239 results on '"Marcelo Sobral da Silva"'
Search Results
2. Integrative investigation of the potential impacts of Pilosocereus gounellei (A. Weber ex K. Schum. Bly. Ex Rowl) cladodes on the human intestinal microbiota
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Sabrina Radames Ferreira da Silva, Sara de Sousa Rocha, Jaielison Yandro Pereira da Silva, Viviane Priscila Barros de Medeiros, Flávia Figueira Aburjaile, Rodrigo Dias de Oliveira Carvalho, Marcelo Sobral da Silva, Josean Fechine Tavares, Yuri Mangueira do Nascimento, Marcos dos Santos Lima, Cristiane Francisca Costa Sassi, Mariana Monteiro, José Luiz de Brito Alves, Thatyane Mariano Rodrigues de Albuquerque, Maria Elieidy Gomes de Oliveira, and Evandro Leite de Souza
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Cactaceae ,Xique-xique ,Intestinal microbiota ,Antioxidant activity ,Colonic fermentation ,Nutrition. Foods and food supply ,TX341-641 - Abstract
Pilosocereus gounellei A. Weber ex K. Schum. Bly. Ex Rowl (xique-xique) is a cactus native to the Brazilian Caatinga biome and considered a non-conventional food plant. This study evaluated the physicochemical characteristics, antioxidant capacity, and impacts on the composition and metabolic activity of human intestinal microbiota of freeze-dried P. gounellei cladodes (FDPg) during 48 h of in vitro colonic fermentation. FDPg had a high nutritional value, the presence of bioactive compounds, and antioxidant capacity. The colonic fermentation of FDPg decreased the Firmicutes/Bacteroidetes ratio and increased bacterial diversity. It also increased the relative abundance of bacterial groups considered beneficial, such as Mitsuokella, Bacteroides, Megasphaera, and Acidaminococcus, and decreased the relative abundance of bacterial groups considered non-beneficial, such as Succinivibrio, Citrobacter, Escherichia-Shigella, Faecalibacterium, and Blautia. The colonic fermentation of FDPg induced the production of various metabolites related to host health promotion. The results show the potential beneficial impacts of FDPg on human intestinal microbiota.
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- 2024
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3. (-)-Fenchone Ameliorates TNBS-Induced Colitis in Rats via Antioxidant, Immunomodulatory, and Cytoprotective Mechanisms
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Maria Elaine Cristina Araruna, Edvaldo Balbino Alves Júnior, Catarina Alves de Lima Serafim, Matheus Marley Bezerra Pessoa, Michelle Liz de Souza Pessôa, Vitória Pereira Alves, Marianna Vieira Sobral, Marcelo Sobral da Silva, Adriano Francisco Alves, Maria Carolina de Paiva Sousa, Aurigena Antunes Araújo, and Leônia Maria Batista
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(-)-fenchone ,ulcerative colitis ,antioxidant ,immunomodulatory ,cytoprotection ,Medicine ,Pharmacy and materia medica ,RS1-441 - Abstract
Background: (-)-Fenchone is a bicyclic monoterpene present in the plant species Foeniculum vulgare Mill, Thuja occidentalis L. (tuja), and Lavandula stoechas (lavender). These plants have therapeutic value in the treatment of intestinal disorders. Aim: To evaluate intestinal anti-inflammatory activity in an acute and chronic trinitrobenzene sulphonic acid (TNBS)-induced colitis model in rats. Methods: Intestinal anti-inflammatory effects were assessed using the acute and chronic TNBS-induced colitis model in rats. The mechanisms were evaluated from colonic tissue fragments of the acute and chronic models. Results: Oral administration of the (-)-fenchone (37.5–300 mg/kg) acute phase or (150 mg/kg) (p < 0.001) chronic phase reduced the macroscopic lesion score, ulcerative area, intestinal weight/length ratio, and diarrheal index in TNBS-treated animals. At a dose of 150 mg/kg, the acute and chronic phase decreased malondialdehyde (MDA) and myeloperoxidase (MPO) (p < 0.001), restored glutathione (GSH) levels and superoxide dismutase (SOD) (p < 0.001), decreased immunomarking for factor nuclear kappa B (NF-κB) and levels of interleukin (IL)-1 and tumor necrosis factor α (TNF-α), and maintained IL-10 and TGF-β basal levels. Furthermore, increased immunostaining for zonula occludens 1 (ZO-1) was observed. Conclusions: (-)-fenchone has intestinal anti-inflammatory activity related to cytoprotection of the intestinal barrier, as well as antioxidant and immunomodulatory effects.
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- 2024
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4. Exploring the potential prebiotic effects of Opuntia dillenii (Ker Gawl). Haw (Cactaceae) cladodes on human intestinal microbiota
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Sara de Sousa Rocha, Sabrina Radames Ferreira da Silva, Jaielison Yandro Pereira da Silva, Viviane Priscila Barros de Medeiros, Flávia Figueira Aburjaile, Rodrigo Dias de Oliveira Carvalho, Marcelo Sobral da Silva, Josean Fechine Tavares, Yuri Mangueira do Nascimento, Marcos dos Santos Lima, Cristiane Francisca Costa Sassi, Mariana Monteiro, José Luiz de Brito Alves, Thatyane Mariano Rodrigues de Albuquerque, Maria Elieidy Gomes de Oliveira, and Evandro Leite de Souza
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Cactaceae ,Palm ,Functional food ,Intestinal microbiota ,Modulatory effects ,Antioxidant capacity ,Nutrition. Foods and food supply ,TX341-641 - Abstract
This study evaluated the physicochemical properties, antioxidant capacity, and potential prebiotic effects on the human intestinal microbiota of freeze-dried Opuntia dillenii (Ker Gawl). Haw] (Cactaceae) cladodes (FDOd). FDOd had high levels of total fiber (52.36 g/100 g), especially soluble fiber (33.36 g/100 g), as well as minerals, such as potassium (4415.49 mg/100 g), calcium (1593.25 mg/100 g), magnesium (853.55 mg/100 g), and phosphorus (209.04 mg/100 g), high total chlorophyll content (912.00 mg/100 g), presence of various phenolic compounds, such as catechin (41.00 mg/100 g), myricetin (785.00 mg/100 g), isorhamnetin (5.00 mg/100 g), rutin (42 mg/100 g), and antioxidant activity (ABTS•+: 0.51 µmol TEAC/g; DPPH•: 0.32 µmol TEAC/g; FRAP: 2.75 µmol FeSO4/g). Fermentation of FDOd using human fecal inoculum changed the composition and metabolic activity of intestinal microbiota, increasing the relative abundance of Ligilactobacillus (0.03 %–16.44 %), Lactiplantibacillus (0.00 %–1.11 %), and Agathobacter (1.80 %–4.23 %), and decreasing the relative abundance of Prevotella_9 (25.08 %–0.15 %) and Succinivibrio (24.77 %–1.54 %). FDOd influenced the metabolic profile of the intestinal microbiota with the production of various metabolites, including short- and medium-chain fatty acids, organic acids, essential amino acids, and other compound classes with health-promoting properties. The results indicate FDOd as a new ingredient with prebiotic properties in the human intestinal microbiota.
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- 2024
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5. AMTAC-19, a Spiro-Acridine Compound, Induces In Vitro Antitumor Effect via the ROS-ERK/JNK Signaling Pathway
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Valgrícia Matias de Sousa, Sâmia Sousa Duarte, Rafael Carlos Ferreira, Natália Ferreira de Sousa, Marcus Tullius Scotti, Luciana Scotti, Marcelo Sobral da Silva, Josean Fechine Tavares, Ricardo Olímpio de Moura, Juan Carlos Ramos Gonçalves, and Marianna Vieira Sobral
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colorectal carcinoma ,oxidative stress ,MAPKs ,Organic chemistry ,QD241-441 - Abstract
Colorectal cancer remains a significant cause of mortality worldwide. A spiro-acridine derivative, (E)-1′-((4-bromobenzylidene)amino)-5′-oxo-1′,5′-dihydro-10H-spiro[acridine-9,2′-pyrrole]-4′-carbonitrile (AMTAC-19), showed significant cytotoxicity in HCT-116 colorectal carcinoma cells (half maximal inhibitory concentration, IC50 = 10.35 ± 1.66 µM) and antioxidant effects after 48 h of treatment. In this study, Molegro Virtual Docker v.6.0.1 software was used to investigate the interactions between AMTAC-19 and the Extracellular Signal-Regulated Kinase 1 (ERK1), c-Jun N-terminal Kinase 1 (JNK1), and p38 Mitogen-Activated Protein Kinase α (p38α MAPK). In vitro assays were conducted in HCT-116 cells to evaluate the effect of AMTAC-19 on the modulation of these proteins’ activities using flow cytometry. Furthermore, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in the presence or absence of ERK1/2, JNK, and p38 MAPK inhibitors was used to evaluate the involvement of these enzymes in AMTAC-19 cytotoxicity. ROS production was assessed using the 2,7-dichlorodihydrofluorescein diacetate (DCFH-DA) assay at various incubation times (30 min, 1 h, 6 h, 12 h, and 24 h), and the MTT assay using N-acetyl-L-cysteine (NAC) was performed. In silico results indicated that AMTAC-19 interacts with ERK1, JNK1, and p38α MAPK. Additionally, AMTAC-19 activated ERK1/2 and JNK1 in HCT-116 cells, and its cytotoxicity was significantly reduced in the presence of ERK1/2 and JNK inhibitors. AMTAC-19 also induced a significant increase in ROS production (30 min and 1 h), while NAC pretreatment reduced its cytotoxicity. These findings support AMTAC-19′s in vitro antitumor effect through ROS-dependent activation of ERK and JNK pathways.
