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

Vinylogous aldol reaction of heterocyclic silyloxy dienes. Application in synthesis

A versatile, readily accessible triad of 2-enoxy silane synthons derived from furan, pyrrole, and thiophene is presented. These heterocycles, in reacting with carbonyl and carbonyl- related acceptors, act as vinylogous nucleophile modules, giving rise to diverse, functionality- rich, γ-substituted α,β-unsaturated carbonyl constructs. These, in turn, are invaluable platforms onto which further functional elements and chirality may be introduced. A couple of appealing applications—the variable construction of a repertoire of carbasugars and a library of annonaceous acetogenin segments—have been chosen to illustrate the viability of this vinylogous aldol approach

First report on the termiticidal activity of extracts of Annona squamosa (Annonaceae) seeds and on its active constituent squamocins

Termites inflict severe damage on wood and impede usage of several forest species. The biological metabolites could potentially replace synthetic termiticidal products which are becoming more restricted to use. Annona squamosa is well known for its edible fruits - tropical custard apple. Annonaceous tetrahydrofuran acetogenins have attracted much interest due to their broad range of biological activities, and seeds containing them are reported to show insecticidal and abortifacient properties. Under the course our exploratory investigation of non food valuable products from less known forest species (here from Benin), the fractions obtained from defatted cake of Annona squamosa seeds with solvents covering a broad range of polarity, revealed a significant termiticidal activity, when applied at 5 - 10 mg/cm² (non-polar solvent) and 1.2 - 5 mg/cm² (case of a more polar solvent). Based on the result (0: no attack) from the standard procedure EN 118, these extracts could be used for preserving wood under class of use number 1. A derivatization step with Kedde reagents A and B, elemental analysis C,H,O, HPLC/MS and proton NMR showed the presence of squamocin type acetogenins (MW 594 and 622 g/mole: C35H62O7 and C37H66O7) as main components of the most active fraction (100% mortality within 7 days for a sample applied at 2 mg/cm²). Additional work will be undertaken to confirm the structure of most active compounds in the extracts, and to check whether some Annona squamosa seed extracts (non timber products of sustainable management of native forest) could show even higher activity to protect wood under more adverse conditions and be alternative active natural products to synthetic compounds. (Résumé d'auteur

Annona muricata (graviola): toxic or therapeutic

This paper examines annona muricata (graviola): toxic or therapeutic

Evaluación preliminar de la actividad insecticida contra puto barberi (cochinilla harinosa) del extracto etanolico de las semillas desengrasadas de annona muricata

Se evaluó la bioactividad del extracto etanólico crudo de semillas desengrasadas de Annona muricata, el cual presento actividad citotóxica frente a Artemia salina y actividad insecticida frente a Puto barberi. Este último bioensayo fue evaluado a concentraciones de 25, 15 y 9 ppm del extracto variando el tiempo de exposición (5, 15 y 30 minutos) de las raíces de Talinum paniculatum en el extracto, empleadas como alimento del Puto barberi y la movilidad de los insectos a las 24 horas. El efecto del extracto fue comparado con Lorsban 4E®, utilizado como control positivo. Se obtuvieron resultados prometedores con CL50 bajos, indicando una alta actividad insecticida del extracto. Se verificó la presencia de las acetogeninas con anillo ?-lactónico a, ß- insaturado por cromatografía en capa delgada (CCD) y se cuantificaron siete acetogeninas por cromatografía de alta eficiencia (CLAE) en el extracto etanólico crudo de semillas desengrasadas de Annona muricata.In this experience the bioactivity of the crude ethanolic extract of the degreased seeds of Annona muricata was evaluated, which presented cytotoxic activity against Artemia salina and insecticide activity against Puto barberi. This last bioassay was evaluated with concentrations of 25, 15 and 9 ppm of the extract, changing the exposition time (5, 15 and 30 minutes)of the roots of Talinum paniculatum in the extract, it was used like feed to the Puto barberi and the mobility of the insects after 24 hours. The effect of the extract was compared with Lorsban 4E®, used like a positive control. The results obtained with CL50 were promising; this indicates a high insecticide activity of the extract. The presence of acetogenins with a γ-lactone α, β-unsaturated ring was checked with high performance liquid chromatography (HPLC) in the crude ethanolic extract of the degreased seeds of Annona muricata

The catalytic hydrogenation of 3-(2-fluorophenyl)- and 3-(4-fluorophenyl)-4,4-ethylenedioxycyclopenta[d]isoxazolines

