Flavonoides de Dahlstedtia grandiflora

Orientadora: Profa. Dra. Beatriz Helena Lameiro de Noronha Sales MaiaDissertação (mestrado) - Universidade Federal do Paraná, Setor de Ciências Exatas, Programa de Pós-Graduação em Química. Defesa : Curitiba, 09/07/2015Inclui referências: p. 105-115Área de concentração: Química orgânicaResumo: Neste trabalho foi realizado o fracionamento do extrato em diclorometano (DCM) das raízes de Dahlstedtia grandiflora que resultou na identificação de 42 compostos sendo 5 chalconas, 5 flavanonas, 5 flavonas, 5 flavonóis, 5 derivados de dibenzoilmetano, 3 retrochalconas, 1 diidroretrochalcona, 3 rotenoides, 7 biflavonoides e 3 outras substâncias. As estruturas dos compostos foram determinadas utilizando técnicas espectroscópicas de RMN 1D e 2D e espectrometria de massas, todos os compostos identificados são descritos pela primeira vez para esta espécie vegetal, sendo que doze das substâncias identificadas são inéditas na literatura, três são inéditas como produto natural mas conhecidas como produto de síntese e outras doze nunca haviam sido relatadas no gênero Dahlstedtia. Os extratos em éter de petróleo, diclorometano e metanol das raízes de D. grandiflora foram comparados quanto à composição química utilizando um cromatógrafo de fase líquida de alta eficiência acoplado a um detector de arranjo de fotodiodos e concluiu-se que os extratos em éter de petróleo e diclorometano possuem cromatogramas sobreponíveis, indicando que a composição química dos extratos é semelhante, porém, o extrato metanólico apresentou um perfil diferente dos outros. O extrato em DCM apresentou atividade significativa contra duas linhagens de células in vitro, câncer de mama e de rim, além de menor toxicidade em relação às células normais quando comparado ao controle positivo (doxorrubicina), sugerindo que a espécie estudada possui potencial como um agente anti-câncer. A avaliação da atividade antimicrobiana dos extratos não apresentou nenhuma atividade significativa. Palavras chaves: Dahlstedtia grandiflora; Fitoquímica; Flavonoides prenilados.Abstract: The phytochemical study of roots from Dahlstedtia grandiflora lead to the identification of 42 substances: five chalcones, five flavanones, five flavones, five flavonols, five derivatives from dibenzoylmethane, three retrochalcones, one dihydroretrochalcone, three rotenoids, seven biflavonoids and three other substances. The structures were determined using 1D and 2D NMR and mass spectrometry techniques. All the identified substances are being described for the first time in this species, twelve substances are reported for the first time, three are new as natural compounds but known as synthesis product and twelve are reported in the genus Dahlstedtia for the first time in the literature. The petroleum ether, dichloromethane and methanol extracts of roots of D. grandiflora were compared with each other regarding the chemical composition using high performance liquid chromatography coupled with a photodiode array detector and was observed that the petroleum ether and dichloromethane extracts have very similar chromatogram, which indicates that the chemical composition of both extracts is very alike. On the other hand, the methanolic extract exhibited a different profile from the others. The antiproliferative assays showed that the dichloromethane extract presented potent activity against cell lines human of breast and kidney and revealed less toxicity relative to normal cells compared to positive control (doxorubicin). These results indicate that this species have potential as an anti-cancer agent. The evaluation of the antimicrobial activity of the extracts did not show significant activity. Keywords: Dahlstedtia grandiflora, Phytochemistry, Prenylated flavonoids

