Luiz Claudio de Almeida Barbosa
@ufmg.br
Department of Chemistry
Instituto de Ciências Exatas - Universidade Federal de Minas Gerais
LUIZ CLÁUDIO de Almeida Barbosa, natural de Além Paraíba, MG, é graduado em Química e mestre em Agroquímica pela Universidade Federal de Viçosa (UFV) – com aperfeiçoamento em Química de Produtos Naturais pela Universidade Federal de Minas Gerais (UFMG) – e Ph.D. na área de Síntese Orgânica pela Universidade de Reading (Inglaterra). Realizou estágio de pós-doutoramento na Universidade de Oxford (Inglaterra). Foi Professor Titular do Departamento de Química da UFV até 2012, quando se tornou professor da UFMG. Pesquisador do CNPq desde 1992, publicou mais de 270 artigos científicos. É autor do livro-texto INTRODUÇÃO À QUÍMICA pela Pearson Education do Brasil (. Publicou também pela Editora UFV “Os Pesticidas, o Homem e o Meio Ambiente” e “Espectroscopia no Infravermelho na Caracterização de Compostos Orgânicos”; pela Editora Letramento o livro Nitrogênio: o sétimo elemento.
EDUCATION
PhD - University of Reading (1991); Post-doctoral research Fellow, University of Oxford (2009)
RESEARCH INTERESTS
Organic Synthesis; Natural Products; Essential Oils; History of Chemistry.
Scopus Publications
Scholar Citations
Scholar h-index
Scholar i10-index
Scopus Publications
Seyyed Khalil Hosseinihashemi, Sayed Khosrow Hosseinashrafi, Mehrnoush Kelkian, Zohreh Shafighi, and Luiz Claudio Almeida Barbosa
BioResources
The essential oils extracted from the cone scale (CS), seed (SE), and thin branch with leaf (BL) of Taxodium distichum harvested during the winter season were analyzed by gas chromatography-mass spectrometry. Up to 37 components were identified, accounting for more than 96% of the total oil volume in all samples. Monoterpenes (CS 93.4%, SE 85.2%, and BL 72.8%) represented the major constituents of the essential oils, followed by smaller quantities of sesquiterpenoids. Monoterpene hydrocarbons (MH) dominated, with limonene (CS 56.5%, SE 50.5%, and BL 43.8%) and α-pinene (CS 31.7%, SE 26.1%, and BL 16.2%) being the main constituents. Representative minor constituents in the CS oil are camphene (1.3%) and bornyl acetate (2.6%); in the SE oil, β-myrcene (1.7%) and bornyl acetate (5.1%) were found; and in BL essential oil, β-myrcene (3.1%) and bornyl acetate (6%). Sesquiterpene hydrocarbons (CS 4.6%, SE 7.8%, and BL 12.9%) were the other major subclasses of components, with caryophyllene (CS 4.1%, SE 6.8%, and BL 9.3%) as the main constituent. The only oxygen-containing sesquiterpene found was caryophyllene oxide (CS 1.5%, SE 5.5%, and BL 8.3%). The compounds could be of great interest in food, cosmetics, and pharmaceutical applications.
Sweta Roy, Jaime A. M. Acosta, Milandip Karak, Isabela Ramirez-Velez, Kohei Torikai, Dacheng Ren, and Luiz C. A. Barbosa
American Chemical Society (ACS)
Detrimental biofilms of bacterial pathogens cause chronic infections with a high-level tolerance to antibiotics. To identify new control agents, we synthesized and tested a total of 14 tetronamides (including 5 new compounds) and 6 denigrin intermediates on the model species Escherichia coli. At a concentration of 50 μg/mL, two tetronamides and two methylated denigrins exhibited significant inhibitory effects against biofilm formation of E. coli RP437, e.g., by 60 and 94%, respectively. Structural analysis of the tested compounds revealed that p-methoxybenzylidene and p-methoxyphenethyl moieties of denigrins are important for biofilm inhibition, while the former group is also essential to the activity against quorum sensing (QS) via AI-2. Specifically, tetramethyldenigrin B has strong inhibitory effects against both E. coli biofilm formation and AI-2-mediated QS and thus provides a promising lead structure for designing better control agents. Consistently, tetramethyldenigrin B also showed inhibitory activity against biofilm formation of uropathogenic E. coli. Together, these findings provide new insights for the rational design of novel biofilm and QS inhibitors.
