Chemical Constituents and Evaluation of Antimicrobial and Cytotoxic Activities of Kielmeyera coriacea

Many essential oils (EOs) of different plant species possess interesting antimicrobial effects on buccal microorganisms and cytotoxic properties. EOs of Kielmeyera coriacea Mart. & Zucc. were analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The EO from leaves is rich in sesquiterpenes hydrocarbons and oxygenated sesquiterpenes. The three major compounds identified were germacrene-D (24.2%), (E)-caryophyllene (15.5%), and bicyclogermacrene (11.6%). The inner bark EO is composed mainly of sesquiterpenes hydrocarbons and the major components are alpha-copaene (14.9%) and alpha-(E)-bergamotene (13.0%). The outer bark EO is composed mainly of oxygenated sesquiterpenes and long-chain alkanes, and the major components are alpha-eudesmol (4.2%) and nonacosane (5.8%). The wood EO is mainly composed of long-chain alkanes and fatty acids, and the major components are nonacosane (9.7%) and palmitic acid (16.2%). The inner bark EO showed the strongest antimicrobial activity against the anaerobic bacteria Prevotella nigrescens (minimum inhibitory concentration-MIC of 50 µg mL−1). The outer bark and wood EOs showed MICs of 100 µg mL−1 for all aerobic microorganisms tested. The EOs presented low toxicity to Vero cells. These results suggest that K. coriacea, a Brazilian plant, provide initial evidence of a new and alternative source of substances with medicinal interest

Chemical Composition, Cytotoxic and Antimicrobial Activity of Essential Oils from Cassia bakeriana Craib. against Aerobic and Anaerobic Oral Pathogens

The chemical composition of the essential oils from leaves, bark and wood of Cassia bakeriana Craib. was determined by gas chromatography (GC) and gas chromatography–mass spectrometry (GC-MS). Alcohols, aldehydes and fatty acids were the major components in leaf and bark oil, while wood essential oil was rich in fatty acids. Terpenes such as linalool, (E)-nerolidol and phytol were present in low concentrations. The antimicrobial activity against aerobic and anaerobic oral bacteria was evaluated using the microdilution method, as was the cell viability test carried out with Vero cells. The oils from leaves and bark showed high antimicrobial activity, with minimum inhibitory concentrations between 62.5 and 125 µg·mL−1 for most of the tested bacteria, including Streptococcus mutans, the main etiological agent of dental caries. Leaves oil displayed the lowest cytotoxic effect (EC50 of 153 µg·mL−1), while wood oil exhibited the highest toxicity to Vero cells. C. bakeriana oils are thus a source of biologically active compounds against aerobic and anaerobic oral microorganisms. This study is the first report on the chemical composition, antimicrobial activity and cytotoxicity of C. bakeriana

Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: Synthesis of Copper(II) Complexes and Studies of Antibacterial and Antitumor Activities

Submitted by Sandra Infurna ([email protected]) on 2018-11-29T13:02:09Z No. of bitstreams: 1 jussarap_barbosa_etal_IOC_2010.pdf: 1564535 bytes, checksum: b114a73b75a02eda0887520d01d69d53 (MD5)Approved for entry into archive by Sandra Infurna ([email protected]) on 2018-11-29T13:12:59Z (GMT) No. of bitstreams: 1 jussarap_barbosa_etal_IOC_2010.pdf: 1564535 bytes, checksum: b114a73b75a02eda0887520d01d69d53 (MD5)Made available in DSpace on 2018-11-29T13:12:59Z (GMT). No. of bitstreams: 1 jussarap_barbosa_etal_IOC_2010.pdf: 1564535 bytes, checksum: b114a73b75a02eda0887520d01d69d53 (MD5) Previous issue date: 2010Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Universidade Federal Fluminense. Instituto de Química. Campus do Valonguinho, Niterói. RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ. Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Ceará. Depto de Fisiologia e Farmacologia. Campus do Porangabussu, Fortaleza, CE, Brasil.Universidade Federal do Paraná. Departamento de Química. Curitiba, PR, Brasil.DFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol-1) and III (by approximately 6 kcal mol-1), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)2], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)2] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60).Cálculos teóricos utilizando os funcionais B3LYP e PBE1PBE e as bases 6-31G(d) e 6-311+G(2d,p) para o sistema 3-(2-fenil-hidrazona)-naftaleno-1,2,4-triona, em solução (dmso) e em fase gasosa, evidenciaram, em ambos os casos, a maior estabilidade da forma ceto-hidrazona (rotâmeros Ia e Ib) comparada às formas enol-azo (rotâmeros IIa/IIb, por volta de 14 kcal mol-1) e III (aproximadamente 6 kcal mol-1). A natureza do substituinte no grupo fenil não influenciou a estabilidade relativa dos tautômeros. Estes resultados foram confirmados por dados espectroscópicos dos derivados HL1-HL13, sintetizados a partir da 2-hidroxi-1,4-naftoquinona e arilaminas (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). A avaliação da atividade anticâncer in vitro (contra linhagens de células cancerosas SF-295, HCT‑8, MDAMB-435 e HL-60) e bactericida (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia e Pseudomonas aeruginosa) dos compostos HL1-HL13 e dos seus respectivos complexos de cobre(II), [Cu(L1-13)2], foi avaliada. Em geral a atividade bactericida foi baixa, exceto para o derivado HL5 (R = 3-I), mais ativo do que o controle; entretanto, seu complexo não foi ativo. Por outro lado, a complexação levou, em geral, ao aumento da atividade antitumoral dos pré-ligantes. O complexo [Cu(L13)2] (R = 3-NO2) apresentou moderada citotoxicidade contra leucemia humana (HL-60)