Artigos - Química Orgânica - IQ

URI Permanente para esta coleçãohttps://hdl.handle.net/11449/26196

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Dark Fermentation and Principal Routes to Produce Hydrogen
(2023-01-01) Grangeiro, Luana C. ; de Mello, Bruna S. ; Rodrigues, Brenda C. G. ; Rodrigues, Caroline Varella ; Marin, Danieli Fernanda Canaver ; de Carvalho Junior, Romario Pereira ; Pires, Lorena Oliveira ; Maintinguer, Sandra Imaculada ; Sarti, Arnaldo ; Dussán, Kelly J. ; Universidade Estadual Paulista (UNESP) ; UNIARA -University of Araraquara
Interest in biohydrogen (bioH2) production from dark fermentation (DF) has increased due to green routes involving reusing by-products, wastewater, and residues from agroindustry. Moreover, bioH2 as an energy carrier of the future leads to clean combustion with the formation of a single product (water) and also releases 242 kJ mol−1 or 121 kJ g−1 energy per mass unit. As a result, it could be transformed into electrical energy using a fuel cell or an internal combustion engine. However, several studies state that the yield of bioH2 production in anaerobic reactors by dark fermentation (DF) is still low when compared to the yields of conventional hydrogen processes and technologies such as water electrolysis CH4 reform, and gasification coal, among others. Therefore, in the literature, different anaerobic technologies have been investigated, for example, changing the conventional systems to high-rate reactors and studies on the pre-treatment of inoculum, types of substrates, and genetic modifications of hydrogen-producing microorganisms. Therefore, this chapter shows the principal biochemical routes and main types of reactors used in wastewater-fed bioH2-producing systems. Finally, essential recommendations are highlighted.
Theoretical and experimental study of the diastereoisomers (2S) and (2R)-naringenin-6-C-β-D-glucopyranoside obtained from Clitoria guianensis
(2023-03-01) Cruz, Állefe Barbosa ; Ciribelli, Nicolas Nascimento ; Cunha, Camila Luiza ; Nascimento, Isabele Rodrigues ; Holzbach, Juliana Cristina ; Pereira, Douglas Henrique ; Universidade Federal do Tocantins ; Universidade Estadual Paulista (UNESP)
Abstract: In this work the diastereoisomers (2S) and (2R)-naringenin-6-C-β-D-glucopyroside, isolated for the first time from Clitoria guianensis, were studied using the density functional theory. The frontier molecular orbitals and structural properties showed that the diastereoisomers exhibit the same energy gap 166.61 kcal mol−1 and structural properties different, where in the S diastereoisomer, the bond length between the chiral carbon and the phenolic group is greater (difference of 0.0126 Å). The HPLC data showed that the retention time of the S-diastereoisomer (16.7 min) is shorter than that of R, suggesting that the S compound is more polar than R. The HPLC results corroborates with the molecular electrostatic potential which showed that in the S configuration, the electronegative density was more intense overall, particularly in the glucose molecule. The reactivity indices showed that the diastereoisomers are good electrophiles and reactive species. Finally, the absolute configuration of the diastereoisomers were determined using electronic circular dichroism (ECD) spectroscopy and the theoretical spectra were similar to the experimental. Methods: All calculations of Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TDDFT) were performed using the program Gaussian 09 and the structures of the diastereoisomers were generated and analyzed using the GaussView program. The optimization and vibrational frequency calculations were performed using the functional CAM-B3LYP and 6–311 + + G(2d,2p) basis set. Conformational searches were performed for R configuration, by molecular mechanics using the MM + , MMFF, and OPLS05 force fields; the entire molecular mechanics simulation was performed using the Maestro/MacroModel software. The calculations for the simulations of the ECD spectra were performed for the eight lowest energy conformers obtained in the geometric optimization step, and the TDDFT at the CAM-B3LYP/6–311 + + G(2d,2p) theory level used. The effects of methanol and chloroform were calculated using the SMD implicit solvent model.