Jodieh Oliveira Santana Varejão, Luiz Cláudio Almeida Barbosa, Eduardo Vinícius Vieira Varejão, Nidia Magally Galdámez Coreas, Vinicius Stefano Santos Morais, André Mauricio de Oliveira, Rosimeire Coura Barcelos, Célia Regina Álvares Maltha, and Luzia Valentina Modolo
Springer Science and Business Media LLC
Paula Tatiana Lopes Seixas, Antonio Jacinto Demuner, Luiz Claudio Almeida Barbosa, Cristiane Isaac Cerceau, Daiane Einhardt Blank, Marcelo Henrique Dos Santos, Elizeu de Sá Farias, and Marcelo Coutinho Picanço
Wiley
Dayana A. Rodrigues, Antonio J. Demuner, Luiz C. A. Barbosa, Gustavo A. M. Pereira, José D. Fabris, Félix G. de Siqueira, Márcio T. Pereira, Abelardo Silva Junior, and Otávio V. Carvalho
Springer Science and Business Media LLC
Seyyed Khalil Hosseinihashemi, Fatemeh Barzegari, Hadi Baseri, and Luiz Claudio Almeida Barbosa
Informa UK Limited
The composition and antioxidant activity of the essential oil obtained from the female cones and leaves of Cupressus arizonica were assessed using the DPPH assay. The total oil yields obtained through hydrodistillation from the female cones and leaves were 1.9% (v/w) and 0.65% (v/w), respectively. The GC-MS chemical analysis of the oils from the female cones and leaves resulted in the identification of 17 and 45 compounds, respectively. Moreover, the essential oils obtained from C. arizonica female cones were predominantly composed of monoterpene hydrocarbons, with α-pinene being the most abundant component at 72.20%. In contrast, the oil extracted from the leaves was rich in oxygenated monoterpenes, particularly umbellulone (17.33%). The oils extracted from the leaves exhibited remarkable DPPH radical scavenging activity, displaying a value of 95.6%. This value was comparable to that of ascorbic acid (99.6%) and BHT (96.9%) when tested at a concentration of 59 mg/mL.
Júnio G. Silva, Tatiane F. Borgati, Samuel M.G. Lopes, Niels Heise, Sophie Hoenke, René Csuk, and Luiz C.A. Barbosa
Elsevier BV
Gottimukkala Rambabu, Yarragudi Bathal Reddy Kiran, Yadamari Tarakeswar, Shaik Ibrahim Khalivulla, Luiz Claudio Almeida Barbosa, and Vijayaparthasarathi Vijayakumar
Wiley
An efficient and reusable green catalyst for the synthesis of β-aminocarbonyl compounds has been developed. In this new and greener approach, β-aminocarbonyl compounds (1a-1r) were obtained by Montmorillonite K10 clay catalyzed reaction of aryl amines, aliphatic/aromatic aldehydes and β-ketoesters. Molecular docking investigations were performed for all compounds (1a-1r) with the proteins PDB ID: 1JIJ and 1KZN for S. aureus and E. coli, respectively. For all compounds good to strong interactions with the active sites were observed. The biological activities of β-aminocarbonyl compounds were further assessed for their antibacterial and antioxidant activities. The results confirmed that β-aminocarbonyl compounds could be further developed into new drugs with potent antibacterial and antioxidant activities.
Júnio G. Silva, Amanda S. de Miranda, Fyaz M.D. Ismail, and Luiz C.A. Barbosa
Elsevier BV
Thaise C. Geremias, Marcos A. Batistella, Ricardo R. S. Magini, Selene M. A. Guelli U. de Souza, Cesar V. Franco, Luiz C. A. Barbosa, Ulisses A. Pereira, Juan P. Hinestroza, Andréa L. Pimenta, and Antônio A. Ulson de Souza
Wiley
Thais A. Moreira, Isabel V. Antolínez, Wagner O. Valença, Sweta Roy, Isabela Ramirez, Luiz C.A. Barbosa, and Dacheng Ren
Elsevier BV
Ye Zheng, Jaime A. Martinez‐Acosta, Mohammed Khimji, Luiz C. A. Barbosa, Guy J. Clarkson, and Martin Wills.
