Centro de Ciências Exatas e Tecnológicas
URI permanente desta comunidadehttps://locus.ufv.br/handle/123456789/9791
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Resultados da Pesquisa
Item Isolamento e avaliação da atividade nematicida de constituintes químicos de Mucuna cinerea contra Meloidogyne incognita e Heterodera glycine(Química Nova, 2003-05) Demuner, Antonio Jacinto; Barbosa, Luiz Cláudio de Almeida; Nascimento, Jeferson Chagas do; Vieira, Jessy James; Santos, Maria Amelia dosPhytochemical investigation of the aerial parts and roots of Mucuna cinerea led to the isolation of a mixture of fatty acids, triacylglicerols, b-sitosterol, stigmasterol, stigmasterol glucoside, daucosterol, asperglaucide (4) and the isoflavonoids prunetin (1), genistein (2), medicarpin (3), daidzein (5), 7-O-a-glycopiranosyl daidzein (6). An in vitro bioassay was carried out with compounds 1-4, at the concentration of 50 and 5 mg mL-1 against the phytonematodes M. incognita and H. glycines. Although the four compounds showed some nematocidal property, the most active was (1), causing 70% mortality of M. incognita at the concentration of 50 mg mL-1.Item Síntese de novos herbicidas derivados do 1, 2a, 4a, 5- tetrametil- 8- oxabiciclo[ 3. 2. 1] oct- 6- en- 3- ona(Química Nova, 2004-03) Barbosa, Luiz Cláudio de Almeida; Maltha, Célia Regina Álvares; Demuner, Antônio Jacinto; Filomeno, Claudinei Andrade; Silva, Antônio Alberto daIn this paper we report the synthesis of biologically active compounds through a [3+4] cycloaddition reaction to produce the main frame structure, followed by several conventional transformations. The 1,2a,4a,5-tetramethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (11) obtained from a [3+4] cycloaddition reaction was converted into 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8 -oxabicyclo[3.2.1]octan-3-one (13) in 46% yield. This was further converted into the alcohols 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (14), 1,2a,4a,5-tetramethyl-6,7-exo-isopropylidenedioxi-8 -oxabicyclo[3.2.1]octan-3b-ol (15), 1,2a,4a,5-tetramethyl-3-butyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (17), 1,2a,4a,5-tetramethyl-3-hexyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (18) and 1,2a,4a,5-tetramethyl-3-decyl-6,7-exo-isopropylidenedioxi-8-oxabicyclo[3.2.1]octan-3 a-ol (19). Dehydration of 17, 18 and 19 with thionyl chloride in pyridine resulted in the alkenes 20, 21 and 22 in ca. 82% - 89% yields from starting alcohols. The herbicidal activity of the compounds synthesized was evaluated at a concentration of 100 µg g-1. The most active compound was 21 causing 42,7% inhibition against Cucumis sativus L.Item Preparation and phytotoxicity of sorgoleone analogues(Química Nova, 2001-11) Barbosa, Luiz Cláudio de Almeida; Ferreira, Maria Lúcia; Demuner, Antonio Jacinto; Silva, Antonio Alberto da; Pereira, Rita de Cássia3,5-Dimethoxybenzylic alcohol was converted into the 2-acetoxy-5-methoxy-3-(pent-1-yl)-1,4-benzoquinone (12), in seven steps, with an overall yield of 14.6%. The natural quinone sorgoleone (1) was isolated from Sorghum bicolor and converted into the corresponding quinone (13) having a saturated side chain. The selective effects of these compounds (1, 12 and 13), at the dose of 5.6 mg of a.i./ g of substrate, on the growth of Cucumis sativus, Lactuca sativa, Desmodium tortuosum, Hyptis suaveolens and Euphorbia heterophylla were evaluated. All three compounds caused some inhibition on the root growth of the test plants (0.0-69.19%) with the aerial parts less affected. The results showed that the triene unit of the sorgoleone side chain is not essential for the phytotoxicity and also the synthetic quinone was as active as the natural product.Item Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico(Química Nova, 2003-09) Barbosa, Luiz Cláudio de Almeida; Demuner, Antônio Jacinto; Maltha, Célia Regina Álvares; Silva, Patrícia Silvana da; Silva, Antônio Alberto daSeveral compounds related to helminthosporic acid (3) were synthesized via the [3+4] cycloaddition. The reaction of 3-hydroxymethyl-2-methylfuran (12) with 1,1,3,3-tetrabromo-4-methylpentan-2-one (13) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (8) (37%) and 7-hydroxymethyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (14) (12%), which were converted into 7-formyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (16) (32% from 8) and 7-formyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (18) (40% from 14), respectively. Reduction of (8) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6 -en-3a-ol (11) (63% from 8) and 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3 b-ol (15) (30% from 8). The 4a-isopropyl-1a-methyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-7-oic acid (19) was obtained by oxidation of (16) (78%). The results of biological tests are described in details. The best result was observed for compound (15) that caused 76% inhibition on the root growth of D. tortuosum.Item Síntese e avaliação da atividade fitotóxica de lactonas derivadas do 2, 4- dimetil- 8- oxabiciclo[ 3. 2. 1]- oct- 6- en- 3- ona(Química Nova, 2002-04) Barbosa, Luiz Cláudio de Almeida; Maltha, Célia Regina Álvares; Borges, Eduardo Euclides LimaThe alkene 2,4-dimethyl-8-oxabicyclo[3.2.1]-oct-6-en-3-one (3) was converted to 1,3,10-trimethyl-8-oxabicyclo[5.3.0]-dec-3-ene-2,9-dione (7) and 1,3-dimethyl-8-oxabicyclo[5.3.0]-dec-3-ene-2,9-dione (8) with a 55% overall yield in both cases. Lactones (7) and (8) were converted in two steps to 1,3,4-trimethyl-13-methylene-6-oxatricyclo[8.3.0.0 3,7]-trideca-2,5,12-trione (12) (63%) and 1,3-dimethyl-13-methylene-6-oxatricycle[8.3.0.0 3,7]-trideca-2,5,12-trione (13) (45% from 8). The effect of lactones (7), (8), (12), (13) and the intermediates (5) and (6), at the concentration of 250 mg mL-1, on the growth of Cucumis sativus L. and Sorghum bicolor L. was evaluated. The best results were observed for lactone (13) that caused 100% inhibition on the root growth of C. sativus and lactone (12) that inhibited 90% of the root growth for S. bicolor.Item Determinação de constituintes químicos em madeira de eucalipto por Pi-CG/EM e calibração multivariada: comparação entre redes neurais artificiais e máquinas de vetor suporte(Química Nova, 2011) Nunes, Cleiton Antônio; Lima, Claudio Ferreira; Barbosa, Luiz Cláudio de Almeida; Colodette, Jorge Luiz; Fidêncio, Paulo HenriqueMultivariate models were developed using Artificial Neural Network (ANN) and Least Square - Support Vector Machines (LS-SVM) for estimating lignin siringyl/guaiacyl ratio and the contents of cellulose, hemicelluloses and lignin in eucalyptus wood by pyrolysis associated to gaseous chromatography and mass spectrometry (Py-GC/MS). The results obtained by two calibration methods were in agreement with those of reference methods. However a comparison indicated that the LS-SVM model presented better predictive capacity for the cellulose and lignin contents, while the ANN model presented was more adequate for estimating the hemicelluloses content and lignin siringyl/guaiacyl ratio.Item Harvest time on the content and chemical composition of essential oil from leaves of guava(Ciência Rural, 2016-10) Silva, Elizabeth Aparecida Josefi da; Silva, Vanessa Paula da; Alves, Cassia Cristina Fernandes; Alves, José Milton; Souchie, Edson Luiz; Barbosa, Luiz Cláudio de AlmeidaThe essential oil plants contents can be affected by several factors. For example, in certain plants, collection time has been observed to affect the content and chemical composition of the essential oil obtained from the plant. The objective of this study was to evaluate the effect of collection time on the content and chemical composition of the essential oil from guava ( Psidium guajava L.) leaves. Leaves were collected at different times of the day and the content and chemical composition of their essential oil was determined. Collection time did not qualitatively affect the chemical composition of the essential oil. However, concentration of certain substances in the oil, such as α-humulene and trans-caryophyllene, did significantly vary at different collection times. The main constituents of the