Reaction of the Phytochemistry Community to Green Chemistry: Insights Obtained Since 1990
(2023-02-24) Funari, Cristiano S. ; Rinaldo, Daniel ; Bolzani, Vanderlan S. ; Verpoorte, Robert ; Universidade Estadual Paulista (UNESP) ; Leiden University
This review article aims to study how phytochemists have reacted to green chemistry insights since 1990, the year when the U.S. Environmental Protection Agency launched the “Pollution Prevention Act”. For each year in the period 1990 to 2019, three highly cited phytochemistry papers that provided enough information about the experimental procedures utilized were sampled. The “greenness” of these procedures was assessed, particularly for the use of solvents. The highly hazardous diethyl ether, benzene, and carbon tetrachloride did not appear in the papers sampled after 2010. Advances in terms of sustainability were observed mainly in the extraction stage. Similar progress was not observed in purification procedures, where chloroform, dichloromethane, and hexane regularly have been employed. Since replacing such solvents in purification procedures should be a major goal, potential alternative approaches are discussed. Moreover, some current initiatives toward a more sustainable phytochemical research considering aspects other than only solvents are highlighted. Although some advances have been achieved, it is believed that natural products chemists can play a major role in developing a novel ecological paradigm in chemistry. To contribute to this objective, six principles for performing natural products chemistry consistent with the guidelines of green chemistry are proposed.
Methyl jasmonate induces selaginellin accumulation in Selaginella convoluta
(2023-01-01) Reginaldo, Fernanda Priscila Santos ; Bueno, Paula Carolina Pires ; Lourenço, Estela Mariana Guimarães ; de Matos Costa, Isabelly Cristina ; Moreira, Letícia Gondim Lambert ; de Araújo Roque, Alan ; Barbosa, Euzébio Guimarães ; Fett-Neto, Arthur Germano ; Cavalheiro, Alberto José ; Giordani, Raquel Brandt ; Federal University of Rio Grande do Norte (UFRN) ; Leiden University ; Federal University of Alfenas (UNIFAL) ; Max-Planck Institute of Molecular Plant Physiology ; Federal University of Mato Grosso Do Sul ; Institute for Sustainable Development and Environment ; Federal University of Rio Grande Do Sul (UFRGS) ; Universidade Estadual Paulista (UNESP)
Introduction: Selaginellins are specialized metabolites and chemotaxonomic markers for Selaginella species. Despite the growing interest in these compounds as a result of their bioactivities, they are accumulated at low levels in the plant. Hence, their isolation and chemical characterization are often difficult, time consuming, and limiting for biological tests. Elicitation with the phytohormone methyl jasmonate (MeJA) could be a strategy to increase the content of selaginellins addressing their low availability problem, that also impairs pharmacological investigations. Matherials and methods: In this study, we examined MeJA elicitation in Selaginella convoluta plants, a medicinal plant found in northeastern Brazil, by treating them with two different concentrations (MeJA: 50 and 100 µM), followed by chemical profiling after 12, 24 and 48 h after application. Samples were harvested and analyzed by liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS). Results and discusscion: MeJA treatment significantly impacted the chemical phenotype. Regarding shoots differences in the time-dependent increased accumulation of all metabolites when plants were subjected to 100 µM MeJA were observed while in roots, most metabolites had their concentrations decreased in a time-dependent fashion at the same conditions. Results support organ, MeJA concentration and time post-treatment dependence of specialized metabolite accumulation, mainly the flavonoids and selaginellins. The amount of Selaginellin G in shoots of MeJA-treated specimens increased in 5.63-fold relative to control. The molecular networking approach allowed for the putative annotation of 64 metabolites, among them, the MeJA treatment followed by targeted metabolome analysis also allowed to annotate seven unprecedented selaginellins. Additionally, the in silico bioactive potential of the annotated selaginellins highlighted targets related to neurodegenerative disorders, antiproliferative, and antiparasitic issues. Taken together, data point out MeJA exposure as a strategy to induce potentially bioactive selaginellins accumulation in S. convoluta, this approach could enable a deep investigation about the metabolic function of these metabolites in the genus as well as regarding pharmacological exploration of the undervalued potential.