Wiley
Katalin C. Geöcze, Luiz C.A. Barbosa, Cláudio F. Lima, Mário G. Ferruzzi, Paulo H. Fidêncio, Helena M.P. Sant’ana, and Flaviano O. Silvério
Elsevier BV
Abstract Caryocar brasiliense Camb. is the best-known fruit of the Brazilian Cerrado. This fruit has yellow pulp containing several carotenoids and has a strong and exotic flavor; however, its composition may vary due to factors such as genotypic differences, seasonality, cultivation forms, climatic and soil characteristics, maturation stage, type of storage and processing. Therefore, the present study aimed to determine the chemical composition of carotenoids with pro-vitamin A activity of C. brasiliense fruits from 18 Brazilian municipalities. The vitamin A value expressed as μg Retinol Activity Equivalent (RAE) in the fresh fruit and carotenoid profile were determined by high-performance liquid chromatography coupled to a diode array detector (HPLC- DAD). The main carotenoids found were β-cryptoxanthin and β-carotene. High variation in vitamin A values were observed, especially among the fruits from Gato-Preto-MA with (1.4 µg RAE/100 g fresh fruit) and Januaria-MG (719 µg RAE/100 g fresh fruit). PC1 and PC2 explored about 98.80% of the data variance in the multivariate analysis, Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA) and organized the C. brasiliense fruits in three clusters by decreasing vitamin A values. The fruits from the municipalities of Januaria, Japonvar, Arinos, Salinas and Montes Claros showed higher carotenoid content.
Y. B. Kiran, G. Rambabu, V. Vijayakumar, and L. C. A. Barbosa
Pleiades Publishing Ltd
A green acetic acid-mediated synthesis of kojic acid derivatives through a multicomponent reaction (MCR) has been developed. This new protocol is simple and efficient; it involves a one-pot reaction of equimolar amounts of kojic acid, aromatic aldehydes, and several active methylene compounds at 90°C in 3 h and results in the formation of a wide range of kojic acid derivatives with high yields. Furthermore, the formation of acyclic product when only kojic acid reacted with benzaldehyde under similar reaction conditions has been explored.
Amalyn Nain‐Perez, Luiz C. A. Barbosa, Maria H. Araujo, João P. A. Martins, Jacqueline A. Takahashi, Geane Oliveira, Renata Diniz, Lucie Heller, Sophie Hoenke, and René Csuk
Wiley
Lauro J.C. da Silva, Léia A. Alves, Valdenizia R. Silva, Luciano S. Santos, Daniel P. Bezerra, Milena B.P. Soares, Antonio C. Doriguetto, Luiz C.A. Barbosa, Jeferson C. do Nascimento, Guadalupe E.L. Macedo,et al.
Elsevier BV
Abstract A new tropane alkaloid 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane (1) was isolated from the twigs of Erythroxylum macrocalyx Mart. (Erythroxylaceae), along with the known substances: 6β,7β-dibenzoyloxy-3α-hydroxytropane (2), 6β,7β-dihydroxy-3α-(phenylacetoxy)tropane (3), 3α-benzoyloxy-6β,7β-dihydroxytropane (4), 6β-benzoyloxy-3α-(4-hydroxy-3,5-dimetoxybenzoyloxy)tropane (5), ombuin-3-rutinoside-5-glucoside (6), lupeol (7), taraxerol (8) and lupenone (9). Compounds 1 and 2 were also isolated from the leaves. The structures were established by analyses of 1D- and 2D-NMR and MS data, as well as by comparison with literature data for known compounds. The structure of 2 was also supported by X-ray crystallography analyses. The compounds were evaluated in vitro for their antibacterial and antiproliferative activities. Compound 5 showed high antiproliferative activity on liver hepatocellular carcinoma cells (HepG2) with IC50 value of 3.66 μg mL−1 (8.29 μmol L-1), but no cytotoxic effect (IC50 > 25 μg mL-1) on human lymphoblast cell line. This study reveals the potential use of 5 as prototype for the synthesis of new antiproliferative agents.