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- 2024
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6. (-)-Fenchone Prevents Cysteamine-Induced Duodenal Ulcers and Accelerates Healing Promoting Re-Epithelialization of Gastric Ulcers in Rats via Antioxidant and Immunomodulatory Mechanisms
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Maria Elaine Cristina Araruna, Edvaldo Balbino Alves Júnior, Catarina Alves de Lima Serafim, Matheus Marley Bezerra Pessoa, Michelle Liz de Souza Pessôa, Vitória Pereira Alves, Marcelo Sobral da Silva, Marianna Vieira Sobral, Adriano Francisco Alves, Mayara Karla dos Santos Nunes, Aurigena Antunes Araújo, and Leônia Maria Batista
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(-)-Fenchone ,gastric ulcer ,duodenal ulcer ,healing ,monoterpene ,immunomodulatory ,Medicine ,Pharmacy and materia medica ,RS1-441 - Abstract
Background: (-)-Fenchone is a naturally occurring monoterpene found in the essential oils of Foeniculum vulgare Mill., Thuja occidentalis L., and Peumus boldus Molina. Pharmacological studies have reported its antinociceptive, antimicrobial, anti-inflammatory, antidiarrheal, and antioxidant activities. Methods: The preventive antiulcer effects of (-)-Fenchone were assessed through oral pretreatment in cysteamine-induced duodenal lesion models. Gastric healing, the underlying mechanisms, and toxicity after repeated doses were evaluated using the acetic acid-induced gastric ulcer rat model with oral treatment administered for 14 days. Results: In the cysteamine-induced duodenal ulcer model, fenchone (37.5–300 mg/kg) significantly decreased the ulcer area and prevented lesion formation. In the acetic acid-induced ulcer model, fenchone (150 mg/kg) reduced (p < 0.001) ulcerative injury. These effects were associated with increased levels of reduced glutathione (GSH), superoxide dismutase (SOD), interleukin (IL)-10, and transforming growth factor-beta (TGF-β). Furthermore, treatment with (-)-Fenchone (150 mg/kg) significantly reduced (p < 0.001) malondialdehyde (MDA), myeloperoxidase (MPO), interleukin-1 beta (IL-1β), tumor necrosis factor-alpha (TNF-α), and nuclear transcription factor kappa B (NF-κB). A 14-day oral toxicity investigation revealed no alterations in heart, liver, spleen, or kidney weight, nor in the biochemical and hematological parameters assessed. (-)-Fenchone protected animals from body weight loss while maintaining feed and water intake. Conclusion: (-)-Fenchone exhibits low toxicity, prevents duodenal ulcers, and enhances gastric healing activities. Antioxidant and immunomodulatory properties appear to be involved in its therapeutic effects.
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- 2024
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7. Cleomin Exerts Acute Antinociceptive Effects in Mice via GABAB and Muscarinic Receptors
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Luíza Carolina França Opretzka, Max Denisson Maurício Viana, Alyne Almeida de Lima, Thalisson Amorim de Souza, Marcus Tullius Scotti, Josean Fechine Tavares, Marcelo Sobral da Silva, Milena Botelho Pereira Soares, and Cristiane Flora Villarreal
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cleomin ,antinociception ,GABAergic receptor ,cholinergic receptor ,pain ,Neocalyptrocalix longifolium ,Medicine ,Pharmacy and materia medica ,RS1-441 - Abstract
Cleomin, a 1,3-oxazolidine-2-thione, was recently isolated from Neocalyptrocalyx longifolium, a species traditionally used for treating painful conditions. Reports about the pharmacological activities of cleomin are lacking. Here, the antinociceptive effects of cleomin were investigated using mice models of pain, namely the formalin, the cold plate, and the tail flick tests. Motor integrity was assessed in the rota-rod test. Antagonism assays and in silico docking analyses were performed to investigate the putative mechanisms of action. Cleomin (12.5–25 mg/kg), at doses that did not induce motor impairment, induced dose-dependent antinociception in both early and late phases of the formalin test and reduced nociceptive behaviors in both the cold plate and tail flick tests. Pretreatments with phaclofen and atropine attenuated the antinociceptive effects of cleomin, implicating the involvement of GABAB and muscarinic receptors. In silico docking studies suggested satisfactory coupling between cleomin and GABAB and M2 receptors, hence corroborating their role in cleomin’s activity. Pretreatments with naloxone, yohimbine, bicuculline, and methysergide did not affect the antinociception of cleomin. In silico pharmacokinetics prediction showed a good drug ability profile of cleomin. In conclusion, cleomin promoted antinociception mediated by GABAB and muscarinic receptors. These findings support further investigation of the analgesic potential of cleomin.
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- 2023
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8. The Essential Oil from Conyza bonariensis (L.) Cronquist (Asteraceae) Exerts an In Vitro Antimelanoma Effect by Inducing Apoptosis and Modulating the MAPKs, NF-κB, and PKB/AKT Signaling Pathways
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Rafael Carlos Ferreira, Sâmia Sousa Duarte, Valgrícia Matias de Sousa, Ramon Ramos Marques de Souza, Karinne Kelly Gadelha Marques, Renata Albuquerque de Abrantes, Yuri Mangueira do Nascimento, Natália Ferreira de Sousa, Marcus Tullius Scotti, Luciana Scotti, Josean Fechine Tavares, Juan Carlos Ramos Gonçalves, Marcelo Sobral da Silva, and Marianna Vieira Sobral
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natural products ,essential oil ,antitumor effect ,Medicine ,Pharmacy and materia medica ,RS1-441 - Abstract
The characterization and cytotoxicity of the essential oil from Conyza bonariensis (L.) aerial parts (CBEO) were previously conducted. The major compound was (Z)-2-lachnophyllum ester (EZ), and CBEO exhibited significant ROS-dependent cytotoxicity in the melanoma cell line SK-MEL-28. Herein, we employed the Molegro Virtual Docker v.6.0.1 software to investigate the interactions between the EZ and Mitogen-Activated Protein Kinases (MAPKs), the Nuclear Factor kappa B (NF-κB), and the Protein Kinase B (PKB/AKT). Additionally, in vitro assays were performed in SK-MEL-28 cells to assess the effect of CBEO on the cell cycle, apoptosis, and these signaling pathways by flow cytometry and the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay using MAPKs inhibitors. CBEO induced a significant increase in the sub-G1 peak, as well as biochemical and morphological changes characteristic of apoptosis. The in-silico results indicated that EZ interacts with Extracellular Signal-Regulated Kinase 1 (ERK1), c-Jun N-terminal Kinase 1 (JNK1), p38α MAPK, NF-κB, and PKB/AKT. Moreover, CBEO modulated the ERK1/2, JNK, p38 MAPK, NF-κB, and PKB/AKT activities in SK-MEL-28 cells. Furthermore, CBEO’s cytotoxicity against SK-MEL-28 cells was significantly altered in the presence of MAPKs inhibitors. These findings support the in vitro antimelanoma effect of CBEO through apoptosis induction, and the modulation of ERK, JNK, p38 MAPK, NF-κB, and PKB/AKT activities.
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- 2023
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9. Chemical Composition, In Vitro Antitumor Effect, and Toxicity in Zebrafish of the Essential Oil from Conyza bonariensis (L.) Cronquist (Asteraceae)
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Rafael Carlos Ferreira, Yuri Mangueira do Nascimento, Paulo Bruno de Araújo Loureiro, Rafael Xavier Martins, Maria Eduarda de Souza Maia, Davi Felipe Farias, Josean Fechine Tavares, Juan Carlos Ramos Gonçalves, Marcelo Sobral da Silva, and Marianna Vieira Sobral
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essential oil ,antiproliferative effect ,embryotoxicity ,Microbiology ,QR1-502 - Abstract
The essential oil from Conyza bonariensis (Asteraceae) aerial parts (CBEO) was extracted by hydrodistillation in a Clevenger-type apparatus and was characterized by gas chromatography–mass spectrometry. The antitumor potential was evaluated against human tumor cell lines (melanoma, cervical, colorectal, and leukemias), as well as non-tumor keratinocyte lines using the MTT assay. The effect of CBEO on the production of Reactive Oxygen Species (ROS) was evaluated by DCFH-DA assay, and a protection assay using the antioxidant N-acetyl-L-cysteine (NAC) was also performed. Moreover, the CBEO toxicity in the zebrafish model was assessed. The majority of the CBEO compound was (Z)-2-lachnophyllum ester (57.24%). The CBEO exhibited selectivity towards SK-MEL-28 melanoma cells (half maximal inhibitory concentration, IC50 = 18.65 ± 1.16 µg/mL), and induced a significant increase in ROS production. In addition, the CBEO’s cytotoxicity against SK-MEL-28 cells was reduced after pretreatment with NAC. Furthermore, after 96 h of exposure, 1.5 µg/mL CBEO induced death of all zebrafish embryos. Non-lethal effects were observed after exposure to 0.50–1.25 µg/mL CBEO. Additionally, significant alterations in the activity of enzymes associated with oxidative stress in zebrafish larvae were observed. These results provide evidence that CBEO has a significant in vitro antimelanoma effect by increasing ROS production and moderate embryotoxicity in zebrafish.
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- 2023
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10. HPLC-DAD-ESI-MS profile, antibacterial activity, and modulation of the activity of antibiotics by Carica papaya L. against Escherichia coli serotypes
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Cícera Natalia Figueiredo Leite Gondim, Denise Aline Casimiro Bezerra, Nadghia Figueiredo Leite Sampaio, Maria Anésia Sousa de.Alencar, Roger Henrique Sousa da.Costa, Lucas Silva Abreu, Joanda Paolla Raimundo.e.Silva, Francisco Nascimento Pereira Junior, Josean Fechine Tavares, Marcelo Sobral da Silva, Jaime Ribeiro-Filho, and Henrique Douglas Melo Coutinho
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Carica papaya ,HPLC-DAD-ESI-MS ,Antibacterial activity ,Antibiotic resistance ,E․ coli ,Other systems of medicine ,RZ201-999 - Abstract
Background: Diarrhea is currently the second leading cause of death among children under five years old in the world and therefore, remains a global public health problem. Considering that most cases of diarrhea are due to gastrointestinal infections, and medicinal plants have been traditionally used to treat such conditions, this work aimed to evaluate the chemical composition, antibacterial activity, and antibiotic-enhancing properties of C. papaya against Escherichia coli, EPEC (Enteropathogenic E. coli), and ETEC (Enterotoxigenic E. coli) serotypes.Methods: The chemical profile of the aqueous extract obtained from C. papaya leaves was determined by HPLC-DAD-ESI-MS. The antibacterial and antibiotic-enhancing activities were evaluated through the determination of the MIC, following the microdilution method.Results: A total of 17 compounds were identified by HPLC-DAD-ESI-MS. However, the extract of C. papaya did not present an intrinsic antibacterial effect, in addition to showing no modulatory effect when associated with antibiotics.Conclusions: Despite the presence of bioactive compounds, the aqueous extract C. papaya does not present antibacterial or antibiotic-enhancing effects against the ETEC and EPEC strains of E. coli. Nevertheless, further research is required to determine if its isolated components are potential drug candidates for the therapy of infections caused by these strains.