Proteome profiling of methyl jasmonate elicitation of Maytenus ilicifolia in vitro roots reveals insights into sesquiterpene pyridine alkaloids
(2022-12-01) Santos, Vânia A. F. F. M. dos ; Coppede, Juliana da Silva ; Dias, Nathalia Batista ; Pereira, Ana Maria Soares ; Palma, Mario Sergio ; Furlan, Maysa ; Universidade Estadual Paulista (UNESP) ; Universidade de Ribeirão Preto (UNAERP) ; Universidad de La Frontera (UFRO)
Maytenus ilicifolia (Celastraceae) is an important medicinal plant widely used in Brazil and a rich source of sesquiterpene pyridine alkaloids (SPAs) with relevant biological activities. They exhibit great chemical diversity and high structural complexity, and show accumulation in very low concentrations. Thus, to determine whether in vitro cultured adventitious roots of M. ilicifolia could provide alternative sources for the production of these compounds, the accumulation of SPAs ilicifoliunine A and aquifoliunine E-I, as well as the time of production and the content of these alkaloids were evaluated using methyl jasmonate (MeJA) as an elicitor. The results showed the accumulation ilicifoliunine A and aquifoliunine E-I and an increase in the contents of these alkaloids when elicited with MeJA at 7 and 28 days, respectively. To characterize and identify the proteins present in the enzymatic system and contribute to the understanding of the metabolic pathways involved in the biosynthesis of SPAs, was carried out in vitro proteomic profiling of adventitious roots elicited and non-elicited with MeJA. The shotgun proteomic analyses led to the identification of important proteins involved in the biosynthetic pathway of SPAs, including germacrene A synthase, β-eudesmol synthase, and L-aspartate oxidase. Additionally, many proteins that participate in the biosynthesis of other alkaloids (e.g., tropane, pyrrolidine, terpenoid indole, and isoquinoline) and phenylpropanoids have been identified. In conclusion, the study report for the first time, proteins involved in the biosynthetic pathway of SPAs by using the adventitious roots in vitro system of M. ilicifolia and a shotgun proteomic approach.
Endophytic fungus Phomopsis sp. as a source of 3-nitropropionic acid with larvicidal activity against Aedes aegypti (Linnaeus 1762, Diptera: Culicidae)
(2022-01-01) Garcia, Armando da Costa ; Júnior, Orivaldo Teixeira de Menezes ; Mariano, Lissa Apolonia ; Santiago, Letícia Corrêa ; Araújo, Ângela Regina ; Monfardini, Julia Dietsche ; Simões, Rejane de Castro ; de Oliveira, André Correa ; Roque, Rosemary Aparecida ; Tadei, Wanderli Pedro ; Teles, Helder Lopes ; de Oliveira, Camila Martins ; Instituto de Ciências Exatas e Tecnologia ; Universidade Estadual Paulista (UNESP) ; Instituto Nacional de Pesquisas da Amazônia ; Instituto de Ciências Exatas e Naturais
Background: Aedes aegypti is the primary vector of viruses, such as Zika, chikungunya, yellow fever, and dengue. In this context, a biomonitored chemical study was conducted to evaluate the activity of the crude extract of the endophytic fungus Phomopsis sp. against the larvae of Aedes aegypti. Methods: Crude extract, fractions, and isolated substances were evaluated in in-vitro assays against third-stage larvae of Aedes aegypti. Results: We isolated 3-nitropropionic acid with an LC50 of 15.172 ppm and LC90 of 18.178 ppm after 24 hours of larval exposure. Conclusions: The results indicated that 3-nitropropionic acid exerted larvicidal activity.
Phenylalanine ammonia lyase: new insights from Piperaceae species
(2022-01-01) de Araújo Morandim-Giannetti, Andreia ; Felippe, Lidiane Gaspareto ; de Freitas Formenton Macedo dos Santos, Vânia Aparecida ; Kato, Massuo Jorge ; Furlan, Maysa ; FEI University Center ; Universidade Estadual Paulista (UNESP) ; Universidade de São Paulo (USP)
The enzyme PAL (phenylalanine ammonia lyase) mediates the key entry point to the general phenylpropanoid pathway, which is involved in the lignification process and in the formation of a myriad of secondary compounds in plants that show a variety of biological activities. Soluble fractions containing PAL extracted from Piper and Peperomia species had the optimal catalytic activity analyzed by statistical design model. This analysis revealed that the best conversion of L-phenylalanine to trans-cinnamic acid was pH 9.3 and 58 °C after 25 h, corroborating interesting thermal stability. Additionally, the pre-purification of PAL using ammonium sulfate precipitation (25-55%) increased its specific activity, approximately 133% in P. aduncum and more than 900% in P. crassinervium. The content of lignin was higher for P. tuberculatum (25.71%), while only a small amount of lignin was observed in Peperomia blanda (11.95%). It is interesting to note that Peperomia plants are succulent and without significant amounts of lignin. However, the phenylpropanoid biosynthetic pathway is apparently addressed to produce predominantly tetrahydrofuran lignans with biological interest.
Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant
(2022-09-08) Chacon, Daisy Sotero ; Santos, Marlon Dias Mariano ; Bonilauri, Bernardo ; Vilasboa, Johnatan ; da Costa, Cibele Tesser ; da Silva, Ivanice Bezerra ; Torres, Taffarel de Melo ; de Araújo, Thiago Ferreira ; Roque, Alan de Araújo ; Pilon, Alan Cesar ; Selegatto, Denise Medeiros ; Freire, Rafael Teixeira ; Reginaldo, Fernanda Priscila Santos ; Voigt, Eduardo Luiz ; Zuanazzi, José Angelo Silveira ; Scortecci, Kátia Castanho ; Cavalheiro, Alberto José ; Lopes, Norberto Peporine ; Ferreira, Leandro De Santis ; Santos, Leandro Vieira dos ; Fontes, Wagner ; Sousa, Marcelo Valle de ; Carvalho, Paulo Costa ; Fett-Neto, Arthur Germano ; Giordani, Raquel Brandt ; Federal University of Rio Grande do Norte (UFRN) ; Carlos Chagas Institute ; Stanford University School of Medicine ; Federal University of Rio Grande do Sul ; Rural Federal University of the Semiarid ; Institute for Sustainable Development and Environment ; Universidade de São Paulo (USP) ; Structural and Computational Biology Unit ; Barcelona Institute of Science and Technology ; Leiden University ; Federal University of Rio Grande do Norte ; Universidade Estadual Paulista (UNESP) ; Universidade Estadual de Campinas (UNICAMP) ; University of Brasilia
Erythrina velutina is a Brazilian native tree of the Caatinga (a unique semiarid biome). It is widely used in traditional medicine showing anti-inflammatory and central nervous system modulating activities. The species is a rich source of specialized metabolites, mostly alkaloids and flavonoids. To date, genomic information, biosynthesis, and regulation of flavonoids remain unknown in this woody plant. As part of a larger ongoing research goal to better understand specialized metabolism in plants inhabiting the harsh conditions of the Caatinga, the present study focused on this important class of bioactive phenolics. Leaves and seeds of plants growing in their natural habitat had their metabolic and proteomic profiles analyzed and integrated with transcriptome data. As a result, 96 metabolites (including 43 flavonoids) were annotated. Transcripts of the flavonoid pathway totaled 27, of which EvCHI, EvCHR, EvCHS, EvCYP75A and EvCYP75B1 were identified as putative main targets for modulating the accumulation of these metabolites. The highest correspondence of mRNA vs. protein was observed in the differentially expressed transcripts. In addition, 394 candidate transcripts encoding for transcription factors distributed among the bHLH, ERF, and MYB families were annotated. Based on interaction network analyses, several putative genes of the flavonoid pathway and transcription factors were related, particularly TFs of the MYB family. Expression patterns of transcripts involved in flavonoid biosynthesis and those involved in responses to biotic and abiotic stresses were discussed in detail. Overall, these findings provide a base for the understanding of molecular and metabolic responses in this medicinally important species. Moreover, the identification of key regulatory targets for future studies aiming at bioactive metabolite production will be facilitated.
Application of a Two-Stage Anaerobic System from Guava Processing Waste to Bioenergy
(2022-08-01) De Carvalho, Romário P. ; Maintinguer, Sandra Imaculada ; Universidade Estadual Paulista (UNESP) ; University of Araraquara
The application of maximum feedstock capacity through the treatment of organic wastes generated in the industrial chain is necessary for environmental preservation. Agro-industrial waste, such as from fruit processing, can be treated by anaerobic digestion with bioenergy generation. This study aimed to evaluate the consumption of guava processing waste on hydrogen (H2) and methane (CH4) production in a two-stage anaerobic system under four different conditions (substrate/inoculum ratios of 0.67, 1.0, 2.0, and 3.0 g COD g-1 VS). Bio-H2 (5.26-3.50 mL H2 g-1 VS) and bio-CH4 (266.27-104.67 mL CH4 g-1 VS) were produced, with consequent high efficiencies of organic matter (75-90% to total COD) and carbohydrates (98-99%) removals. Paraclostridium and Clostridium genera were used in ethanol, acetic, propionic, and butyric acids generation in the first stage, and these metabolites were consumed in the second stage. The estimated energy yields of the two-stage system were 1.1-2.7 kJ kg-1 residue. Guava residues can be recovered by application in anaerobic processes for the generation of biofuels and other added-value bioproducts.
