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1 JBCS 30th AnniversaryPaulo Cezar Vieira

Editorial

Contents

Vol. 30, No. 1, January, 2019

ISSN 0103-5053JBCSJournal of the Brazilian Chemical Society

Several studies have reported the anticarcinogenic activity of conjugated linoleic acid (CLA) naturally found in the meat of ruminants (cattle, goats, and sheep) and in dairy products. The anticarcinogenic effect of the cis-9, trans-11 isomer of CLA was studied using two breast cancer (BC) cell lines, one positive (MCF-7) and the other negative (MDA-MB-231) for estrogen receptors. The nuclear magnetic resonance (NMR) metabolomics studies of intact BC cells demonstrate that CLA reduces the level of phosphocholine, a BC malignancy biomarker, in both cell lines. CLA also strongly interferes in acetone metabolism, mainly in the MCF-7 cell line, indicating an effect on fatty acid metabolism. Details are presented in the Communication Effect of cis-9, trans-11 Conjugated Linoleic Acid (CLA) on the Metabolism Profile of Breast Cancer Cells Determined by 1H HR-MAS NMR Spectroscopy by Roberta M. Maria, Wanessa F. Altei, Napoleão F. Valadares, Richard C. Garratt, Adriano D. Andricopulo, Tiago Venâncio and Luiz A. Colnago on page 3.

J. Braz. Chem. Soc.iv

8 Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy-1,4-Naphthoquinones Obtained by an Efficient Knoevenagel CondensationCibelle C. David, Antonio C. S. Lins, Tania M. S. Silva, Júlia F. Campos, Teresinha G. Silva, Gardenia C. G. Militão and Celso A. Camara

Graphical AbstractAn efficient Knoevenagel condensation between aldehydes and lawsone was performed under new conditions showing good isolated yields in a

short reaction time and simple conditions.

19 Synthesis of Spiro-Pyrrolidinyloxindoles by Oxidative Rearrangement of N-Acyltetrahydro-β-carbolines Using an Oxone/Aqueous Acetone MixtureLuisa L. Marçal and Simon J. Garden

Graphical AbstractSubstrate face controlled concerted oxidative rearrangement

of N-acyltetrahydro-β-carbolines stereoselectively gives spiropyrrolidinyloxindoles.

33 Pyrazolyl-Tetrazoles and Imidazolyl-Pyrazoles as Potential Anticoagulants and their Integrated Multiplex Analysis Virtual ScreeningAndré L. P. G. Lourenço, Percilene F. Vegi, Jéssica V. Faria, Gustavo S. P. Pinto, Maurício S. dos Santos, Plínio C. Sathler, Max S. Saito, Marcos Santana, Tatiana P. P. Dutra, Carlos R. Rodrigues, Robson Q. Monteiro, Alice M. R. Bernardino and Helena C. Castro

Graphical AbstractFourteen pyrazole compounds were synthesized and evaluated with

regard to anticoagulant and antithrombotic activities. These derivatives were investigated through an integrated multiplex analysis virtual

screening (IMA-VS) pipeline.

3 Effect of cis-9, trans-11 Conjugated Linoleic Acid (CLA) on the Metabolism Profile of Breast Cancer Cells Determined by 1H HR-MAS NMR SpectroscopyRoberta M. Maria, Wanessa F. Altei, Napoleão F. Valadares, Richard C. Garratt, Adriano D. Andricopulo, Tiago Venâncio and Luiz A. Colnago

Graphical AbstractThe effects of cis-9, trans-11 conjugated linoleic acid (CLA) on the

metabolic profile of MCF-7 and MDA-MB-231 breast cancer cells were evaluated using high-resolution magic angle spinning (HR-MAS) nuclear

magnetic resonance (NMR) spectroscopy.

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Communication

Articles

vVol. 30, No. 1, 2019

60 Analysis of Isomeric Cannabinoid Standards and Cannabis Products by UPLC-ESI-TWIM-MS: a Comparison with GC-MS and GC × GC-QMSNayara A. dos Santos, Lilian V. Tose, Samantha R. C. da Silva, Michael Murgu, Ricardo M. Kuster, Rafael S. Ortiz, Flavio A. O. Camargo, Boniek G. Vaz, Valdemar Lacerda Jr. and Wanderson Romão

Graphical AbstractAnalysis of cannabinoid standards by ultra performance liquid

chromatography coupled with electrospray ionization-quadrupole-time of flight-mass spectrometry (UPLC-ESI-QTOF-MS) and UPLC-ESI-travelling

wave ion mobility (TWIM)-MS.