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- 2022
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11. A NEW SECO-LIMONOID FROM THE INFLORESCENCES OF Dictyoloma vandellianum
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Laiane Caline Oliveira Pereira, Lucas Silva Abreu, Mayra Bitencourt Silveira, Yuri Mangueira do Nascimento, Thalisson Amorim de Souza, Mireille Le Hyaric, Thaís Mangeon Honorato Lisboa, Marianna Vieira Sobral, Eudes da Silva Velozo, Josean Fechine Tavares, and Marcelo Sobral da Silva
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A-seco-limonoid ,alkaloid ,Dictyoloma vandellianum ,Rutaceae ,cytotoxicity ,Chemistry ,QD1-999 - Abstract
Phytochemical investigation of the inflorescences of Dictyoloma vandellianum A. Juss. (Rutaceae) has led to the isolation of a new A-seco-limonoid, named dictyolomol (1), along with a known quinolone alkaloid, casimiroine (2), previously isolated from the same species. The structures were established by spectroscopic analysis such as one- and two-dimensional NMR, IR, high-resolution mass spectrometry and chemical transformations. The isolated compounds (1 and 2) and O-acetyl derivative (1a) were evaluated for their cytotoxicity against MCF-7 and HeLa cancer cell lines. The results indicated that 1, 1a and 2 showed no significant cytotoxicity.
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- 2020
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12. Dolichocarpols A‑F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa
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Kaio Aragão Sales, Anderson Angel Vieira Pinheiro, Diego Igor Alves Fernandes de Araújo, Lucas Silva Abreu, Rodrigo Silva de Andrade, Maria de Fátima Agra, Marianna Vieira Sobral, Rafael Carlos Ferreira, Raimundo Braz-Filho, Marcus Tullius Scotti, Josean Fechine Tavares, and Marcelo Sobral da Silva
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Chemistry ,QD1-999 - Published
- 2020
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13. Psychopharmacological effects of riparin III from Aniba riparia (Nees) Mez. (Lauraceae) supported by metabolic approach and multivariate data analysis
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Sócrates Golzio dos Santos, Isis Fernandes Gomes, Adriana Maria Fernandes de Oliveira Golzio, Augusto Lopes Souto, Marcus Tullius Scotti, Josean Fechine Tavares, Stanley Juan Chavez Gutierrez, Reinaldo Nóbrega de Almeida, José Maria Barbosa-Filho, and Marcelo Sobral da Silva
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Metabolomics analysis ,Footprint ,Urine ,Aniba riparia ,Riparin ,Anxiety animal model ,Other systems of medicine ,RZ201-999 - Abstract
Abstract Background Currently there is a high prevalence of humor disorders such as anxiety and depression throughout the world, especially concerning advanced age patients. Aniba riparia (Nees) Mez. (Lauraceae), popular known as “louro”, can be found from the Amazon through Guianas until the Andes. Previous studies have already reported the isolation of alkamide-type alkaloids such as riparin III (O-methyl-N-2,6-dyhydroxy-benzoyl tyramine) which has demonstrated anxiolytic and antidepressant-like effects in high doses by intraperitoneal administration. Methods Experimental protocol was conducted in order to analyze the anxiolytic-like effect of riparin III at lower doses by intravenous administration to Wistar rats (Rattus norvegicus) (n = 5). The experimental approach was designed to last 15 days, divided in 3 distinct periods of five days: control, anxiogenic and treatment periods. The anxiolytic-like effect was evaluated by experimental behavior tests such as open field and elevated plus-maze test, combined with urine metabolic footprint analysis. The urine was collected daily and analyzed by 1H NMR. Generated data were statistically treated by Principal Component Analysis in order to detect patterns among the distinct periods evaluated as well as biomarkers responsible for its distinction. Results It was observed on treatment group that cortisol, biomarker related to physiological stress was reduced, indicating anxiolytic-like effect of riparin III, probably through activation of 5-HT2A receptors, which was corroborated by behavioral tests. Conclusion 1H NMR urine metabolic footprint combined with multivariate data analysis have demonstrated to be an important diagnostic tool to prove the anxiolytic-like effect of riparin III in a more efficient and pragmatic way.
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- 2020
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14. Antimicrobial Potential of Betulinic Acid and Investigation of the Mechanism of Action against Nuclear and Metabolic Enzymes with Molecular Modeling
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Gabriela Cristina Soares Rodrigues, Mayara dos Santos Maia, Thalisson Amorim de Souza, Edeltrudes de Oliveira Lima, Luiz Eduardo Carneiro Gomes dos Santos, Shellygton Lima Silva, Marcelo Sobral da Silva, José Maria Barbosa Filho, Valnês da Silva Rodrigues Junior, Luciana Scotti, and Marcus Tullius Scotti
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betulinic acid ,antimicrobial activity ,triterpenoids ,M. tuberculosis ,E. coli ,Medicine - Abstract
Natural products have important pharmacological activities. This study sought to investigate the activity of the compound betulinic acid (BA) against different strains of bacteria and fungi. The minimum inhibitory concentration (MIC) was determined and then the minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC). After performing the in vitro tests, molecular modeling studies were carried out to investigate the mechanism of action of BA against the selected microorganisms. The results showed that BA inhibited the growth of microbial species. Among the 12 species (Staphylococcus aureus, S. epidermidis, Pseudomonas aeruginosa, Escherichia coli, Mycobacterium tuberculosis, Candida albicans, C. tropicalis, C. glabrata, Aspergillus flavus, Penicillium citrinum, Trichophyton rubrum, and Microsporum canis) investigated, 9 (75%) inhibited growth at a concentration of 561 µM and 1 at a concentration of 100 µM. In general, the MBC and MFC of the products were between 561 and 1122 μM. In silico studies showed that BA presented a mechanism of action against DNA gyrase and beta-lactamase targets for most of the bacteria investigated, while for fungi the mechanism of action was against sterol 14α-demethylase (CYP51) targets and dihydrofolate reductase (DHFR). We suggest that BA has antimicrobial activity against several species.
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- 2023
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15. (-)-Carveol Prevents Gastric Ulcers via Cytoprotective, Antioxidant, Antisecretory and Immunoregulatory Mechanisms in Animal Models
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Catarina Alves de Lima Serafim, Maria Elaine Cristina Araruna, Edvaldo Balbino Alves Júnior, Leiliane Macena Oliveira Silva, Alessa Oliveira Silva, Marcelo Sobral da Silva, Adriano Francisco Alves, Aurigena Antunes Araújo, and Leônia Maria Batista
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(-)-Carveol ,gastric ulcer ,gastroprotection ,cytoprotection ,antioxidant ,immunoregulatory mechanism ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Background: (-)-Carveol (p-Mentha-6,8-dien-2-ol) is a monocyclic monoterpenic alcohol, present in essential oils of plant species such as Cymbopogon giganteus, Illicium pachyphyllum and in spices such as Carum carvi (cumin). Pharmacological studies report its antitumor, antimicrobial, neuroprotective, vasorelaxant, antioxidant and anti-inflammatory activity.Hypothesis/Purpose: The objective of this study was to evaluate the acute non-clinical oral toxicity, gastroprotective activity of monoterpene (-)-Carveol in animal models and the related mechanisms of action.Methods: Acute toxicity was assessed according to OECD guide 423 in mice. Ethanol, stress, NSAIDs and pylorus ligation-induced gastric ulcer models were used to investigate antiulcer properties. The related mechanisms of action were using the ethanol-gastric lesions protocol.Results: (-)-Carveol has low toxicity, with a lethal dose 50% (LD50) equal to or greater than 2,500 mg/kg according to OECD guide nº 423. In all gastric ulcer induction methods evaluated, (-)-Carveol (25, 50, 100 and 200 mg/kg, p.o.) significantly reduced the ulcerative lesion in comparison with the respective control groups. To investigate the mechanisms involved in the gastroprotective activity, the antisecretory or neutralizing of gastric secretion, cytoprotective, antioxidant and immunoregulatory effects were evaluated. In the experimental protocol of pylorus ligation-induced gastric ulcer, (-)-Carveol (100 mg/kg) reduced (p < 0.001) the volume of gastric secretion in both routes (oral and intraduodenal). The previous administration of blockers NEM (sulfhydryl groups blocker), L-NAME (nitric oxide synthesis inhibitor), glibenclamide (KATP channel blocker) and indomethacin (cyclo-oxygenase inhibitor), significantly reduced the gastroprotection exercised by (-)-Carveol, suggesting the participation of these pathways in its gastroprotective activity. In addition, treatment with (-)-Carveol (100 mg/kg) increased (p < 0.001) mucus adhered to the gastric wall. Treatment also increased (p < 0.001) levels of reduced glutathione (GSH), superoxide dismutase (SOD) and interleukin-10 (IL-10). It also reduced (p < 0.001) malondialdehyde (MDA), myeloperoxidase (MPO), interleukin-1 beta (IL-1β) and tumor necrosis factor-alpha (TNF-α) levels.Conclusion: Thus, it is possible to infer that (-)-Carveol presents gastroprotective activity related to antisecretory, cytoprotective, antioxidant and immunomodulatory mechanisms.