Nematostatic activity of isoprenylated guanidine alkaloids from Pterogyne nitens and their interaction with acetylcholinesterase
(2023-07-01) Coqueiro, Aline ; Fernandes, Daniara Cristina ; Danuello, Amanda ; Regasini, Luis Octávio ; Cardoso-Lopes, Elaine Monteiro ; Young, Maria Cláudia Marx ; Brandão Torres, Luce Maria ; Campos, Vicente Paulo ; Silva, Dulce Helena Siqueira ; da Silva Bolzani, Vanderlan ; de Oliveira, Denilson Ferreira ; Universidade Estadual Paulista (UNESP) ; Federal University of Technology – Paraná (UTFPR) ; Science and Technology of São Paulo (IFSP) ; Universidade Federal de Uberlândia (UFU) ; Institute of Environmental Research ; Universidade Federal de Lavras (UFLA)
Although new nematicides have appeared, the demand for new products less toxic and more efficient for the control of plant-parasitic nematodes are still high. Consequently, studies on natural secondary metabolites from plants, to develop new nematicides, have increased. In this work, nineteen extracts from eleven Brazilian plant species were screened for activity against Meloidogyne incognita. Among them, the extracts of Piterogyne nitens showed a potent nematostatic activity. The alkaloid fraction obtained from the ethanol extract of leaves of P. nitens was more active than the coming extract. Due to the promising activity from the alkaloid fraction, three isoprenylated guanidine alkaloids isolated from this fraction, galegine (1), pterogynidine (2), and pterogynine (3) were tested, showing similar activity to the alkaloid fraction, which was comparable to that of the positive control Temik at 250 μg/mL. At lower concentrations (125−50 μg/mL), compound 2 showed to be the most active one. As several nematicides act through inhibition of acetylcholinesterase (AChE), the guanidine alkaloids were also employed in two in vitro AChE assays. In both cases, compound 2 was more active than compounds 1 and 3. Its activity was considered moderated compared to the control (physostigmine). Compound 2 was selected for an in silico study with the electric eel (Electrophorus electricus) AChE, showing to bind mostly to the same site of physostigmine in the AChEs, pointing out that this could be the mechanism of action for this compound. These results suggested that the guanidine alkaloids 1, 2 and 3 from P. nitens are promising for the development of new products to control M. incognita, especially guanidine 2, and encourage new investigations to confirm the mechanism of action, as well as to determine the structure-activity relationship of the guanidine alkaloids.
Cytotoxic Activity of Baccharis trimera (Less.) DC. Essential Oil in Tumor Cell Lines and its Role in Associated Death Mechanisms
(2023-01-01) Moro, Isabela Jacob ; Carvalho, Flavio Alexandre ; Moreira, Thais Fernanda ; Souza, Felipe de Oliveira ; da Silva, Alexander Alves ; Politi, Flávio ; Soares, Christiane Pienna ; Dos Santos, André Gonzaga ; Universidade Estadual Paulista (UNESP)
This study evaluated the potential of Baccharis trimera essential oil (EO) and its components in cancer therapy through the application of cytotoxicity and cell death assays. Using gas chromatography analysis, the major components of the aerial parts of the essential oil were identified as (E)-caryophyllene (18.9%), bicyclogermacrene (15.6%), and germacrene D (10.5%). Baccharis trimera essential oil (5.8 μg/mL) and α-humulene (7.8 μg/mL) presented strong cytotoxic activity, while (E)-caryophyllene (11.5 μg/mL) and caryophyllene oxide (> 100.0 μg/mL) showed moderate and low activities, respectively, against MCF-7 cell lines. Against HepG2 cell lines, B. trimera essential oil (10.4 μg/mL), α-humulene (17.1 μg/mL), and caryophyllene oxide (19.4 μg/mL) exhibited moderate activity, while (E)-caryophyllene (52.3 μg/mL) displayed low activity against HepG2 cell lines. The selectivity index values of EO (MCF-7 and HepG2), α-humulene and (E)-caryophyllene (MCF-7), and caryophyllene oxide (HepG2) were found between 1.1 and 2.8, compared with MCF-10A cells. The annexin-V and Hoechst / propidium iodide assays performed with essential oil, (E)-caryophyllene, α-humulene, and caryophyllene oxide showed apoptosis and necrosis mechanisms for all cell lines. Based on these findings, B. trimera essential oil and its components can be considered as potential therapeutic agents against cancer.