1JCH Coupling in Benzaldehyde Derivatives: Ortho Substitution Effect

The natural J-coupling (NJC) method is applied to analyze the Fermi contact contribution of the NMR spin–spin coupling constant decomposing this contribution in terms of natural localized molecular orbitals. We investigated the influence of the basis set on the NJC analysis for the formyl group coupling constant (1JCHf) of benzaldehyde derivatives. NJC and other NBO analyses, like steric and natural Coulombic energy, were chosen to explain the influence of electron-donating and electron-withdrawing groups on 1JCHf for some substituted benzaldehydes (Me, OH, OMe, F, Cl, Br, I, and NO2). For the ortho derivatives, electronegative substituents near the C–Hf bond increase the 1JCHf coupling. This effect could be related to an increase in formyl carbon s character and changes in the carbon and hydrogen natural charges. This indicates that the substituents in ortho have a proximity effect on 1JCHf coupling mainly of electrostatic origin instead of the expected hyperconjugative interactions9114941503CAPES - Coordenação de Aperfeiçoamento de Pessoal e Nível SuperiorCNPQ - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPESP – Fundação de Amparo à Pesquisa Do Estado De São PauloNÃO TEMNÃO TEM2015/08541-6; 2017/20890-

VOLATILE CONSTITUENTS OF Aristolochia trilobata

Analysis of the volatile fraction of Aristolochia trilobata stem led to the identification of 6-methyl-5-hepten-2-yl acetate (23.31 ± 0.28%), limonene (15.43 ± 0.030%), linalool (8.70 ± 0.29%), p-cymene (7.81 ± 0.12%), bicyclogermacrene (4.21 ± 0.11%), and spathulenol (4.17 ± 0.14%) as the major constituents of the essential oil. Linalool (29.51 ± 0.49%), 6-methyl-5-hepten-2-ol (19.54 ± 0.82%), 6-methyl-5-hepten-2-yl acetate (8.92 ± 0.16%), and a-terpineol (4.62 ± 0.05%) were identified as major constituents of the hydrolate. The compound 6-methyl-5-hepten-2-yl acetate was isolated for the first time from this plant and was identified as the major component of the volatile fraction

Artigo doi number VOLATILE CONSTITUENTS OF Aristolochia trilobata L. (Aristolochiaceae): A RICH SOURCE OF SULCATYL ACETATE

publicado na web em 17/06/2014 Analysis of the volatile fraction of Aristolochia trilobata stem led to the identification of 6-methyl-5-hepten-2-yl acetate (23.31 ± 0.28%), limonene (15.43 ± 0.030%), linalool (8.70 ± 0.29%), p-cymene (7.81 ± 0.12%), bicyclogermacrene (4.21 ± 0.11%), and spathulenol (4.17 ± 0.14%) as the major constituents of the essential oil. Linalool (29.51 ± 0.49%), 6-methyl-5-hepten-2-ol (19.54 ± 0.82%), 6-methyl-5-hepten-2-yl acetate (8.92 ± 0.16%), and a-terpineol (4.62 ± 0.05%) were identified as major constituents of the hydrolate. The compound 6-methyl-5-hepten-2-yl acetate was isolated for the first time from this plant and was identified as the major component of the volatile fraction

CONSTITUENTS OF ESSENTIAL OIL AND HYDROLATE OF LEAVES OF Campomanesia viatoris LANDRUM

The chemical composition of the essential oil and hydrolates of Campomanesia viatoris Landrum were investigated by gas chromatography/mass spectrometry (GC/MS) and a GC flame ionization detector (GC-FID). The major constituents were tasmanone (70.50, essential oil; 74.73%, hydrolate), flavesone (12.77, essential oil; 12.24%, hydrolate) and agglomerone (6.79, essential oil; 10.84%, hydrolate). Tasmonone was isolated and its structure was characterized by spectrometric analysis, specifically 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS). These findings supports the quimiotaxonomic relationship with Campomanesia and Eucalyptus genera

ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.