essential oil of Psidium guajava are limonene (2.2-4.4%), trans-caryophyllene (18.1-17.1%), α-humulene (26.3-20.4%), aromadendrene (7.6-12.2%), α-selinene (7.3-11.3%), caryophyllene oxide (3.7-3.3%), humulene epoxide II (4.1-1.9%), and selin-11-en-4α-ol (7.2-11.1%). Leaves collected at 7:00 AM had higher essential oil production, with a content of 0.38% (d.b.), whereas leaves collected at 7:00 PM had lower essential oil production, 0.24% (d.b.). Chemical analysis showed that sesquiterpene compounds represented the highest concentration (62.0%), and monoterpenoids and monoterpenes represented the lowest concentrations (1.1 and 2.2%, respectively). Chemical classes that underwent major changes with respect to collection time were monoterpenes, sesquiterpenes, and sesquiterpenoids (2.2-4.4%, 63.8-61.7%, and 15.9-13.2%, respectively).Item A pentacyclic triterpene from Maytenus imbricata: structure elucidation by X-ray crystallography(Structural Chemistry, 2006-02) Pimenta Jr., Alécio Antonio; Silva, Sílvia Ribeiro de Souza e; Silva, Grácia Divina de Fátima; Barbosa, Luiz Cláudio de Almeida; Ellena, Javier; Doriguetto, Antonio CarlosA pentacyclic triterpene, 3β,30-dihydroxy-lup-20(29)-ene, was isolated from the powder extract of Maytenus imbricata. The structure and stereochemistry of the compound were established by spectroscopic techniques and unambiguously determined by single crystal X-ray crystallography. The crystal structure shows one molecule in the asymmetric unit. The crystal packing is stabilized by O–H···O intermolecular hydrogen bonds, which give rise to infinite helical chains along the c unit cell axis. The intra-molecular geometry was analyzed using MOGUL, a knowledge base of molecular geometry derived from the Cambridge Structural Database (CSD).Item A comparative study on the crystal structure of bicycle analogues to the natural phytotoxin helminthosporins(Journal of Molecular Structure, 2016-02-05) Barbosa, Luiz Cláudio de Almeida; Teixeira, Robson Ricardo; Nogueira, Leonardo Brandão; Maltha, Celia Regina Alvares; Doriguetto, Antônio Carlos; Martins, Felipe TerraHerein we described structural insights of a series of analogues to helminthosporin phytotoxins. The key reaction used to prepare the compounds corresponded to the [3 + 4] cycloaddition between the oxyallyl cation generated from 2,4-dibromopentan-3-one and different furans. Their structures were confirmed upon IR, NMR and X-ray diffraction analyses. While bicycles 7, 8 and 9 crystallize in the centrosymmetric monoclinic space group P21/c, compound 10 was solved in the noncentrosymmetric orthorhombic space group P212121. The solid materials obtained were shown to be racemic crystals (7, 8, 9) or racemic conglomerate (10). In all compounds, there is formation of a bicycle featured by fused tetrahydropyranone and 2,5-dihydrofuran rings. They adopt chair and envelope conformations, respectively. Crystal packing of all compounds is stabilized through C–H•••O contacts. Conformational aspects as well as similarities and differences among the crystal structures of the synthesized analogues are discussed.Item Phytotoxic effectes of metabolites from Alternaria euphorbiicola against its host plant Euphorbia heterophylla(Química Nova, 2013-05-24) Varejão, Eduardo Vinícius Vieira; Demuner, Antônio Jacinto; Barbosa, Luiz Cláudio de Almeida; Barreto, Robert WeingartA bioassay-guided fractionation of culture filtrates of the fungus Alternaria euphorbiicola, a pathogen of the weed Euphorbia heterophylla, led to the isolation of anhydromevalonolactone (1), tyrosol (2), (R)-( - )-mevalonolactone (3), and cycloglycylproline (4). When tested on the punctured leaves of the host plant, these compounds produced bleached lesions with dark brown margins at concentrations as low as 80 µM. When tested on the leaves of other relevant weeds, only cycloglycylproline showed selective activity against E. heterophylla. This is the first report on the isolation of phytotoxins from A. euphorbiicola and on the phytotoxicity of anhydromevalonolactone, (R)-( - )-mevalonolactone, and cycloglycylproline.