Effect of Extracts, Fractions, and Isolated Molecules of Casearia sylvestris to Control Streptococcus mutans Cariogenic Biofilm
(2023-02-01) Ribeiro, Sabrina M. ; Bueno, Paula C. P. ; Cavalheiro, Alberto José ; Klein, Marlise I. ; Universidade Estadual Paulista (UNESP) ; Universidade de São Paulo (USP) ; Federal University of Alfenas ; Universidade Estadual de Campinas (UNICAMP)
The effects of extracts, fractions, and molecules of Casearia sylvestris to control the cariogenic biofilm of Streptococcus mutans were evaluated. First, the antimicrobial and antibiofilm (initial and pre-formed biofilms) in prolonged exposure (24 h) models were investigated. Second, formulations (with and without fluoride) were assessed for topical effects (brief exposure) on biofilms. Third, selected treatments were evaluated via bacterium growth inhibition curves associated with gene expression and scanning electron microscopy. In initial biofilms, the ethyl acetate (AcOEt) and ethanolic (EtOH) fractions from Brasília (BRA/DF; 250 µg/mL) and Presidente Venceslau/SP (Water/EtOH 60:40 and Water/EtOH 40:60; 500 µg/mL) reduced ≥6-logs vs. vehicle. Only the molecule Caseargrewiin F (CsF; 125 µg/mL) reduced the viable cell count of pre-formed biofilms (5 logs vs. vehicle). For topical effects, no formulation affected biofilm components. For the growth inhibition assay, CsF yielded a constant recovery of surviving cells (≅3.5 logs) until 24 h (i.e., bacteriostatic), and AcOEt_BRA/DF caused progressive cell death, without cells at 24 h (i.e., bactericidal). CsF and AcOEt_BRA/DF damaged S. mutans cells and influenced the expression of virulence genes. Thus, an effect against biofilms occurred after prolonged exposure due to the bacteriostatic and/or bactericidal capacity of a fraction and a molecule from C. sylvestris.
Rosmarinus officinalis extract-loaded emulgel prevents UVB irradiation damage to the skin
(2022-01-01) Takayama, Kátia S. ; Monteiro, Mariana C. ; Saito, Priscila ; Pinto, Ingrid C. ; Nakano, Claudia T. ; Martinez, Renata M. ; Thomaz, Douglas V. ; Verri, Waldiceu A. ; Baracat, Marcela M. ; Arakawa, Nilton S. ; Russo, Helena M. ; Zeraik, Maria L. ; Casagrande, Rubia ; Do Couto, Renê O. ; Georgetti, Sandra Regina ; Universidade Estadual de Londrina (UEL) ; Universidade Federal de Goiás (UFG) ; Universidade Estadual Paulista (UNESP) ; Laboratório de Desenvolvimento Farmacotécnico-LADEF
UVB-irradiation increases the risk of various skin disorders, therefore leading to inflammation and oxidative stress. In this sense, antioxidant-rich herbs such as Rosmarinus officinalis may be useful in minimizing the damage promoted by reactive oxygen species. In this work, we report the efficacy of a R. officinalis hydroethanolic extract (ROe)-loaded emulgel in preventing UVB-related skin damage. Total phenols were determined using Folin-Ciocalteu assay, and the main phytocomponents in the extract were identified by UHPLC-HRMS. Moreover, in vitro sun protection factor (SPF) value of ROe was also assessed, and we investigated the in vivo protective effect of an emulgel containing ROe against UVB-induced damage in an animal model. The ROe exhibited commercially viable SPF activity (7.56 ± 0.16) and remarkable polyphenolic content (24.15 ± 0.11 mg (Eq.GA)/g). HPLC-MS and UHPLC-HRMS results showcased that the main compounds in ROe were: rosmarinic acid, carnosic acid and carnosol. The evaluation of the in vitro antioxidant activity demonstrated a dose-dependent effect of ROe against several radicals and the capacity to reduce iron. Therefore, we demonstrated that topical application of the formulation containing ROe inhibited edema formation, myeloperoxidase activity, GSH depletion and maintained ferric reducing (FRAP) and ABTS scavenging abilities of the skin after UVB exposure.