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- 2021
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16. Toxicological and Pharmacological Activities of Leptohyptis macrostachys (Benth.) Harley and J.F.B.Pastore (Lamiaceae) on Intestinal Smooth Muscle
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Iara Leão Luna de Souza, Maria Allynne de Vasconcelos, Anne Dayse Soares da Silva, Polyana Cristina Barros Silva, Carlos Arthur Gouveia Veloso, Diego Igor Alves Fernandes de Araújo, Vicente Carlos de Oliveira Costa, Hilzeth Luna Freire Pessôa, Josean Fechine Tavares, Marcelo Sobral da Silva, Bagnólia Araújo da Silva, and Fabiana de Andrade Cavalcante
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Leptohyptis macrostachys ,Lamiaceae ,spasmolytic activity ,antidiarrheal activity ,potassium channel ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Leptohyptis macrostachys, previously known as Hyptis macrostachys Benth., is used in folk medicine to relieve the symptoms of asthma, cough, and bronchitis. Recently, we showed that the ethanol extract obtained from Leptohyptis macrostachys has selective spasmolytic activity on guinea pig ileum. Therefore, the aim of this study was to characterize the spasmolytic mechanism of this extract, investigated whether it presents toxicological and antidiarrheal activities. Therefore, the crude ethanolic extract of Leptohyptis macrostachys was analyzed by high-performance liquid chromatographic-diode array detection (HPLC–DAD). The spasmolytic effect was evaluated on guinea pig ileum, toxicological activity using rats and antidiarrheal activity using male and female mice. In HPLC-DAD analysis, Rosmarinic acid (5.44%) was the most abundant phenolic compound, being considered as a chemical marker. The spasmolytic potency of the extract on histamine-induced contraction was reduced in the presence of 1 mM TEA+, a selective big–conductance K+ channels blocker (BKCa). The extract produces a dose–dependent antidiarrheal activity, inhibiting equipotently defecation frequency and liquid stool formation. In addition, the extract has inhibited in a dose–dependent manner both castor oil–induced intestinal transit and intestinal fluid content. Thus, the spasmolytic activity of the extract involves positive modulation of BKCa and its antidiarrheal activity is related to inhibition of intestinal motility and secretion.
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- 2020
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17. Toxicity and antitumor potential of Mesosphaerum sidifolium (Lamiaceae) oil and fenchone, its major component
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Thaísa Leite Rolim, Déborah Ribeiro Pessoa Meireles, Tatianne Mota Batista, Tatyanna Kelvia Gomes de Sousa, Vivianne Mendes Mangueira, Renata Albuquerque de Abrantes, João Carlos Lima Rodrigues Pita, Aline Lira Xavier, Vicente Carlos Oliveira Costa, Leônia Maria Batista, Marcelo Sobral da Silva, and Marianna Vieira Sobral
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Mesosphaerum sidifolium ,Lamiaceae ,Fenchone ,Hemolysis ,Ehrlich ascites carcinoma ,Genotoxicity ,Other systems of medicine ,RZ201-999 - Abstract
Abstract Background The essential oil from Mesosphaerum sidifolium (L’Hérit.) Harley & J.F.B.Pastore (syn. Hyptis umbrosa), Lamiaceae (EOM), and its major component, have been tested for toxicity and antitumor activity. Methods EOM was obtained from aerial parts of M. sidifolium subjected to hydro distillation, and gas chromatography-mass spectrometry was used to characterize the EOM chemical composition. The toxicity was evaluated using haemolysis assay, and acute toxicity and micronucleus tests. Ehrlich ascites carcinoma model was used to evaluate the in vivo antitumor activity and toxicity of EOM (50, 100 and 150 mg/kg), and fenchone (30 and 60 mg/kg) after 9 d of treatment. Results The EOM major components were fenchone (24.8%), cubebol (6.9%), limonene (5.4%), spathulenol (4.5%), β-caryophyllene (4.6%) and α-cadinol (4.7%). The HC50 (concentration producing 50% haemolysis) was 494.9 μg/mL for EOM and higher than 3000 μg/mL for fenchone. The LD50 for EOM was approximately 500 mg/kg in mice. The essential oil induced increase of micronucleated erythrocytes only at 300 mg/kg, suggesting moderate genotoxicity. EOM (100 or 150 mg/kg) and fenchone (60 mg/kg) reduced all analyzed parameters (tumor volume and mass, and total viable cancer cells). Survival also increased for the treated animals with EOM and fenchone. For EOM 150 mg/kg and 5-FU treatment, most cells were arrested in the G0/G1 phase, whereas for fenchone, cells arrested in the S phase, which represents a blockage in cell cycle progression. Regarding the toxicological evaluation, EOM induced weight loss, but did not induce hematological, biochemical or histological (liver and kidneys) toxicity. Fenchone induced decrease of AST and ALT, suggesting liver damage. Conclusions The data showed EOM caused in vivo cell growth inhibition on Ehrlich ascites carcinoma model by inducing cell cycle arrest, without major changes in the toxicity parameters evaluated. In addition, this activity was associated with the presence of fenchone, its major component.
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- 2017
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18. Seasonal Variations of Polyphenols Content, Sun Protection Factor and Antioxidant Activity of Two Lamiaceae Species
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Juliana de Medeiros Gomes, Márcio Vinícius Cahino Terto, Sócrates Golzio do Santos, Marcelo Sobral da Silva, and Josean Fechine Tavares
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photoprotection ,M. villosa ,P. amboinicus ,ultraviolet radiation ,PCA ,seasonality ,Pharmacy and materia medica ,RS1-441 - Abstract
Secondary metabolite production by plants is influenced by external environmental factors that can change depending on the seasons, which makes it important to know how the plant, through its metabolism, is able to adapt to these variations. Mentha x villosa and Plectranthus amboinicus present in their chemical composition polyphenols, and through previous studies, it has been seen that these two species present promising in vitro photoprotective activity. The aim of this study was to evaluate seasonal alterations in photoprotective and antioxidant activities and the influence of factors such as precipitation levels and sun radiation incidence. Thus, polyphenol quantification, cromatographics (HPLC-DAD) and multivariate (PCA) analyses of extracts of the two species through twelve months were done. It was observed that the best months for photoprotective and antioxidant activities were September for M. villosa and July for P. amboinicus (SPF = 14.79). It was possible to conclude that solar radiation more clearly influences the production of phenolics and the increase of SPF in M. villosa, in addition to favoring the antioxidant activity of the two species, while precipitation seems to have no influence.
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- 2021
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19. Antinociceptive compounds and LC-DAD-ESIMSn profile from Dictyoloma vandellianum leaves.
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Lucas Silva Abreu, Iura Muniz Alves, Renan Fernandes do Espírito Santo, Yuri Mangueira do Nascimento, César Augusto Gonçalves Dantas, Gisele Graça Leite Dos Santos, Mireille Le Hyaric, Maria Lenise Silva Guedes, Marcelo Sobral da Silva, Cristiane Flora Villarreal, Eudes da Silva Velozo, and Josean Fechine Tavares
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Medicine ,Science - Abstract
Limonoids, quinolone alkaloids and chromones have been reported as constituents of Dictyoloma vandellianum Adr. Juss. (Rutaceae). Although those compounds are known for their biological activities, only the anti-inflammatory activity of chromones isolated from the underground parts has been evaluated. There are no studies of the pharmacological properties of the aerial parts of D. vandellianum. The present study was carried out to determine the phytochemical profile and antinociceptive activity of the methanol extract, fractions and isolated compounds of leaves of D. vandellianum. The phytochemical profile was performed by HLPC-DAD-ESIMSn and pure substances obtained were characterized by MS and NMR spectroscopy. The antinociceptive activity was assessed using the formalin assay in mice, and the motor function in the rotarod test. ME and all the fractions obtained from ME produced antinociceptive effects. Among them, the ethyl ether fraction was the most active. Data from HPLC-DAD-ESIMSn showed that the ethyl ether fraction presented 42 compounds. The major compounds isolated from this fraction-gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose-were tested and produced antinociceptive effects. Gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose at antinociceptive doses did not affect the motor performance in mice in the rotarod test. This work is the first report of the occurrence of gallotanins in D. vandellianum. In addition, the pharmacological study showed that D. vandellianum leaves present antinociceptive activity, probably induced by gallic acid, methyl gallate and 1,2,6-tri-O-galloyl-β-d-glucopyranose.
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- 2019
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20. Computer-Aided Chemotaxonomy and Bioprospecting Study of Diterpenes of the Lamiaceae Family
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Andreza Barbosa Silva Cavalcanti, Renata Priscila Costa Barros, Vicente Carlos de Oliveira Costa, Marcelo Sobral da Silva, Josean Fechine Tavares, Luciana Scotti, and Marcus Tullius Scotti
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lamiaceae ,database ,diterpenes ,chemotaxonomic ,soms ,Organic chemistry ,QD241-441 - Abstract
Lamiaceae is one of the largest families of angiosperms and is classified into 12 subfamilies that are composed of 295 genera and 7775 species. It presents a variety of secondary metabolites such as diterpenes that are commonly found in their species, and some of them are known to be chemotaxonomic markers. The aim of this work was to construct a database of diterpenes and to use it to perform a chemotaxonomic analysis among the subfamilies of Lamiaceae, using molecular descriptors and self-organizing maps (SOMs). The 4115 different diterpenes corresponding to 6386 botanical occurrences, which are distributed in eight subfamilies, 66 genera, 639 different species and 4880 geographical locations, were added to SistematX. Molecular descriptors of diterpenes and their respective botanical occurrences were used to generate the SOMs. In all obtained maps, a match rate higher than 80% was observed, demonstrating a separation of the Lamiaceae subfamilies, corroborating with the morphological and molecular data proposed by Li et al. Therefore, through this chemotaxonomic study, we can predict the localization of a diterpene in a subfamily and assist in the search for secondary metabolites with specific structural characteristics, such as compounds with potential biological activity.
