Synthesis of Some Novel Fused Substituted 3-(4-substitutedphenyl)-6,6-diphenyl-3,3a dihydroimidazo [2',1':2,3][1,3] thiazolo[4,5-c][1,2] Isoxazoles

The present study describes the synthesis of some novel arylidene cyclic chalcones 2-(4-substituted benzylidene)-6,6-diphenylimidazo[2,1-b][1,3]thiazole-3,5-diones and their transformation to 3-(4-substitutedphenyl)-6,6-diphenyl-3,3a- dihydroimidazo[2´,1´:2,3][1,3]thiazolo[4,5-c][1,2]oxazol-7(6H)-ones via cyclization using hydroxylamine hydrochloride. The starting chalcones have been synthesized by the condensation of various aromatic aldehydes and methylene entity of synthesized imidazothiazole-3,5-diones which were obtained by the cyclization of 5,5-diphenyl-2-thioxoimidazolidin-4-ones and chloroacetic acid. The intermediate 5,5-diphenyl-2-thioxoimidazolidin-4-ones have been synthesized by the condensation of α-diketone (benzil) with thiourea in presence of ethanolic alkali followed by Pinacol-Pinacolone rearrangement. Structures of all the newly synthesized compounds were confirmed by chemical, analytical and spectral data.Fil: Dangi, R. R.. Mody University Of Science And Technology; IndiaFil: Kumari, Maya. Mody University Of Science And Technology; IndiaFil: Khyaliya, Priyanka. Mody University Of Science And Technology; IndiaFil: Parellada, Eduardo Alberto. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Ameta, K. L.. Mody University Of Science And Technology; Indi

Polycyclic aromatic hydrocarbons removal by immobilized bacterial cells using annonaceous acetogenins for biofilm formation stimulation on polyurethane foam

Wastewaters containing polycyclic aromatic hydrocarbons (PAH) must be treated before discharge in water bodies to avoid environmental pollution and comply with environmental protection regulations. The development of novel PAH removal technologies from wastewaters is thus of great importance. The aim of this work was to use immobilized bacteria on polyurethane foam (PUF) for acenaphthene, fluoranthene and pyrene removal using annonaceous acetogenins (ACG) to stimulate biofilm and possibly enhance PAH removal activity. Different ACG were tested for their capacity to stimulate biofilm formation on Pseudomonas monteilii P26, a known naphthalene degrader. Itrabin, jetein and an ethanolic extract of Annona cherimola pulp were selected for showing a high stimulation level at low concentration in microplate biofilm formation assay. On PUF, the biofilm formation was strongly stimulated by itrabin and the ethanolic extract. However, there was no difference between the PAH removal percentages of the different systems (sterile PUF, cell immobilized in presence of ACG and cells immobilized without ACG). In average, 99% acenaphthene, 98% fluoranthene and 92.5% pyrene were removed in 7 days mostly by sorption (initial PAH concentration was 50 ppm). A 15–22% removal was attributed to biodegradation or bioaccumulation in the systems with immobilized cells. In this case, stimulating biofilm formation did not enhance PAH removal by immobilized bacteria on PUF.Fil: Alessandrello, Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucuman. Planta Piloto de Procesos Industriales Microbiologicos; ArgentinaFil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Juárez Tomás, María Silvina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucuman. Planta Piloto de Procesos Industriales Microbiologicos; ArgentinaFil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Vullo, Diana Lia. Universidad Nacional de General Sarmiento. Instituto de Ciencias; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ferrero, Marcela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucuman. Planta Piloto de Procesos Industriales Microbiologicos; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentin

Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I

A new β-hydroxy-γ-methyl-γ-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/ threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin) was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex 1 in the 0.18 - 1.55 nM range.Fil: Barrachina, Isabel. Universidad de Valencia; EspañaFil: Neske, Adriana. Universidad Nacional de Tucumán; ArgentinaFil: Granell, Susana. Universidad de Valencia; EspañaFil: Bermejo, Almudena. Universidad de Valencia; EspañaFil: Chahboune, Nadia. Universidad de Valencia; EspañaFil: El Aouad, Noureddine. Universidad de Valencia; EspañaFil: Alvarez, Olga. Universidad Nacional de Tucumán; ArgentinaFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaFil: Zafra Polo, M. Carmen. Universidad de Valencia; Españ

Stimulation of biofilm formation by hydrocarbon degrading strains in the presence of squamocin