71 Occurrence of Pesticides and PPCPs in Surface and Drinking Water in Southern Brazil: Data on 4-Year MonitoringSergiane S. Caldas, Jean Lucas O. Arias, Caroline Rombaldi, Lucas L. Mello, Maristela B. R. Cerqueira, Ayrton F. Martins and Ednei G. Primel

Graphical AbstractFifty-one compounds including PPCPs and pesticides were

monitored from 2011 to 2014 in drinking and surface waters in Rio Grande do Sul State.

48 Determination of Parabens in Breast Milk Samples by Dispersive Liquid-Liquid Microextraction (DLLME) and Ultra-High-Performance Liquid Chromatography Tandem Mass SpectrometryCaroline F. Grecco, Israel D. Souza, Vinicius R. Acquaro Junior and Maria E. C. Queiroz

Graphical AbstractDetermination of parabens in breast milk samples by dispersive

liquid-liquid microextraction (DLLME) and ultra-high-performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS).

81 Synthesis, Photophysical and Electrochemical Properties of Novel D-π-D and D-π-A Triphenylamino-Chalcones and β-ArylchalconesRafaela G. M. da Costa, Francisco R. L. Farias, Luis Maqueira, Carlos Castanho Neto, Leonardo S. A. Carneiro, Joseany M. S. Almeida, Camilla D. Buarque, Ricardo Q. Aucélio and Jones Limberger

Graphical AbstractA series of triphenylamino (TPA)-chalcones and β-arylchalcones,

displaying either D-π-D or D-π-A architecture, were synthesized and characterized. Photophysical and electrochemical properties of these

compounds were evaluated.

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J. Braz. Chem. Soc.vi

97 S y n t h e s i s o f 1 , 2 , 3 - Tr i a z o l e D e r i v a t i v e s o f 4,4’-Dihydroxybenzophenone and Evaluation of Their Elastase Inhibitory ActivityMaria C. F. Dias, Thiago Q. Gularte, Róbson R. Teixeira, Jorge A. N. Santos, Eduardo J. Pilau, Tiago A. O. Mendes, Antônio J. Demuner and Marcelo H. dos Santos

Graphical AbstractThe conversion of 4,4’-dihydroxybenzophenone into a series of

1,2,3-triazolic derivatives resulted in the identification of bis(4-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)benzophenone with

significant elastase inhibitory activity (IC50 = 16.6 ± 1.9 µM, inhibition constant (Ki) of 11.12 µM).

108 In vitro Evaluation of Ca, Cu, and Mg Bioaccessibility in Fresh and Dried FruitsThais T. Mingroni, Juliana Hamada, Alexsandra D. S. Xavier, Cleusa Cavalcante and Angerson N. do Nascimento

Graphical AbstractAn in vitro evaluation of Ca, Cu, and Mg bioaccessibility in fresh and

dried fruits was carried out, with results demonstrating that the dehydration process negatively affects bioaccessibility of Ca and Mg in

dried fruits.

90 Influence of Copper and Metallic Alloys on the Oxidation Reaction of Commercial Biodiesel in Mixture with Natural AntioxidantLetícia T. Chendynski, Érica S. Romagnoli, Ana Carolina G. Mantovani, Marissa Kimura, Leonardo C. Marques and Dionisio Borsato

Graphical AbstractInfluence of copper and metallic alloys on the biodiesel oxidation

reaction.

116 Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamidesManuel Pastrana Restrepo, Verónica Surmay Surmay, Elkin Galeano Jaramillo and Sara Robledo Restrepo

Graphical AbstractNovel 3,5-diiodophenethyl-benzamides as new lead compounds for the

development of new anti-parasites treatment.

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viiVol. 30, No. 1, 2019

132 Ultrasonic Extracts of Morinda citrifolia L.: Characterization of Volatile Compounds by Gas Chromatography-Mass SpectrometryDaiane B. M. Lima, Anaí L. dos Santos, Ariel O. Celestino, Nayna Sampaio, Jéssica Baldez, Maria I. S. Melecchi, Thiago R. Bjerk, Laíza C. Krause and Elina B. Caramão

Graphical AbstractSonication extraction from leaves and fruits using response surface

methodology and analysis of the extracts by gas chromatography-mass spectrometry (GC-MS) showing as major compounds: octanoic acid,

vitamin E, phytol and hydroxymethylfurfural.