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- 2019
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21. Flavonoides glicosilados de Erythroxylum pulchrum a. st.-hil. (Erythroxylaceae)
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Camila Holanda de Albuquerque, Josean Fechine Tavares, Steno Lacerda de Oliveira, Tainá Souza Silva, Gregório Fernandes Gonçalves, Vicente Carlos de Oliveira Costa, Maria de Fátima Agra, Hilzeth de Luna Freire Pessôa, and Marcelo Sobral da Silva
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Erythroxylum pulchrum ,flavonoid glycosides ,antimicrobial activity ,Chemistry ,QD1-999 - Abstract
The phytochemical investigation of Erythroxylum pulchrum St. Hil. (Erythroxylaceae) led to the isolation of three known flavonoid glycosides quercetin-3-O-α-L-rhaminoside, ombuin-3-ruthinoside and ombuin-3-ruthinoside-5-glucoside. These flavonoids are being described for the first time in this E. pulchrum. The structures of the compounds were determined by analysis of IR, MS and NMR data, as well as by comparison with literature data. The methanolic extract of leaves from E. pulchrum inhibited the growth of the Bacillus subtilis CCT 0516, Escherichia coli ATCC 2536, Pseudomonas aeruginosa ATCC 8027, P. aeruginosa ATCC 25619, Staphylococcus aureus ATCC 6538, S. aureus ATCC 25925, Streptococcus sanguinis ATCC 15300, S. salivarius ATCC 7073, S. mutans ATCC 25175 and Streptococcus ATCC. S. aureus ATCC 25925 was the most sensitive among the other S. sanguinis while S. salivarius proved the most resistant.
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- 2014
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22. In Vitro and in Vivo Antitumor Effect of Trachylobane-360, a Diterpene from Xylopia langsdorffiana
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João Carlos Lima Rodrigues Pita, Aline Lira Xavier, Tatyanna Kelvia Gomes de Sousa, Vivianne Mendes Mangueira, Josean Fechine Tavares, Robson José de Oliveira Júnior, Robson Cavalcante Veras, Hilzeth de Luna Freire Pessoa, Marcelo Sobral da Silva, Sandra Morelli, Veridiana de Melo Rodrigues Ávila, Teresinha Gonçalves da Silva, Margareth de Fátima Formiga Melo Diniz, and Marianna Vieira Sobral Castello-Branco
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trachylobane-360 ,Xylopia langsdorffiana ,antitumor activity ,toxicity ,hemolytic activity ,Organic chemistry ,QD241-441 - Abstract
Trachylobane-360 (ent-7α-acetoxytrachyloban-18-oic acid) was isolated from Xylopia langsdorffiana. Studies have shown that it has weak cytotoxic activity against tumor and non-tumor cells. This study investigated the in vitro and in vivo antitumor effects of trachylobane-360, as well as its cytotoxicity in mouse erythrocytes. In order to evaluate the in vivo toxicological aspects related to trachylobane-360 administration, hematological, biochemical and histopathological analyses of the treated animals were performed. The compound exhibited a concentration-dependent effect in inducing hemolysis with HC50 of 273.6 µM, and a moderate in vitro concentration-dependent inhibitory effect on the proliferation of sarcoma 180 cells with IC50 values of 150.8 µM and 150.4 µM, evaluated by the trypan blue exclusion test and MTT reduction assay, respectively. The in vivo inhibition rates of sarcoma 180 tumor development were 45.60, 71.99 and 80.06% at doses of 12.5 and 25 mg/kg of trachylobane-360 and 25 mg/kg of 5-FU, respectively. Biochemical parameters were not altered. Leukopenia was observed after 5-FU treatment, but this effect was not seen with trachylobane-360 treatment. The histopathological analysis of liver and kidney showed that both organs were mildly affected by trachylobane-360 treatment. Trachylobane-360 showed no immunosuppressive effect. In conclusion, these data reinforce the anticancer potential of this natural diterpene.
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- 2012
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23. Experimental Methodologies and Evaluations of Computer-Aided Drug Design Methodologies Applied to a Series of 2-Aminothiophene Derivatives with Antifungal Activities
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Ricardo Olímpio de Moura, Rayssa Marques Duarte da Cruz, Francisco Jaime Bezerra Mendonça, Jaismary Gonzaga Batista de Oliveira, Edeltrudes de Oliveira Lima, Marcelo Sobral da Silva, Maria do Carmo Alves de Lima, Ivan da Rocha Pitta, Luciana Scotti, and Marcus Tullius Scotti
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2-aminothiophene derivatives ,antifungal activity ,molecular modelling ,computer-aided drug design ,density functional theory ,Organic chemistry ,QD241-441 - Abstract
Fifty 2-[(arylidene)amino]-4,5-cycloalkyl[b]thiophene-3-carbonitrile derivatives were screened for their in vitro antifungal activities against Candida krusei and Cryptococcus neoformans. Based on experimentally determined minimum inhibitory concentration (MIC) values, we conducted computer-aided drug design studies [molecular modelling, chemometric tools (CPCA, PCA, PLS) and QSAR-3D] that enable the prediction of three-dimensional structural characteristics that influence the antifungal activities of these derivatives. These predictions provide direction with regard to the syntheses of new derivatives with improved biological activities, which can be used as therapeutic alternatives for the treatment of fungal infections.
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- 2012
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24. Chemotaxonomy of three genera of the annonaceae family using self-organizing maps and 13C NMR data of diterpenes
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Luciana Scotti, Josean Fechine Tavares, Marcelo Sobral da Silva, Emanuela Viana Falcão, Luana de Morais e Silva, Gabriela Cristina da Silva Soares, and Marcus Tullius Scotti
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chemotaxonomy ,self-organizing maps ,13C NMR ,Chemistry ,QD1-999 - Abstract
The Annonaceae family is distributed throughout Neotropical regions of the world. In Brazil, it covers nearly all natural formations particularly Annona, Xylopia and Polyalthia and is characterized chemically by the production of sources of terpenoids (mainly diterpenes), alkaloids, steroids, polyphenols and, flavonoids. Studies from 13C NMR data of diterpenes related with their botanical occurrence were used to generate self-organizing maps (SOM). Results corroborate those in the literature obtained from morphological and molecular data for three genera and the model can be used to project other diterpenes. Therefore, the model produced can predict which genera are likely to contain a compound.
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- 2012
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25. Licanol, um novo flavanol, e outros constituintes de Licania macrophylla Benth
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Fernando Antônio de Medeiros, Alessandra A. N. Medeiros, Josean Fechine Tavares, José Maria Barbosa Filho, Edeltrudes de Oliveira Lima, and Marcelo Sobral da Silva
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Licania macrophylla ,Chrysobalanaceae ,(-)-4'-O-methyl-epigallocatechin-3'-O-α-L-rhamnoside ,Chemistry ,QD1-999 - Abstract
The phytochemical investigation of L. macrophylla Benth led to the isolation of a new flavanol named licanol: (-)-4'-O-methyl-epigallocatechin-3'-O-α-L-rhamnoside, along with nine known compounds, identified as: (-)-4'-O-methyl-epigallocatechin, pheophytin A, 13²-hydroxy-(13²-S)-pheophytin A, pheophytin B, sitosterol, stigmasterol, sitosterol-β-O-glucoside, betulinic alcohol and oleanolic acid. The structures were established based on IR, HR-ESI-MS, and NMR spectrometric data analysis with the aid of 2D techniques. The methanolic extracts of leaves and stem bark as well as the compounds licanol, 13²-hidroxi-(13²-S)-feofitina A, and betulinic alcohol demonstrated antimicrobial activity against several bacterial strains.
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- 2012
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26. Aplysfistularine: a novel dibromotyrosine derivative isolated from Aplysina fistularis
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Narlize Silva Lira, Rubens L. Monte-Neto, João Guilherme B. Marchi, Antônio Cláudio da Silva Lins, Josean Fechine Tavares, Marcelo Sobral da Silva, Celidarque da Silva Dias, José Maria Barbosa-Filho, Creusioni Figueredo dos Santos, Emídio Vasconcelos Leitão da Cunha, Ulisses dos Santos Pinheiro, and Raimundo Braz-Filho
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Aplysina fistularis ,aplysfistularine ,topoisomerase activity ,Chemistry ,QD1-999 - Abstract
The new dibromotyrosine derivative 3,5-dibromo-4-[3'dimethylamonium]propoxyphenyl]-N,N,N-trimethylethanamonium, here referred to as aplysfistularine (1), was isolated from the marine sponge Aplysina fistularis along with 2-(3,5-dibromo-4methoxyphenyl)-N,N,N-trimethylethanamonium (2), aplysterol (3) and 24,28-didehydroaplysterol (4). Their identification was performed by mass spectrometry, infrared, ¹H and 13C NMR, and by comparison with literature data. Compound 2 and the mixture of 3 and 4 were tested in vitro (inhibitory activity) with supercoiled DNA relaxation techniques, and showed inhibitory activity on human DNA topoisomerase II-α. Compound 1 was not tested due to paucity of the material.
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- 2012
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27. Constituintes químicos das folhas de Rollinia leptopetala R. E. Fries
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Vicente Carlos de O. Costa, Josean F. Tavares, Cinthia S. Queiroga, Marianna V. S. Castello-Branco, Margareth F. F. Melo Diniz, Carolina Uchôa G. B. de Lima, Bárbara Viviana de O. Santos, João Carlos L. R. Pita, Marcelo Sobral da Silva, and Ivana Maria Fechine Sette
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Rollinia leptopetala ,α-terpinyl caffeate ,alkaloids ,Chemistry ,QD1-999 - Abstract
The phytochemical investigation of Rollinia leptopetala led to the isolation of a new compound named α-terpinyl caffeate, and five known compounds, being three sesquiterpenes, spathulenol, β-caryophyllene and 4β,10α-aromadendrane-diol, and two alkaloids, (-)-3-hydroxynornuciferine and (+)-norisocorydine. These alkaloids are being described for the first time in this genus. The structures of the compounds were determined by analysis of IR, MS and NMR data, as well as by comparison with literature data. The crude extract of R. leptopetala leaves demonstrated a weak cytotoxicity on sarcoma 180 cells with an IC50 of 512.3 µg/mL. However, the in vivo results showed that the extract exhibited a significant dose-dependent tumor growth reduction.