Chemoinformatics and artificial intelligence colloquium: progress and challenges in developing bioactive compounds
(2022-12-01) Bajorath, Jürgen ; Chávez-Hernández, Ana L. ; Duran-Frigola, Miquel ; Fernández-de Gortari, Eli ; Gasteiger, Johann ; López-López, Edgar ; Maggiora, Gerald M. ; Medina-Franco, José L. ; Méndez-Lucio, Oscar ; Mestres, Jordi ; Miranda-Quintana, Ramón Alain ; Oprea, Tudor I. ; Plisson, Fabien ; Prieto-Martínez, Fernando D. ; Rodríguez-Pérez, Raquel ; Rondón-Villarreal, Paola ; Saldívar-Gonzalez, Fernanda I. ; Sánchez-Cruz, Norberto ; Valli, Marilia ; Rheinische Friedrich-Wilhelms-Universität ; National Autonomous University of Mexico ; Ersilia Open Source Initiative ; The Barcelona Institute of Science and Technology ; International Iberian Nanotechnology Laboratory ; University of Erlangen-Nuremberg ; Center for Research and Advanced Studies of the National Polytechnic Institute (CINVESTAV) ; University of Arizona ; Recursion Pharmaceuticals ; Parc Cientific de Barcelona (PCB) ; Parc de Recerca Biomedica (PRBB) ; University of Florida ; University of New Mexico School of Medicine ; Sahlgrenska Academy at Gothenburg University ; University of Copenhagen ; Inc. ; Irapuato Unit ; Novartis Institutes for Biomedical Research ; Instituto de Investigación Masira ; Universidad Nacional Autónoma de México ; Universidade Estadual Paulista (UNESP)
We report the main conclusions of the first Chemoinformatics and Artificial Intelligence Colloquium, Mexico City, June 15–17, 2022. Fifteen lectures were presented during a virtual public event with speakers from industry, academia, and non-for-profit organizations. Twelve hundred and ninety students and academics from more than 60 countries. During the meeting, applications, challenges, and opportunities in drug discovery, de novo drug design, ADME-Tox (absorption, distribution, metabolism, excretion and toxicity) property predictions, organic chemistry, peptides, and antibiotic resistance were discussed. The program along with the recordings of all sessions are freely available at https://www.difacquim.com/english/events/2022-colloquium/.
Identification of natural cytochalasins as leads for neglected tropical diseases drug discovery
(2022-10-01) Valli, Marilia ; Souza, Julia Medeiros ; Chelucci, Rafael Consolin ; Biasetto, Carolina Rabal ; Araujo, Angela Regina ; da Silva Bolzani, Vanderlan ; Andricopulo, Adriano Defini ; Universidade de São Paulo (USP) ; Universidade Estadual Paulista (UNESP)
Investigating the chemical diversity of natural products from tropical environments is an inspiring approach to developing new drug candidates for neglected tropical diseases (NTDs). In the present study, phenotypic screenings for antiprotozoal activity and a combination of computational and biological approaches enabled the identification and characterization of four cytochalasins, which are fungal metabolites from Brazilian biodiversity sources. Cytochalasins A-D exhibited IC50 values ranging from 2 to 20 μM against intracellular Trypanosoma cruzi and Leishmania infantum amastigotes, values comparable to those of the standard drugs benznidazole and miltefosine for Chagas disease and leishmaniasis, respectively. Furthermore, cytochalasins A-D reduced L. infantum infections by more than 80% in THP-1 cells, most likely due to the inhibition of phagocytosis by interactions with actin. Molecular modelling studies have provided useful insights into the mechanism of action of this class of compounds. Furthermore, cytochalasins A-D showed moderate cytotoxicity against normal cell lines (HFF-1, THP-1, and HepG2) and a good overall profile for oral bioavailability assessed in vitro. The results of this study support the use of natural products from Brazilian biodiversity sources to find potential drug candidates for two of the most important NTDs.
Evaluation of the Metabolic Production from the Co-Culture of Saccharicola sp. and Botryosphaeria parva, an Endophytic Fungi Associated with Eugenia jambolana Lam.
(Soc Brasileira Quimica, 2023-03-31) Costa, Mayra F. ; Borges, Maiara S. ; Chapla, Vanessa M. ; Biasetto, Carolina R. ; Nascimento, Isabele R. ; Bolzani, Vanderlan S. ; Araujo, Angela R. ; Universidade Estadual Paulista (UNESP) ; Univ Fed Tocantins UFT
A new compound, (6R,7S,2E,4E)-6,7-dihydroxy-4,6-dimethylocta-2,4-dienoic acid (1), together with eight known compounds were isolated from the co-culture of Saccharicola sp. and Botryosphaeria parva, an endophytic fungi associated with Eugenia jambolana Lam. (Myrtaceae) plant species. The structures were elucidated by spectroscopic analysis of the one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) data as well as by comparison with literature data. The bioactivity (antioxidant and antifungal) of the crude EtOAc was evaluated. All crude extracts presented antioxidant activity and only the crude extract from the co-culture was active on the fungus Cladosporium sphaerospermum. This investigation contributed to the knowledge about the metabolic production of two endophytic fungi Saccharicola sp. and Botryosphaeria parva in co-culture, once, until the present date, there are no studies in the literature that report the understanding of the chemical interaction of both grown in the same environment.