The catalytic hydrogenation of 3-(2-fluorophenyl)- and 3-(4-fluorophenyl)-4,4-ethylenedioxycyclo-penta[d ]isoxazolines led with good yields to corresponding fluorinated β -hydroxyketones. The synthesized compounds are precursors of new fluorinated prostanoids and carbocyclic analogs of acetogenins being of great interest as potential bi ologically active substances as well

Chemical composition of laurencia obtusa extract and isolation of a new C15-acetogenin

A new C15-acetogenin, sagonenyne (20), exhibiting an unusual single tetrahydropyran ring was isolated from an ethyl acetate extract of Laurencia obtusa collected on the Corsican coastline. Its structure was established by detailed NMR spectroscopic analysis, mass spectrometry, and comparison with literature data. Twenty-three known compounds were identified in the same extract by means of column chromatography steps, using a (13)C-NMR computer aided method developed in our laboratory. In addition to sesquiterpenes, which represent the main chemical class of this extract, diterpenes, sterols, and C15-acetogenins were identified. The crude extract was submitted to a cytotoxicity assay and was particularly active against THP-1 cells, a human leukemia monocytic cell line.info:eu-repo/semantics/publishedVersio

Chemical constituents of the volatile oil from leaves of Annona coriacea and in vitro antiprotozoal activity

The essential oil of the leaves from Annona coriacea Mart., Annonaceae, was extracted by hydrodistillation in a Clevenger apparatus and analyzed by GC/MS and GC/FID. The oil yield was 0.05% m/m. Sixty compounds were identified, in a complex mixture of sesquiterpenes (76.7%), monoterpenes (20.0%) and other constituents (3.3%). Bicyclogermacrene was its major compound (39.8%) followed by other sesquiterpenes. Most of the monoterpenes were in low concentration (<1%). Only &#946;-pinene and pseudolimonene presented the highest level of 1.6%. The volatile oil presented anti-leishmanial and trypanocidal activity against promastigotes of four species of Leishmania and trypomastigotes of Trypanosoma cruzi, showing to be more active against Leishmania (L.) chagasi (IC50 39.93 µ g/mL) (95% CI 28.00-56.95 µ g/mL)

PERBANDINGAN EKSTRAK DAUN SIRSAK, EKSTRAK ROSELLA, DAN MADU TERHADAP KARAKTERISTIK MINUMAN FUNGSIONAL DAUN SIRSAK (Annona muricata Linn.)

Tujuan dari penelitian ini adalah untuk membuat produk baru dengan berbahan dasar daun sirsak, kelopak bunga rosella dan madu yang menyehatkan tubuh dan menyegarkan serta untuk mengetahui pengaruh perbandingan antara ekstrak daun sirsak, ekstrak rosella, dan madu terhadap antioksidan pada karakteristik minuman fungsional daun sirsak. Rancangan percobaan yang digunakan dalam penelitian ini adalah Rancangan Acak Kelompok (RAK) dengan pola factorial 1 x 5 sebanyak 5 kali ulangan. Variable yang digunakan dalam penelitian ini adalah perbandingan ekstrak daun sirsak, ekstrak rosela, dan madu yang berbeda-beda. Analisis kimia yang dilakukan dalam penelitian ini adalah analisis kadar tannin, selain itu juga dilakukan uji organoleptik dengan penilaian warna, rasa, dan aroma terhadap minuman fungsional daun sirsak. Hasil penilaian menunjukan bahwa perbandingan ekstrak daun sirsak, ekstrak rosela, dan madu tidak berpengaruh nyata terhadap warna, aroma, dan kadar tannin, namun berpengaruh nyata terhadap penilaian rasa minuman The result of this research is to create new products with soursop leaf-based, rosella flower petals, and honey nourish the body and refreshing as well as to determine the effect a comparison between soursop leaf extract, extract rosella, and honey to the antioxidants in functional drinks soursop leaf characteristics. The experimental design used in this study is a randomized block design (RAK) with factorial pattern of 1 x 5 by 5 repetitions. Variables used in this study is a comparison of soursop leaf extract, extract of roselle, and different honey. Chemical analysis performed in this study is the analysis of the levels of tannin, but it also conducted organoleptic tests with assessment of color, flavor, and aroma of the leaves of the soursop functional drinks. Results of the assessment showed that the ratio of soursop leaf extract, extract of roselle, and honey did not significantly affect the color, aroma and tannin levels, but significantly affect the assessment flavored drinks