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- 2012
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28. Brominated Compounds from Marine Sponges of the Genus Aplysina and a Compilation of Their 13C NMR Spectral Data
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Jose Maria Barbosa-Filho, Celidarque da Silva Dias, Luis Cezar Rodrigues, Narlize Silva Lira, Petronio Filgueiras de Athayde-Filho, Emidio V. L. da Cunha, Josean Fechine Tavares, Ricardo Carneiro Montes, and Marcelo Sobral da Silva
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Aplysina ,marine sponges ,halogenated substances ,13C NMR ,review ,Biology (General) ,QH301-705.5 - Abstract
Aplysina is the best representative genus of the family Aplysinidae. Halogenated substances are its main class of metabolites. These substances contribute greatly to the chemotaxonomy and characterization of the sponges belonging to this genus. Due to their pharmacological activities, these alkaloids are of special interest. The chemistry of halogenated substances and of the alkaloids has long been extensively studied in terrestrial organisms, while the number of marine organisms studied has just started to increase in the last decades. This review describes 101 halogenated substances from 14 species of Aplysina from different parts of the world. These substances can be divided into the following classes: bromotyramines (A), cavernicolins (B), hydroverongiaquinols (C), bromotyrosineketals (D), bromotyrosine lactone derivatives (E), oxazolidones (F), spiroisoxazolines (G), verongiabenzenoids (H), verongiaquinols (I), and dibromocyclohexadienes (J). A compilation of their 13C NMR data is also part of the review. For this purpose 138 references were consulted.
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- 2011
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29. Anti-Inflammatory Activity of Alkaloids: An Update from 2000 to 2010
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Margareth de Fátima Formiga Melo Diniz, José Maria Barbosa Filho, Petrônio Filgueiras de Athayde-Filho, Marcelo Sobral da Silva, Josean Fechine Tavares, and Augusto Lopes Souto
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alkaloids ,anti-inflammatory activity ,inflammation ,experimental models ,review ,Organic chemistry ,QD241-441 - Abstract
Many natural substances with proven anti-inflammatory activity have been isolated throughout the years. The aim of this review is to review naturally sourced alkaloids with anti-inflammatory effects reported from 2000 to 2010. The assays were conducted mostly in vivo, and carrageenan-induced pedal edema was the most used experimental model. Of the 49 alkaloids evaluated, 40 demonstrated anti-inflammatory activity. Of these the most studied type were the isoquinolines. This review was based on NAPRALERT data bank, Web of Science and Chemical Abstracts. In this review, 95 references are cited.
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- 2011
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30. Azaphenanthrene Alkaloids with Antitumoral Activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)
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Josean Fechine Tavares, Emidio V.L. Da-Cunha, Marcelo Sobral Da Silva, Maria De Fátima Agra, Margareth De Fátima Formiga Melo Diniz, Marianna Vieira Sobral Castello Branco, Ana Silvia Suassuna Carneiro Lúcio, João Carlos Lima Rodrigues Pita, José Maria Barbosa-Filho, and Jackson Roberto Guedes Da Silva Almeida
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Annonaceae ,Anaxagorea dolichocarpa ,azaphenanthrene alkaloid ,antitumor activity ,Organic chemistry ,QD241-441 - Abstract
Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC50 of 18.97 and 10.95 µg/mL, respectively.
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- 2011
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31. 13C NMR spectral data and molecular descriptors to predict the antioxidant activity of flavonoids
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Luciana Scotti, Mariane Balerine Fernandes, Eric Muramatsu, Vicente de Paula Emereciano, Josean Fechine Tavares, Marcelo Sobral da Silva, and Marcus Tullius Scotti
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RMN 13C ,Flavonóides ,Mapa auto-organizável de Kohonen ,Flavonoids ,13C NMR ,Kohonen self-organizing map ,Pharmacy and materia medica ,RS1-441 - Abstract
Tissue damage due to oxidative stress is directly linked to development of many, if not all, human morbidity factors and chronic diseases. In this context, the search for dietary natural occurring molecules with antioxidant activity, such as flavonoids, has become essential. In this study, we investigated a set of 41 flavonoids (23 flavones and 18 flavonols) analyzing their structures and biological antioxidant activity. The experimental data were submitted to a QSAR (quantitative structure-activity relationships) study. NMR 13C data were used to perform a Kohonen self-organizing map study, analyzing the weight that each carbon has in the activity. Additionally, we performed MLR (multilinear regression) using GA (genetic algorithms) and molecular descriptors to analyze the role that specific carbons and substitutions play in the activity.Danos aos tecidos devido ao estresse oxidativo estão diretamente ligados ao desenvolvimento de muitos, senão todos, os fatores de sedentarismo e de doenças crônicas. Neste contexto, a busca de moléculas naturais, que participam da nossa dieta e que possuam atividade antioxidante, flavonóides, torna-se de grande interesse. Neste estudo, nós investigamos um conjunto de 41 flavonóides (23 flavonas e 18 flavonóis), relacionando suas estruturas e atividade antioxidante. Os dados experimentais foram submetidos à análise de QSAR (relações quantitativas estrutura-atividade). Dados de RMN 13C foram utilizados para realizar um estudo do mapa auto-organizável de Kohonen, analisando o peso que cada carbono tem na atividade. Além disso, realizamos uma MLR (regressão múltipla) usando GA (algoritmos genéticos) e descritores moleculares para avaliar a influência de carbonos e substituições na atividade.
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- 2011
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32. Flavonoids from Praxelis clematidea R.M. King and Robinson Modulate Bacterial Drug Resistance
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José Maria Barbosa-Filho, Marcelo Sobral da Silva, Luis Cezar Rodrigues, José Pinto de Siqueira-Júnior, Josean Fechine Tavares, João Xavier de Araújo-Júnior, Pedro Gregório Vieira Aquino, Vivyanne dos Santos Falcão-Silva, and Gabriela Lemos de Azevedo Maia
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Praxelis clematidea ,Asteraceae ,flavonoids ,antibacterial activity ,bacterial resistance ,efflux pump ,Organic chemistry ,QD241-441 - Abstract
Chemical studies of Praxelis clematidea R.M. King & Robinson resulted in the isolation of six flavones: Apigenine, genkwanine, 7,4’-dimethylapigenin, trimethylapigenin,cirsimaritin and tetramethylscutellarein, which were tested for their toxicity against Staphylococcus aureus SA-1199B, a strain possessing the NorA efflux pump. Efflux pumps are integral proteins of the bacterial membrane and are recognized as one of the main causes of bacterial drug resistance, since they expel antibiotics from the cell. The inhibition of this transporter is one form of modulating bacterial resistance to antimicrobial drugs. The flavones tested did not show any significant antibacterial activity against the Staphylococcus aureus strain used, but were able to modulate bacterial drug resistance. This property might be related to the degree of lipophilicity of the flavones conferred by the methoxyl groups, since 4’,5,6,7 tetramethoxyflavone the most methoxylated compound, reduced the minimal inhibitory concentration of the drug 16-fold.
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- 2011
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33. Chemometric Studies on Natural Products as Potential Inhibitors of the NADH Oxidase from Trypanosoma cruzi Using the VolSurf Approach
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Elizabeth Igne Ferreira, Marcelo Sobral da Silva, Luciana Scotti, and Marcus Tullius Scotti
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natural products ,VolSurf ,antichagasic agents ,Organic chemistry ,QD241-441 - Abstract
Natural products have widespread biological activities, including inhibition of mitochondrial enzyme systems. Some of these activities, for example cytotoxicity, may be the result of alteration of cellular bioenergetics. Based on previous computer-aided drug design (CADD) studies and considering reported data on structure-activity relationships (SAR), an assumption regarding the mechanism of action of natural products against parasitic infections involves the NADH-oxidase inhibition. In this study, chemometric tools, such as: Principal Component Analysis (PCA), Consensus PCA (CPCA), and partial least squares regression (PLS), were applied to a set of forty natural compounds, acting as NADH-oxidase inhibitors. The calculations were performed using the VolSurf+ program. The formalisms employed generated good exploratory and predictive results. The independent variables or descriptors having a hydrophobic profile were strongly correlated to the biological data.
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- 2010
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34. Alcaloides e outros constituintes de Xylopia langsdorffiana (Annonaceae) Alkaloids and other constituents from Xylopia langsdorffiana (Annonaceae)
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Marcelo Sobral da Silva, Josean Fechine Tavares, Karine Formiga Queiroga, Maria de Fátima Agra, José Maria Barbosa Filho, Jackson Roberto Guedes da Silva Almeida, and Sâmia Andrícia Souza da Silva
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Xylopia langsdorffiana ,alkaloids ,atisane diterpene ,Chemistry ,QD1-999 - Abstract
The phytochemical investigation of Xylopia langsdorffiana led to the isolation of corytenchine, xylopinine, discretamine, xylopine, ent-atisan-16α-hydroxy-18-oic acid, 13² (S) hydroxy-17³-ethoxyphaephorbide and quercetin-3-α-rhamnoside. Their structures were assigned based on spectroscopic analyses, including two-dimensional NMR techniques. Antioxidant activities of discretamine were measured using the 1,2-diphenyl- 2-picryl-hydrazyl (DPPH) free radical scavenging assay.