Plant Diversity from Brazilian Cerrado and Atlantic Forest as a Tool for Prospecting Potential Therapeutic Drugs
(Elsevier B.V., 2010-01-01) Siqueira Silva, Dulce Helena ; Castro-Gamboa, Ian ; Bolzani, Vanderlan Da Silva ; Mander, L. ; Liu, H. W. ; Universidade Estadual Paulista (UNESP)
Advanced Glycation End Products Inhibitors from Talisia esculenta
(Soc Brasileira Quimica, 2023-04-24) Alves, Natalia Felix ; Ribeiro, Dayane Castro ; Mannochio-Russo, Helena ; Queiroz, Suzana Aparecida Silva ; Zocolo, Guilherme Juliao ; Bolzani, Vanderlan da Silva ; Valli, Marilia ; Universidade Estadual Paulista (UNESP) ; Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA) ; Universidade de São Paulo (USP)
Advanced Glycation End Products (AGEs) are formed under hyperglycemic conditions but also during the natural aging process. AGEs are associated with skin aging, loss of skin elasticity, and some chronic diseases such as diabetes and Alzheimer ' s, being a research topic of great relevance. Several herbal supplements have beneficial effects on glycemic control and oxidative stress, with the consequent reduction in the volume of AGEs during aging. In this scenario, the search for natural products with AGEs inhibition activity has been gaining prominence due to their importance for innovation in pharmaceuticals and cosmetics. The present study describes the investigation of natural products from Talisia esculenta with antiglycation activity. Ten phenolic compounds were annotated by LC-MS, and the compounds present in the leaves extracts were isolated, characterized by NMR and submitted for further in vitro studies. Rutin and quercitrin were isolated and presented 44% and 86% antiglycation activity at 150 mu g/mL. These results open new possibilities for the use of abundant natural compounds as AGEs inhibitors, and further studies should be performed to evaluate their use and efficacy in cosmetics formulations and even in the treatment of AGEs-associated diseases.
Unraveling the Metabolomic Profile and Bioactivities of the Paratoid Gland Secretion from Rhinella granulosa
(Soc Brasileira Quimica, 2023-04-13) Barros, Elcio Daniel S. ; Moncao Filho, Evaldo S. ; Fonseca, Mariluce G. ; Alves, Patricia S. ; Santos, Antonia Laires S. ; Feitosa, Chistiane M. ; Silva, Dulce Helena S. ; Costa, Pedro Mikael S. ; Pessoa, Claudia ; Campos, Carmem D. L. ; Monteiro, Cristina A. ; Chaves, Mariana Helena ; Vieira Junior, Gerardo M. ; Inst Fed Educ Ciencia & Tecnol Maranhao ; Univ Fed Piaui ; Universidade Estadual Paulista (UNESP) ; Univ Fed Ceara
Toads of the Rhinella genus have a pair of paratoid glands that store biological secretions of high toxicity and varied chemical composition, rich in biologically active compounds. The present work aimed to carry out the investigation of the metabolomic profile and evaluation of the biological potential of the secretion paratoid glands (PGS) from Rhinella granulosa. The paratoid secretion was collected in the Piaui state (Brazil), extracted with methanol and the extract was analyzed by ultra-performance liquid chromatography with quadrupole time-of-flight mass spectrometry. Fifty chemical constituents were identified. The extract showed cytotoxicity against tumor cell lines of the central nervous system (half maximal inhibitory concentration (IC50) = 1.9 mu g mL-1) and prostate (IC50 = 1.6 mu g mL-1), unsatisfactory antimicrobial potential (minimal inhibitory concentration (MIC) > 312 mu g mL-1) and inhibited the enzyme acetylcholinesterase (IC50 = 5.119 mg mL-1). The results presented relevant information about the PGS and contributed to the understanding of the metabolomic and biological potential of R. granulosa.
Potential Use of I. suffruticosa in Treatment of Tuberculosis with Immune System Activation
(Intech Europe, 2012-01-01) Andrade Carli, Camila Bernardes de ; Quilles, Marcela Bassi ; Geraldo Maia, Danielle Cardoso ; Fujimura Leite, Clarice Q. ; Vilegas, Wagner ; Carlos, Iracilda Z. ; Cardona, P. J. ; Universidade Estadual Paulista (UNESP)

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