Maria Cristina de Albuquerque BARBOSA, Queila da Silva ROSA, Leandro de Morais CARDOSO, Antônio Frederico de Freitas GOMIDES, Luiz Cláudio de Almeida BARBOSA, Helena Maria Pinheiro SANT’ANNA, Soraia Silva PINHEIRO, Maria do Carmo Gouveia PELUZIO, Reinaldo Duque Brasil Landulfo TEIXEIRA, and Maria Anete Santana VALENTE
FapUNIFESP (SciELO)
Fruit consumption by humans is recognized to be important because it provides nutrients and bioactive compounds that contribute to reducing the risk of developing various diseases, including non-communicable diseases and chronic diseases (Slavin & Lloyd, 2012). In this context, several fruits underutilized in human food have been receiving special attention from the scientific community as a source of nutrients, bioactive compounds and due to their nutritional and functional properties.
Claudinei Andrade Filomeno, Luiz Claudio Almeida Barbosa, Róbson Ricardo Teixeira, Antônio Lelis Pinheiro, Elizeu de Sá Farias, Jhulyana Sanches Ferreira, and Marcelo Coutinho Picanço
Elsevier BV
Abstract Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae) is one of the main stored grain pests in the world. The present study describes the investigation of the insecticidal activity of essential oils (EOs) extracted from the leaves of twelve Myrtaceae species against this important pest. The essential oils of Eucalyptus resinifera Sm. (Myrtaceae) were the most actives and presented 1,8-cineole (59.3%), p-cymene (12.9%), and α-pinene (9.7%) as the main components. Contact bioassays revealed that the EOs of E. resinifera were less toxic (LD50 = 17.08 μg mg−1 of insect body weight; LD95 = 56.17 μg mg−1) than the commercial insecticide pirimiphos-methyl (LD50 = 0.49 μg mg−1; LD95 = 1.14 μg mg−1) used as positive control. In the fumigation bioassays, however, these EOs were more effective (LC50 = 70.55 μL L−1, LC95 = 266.40 μL L−1) than the commercial insecticide (LC50 = 154.74 μL L−1; LC95 = 334.95 μL L−1). The LT50 on R. dominica adults for the EOs of E. resinifera were 1.75 h and 13.0 h in the contact and fumigation bioassays, respectively. The fumigant effect was due to the terpenoid 1,8-cineole, while the contact effect was caused by the association of the major components of the essential oils of E. resinifera. Thus, the EOs of E. resinifera have potential to be used as an alternative to commercial insecticides in R. dominica management.
Isabel Antolínez, Luiz Barbosa, Célia Maltha, Gustavo Pereira, and Antônio Silva
Sociedade Brasileira de Quimica (SBQ)
Isabel V. Antolíneza, Luiz C. A. Barbosaa,b,*, , Célia R. A. Malthab, Gustavo A. M. M. Pereirac and Antônio A. Silvac Departamento de Química, Universidade Federal de Minas Gerais, Campus Pampulha, 31270-901 Belo Horizonte – MG, Brasil Departamento de Química, Universidade Federal de Viçosa, 36570-900 Viçosa – MG, Brasil Departamento de Ciências Agrárias, Universidade Federal de Viçosa, 36570-900 Viçosa – MG, Brasil
Isabel V. Antolínez, Luiz C. A. Barbosa, Tatiane F. Borgati, Almodvar Baldaia, Sebastião R. Ferreira, Raquel M. Almeida, and Ricardo T. Fujiwara
Wiley
Leishmaniasis is a neglected disease, caused by a parasite of Leishmania genus and widespread in the tropical and subtropical areas of the world. Currents drugs are limited due to their toxicity and parasite resistance. Therefore, the discovery of new treatment, more effective and less toxic, is urgent. In this study, we report the synthesis of six gem‐dihydroperoxides (2a–2f), with yields ranging from 10 % to 90 %, utilizing a new methodology. The dihydroperoxides were converted into ten tetroxanes (3a–3j), among which six (3b, 3c, 3d, 3g, 3h and 3j) showed activity against intracellular amastigotes of Leishmania amazonensis. The cytotoxicity of all compounds was also evaluated against canine macrophages (DH82), human hepatoma (HepG2) and monkey renal cells (BGM). Most compounds were more active and less toxic than potassium antimonyl tartrate trihydrate, used as positive control. Amongst all tetroxanes, 3b (IC50=0.64 μm) was the most active, being more selective than positive control in relation to DH82, HepG2 and BGM cells. In summary, the results revealed a hit compound for the development of new drugs to treat leishmaniasis.