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- 2009
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35. A new arylnaphthalene type lignan from Cordia rufescens A. DC. (Boraginaceae)
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Sâmia Andrícia Souza da Silva, Augusto Lopes Souto, Maria de Fátima Agra, Emídio Vasconcelos Leitão da-Cunha, José Maria Barbosa-Filho, Marcelo Sobral da Silva, and Raimundo Braz-Filho
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Organic chemistry ,QD241-441 - Published
- 2004
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36. Neolignans from Licaria chrysophylla and Licaria aurea with DNA topoisomerase II-α inhibitory activity
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Amanda de Melo Bezerra, Antônio Cláudio da Silva Lins, Petrônio Filgueiras de Athayde-Filho, Marcelo Sobral da Silva, José Maria Barbosa-Filho, Celso Amorim Camara, Tania Maria Sarmento Silva, Vanessa da Silva Luna, and Creusioni Figueredo dos Santos
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Licaria ,lignoids ,topoisomerase ,Chemistry ,QD1-999 - Abstract
Seven natural neolignans isolated from Licaria chrysophylla and Licaria aurea along with five semisynthetic derivatives were tested for their inhibitory action on DNA-topoisomerase by relaxation assays on pBR322 plasmid DNA. All compounds tested showed strong inhibition at a concentration of 100 µM, while none showed activity between 5 and 70 µM. These results indicate that no obvious correlation can be derived between the structure of these compounds and their inhibitory effect on the DNA relaxation activity of topoisomerase II. This is the first report on DNA topoisomerase II inhibitors from Licaria chrysophylla and Licaria aurea leading to the identification of lignoids as topoisomerase II-α inhibitors.
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- 2012
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37. Solid-State Form Characterization of Riparin I
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Elisana Afonso de Moura, Márcio Vinícius Cahino Terto, Elisângela Afonso de Moura Mendonça, José Valdilânio Virgulino Procópio, Vicente Carlos de O. Costa, José Maria Barbosa Filho, Stanley Juan Chavez Gutierrez, Josean Fechine Tavares, Rui Oliveira Macedo, and Marcelo Sobral da Silva
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riparin I ,solid-state characterization ,pharmaceutical analysis ,Organic chemistry ,QD241-441 - Abstract
Riparin I is an alkamide with potential anxiolytic activity in preclinical studies. The characterization and understanding of solid-state properties play an importance role in drug development. For this work, the solid state of five riparin I batches (RIP-1, RIP-2, RIP-3, RIP-4, and RIP-5), obtained by the same synthesis process, were characterized by Scanning Electron Microscopy (SEM), Differential Scanning Calorimetry (DSC), DSC-photovisual, Thermogravimetry (TG), Fourier Transform Infrared (FTIR), Pyrolysis (Pyr-GC/MS), X-ray Powder Diffraction (PXRD), and Solid-State Nuclear Magnetic Resonance (ssNMR) techniques. Batches of riparin I with different crystal habits resulting in crystallization impurities were observed, which can be attributed to the presence of triethylamine. The main differences were observed by DSC, PXRD, and ssNMR analysis. DSC curves of RIP-2 and RIP-3 presented endothermic peaks at different temperatures of fusion, which can be attributed to the mixture of different crystalline forms. PXRD and ssNMR results confirmed crystallinity differences. The results offer evidence of the importance of controlling the reproducibility of the synthesis in order to obtain the adequate morphology for therapeutic efficacy and avoiding future problems in quality control of riparin I products.
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- 2017
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38. Erratum to: toxicity and antitumor potential of Mesosphaerum sidifolium (Lamiaceae) oil and fenchone, its major component
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Thaísa Leite Rolim, Déborah Ribeiro Pessoa Meireles, Tatianne Mota Batista, Tatyanna Kelvia Gomes de Sousa, Vivianne Mendes Mangueira, Renata Albuquerque de Abrantes, João Carlos Lima Rodrigues Pita, Aline Lira Xavier, Vicente Carlos Oliveira Costa, Leônia Maria Batista, Marcelo Sobral da Silva, and Marianna Vieira Sobral
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Other systems of medicine ,RZ201-999 - Published
- 2017
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39. Identification of Phenolic Compounds from Hancornia speciosa (Apocynaceae) Leaves by UHPLC Orbitrap-HRMS
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Katherine Xavier Bastos, Clarice Noleto Dias, Yuri Mangueira Nascimento, Marcelo Sobral da Silva, Silvana Maria Zucolotto Langassner, Ludger A. Wessjohann, and Josean Fechine Tavares
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Hancornia speciosa ,mangabeira ,UHPLC ,Orbitrap ,chemical composition ,phenolic compounds ,Organic chemistry ,QD241-441 - Abstract
Apocynaceae is a botanical family distributed mainly in tropical and subtropical regions of the world. In Brazil, they comprise about 90 genera and 850 species, inhabiting various types of vegetation. Within this large botanical family, the genus Hancornia is considered monotypic, with its only species Hancornia speciosa Gomes. Antihypertensive, antidiabetic, and antiviral activities are described for this species. Despite having been the target of some studies, knowledge of its chemical composition is still limited. In this study, the phenolics of H. speciosa leaves were analyzed using ultra-high performance liquid chromatography (UHPLC) coupled to Orbitrap high-resolution mass spectrometry (HRMS). As a result, 14 compounds were identified viz. protocatechuic acid, catechin, and quercetin, and another 14 were putatively identified viz. B- and C-type procyanidins, while just one compound remained unknown. From the identified compounds, 17 are reported for the first time viz. coumaroylquinic acid isomers and eriodyctiol. The results show that Hancornia speciosa can serve as source of valuable phenolics.
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- 2017
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40. Structure Revision of the Sesquiterpene Nordine Based on NMR Spectroscopic Analysis and X-ray Crystallography
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Rodrigo Silva de Andrade, Kaio Aragão Sales, Lucas Silva Abreu, Vinícius Rangel Campos, Fernando Martins dos Santos Junior, Raimundo Braz-Filho, Marcus Tullius Scotti, Josean Fechine Tavares, and Marcelo Sobral da Silva
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Pharmacology ,Magnetic Resonance Spectroscopy ,Molecular Structure ,Complementary and alternative medicine ,Organic Chemistry ,Drug Discovery ,Pharmaceutical Science ,Molecular Medicine ,Crystallography, X-Ray ,Sesquiterpenes ,Ethers ,Analytical Chemistry - Abstract
Nordine was reported to be an unusual humulene-type macrocyclic sesquiterpenoid that contains an ether-bridged bicyclic ring between C-10 and C-6 with a hydroxy group at position 2. Here, we report the structure revision of nordine based on incongruities found for carbon chemical shifts in the originally proposed structure, in addition to formation of a diacetylated derivative. As expected, a single-crystal X-ray diffraction analysis unambiguously confirmed our proposal that the nordine (
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- 2022
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41. Sucrose Diester of Aryldihydronaphthalene-Type Lignan with Anti-inflammatory Activity from Heliotropium angiospermum
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George Luís Dias dos Santos, Diego Igor Alves Fernandes de Araújo, Joanda Paola Raimundo e Silva, Yuri Mangueira do Nascimento, Thalisson Amorim de Souza, Luiza Carolina França Opretzka, Cristiane Flora Villarreal, Lucas Silva Abreu, Fernando Martins dos Santos Junior, José Iranildo Miranda de Melo, Ivana Maria Fechine, Josean Fechine Tavares, and Marcelo Sobral da Silva
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General Pharmacology, Toxicology and Pharmaceutics - Published
- 2022
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42. ISCOM-Matrices Nanoformulation Using the Raw Aqueous Extract of Quillaja lancifolia (Q. brasiliensis)
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Samuel Cibulski, Thalisson Amorim de Souza, Joanda Paola Raimundo, Yuri Mangueira Nascimento, Lucas Silva Abreu, Norma Suarez, Iris Miraballes, Paulo Michael Roehe, Demetrius Antonio Machado de Araújo, Josean Fechine Tavares, Marcelo Sobral da Silva, and Fernando Silveira
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Biomedical Engineering ,Bioengineering - Published
- 2022
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43. New ent-kaurene-type nor-diterpene and other compounds isolated from Annona vepretorum Mart. (Annonaceae)
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Camila de Souza Araújo, Daniel Amando Nery, Ana Paula de Oliveira, Raimundo Gonçalves de Oliveira-Júnior, Larissa Araújo Rolim, Norberto Peporine Lopes, Maria Francilene de Souza Silva, Cláudia do Ó Pessoa, Raimundo Braz-Filho, Lívia Macedo Dutra, Josean Fechine Tavares, Lucas Silva Abreu, Marcelo Sobral da Silva, and Jackson Roberto Guedes da Silva Almeida
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Organic Chemistry ,Plant Science ,Biochemistry ,Analytical Chemistry - Published
- 2022
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44. Effects of Simulated Gastrointestinal Conditions on Combined Potentially Probiotic Limosilactobacillus fermentum 296, Quercetin, and/or Resveratrol as Bioactive Components of Novel Nutraceuticals
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Karoliny Brito Sampaio, José Luiz de Brito Alves, Yuri Mangueira do Nascimento, Josean Fechine Tavares, Marcelo Sobral da Silva, Davi dos Santos Nascimento, Noádia Priscila de Araújo Rodrigues, Mariana Costa Monteiro, Estefânia Fernandes Garcia, and Evandro Leite de Souza
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Molecular Medicine ,Molecular Biology ,Microbiology - Published
- 2023
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45. Lupanes and friedelanes, the first chemical constituents of the aerial parts of Maytenus erythroxylon Reissek
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Edeltrudes de Oliveira Lima, Emille Wannick Reinaldo da Silva, Vicente Carlos de Oliveira Costa, Josean Fechine Tavares, Pedro Thiago Ramalho de Figueiredo, Marcelo Sobral da Silva, Renata Priscila Costa Barros, Laísa Vilar Cordeiro, and Marcus Tullius Scotti
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Traditional medicine ,biology ,Chemistry ,Maytenus ,Plant Science ,biology.organism_classification ,Biochemistry ,Terpene ,Phytochemical ,Chemical constituents ,Candida spp ,Spectral data ,Agronomy and Crop Science ,Biotechnology - Abstract
The first phytochemical study of the aerial parts of Maytenus erythroxylon Reissek resulted in the isolation of five triterpenes, two with a lupane skeleton: 29-norlupan-3,20-dione (1) and 30-hydroxy-20 (29) -lupen-3-one (2) and three with friedelane skeleton: 3,4-secofriedelan-3-oic acid (3), 3-oxo-30-hydroxyfriedelane (4) and 3β-Hydroxyfriedelane (5), where the compound (1) is reported for the first time in the Maytenus genus. The structures were identified through the analysis of uni and two-dimensional NMR spectral data. The isolated phases and compounds were subjected to in silico and in vitro techniques to evaluate the microbiological potential against microorganisms that cause intestinal disorders, showing that only the compound (3) was able to inhibit Candida spp. strains.