Submitted by Ana Maria Fiscina Sampaio ([email protected]) on 2015-05-19T19:20:02Z No. of bitstreams: 1 Dutra LM ant-kaurane diterpenes.pdf: 499055 bytes, checksum: 997b925a2d8b2fbcc92a1bb4c34cbb80 (MD5)Approved for entry into archive by Ana Maria Fiscina Sampaio ([email protected]) on 2015-05-19T19:36:45Z (GMT) No. of bitstreams: 1 Dutra LM ant-kaurane diterpenes.pdf: 499055 bytes, checksum: 997b925a2d8b2fbcc92a1bb4c34cbb80 (MD5)Made available in DSpace on 2015-05-19T19:36:45Z (GMT). No. of bitstreams: 1 Dutra LM ant-kaurane diterpenes.pdf: 499055 bytes, checksum: 997b925a2d8b2fbcc92a1bb4c34cbb80 (MD5) Previous issue date: 2014Federal University of Sergipe. Department of Chemistry. São Cristóvão, SE, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilHospital São Rafael. Center of Biotechnology and Cell Therapy. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Center of Biotechnology and Cell Therapy. Salvador, BA, BrasilHospital São Rafael. Center of Biotechnology and Cell Therapy. Salvador, BA, BrasilFederal University of Sergipe. Department of Chemistry. Itabaiana, SE, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilThis work describes a novel ent-kaurane diterpene, ent-3ß-hydroxy-kaur-16-en-19-al along with five known ent-kaurane diterpenes, ent-3ß,19-dihydroxy-kaur-16-eno, ent-3ß-hydroxy-kaur-16-eno, ent-3ß-acetoxy-kaur-16-eno, ent-3ß-hydroxy-kaurenoic acid and kaurenoic acid, as well as caryophyllene oxide, humulene epoxide II, ß-sitosterol, stigmasterol and campesterol from the stem bark of Annona vepretorum Mart. (Annonaceae). Cytotoxic activities towards tumor B16-F10, HepG2, K562 and HL60 and non-tumor PBMC cell lines were evaluated for ent-kaurane diterpenes. Among them, ent-3ß-hydroxy-kaur-16-en-19-al was the most active compound with higher cytotoxic effect over K562 cell line (IC50 of 2.49 µg/mL) and lower over B16-F10 cell line (IC50 of 21.02 µg/mL)

A New Source of (R)-Limonene and Rotundifolone from Leaves of Lippia pedunculosa (Verbenaceae) and their Trypanocidal Properties

Submitted by Ana Maria Fiscina Sampaio ([email protected]) on 2017-08-17T17:05:21Z No. of bitstreams: 1 Menezes L A new source....pdf: 240902 bytes, checksum: 6fac98c7e75cc4d38f9095f35e677c25 (MD5)Approved for entry into archive by Ana Maria Fiscina Sampaio ([email protected]) on 2017-08-17T17:17:45Z (GMT) No. of bitstreams: 1 Menezes L A new source....pdf: 240902 bytes, checksum: 6fac98c7e75cc4d38f9095f35e677c25 (MD5)Made available in DSpace on 2017-08-17T17:17:45Z (GMT). No. of bitstreams: 1 Menezes L A new source....pdf: 240902 bytes, checksum: 6fac98c7e75cc4d38f9095f35e677c25 (MD5) Previous issue date: 2014FAPITEC/SE (Editais No 07/2009 and 10/2009), FAPESB, CNPq, FINEP, UFPR and CAPESUniversidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, BrasilUniversidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Universidade do Estado da Bahia. Departamento de Ciências da Vida. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Universidade do Estado da Bahia. Departamento de Ciências da Vida. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, BrasilUniversidade Federal do Paraná. Departamento de Química. Curitiba, PR, BrasilUniversidade Federal do Paraná. Departamento de Química. Curitiba, PR, BrasilUniversidade Federal de Sergipe. Departamento de Química. Itabaiana, SE, BrasilInvestigation by GC-FID and GC-MS of the essential oil (LPOE) from the leaves of Lippia pedunculosa revealed, as the major compounds, the monoterpenes rotundifolone (71.7%) and (R)-limonene (21.8%). These two compounds and the minor constituent piperitenone (1.2%) were also isolated from the leaves and identified by spectrometric analysis. LPOE and isolated compounds were evaluated for their trypanocidal activity against epimastigote and trypomastigote forms of Trypanosoma cruzi. Significant results with IC50 values lower than 34.0 g.mL-1 were observed against these forms of T. cruzi for LPOE and isolated compounds. Rotundifolone was the most active compound with an IC50 lower than 10.0 g.mL-1 for both forms of T. cruzi. The effects of LPOE and isolated compounds were also evaluated in cultures of macrophages infected with T. cruzi. Treatment with (R)-limonene and rotundifolone caused a moderate reduction in the percentage of macrophages infected by T. cruzi and in the number of intracellular parasites at concentrations non-toxic to macrophages