used commercial dispenser, Isomate CPlus. This was done using a genetic programming (GP) algorithm. GP evolved functions able to describe the performance of both dispensers and that support the initial hypothesis.

Development of an attract-and-infect system to control Rhynchophorus ferrugineus with the entomopathogenic fungus Beauveria bassiana : Attract-and-infect device to control red palm weevil

BACKGROUND A new Beauveria bassiana-based attract and infect device (AID) to control Rhynchophorus ferrugineus Olivier (Coleoptera: Curculionidae) was developed. The virulence and persistence of the fungal formulation used in the AID were evaluated in the laboratory. Semi-field and field trials were carried out to validate the results and establish the potential of this device as a control tool. RESULTS In laboratory conditions, a 50% lethal time (LT50 ) of 4.33 days was obtained when adults (7-10 days old) were exposed to the inoculation tunnel (IT) containing 1 × 1010 conidia g-1 in an oil-based fungal formulation. This formulation maintained conidium viability at 50% for up to 2 months. Moreover, when adults were exposed to 2.5-month field-aged ITs, mortality still reached 50% 40 days after exposure. In addition, no differences were observed between ITs aged in early spring and those aged in summer, suggesting that the fungal formulation is not strongly affected by environmental factors in Mediterranean basin conditions. Semi-field assays showed that the device allowed an easy transit of weevils through the IT, which were effectively attracted and infected. Using the AIDs in 4-ha plot field trials, a reduction of >50% in the percentage of infested sentinel palms was obtained. CONCLUSION Based on the results obtained in terms of the efficacy and persistence of this new AID in the field and its potential in reducing R. ferrugineus populations and palm infestation, this device could become a key tool for the management of R. ferrugineus.