Previous studies have shown that annonaceous acetogenins (ACGs) stimulates biofilm formation in a P. aeruginosa strain of clinical origin. ACG squamocin is structurally related to the γ-lactones, a family of bacterial autoinducers that play an essential role in the quorum sensing mechanism to coordinate the biofilm maturation. In this work, 37 polycyclic aromatic hydrocarbon degrading strains were tested for their attachment capability and biofilm development on polystyrene microplates using squamocin as a biofilm inducer. Out of the 37 strains tested, 22% showed natural formation of bacterial biofilms that increased in the presence of squamocin, in some cases up to 40%. In the remaining 12 strains over 60% showed an increase in biofilm production and were therefore selected for future studies.Fil: Rodriguez, Analia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Riva Mercadal, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; ArgentinaFil: Cartagena, Elena. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Ferrero, Marcela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Planta Piloto de Procesos Industriales Microbiológicos; ArgentinaFil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaXXIV Annual Scientific MeetingTafi del ValleArgentinaAsociación de Biología de Tucumá

Montmorrilonite K10 catalyzed efficient synthesis of some 4'-nitrochalcones and their 1, 3, 5-triaryl-2-pyrazolines and in vitro antimicrobial evaluation

An expeditious synthesis of some 4´-nitrochalcones (3a-n) and their subsequent facile one-pot transformation to 1, 3,5-triaryl-2-pyrazolines (4a-n) has been carried out using montmorrilonite K10 via microwave mediated solvent free protocol.An emphasis is given to highlighting the greenness of the processes, and a fair comparison is also provided between differentinorganic solid supports as catalysts. Both conventional as well as non-conventional approaches have been explored bycomparing the reaction conditions and yields. The newly synthesized pyrazolines were studied for their in vitro antimicrobialevaluation against bacterial strains Bacillus pumilus and Escherichia coli and fungal strains Aspergillus niger and Penicilliumchrysogenum. Findings of biological evaluation highlighted 4b, 4e, 4j and 4m as potential new leads in the search of newantimicrobial agents. The structures of newly synthesized compounds have been established on the basis of elemental analysisand spectroscopic studies.Fil: Ameta, K. L.. Faculty Of Arts, Science & Commerce, Mody University Of; IndiaFil: Rathore, Nitu S.. Faculty Of Arts, Science & Commerce, Mody University Of; IndiaFil: Kumari, Maya. Faculty Of Arts, Science & Commerce, Mody University Of; IndiaFil: Khyaliya, Priyanka. University of Science and Technology; IndiaFil: Dangi R. R.. Faculty Of Arts, Science & Commerce, Mody University Of; IndiaFil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; ArgentinaFil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentin

Bis- and mono-substituted Chalcones exert anti-feedant and toxic effects on fall armyworm Spodoptera frugiperda

Spodoptera frugiperda is a highly polyphagous migratory lepidopteran pest species. It causes infestation in crops leading to the severe crop losses. Being a new invasive parasite, its susceptibility to insecticides needs to be explored; and therefore, there is an urgent need to develop the potent insecticides for the effective control of this insect pest. To attain the crop sustainability, the antifeedant, toxicity and nutritional effects on larvae of Spodoptera frugiperda were studied with six mono- and eight bis- substituted chalcones. The antifeedant activity was calculated when 50% of the larvae control ate 50% of the diet through the FR factor. Toxicity was assessed through larval, pupal mortality and the emergence of adults and nutritional effects with consumption rates (IC), growth (GR) and consumption efficiency (EIC). The bis-chalcones 6b, 6e, 6f and 6h caused lethal effect on S. frugiperda in the first larval stages, being 6b the most toxic (85%). Adults who survived showed malformations and decreased size, which led to death. The larvae fed with aggregate in the bis-chalcones diet: 6b, 6e and 6f had the highest percentage of intake and the poorest conversion of nutrient absorption (ECI), which suggests that the larva metabolizes food for energy and results in a decrease of growth and death in early stages. Bis-chalcones showed more toxicity than mono-chalcones and 6b causes the most toxic and dietary change.Fil: Priyanca Devi, Ahanthem. Mody University Of Science And Technology; IndiaFil: Alsulimani, Ahmad. Jazan University; Arabia SauditaFil: Ruiz Hidalgo, José. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Neske, Adriana. Mody University Of Science And Technology; IndiaFil: Sayyed, R. Z.. Psgvp Mandals Arts; IndiaFil: Hassan, Montaser. Taif University; Arabia SauditaFil: Ameta, Keshav Lalit. Mody University Of Science And Technology; IndiaFil: Elshazly, Hayam. Qassim University; Arabia Saudit

Structural factors of annonaceous acetogenins and their semisynthetic analogues related with the toxicity on Spodoptera frugiperda

Toxic and nutritional effects of annonaceous acetogenins and their semisynthetic analogues on Spodoptera frugiperda were evaluated. Structural modification of the natural ACG, blocking the OH flanking THF with MOM, allowed us to suggest the mode of action of ACG in the membrane. Our study emphasizes the role of the flanking OH and acetyl groups of THF with the membrane hydrophilic polar head groups. They are essential structural factors in the ACG that facilitate the intermolecular interaction that dehydrates the membrane and makes it potentially toxic against Spodoptera frugiperda.Fil: Di Toto Blessing, Lilian Edith. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Budeguer, Florencia. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Ramos, Juan. Universidad de la República. Facultad de Química. Departamento de Química Orgánica; UruguayFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Díaz, Sonia Beatriz. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Brovetto, Margarita. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Seoane, Gustavo. Universidad de la República. Facultad de Química. Departamento de Química Orgánica; UruguayFil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentin

Natural and Derivatized Acetogenins Promising for the Control of Spodoptera frugiperda Smith

Annonaceous acetogenins (ACG), belonging to the family Annonaceae, represent aclass of bioactive compounds whose toxic effects have been reported for several species of insects. Given their insecticidal properties, we first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods. ACG analogues were semi-synthesized and characterized by spectroscopic techniques (1H and 13C-NMR). We isolated ten natural acetogenins:squamocin, molvizarin, motrilin, rolliniastatin-2, almuñequin, cherimolin-1, cherimolin-2, annonacin, squamocin D and asiminecin. The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). The natural ACGs squamocin and molvizarin killed 100% of S. frugiperda larvae, followed by motrilin (80%). Acetylated derivatives had less toxic and nutritional effects that led to pupal mortality and adult fatal malformations. The addition of MOM derivatives to the larval diet has not toxic effects on larvae, but ignificantly reduces growth rate and efficiency in conversion of ingested food into biomass, affecting adult survival.Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Parellada, Eduardo Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Universidad Nacional de Santiago del Estero. Instituto de Bionanotecnología del Noa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Bionanotecnología del Noa; ArgentinaFil: Di Toto Blessing, Lilian Edith. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaFil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Ameta, K. L.. Faculty Of Arts, Science & Commerce, Mody University Of; IndiaFil: Vera, Nancy Roxana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Neske, Adriana. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentin

Toxic Effects of Citrus aurantium and C. limon Essential Oils on Spodoptera frugiperda (Lepidoptera: Noctuidae)

Citrus aurantium and C. limon were selected in the search for natural plant insecticides. The essential oils of C. aurantium and C. limon and ethanol extracts of the seeds, pulp, albedo, and peel of C. aurantium were incorporated into the larval diet of the lepidopteran pest Spodoptera frugiperda. Larval and pupal mortality were quantified and adult malformation was observed. C aurantium essential oil bad antifeedant action and the mixture of albedo ethanol extract and C aurantium essential oil had toxic effects on S. frugiperda larvae at early stages, when they had not yet produced major damage to the crop. Our results indicated that a mixture of ethanol extract of albedo and C. auranJium essential oil (250 Jig of extract mix per g of diet) deterred feeding by 46% and had the highest larval mortality (100%) of the materials tested. The peel extract (250 ug per g of diet) produced an increment in growth rate and diet consumption. However, 4()OJO of the larval and 45% of the pupal populations died after 96 h of treatment. The blend of essential oil and C. aurantium albedo ethanol extract showed the lowest consumption and a poor nutrient conversion into biomass. Finally, the presence of D-limonene and nootkatone in the peel ethanol extract, and C. limon and C. aurantium essential oils, may be the cause of the response in the feeding behavior and toxic effects found on S. frugiperda.Fil: Villafañez, Emilio Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Tolosa, Diego. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Neske, Adriana Neske. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentin

Toxic effects of annonaceous acetogenins from Annona cherimolia (Magnoliales: Annonaceae) on Spodoptera frugiperda (Lepidoptera: Noctuidae)

Plants belonging to the family Annonaceae have been commonly described in traditional medicine as remedies against head lice, and for their insecticidal properties. Characteristic constituents from a few genera of these plants are the annonaceous acetogenins. Fourteen annonaceous acetogenins have been isolated from our Argentine collection of the seeds of A. cherimolia. We report herein the antifeedant and insecticidal effects of nine of those acetogenins on Spodoptera frugiperda (J. E. Smith). The acetogenin squamocin, one of the major constituents of the extract, displayed toxic effects on early larval instars when incorporated to the larval diet at a dose of 50 μg per g of diet. The remaining annonaceous acetogenins tested, itrabin, asimicin, neoanonin, cherimolin-1, cherimolin-2, almuñequin, motrilin, and tucumanin produced pupal mortality and adult malformations leading to death, when incorporated to the larval diet at the same dose. The evaluation of indices of food consumption, growth, and food utilization indicated that squamocin was the only tested acetogenin to produce significant decrease in the growth rate and to reduce the efficiency with which larvae converted ingested food into biomass. All the acetogenins produced more than 80% pupal mortality with no dependence on the position of the THF rings or the number and location of the OH groups. © Springer-Verlag 2006.Fil: Álvarez Colom, Olga. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; ArgentinaFil: Neske, Adriana Neske. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Popich, Susana Beatriz. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; ArgentinaFil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica. Cátedra de Química Orgánica III; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentin