RESUMO
Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition of the essential oil was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against three Gram-positive bacteria, one Gram-negative bacterium and one dermatophyte fungus. The radical scavenging properties of the essential oil was evaluated by means of DPPH and ABTS assays. The chemical analysis allowed us to identify thirty-five compounds representing more than 99.95% of the total composition. Aliphatic sesquiterpene hydrocarbon trans-caryophyllene was the main constituent with 20.47 ± 1.25%. Other main compounds were myrcene (11.47 ± 1.56%), ß-phellandrene (10.55 ± 0.02%), germacrene D (7.60 ± 0.60%), and α-humulene (5.49 ± 0.38%). The essential oil from Croton ferrugineus presented moderate activity against Candida albicans (ATCC 10231) with an MIC of 1000 µg/mL, a scavenging capacity SC50 of 901 ± 20 µg/mL with the ABTS method, and very strong antiglucosidase activity with an IC50 of 146 ± 20 µg/mL.
Assuntos
Anti-Infecciosos/química , Antioxidantes/química , Croton/química , Inibidores Enzimáticos/química , Óleos Voláteis/química , Folhas de Planta/química , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/isolamento & purificação , Alcenos/química , Alcenos/isolamento & purificação , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Benzotiazóis/antagonistas & inibidores , Compostos de Bifenilo/antagonistas & inibidores , Candida albicans/efeitos dos fármacos , Candida albicans/crescimento & desenvolvimento , Monoterpenos Cicloexânicos/química , Monoterpenos Cicloexânicos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Escherichia coli/efeitos dos fármacos , Escherichia coli/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Sesquiterpenos Monocíclicos/química , Sesquiterpenos Monocíclicos/isolamento & purificação , Picratos/antagonistas & inibidores , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/isolamento & purificação , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidores , alfa-Glucosidases/químicaRESUMO
This paper proposes a framework with six dimensions that can be useful for evaluating the potential and the current stage of a bio-based platform chemical. The framework considers the technological and strategic challenges to be fulfilled by a company that intends to lead a platform based on a bio-based chemical. A platform chemical should be an intermediate molecule, with a structure able to generate a number of derivatives, that is produced at a competitive cost, capable of allowing exploitation of the scale and scope economies, and inserted within a complete innovation ecosystem that is able to create value with governance mechanisms that are capable of allowing coordination of the innovation process and facilitation of the value capture by the focal company leading the platform, in our case the producer of the platform molecule. Based on these six dimensions, three potential platform chemicals - succinic acid, butanol and farnesene - are compared and discussed. It is possible to identify important differences concerning the technological dimensions and the strategic dimensions as well. Two of the molecules - farnesene and succinic acid - adhere to most of the conditions required to structure a platform chemical. However, the innovation ecosystem is not complete and the governance mechanisms are still under development, so it is not clear if they will be capable of allowing a favorable position for value capture by the platform leader. Butanol structuring for a platform does not seem promising. The potential of the molecule is apparently not high and the strategic initiatives are in general not focused on innovation ecosystem structuring.
Assuntos
Alcenos/isolamento & purificação , Biotecnologia , Butanóis/isolamento & purificação , Ácido Succínico/isolamento & purificação , Alcenos/química , Butanóis/química , Ácido Succínico/químicaRESUMO
This study aimed to determine the volatile profile of cashew apple fibers to verify which compounds are still present after successive washings and thus might be responsible for the undesirable remaining cashew-like aroma present in this co-product, which is used to formulate food products like vegetarian burgers and cereal bars. Fibers were obtained from cashew apple juice processing and washed five times in an expeller press. Compounds were analyzed by the headspace solid-phase micro extraction technique (HS-SPME) and gas chromatography-mass spectrometry (GC-MS), using a DB-5 column. Sensory analysis was also performed to compare the intensity of the cashew-like aroma of the fibers with the original juice. Altogether, 80 compounds were detected, being esters and terpenes the major chemical classes. Among the identified substances, 14 were classified as odoriferous in the literature, constituting the matrix used in the Principal Component Analysis (PCA). Odoriferous esters were substantially reduced, but many compounds were extracted by the strength used in the expeller press and remained until the last wash. Among them are the odoriferous compounds ethyl octanoate, γ-dodecalactone, (E)-2-decenal, copaene, and caryophyllene that may contribute for the mild but still perceptible cashew apple aroma in the fibers that have been pressed and washed five times. Development of a deodorization process should include reduction of pressing force and stop at the second wash, to save water and energy, thus reducing operational costs and contributing to process sustainability.