140 Sample Preparation Applied to Analysis of Proteins in Cowpea Seeds (Vigna unguiculata (L.) Walp.)Thábata L. A. B. Nascimento, Tiago L. S. Coelho, Cícero A. Lopes Júnior, Samuel A. A. Sousa and Herbert S. Barbosa

Graphical AbstractOptimization of sample preparation procedure in the extraction of

cowpea proteins using the high-performance liquid chromatography (HPLC) technique as a comparative tool.

124 Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl3/Al2O3 and Analysis of Large 1H NMR Diastereotopic EffectIsabel Monreal, Mariano Sánchez-Castellanos, Karla Ramírez-Gualito, Gabriel Cuevas, Karla A. Espinoza and Ignacio A. Rivero

Graphical AbstractThe quinazolinones showed a large range diastereotopic effect that was

studied through nuclear magnetic resonance (NMR) and computational calculations.

149 Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl CompoundsValéria B. Riatto, Mauricio M. Victor, Jaqueline F. Sousa and Carla Menegola

Graphical AbstractThis work describes the first use of marine sponge Cliona varians as biocatalytic agents in the stereoselective reduction of a-keto esters

and isatin.

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J. Braz. Chem. Soc.viii

164 Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives Raíssa K. C. de Paiva, Jamerson F. da Silva, Hudieyllen A. Moreira, Osvaldo G. Pinto, Lilian T. F. M. Camargo, Plínio L. F. Naves, Ademir J. Camargo, Luciano Ribeiro and Luciana M. Ramos

Graphical AbstractThe synthesis and antimicrobial activity of thiazolidine-2,4-dione

derivatives are described. The structures of the synthesized compounds were confirmed by infrared and nuclear magnetic resonance. All

compounds were evaluated for their in vitro antibacterial activity. Density functional theory and principal component analysis were used to

discriminate the compounds.

173 On the Use of an Interpolation Approach for the Choice of Gaussian Polarization FunctionsFernando Ratuchne, Ana C. Mora, Ricardo Celeste and Albérico B. F. da Silva

Graphical AbstractThe polarization exponents (aw) vary with the atomic number (Z) for a

sequence of atoms in a row with the same valence structure. Thus, aw can be obtained by interpolation.

158 Male-Specific Volatiles Released by the Big Avocado Seed Weevil Heilipus lauri Boheman (Coleoptera: Curculionidae)Alicia A. Romero-Frías, Diana C. Sinuco and José Maurício S. Bento

Graphical AbstractVolatile organic compounds released by Heilipus lauri

(Coleoptera: Curculionidae).

180 Use of Coconut Charcoal and Menthone-Thiosemicarbazone Polymer as Solid Phase Materials for the Determination of N,N-Dimethyltryptamine, Harmine, Harmaline, Harmalol, and Tetrahydroharmine in Ayahuasca Beverage by Liquid Chromatography-Tandem Mass SpectrometrySandro Navickiene, Luis F. S. Santos, Mônica C. Santos and Alain Gaujac

Graphical AbstractEvaluation of efficiency of coconut charcoal and menthone-

thiosemicarbazone as alternative solid phase extraction adsorbent for the determination of alkaloids in ayahuasca beverage.

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ixVol. 30, No. 1, 2019

198 A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative ActivityIara S. Santos, Fabiana S. Guerra, Lucas F. Bernardino, Patrícia D. Fernandes, Lidilhone Hamerski and Bárbara V. Silva

Graphical AbstractIt was synthesized a new isatinspirooxazine derivative with an half

maximal inhibitory concentration (IC50) = 0.34 μM, more potent than the reference drug, doxorubicin (IC50 = 1.88 µM), in breast cancer line

MDA-MB231.

188 Synthesis, in silico Study and Antimicrobial Evaluation of New SelenoglycolicamidesHelivaldo D. S. Souza, Roxana P. F. de Sousa, Bruno F. Lira, Raquel F. Vilela, Nathalie H. P. B. Borges, José P. de Siqueira-Junior, Edeltrudes O. Lima, Jeane U. G. Jardim, Gracielle A. T. da Silva, José M. Barbosa-Filho and Petrônio F. de Athayde-Filho

Graphical AbstractThe organoselenium compounds presented are prominent in medicinal

chemistry; due to the increase of resistant fungi and bacteria, novel organoselenium compounds have been investigated as potent

antimicrobials.

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Short Reports