Jaime AM Acosta, Milandip Karak, Luiz CA Barbosa, John Boukouvalas, Andrea Straforini, and Giuseppe Forlani
Wiley
BACKGROUND
The increasing frequency and intensity of cyanobacterial blooms pose a serious threat to aquatic ecosystems. These blooms produce potent toxins that can contaminate drinking water and endanger the life of wild and domestic animals as well as humans. Consequently, the development of effective methods for their control is a matter of high priority. We have previously shown that some γ-benzylidenebutenolides, related to the rubrolide family of natural products, are capable of inhibiting the photosynthetic electron transport chain (Hill reaction), a target of commercial herbicides. Here we report the synthesis and biological properties of a new class of rubrolide-inspired molecules featuring a tetronamide motif.
RESULTS
A total of 47 N-aryl tetronamides, including 38 aldol adducts, were prepared bearing phenyl, biphenyl, naphthyl, aliphatic and heteroaromatic groups. Some of the aldol adducts were dehydrated to the corresponding γ-benzylidenetetronamides, although satisfactory yields were obtained in only three cases (52-97%). None of the synthesized compounds were capable of blocking the Hill reaction. This notwithstanding, several aldol adducts equipped with a biphenyl substituent displayed excellent inhibitory activity against Synechococcus elongatus and other cyanobacterial strains (IC50 = 1-5 μM). Further, these tetronamides were found to be essentially inactive against eukariotic microorganisms.
CONCLUSION
Several newly synthesized biphenyl-containing tetronamides were shown to display potent and selective inhibitory activity against cyanobacteria. These compounds appear to exert their biological effects without interfering with the Hill reaction. As such, they represent novel leads in the search of environmentally benign agents for controlling cyanobacterial blooms. This article is protected by copyright. All rights reserved.
Jodieh Varejão, Luiz Barbosa, Eduardo Varejão, Aline Souza, Mateus Lage, and José Carneiro
Sociedade Brasileira de Quimica (SBQ)
Cristiane I. Cerceau, Luiz C.A. Barbosa, Elson S. Alvarenga, Celia R.A. Maltha, and Fyaz M.D. Ismail
Wiley
INTRODUCTION
Essential oils of Cymbopogon nardus and C. winterianus have fungicidal, bactericidal, and insect repellent activities. In addition, they are components of fragrances, cosmetics, and household products. The growing demand for essential oils has intensified adulteration practices of such products.
OBJECTIVES
To evaluate the authenticity and quality of citronella commercial essential oils based on chemical composition [by gas chromatography mass spectrometry (GC-MS)] and the contents of its major constituents [by 1 H-NMR, and gas chromatography with a flame ionisation detector using internal standardisation (GC-IS)].
MATERIALS AND METHODS
The chemical composition of essential oil was determined by GC-MS. Major components were quantified by 1 H-NMR and the results compared to those obtained by GC-IS.
RESULTS
The adulteration of oils was verified by GC and 1 H-NMR. In the pure oils, the results obtained by 1 H-NMR were similar to those obtained by GC-IS for most of the oils. However, in adulterated oils, signal overlap prevented the quantification of citronellol and geraniol by NMR. Importantly, due to dilution with dipropylene glycol it was not possible to quantify citronellal using 1 H-NMR. However, for both pure and adulterated oils, GC-IS method proved successful in quantifying notable constituents.
CONCLUSION
All the methods used proved efficient in detecting adulteration. However, whilst GC-IS provided quantification of constituents of interest, both in pure and adulterated oils, their quantification by NMR was only possible in non-adulterated samples. None of the oils evaluated presented a composition within the threshold established by British Pharmacopoeia quality standards.