Assuntos
Anacardium/química , Bebidas/análise , Frutas/química , Odorantes/análise , Microextração em Fase Sólida/métodos , 4-Butirolactona/análogos & derivados , 4-Butirolactona/isolamento & purificação , Aldeídos/isolamento & purificação , Alcenos/isolamento & purificação , Caprilatos/isolamento & purificação , Odorantes/prevenção & controle , Sesquiterpenos Policíclicos , Pressão , Análise de Componente Principal , Sesquiterpenos/isolamento & purificação , Terpenos/isolamento & purificaçãoRESUMO
Leishmaniasis is a chronic infectious disease caused by different Leishmania species. Global occurrences of this disease are primarily limited to tropical and subtropical regions. Treatments are available; however, patients complain of side effects. Different species of plants have been screened as a potential source of new drugs against leishmaniasis. In this study, we investigated the antileishmanial activity of cilantro (Coriandrum sativum) essential oil and its main components: (E)-2-undecenal, (E)-2-decenal, (E)-2-dodecenal, decanal, dodecanal, and tetradecanal. The essential oil of C. sativum leaves inhibits growth of Leishmani donovani promastigotes in culture with an IC50 of 26.58 ± 6.11 µg/mL. The aliphatic aldehydes (E)-2-decenal (7.85 ± 0.28 µg/mL), (E)-2-undecenal (2.81 ± 0.21 µg/mL), and (E)-2-dodecenal (4.35 ± 0.15 µg/mL), all isolated from C. sativum essential oil, are effective inhibitors of in vitro cultures of L. donovani promastigotes. Aldehydes (E)-2-decenal, (E)-2-undecenal, and (E)-2-dodecenal were also evaluated against axenic amastigotes and IC50 values were determined to be 2.47 ± 0.25 µg/mL, 1.25 ± 0.11 µg/mL, and 4.78 ± 1.12 µg/mL, respectively. (E)-2-Undecenal and (E)-2-dodecenal demonstrated IC50 values of 5.65 ± 0.19 µg/mL and 9.60 ± 0.89 µg/mL, respectively, against macrophage amastigotes. These cilantro compounds showed no cytotoxicity against THP-1 macrophages.
Assuntos
Antiprotozoários/química , Antiprotozoários/farmacologia , Coriandrum/química , Leishmania donovani/efeitos dos fármacos , Aldeídos/química , Aldeídos/isolamento & purificação , Aldeídos/farmacologia , Alcenos/isolamento & purificação , Alcenos/farmacologia , Linhagem Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Avaliação Pré-Clínica de Medicamentos/métodos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Concentração Inibidora 50 , Macrófagos/efeitos dos fármacos , Macrófagos/parasitologia , Estrutura Molecular , Óleos Voláteis/química , Óleos Voláteis/farmacologiaRESUMO
The composition of stink bug allomones is similar for most species and includes hydrocarbons, as well as saturated and unsaturated aldehydes and esters. Analysis of extracts of the metathoracic glands of seven pentatomid species from different genera by gas chromatography/Fourier transform-infrared (GC/FT-IR) showed that the compound previously thought to be 1-tridecene actually showed characteristic bands of an internal as well as terminal double bond, the former compound having (Z)-configuration. The mass spectrum of an epoxy-derivative of the natural material demonstrated that the internal double bound was located at C4. GC/FT-IR and co-injections with synthetic standards on different capillary columns proved that all these stink bugs had 1-tridecene and (Z)-4-tridecene in their defensive secretions.
Assuntos
Alcenos/isolamento & purificação , Glândulas Exócrinas/metabolismo , Heterópteros/fisiologia , Alcenos/química , Animais , Cromatografia Gasosa/métodos , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
BACKGROUND: Termites are degradation agents that inflict severe damage on wood. Some long-lasting Amazonian trees can resist these insects by producing toxic secondary metabolites. These metabolites could potentially replace synthetic termiticidal products which are becoming more restricted to use. RESULTS: Sextonia rubra is resistant to termite-induced degradation. It has been demonstrated that this species naturally produces an ethyl-acetate-soluble termiticidal metabolite, rubrynolide, to protect its wood. Assays in the presence of tropical and invasive termites established that both rubrynolide and crude ethyl acetate extract from S. rubra wood can be used as a treatment for the protection of sensitive woods against termites. CONCLUSION: Rubrynolide and S. rubra extract are promising candidates for the replacement of synthetic termiticides.
Assuntos
Acetais/toxicidade , Alcenos/toxicidade , Inseticidas/toxicidade , Isópteros/efeitos dos fármacos , Lauraceae/química , Acetais/química , Acetais/isolamento & purificação , Alcenos/química , Alcenos/isolamento & purificação , Animais , Guiana Francesa , Inseticidas/química , Inseticidas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Madeira/química , Madeira/toxicidadeRESUMO
Research on antifungal compounds from the durable wood from French Guiana Amazonian forest trees highlights the correlation between the activity of their extracts against wood-rotting fungi and human pathogens. The fractionation of an ethyl acetate extract of Sextonia rubra wood led to the isolation of rubrenolide (1) and rubrynolide (2). The potential of compounds 1 and 2 is described through the evaluation of their activity against 16 pathogenic fungi and their cytotoxicity toward NIH-3T3 mammalian fibroblast cells.
Assuntos
Acetais/isolamento & purificação , Acetais/farmacologia , Alcenos/isolamento & purificação , Alcenos/farmacologia , Alcinos/isolamento & purificação , Alcinos/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Basidiomycota/química , Polyporaceae/química , Árvores/microbiologia , Acetais/química , Alcenos/química , Alcinos/química , Animais , Antifúngicos/química , Guiana Francesa , Lauraceae/microbiologia , Camundongos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Células NIH 3T3 , Caules de Planta/química , Madeira/microbiologiaRESUMO
Heliopsis longipes (Compositae) is a Mexican plant used as analgesic in pain toothache. A solution of 10mug/ml of dichloromethane extract from this plant showed analgesic activity determined by means of GABA release in mice brain slices. Through a bioassay-directed separation, fractions G-1, G-2, G-4 and G-6 at the same concentration were active. Affinin was the unique and common active compound, and evoke the GABA release 0.5min after administration at 1x10(-4)M concentration. Inactive compound were undeca-2E-en-8,10-dyinoic acid isobutylamide, hinokinin, 2'-hydroxyhinokinin, 3beta-sn-glyceroyl-(1''-palmitoxy)urs-12-ene, 13(18)-ursen-3beta-ol, 13(18)-ursen-3beta-acetate, beta-sitosterol and stigmasterol. The analgesic activity of Heliopsis longipes could be associated to affinin.
Assuntos
Alcenos/farmacologia , Amidas/farmacologia , Analgésicos/farmacologia , Asteraceae/química , Dor/tratamento farmacológico , Extratos Vegetais/farmacologia , Alcamidas Poli-Insaturadas/farmacologia , 4-Butirolactona/análogos & derivados , 4-Butirolactona/isolamento & purificação , Alcenos/isolamento & purificação , Amidas/isolamento & purificação , Analgésicos/isolamento & purificação , Animais , Benzodioxóis , Encéfalo/efeitos dos fármacos , Encéfalo/metabolismo , Dioxóis/isolamento & purificação , Feminino , Técnicas In Vitro , Lignanas/isolamento & purificação , Medicina Tradicional , Cloreto de Metileno , México , Camundongos , Plantas Medicinais , Alcamidas Poli-Insaturadas/isolamento & purificação , Ácido gama-Aminobutírico/efeitos dos fármacos , Ácido gama-Aminobutírico/metabolismoRESUMO
Bioactivity-guided fractionation of a MeOH-EtOAc extract from the young leaves of Nectandra lineata (Lauraceae), using a Trypanosoma cruzi bioassay resulted in the isolation of a novel norlignan 3'-methoxy-3,4-methylenedioxy-4',7-epoxy-9-nor-8,5'-neolignan-9'-acetoxy (1), together with the known compound, 3'-methoxy-3,4-methylenedioxy-4'-7-epoxy-9-nor-8,5'-neolignan-7,8'-diene (2). Compounds 1 and 2 were shown to inhibit the growth of T. cruzi epimastigotes in axenic culture.
Assuntos
Alcenos/química , Alcenos/farmacologia , Lauraceae/química , Lignanas/química , Lignanas/farmacologia , Tripanossomicidas/química , Tripanossomicidas/farmacologia , Alcenos/isolamento & purificação , Animais , Lignanas/isolamento & purificação , Folhas de Planta/química , Tripanossomicidas/isolamento & purificação , Trypanosoma cruzi/efeitos dos fármacosRESUMO
Termites have become an important pest of Eucalyptus and Pinus reforestations, sugarcane and other cultures. An alternative for the control of this pest would be the use of attractive traps that take in account the social behavior of these insects. Diverse factors are important for the insects in the localization of the habitat and the choice of the food and specific odors can facilitate this. Studies referring to Heterotermes tenuis (Isoptera: Rhinotermitidae) are scarce. The objective of this work was to analyze the tergal cuticular extract of H. tenuis and determine the selectivity and sensitivity of its antennae to the components of this extract by electroantennography (EAG). The composition of the cuticular extract was determined by GC-MS analysis. The hydrocarbons found were restricted to linear alkanes, being most abundant C24 to C27 that comprises ca. 65% of the total. Olefins were not detected. EAG and behavioral test responses to the cuticular hydrocarbons were greater and significantly different from the control and the high selectivity of the antennae to the extract indicates its potential as chemical messenger. Cuticular hydrocarbons mixture is species-specific and can be used to identify a given taxon without the diagnostic castes, soldiers or imagoes Difference in the composition appears to relate with the type of habitat of specie.
Assuntos
Hidrocarbonetos/isolamento & purificação , Isópteros/fisiologia , Alcanos/química , Alcanos/isolamento & purificação , Alcenos/química , Alcenos/isolamento & purificação , Animais , Brasil , Comportamento de Escolha , Eletrofisiologia/métodos , Meio Ambiente , Cromatografia Gasosa-Espectrometria de Massas , Hidrocarbonetos/química , OdorantesRESUMO
The essential oils from leaves, aerial stems and underground organs of Aristolochia argentina Gris., a medicinal plant popularly known as "charrúa", were obtained by hydrodistillation and analyzed by GC and GC/MS. Forty-three components were identified in the oils. All parts of the plant afforded volatile oils characterized by high levels of argentilactone (57-89%) and the presence of undecatriene isomers (0.3-4.0%), these latter compounds providing the essential oils and extracts with an intense particular odor. Terpenes account for the remaining portion of the essential oils (5-29%). Bicyclogermacrene predominates in the aerial parts of the plant, whereas ishwarane is the main terpene of the subterranean organs. Argentilactone, a suspected carcinogenic compound, was also identified in a medicinal commercial tincture of A. argentina.
Assuntos
Aristolochiaceae/química , Óleos Voláteis/análise , Alcenos/química , Alcenos/isolamento & purificação , Cromatografia Gasosa , Cromatografia Gasosa-Espectrometria de Massas , Isomerismo , Lactonas/isolamento & purificação , Óleos Voláteis/química , Estruturas Vegetais/química , Plantas Medicinais/química , Terpenos/química , Terpenos/isolamento & purificaçãoRESUMO
Four new alkylene resorcinols, (Z,Z)-5-(trideca-4,7-dienyl)resorcinol (1), (Z,Z,Z)-5-(trideca-4,7,10-trienyl)resorcinol (2), (Z,Z,E)-5-(trideca-4,7,10-trienyl)resorcinol (3), and (Z)-5-(trideca-4-enyl)resorcinol (4), were isolated from the MeOH-CH(2)Cl(2) extract of Lithraea molleoides. The structures of these compounds were determined by one- and two-dimensional NMR including selective decoupling experiments. In vitro all four compounds showed strong paralyzing effects on the nematode Caenorhabditis elegans at concentrations between 6 and 50 microg/mL, whereas the activity of compounds 1 and 2 against the nematode Trichostrongylus colubriformis was less pronounced and no activity against this nematode was observed for compounds 1-4 in a rodent model.
Assuntos
Alcenos/isolamento & purificação , Anacardiaceae/química , Antinematódeos/isolamento & purificação , Caenorhabditis elegans/efeitos dos fármacos , Extratos Vegetais/química , Plantas Medicinais/química , Resorcinóis/isolamento & purificação , Trichostrongylus/efeitos dos fármacos , Alcenos/química , Alcenos/farmacologia , Animais , Antinematódeos/química , Antinematódeos/farmacologia , Argentina , Candida/efeitos dos fármacos , Candida/crescimento & desenvolvimento , Cromatografia Líquida de Alta Pressão , Larva/efeitos dos fármacos , Metanol , Conformação Molecular , Estrutura Molecular , Nematoides/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Resorcinóis/química , Resorcinóis/farmacologia , EstereoisomerismoRESUMO
The isolation of eight prenylated chalcones (cordoin, isocordoin, psi-isocordoin, derricin, lonchocarpin, 4-hydroxyderricin, 4-hydroxylonchocarpin, 4-hydroxyisocordoin) and of the flavanone and dihydrochalcone corresponding to cordoin is described. These substances are biogenetically correlated. The structures of the above mentioned substances were established through the examination and comparison of spectral data (U.V., I.R., N.M.R., M.S.) and of the chemical behaviour. Particular interest is shown by psi-isocordoin and 4-hydroxy derivatives. The latter and 4-hydroxyderricin in particular show also a marked inhibition on the growth of gram-positive bacteria.