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- 2021
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46. Evaluating the Stability of a Novel Nutraceutical Formulation Combining Probiotic Limosilactobacillus fermentum 296, Quercetin, and Resveratrol Under Different Storage Conditions
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Davi dos Santos Nascimento, Karoliny Brito Sampaio, Yuri Mangueira do Nascimento, Thalisson Amorim de Souza, Fábio Santos de Souza, José Venancio Chaves Júnior, Josean Fechine Tavares, Marcelo Sobral da Silva, José Luiz de Brito Alves, and Evandro Leite de Souza
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Molecular Medicine ,Molecular Biology ,Microbiology - Abstract
This study evaluated the stability of a novel nutraceutical formulation composed of the probiotic Limosilactobacillus fermentum 296, quercetin (QUE), and resveratrol (RES) (LFQR) under different storage conditions. The effects of different relative humidities (RH; 11, 22, and 33%) and storage temperatures (refrigeration temperature -4 °C and room temperature -25 °C) on the stability of LFQR were evaluated through the determination of thermal stability, viable cell counts, bacterial physiological status, antioxidant capacity, and contents of QUE and RES during long-term storage. RH did not affect endothermic reactions and mass reduction in LFQR. After a 15-day-humidification period, L. fermentum 296 had higher viable cell counts in LFQR under refrigeration temperature storage when compared to room temperature storage regardless of the RH. The physiological status of L. fermentum 296 in LFQR was overall similar during 90 days of storage (11% RH) under refrigeration and room temperature. L. fermentum 296 had the highest viable cell counts ( 6 log CFU/g) in LFQR up to day 90 of refrigeration storage (11% RH). LFQR kept high contents of QUE and RES and maintained antioxidant capacity during 90 days of storage under refrigeration and room temperature. The results showed that the higher stability and functionality of LFQR during long-term storage should be guaranteed under 11% RH and refrigeration temperature.
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- 2022
47. Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MS n and HRESIMS
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César Augusto Gonçalves Dantas, Lucas Silva Abreu, Hidna Nascimento da Cunha, Carlos Arthur Gouveia Veloso, Maria de Fátima Agra, Augusto Lopes Souto, Josean Fechine Tavares, Vicente Carlos de Oliveira Costa, and Marcelo Sobral da Silva
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Chromatography ,Erythroxylaceae ,biology ,010401 analytical chemistry ,Ethyl acetate ,Plant Science ,General Medicine ,Carbon-13 NMR ,biology.organism_classification ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Analytical Chemistry ,Erythroxylum ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Complementary and alternative medicine ,chemistry ,Phytochemical ,Drug Discovery ,Molecular Medicine ,Hplc esi msn ,Natural Product Research ,Spectral data ,Food Science - Abstract
INTRODUCTION Given the diversity of secondary metabolites produced by species of the genus Erythroxylum, in addition to the many methods that have already been described in the literature, modern screening and identification methodologies, such as dereplication, represent an efficient and quick strategy compared to the classic techniques linked to natural product research. OBJECTIVE The objective of the present study was to determine the phenolic profiles obtained from three species of Erythroxylum (Erythroxylum pauferrense Plowman, Erythroxylum pulchrum A.St.-Hil. and Erythroxylum simonis Plowman) by dereplication using liquid chromatography coupled with ESI-MSn and HRESIMS. MATERIAL AND METHODS Ethyl acetate and n-butanolic fractions from crude ethanolic extract of Erythroxylum species were analyzed by HPLC-ESI-MSn and HPLC-HRESIMS, in order to identify its corresponding compounds. Experiments were performed in negative ionization mode, and the metabolites were provisionally identified based on deprotonated molecules, molecular formulas, fragmentation patterns and literature data. The corresponding isolated compounds were characterized by 1 H and 13 C NMR spectroscopy. RESULTS According to the dereplication method, it was possible to establish and compare the phenolic profile of the corresponding species by the assignment of 55 compounds, most of which were first described in these species and among which some were also new to the Erytroxylum genus. Additionally, nine compounds were isolated, including biphenyl-3,3',4,4'-tetraol, where the mass spectral data were not sufficient for their identification, and reported for the first time in the Erythroxylaceae family. CONCLUSION This research contributes to the phytochemical knowledge of the Erythroxylum genus and demonstrates the importance of the dereplication method regarding the investigation of natural products, enabling accurate identification of the metabolites while avoiding the efforts and material expenses involved in the isolation of known compounds.
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- 2021
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48. Four diterpenes identified
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Andreza Barbosa Silva, Cavalcanti, Mayara Dos Santos, Maia, Pedro Thiago Ramalho de, Figueiredo, Renata Priscila Barros de, Menezes, Alex France Messias, Monteiro, Roseana Araújo Ramos, Meireles, Gabriela Cristina Soares, Rodrigues, Ana Rita, Rodrigues de Almeida Silva, Jociano da Silva, Lins, Laísa Vilar, Cordeiro, Valnês S Rodrigues, Junior, Ana Paula O T, Castelo Branco, Maria de Fátima, Agra, Zoe L, Sessions, Eugene N, Muratov, Luciana, Scotti, Marcelo Sobral da, Silva, Vicente Carlos de Oliveira, Costa, Josean Fechine, Tavares, and Marcus Tullius, Scotti
- Abstract
Plants of Hyptidinae subtribe (Lamiaceae - family), as
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- 2022
49. IMXQB-80: A Quillaja brasiliensis saponin-based nanoadjuvant enhances Zika virus specific immune responses in mice
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Matheus Fabião de Lima, Paulo Michel Roehe, Fernando Silveira, Samuel Paulo Cibulski, Diogo O. Souza, Marcelo Sobral da Silva, Yuri Mangueira do Nascimento, Patrícia Sesterheim, Josean Fechine Tavares, Gabriela Casanova, Ana Paula Muterle Varela, and Thais Fumaco Teixeira
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medicine.medical_treatment ,030231 tropical medicine ,Saponin ,Immunoadjuvant ,Quillaja Saponins ,Microbiology ,Mice ,03 medical and health sciences ,0302 clinical medicine ,Immune system ,Adjuvants, Immunologic ,Antigen ,medicine ,Saponaria ,Animals ,030212 general & internal medicine ,chemistry.chemical_classification ,General Veterinary ,General Immunology and Microbiology ,biology ,Zika Virus Infection ,Quillaja ,Immunity ,Public Health, Environmental and Occupational Health ,Zika Virus ,Saponins ,biology.organism_classification ,Infectious Diseases ,chemistry ,biology.protein ,Molecular Medicine ,Antibody ,Adjuvant - Abstract
Vaccine adjuvants are compounds that enhance/prolong the immune response to a co-administered antigen. Saponins have been widely used as adjuvants for many years in several vaccines – especially for intracellular pathogens – including the recent and somewhat revolutionary malaria and shingles vaccines. In view of the immunoadjuvant potential of Q. brasiliensis saponins, the present study aimed to characterize the QB-80 saponin-rich fraction and a nanoadjuvant prepared with QB-80 and lipids (IMXQB-80). In addition, the performance of such adjuvants was examined in experimental inactivated vaccines against Zika virus (ZIKV). Analysis of QB-80 by DI-ESI-ToF by negative ion electrospray revealed over 29 saponins that could be assigned to known structures existing in their congener Q. saponaria, including the well-studied QS-21 and QS-7. The QB-80 saponins were a micrOTOF able to self-assembly with lipids in ISCOM-like nanoparticles with diameters of approximately 43 nm, here named IMXQB-80. Toxicity assays revealed that QB-80 saponins did present some haemolytical and cytotoxic potentials; however, these were abrogated in IMXQB-80 nanoparticles. Regarding the adjuvant activity, QB-80 and IMXQB-80 significantly enhanced serum levels of anti-Zika virus IgG and subtypes (IgG1, IgG2b, IgG2c) as well as neutralized antibodies when compared to an unadjuvanted vaccine. Furthermore, the nanoadjuvant IMXQB-80 was as effective as QB-80 in stimulating immune responses, yet requiring fourfold less saponins to induce the equivalent stimuli, and with less toxicity. These findings reveal that the saponin fraction QB-80, and particularly the IMXQB-80 nanoadjuvant, are safe and capable of potentializing immune responses when used as adjuvants in experimental ZIKV vaccines.
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- 2021
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50. In vitro and in silico studies of 8(17),12E,14-labdatrien-18-oic acid in airways smooth muscle relaxation: new molecular insights about its mechanism of action
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Edilson B. Alencar Filho, Luciano Augusto de Araújo Ribeiro, Luiz Antonio M S Duarte-Filho, Bagnólia Araújo da Silva, Thiego Gustavo Cavalcante de Carvalho, Euzébio Guimarães Barbosa, Pedro Modesto Nascimento Menezes, Marcelo Sobral da Silva, Fabrício Souza Silva, and Josean Fechine Tavares
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Pharmacology ,chemistry.chemical_classification ,0303 health sciences ,Forskolin ,Carboxylic acid ,In silico ,General Medicine ,In vitro ,Guinea pig ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,Mechanism of action ,chemistry ,030220 oncology & carcinogenesis ,medicine ,Biophysics ,medicine.symptom ,Binding site ,Diterpene ,030304 developmental biology - Abstract
In the field of experimental pharmacology, researchers continuously investigate new relaxant agents of the airway smooth muscle cells (ASMCs), since the pathophysiology of respiratory illnesses, such as asthma, involves hyperresponsiveness and changes in ASMC homeostasis. In this scenario, labdane-type diterpenes, like forskolin (FSK), are a class of compounds known for their relaxing action on smooth muscle cells (SMCs), being this phenomenon related to the direct activation of AC-cAMP-PKA pathway. Considering the continuous effort of our group to study the mechanism of action and prospecting for compounds isolated from natural sources, in this paper, we presented how the diterpene 8(17),12E,14-labdatrien-18-oic acid (LBD) promotes relaxant effect on ASMC, performing in vitro experiments using isolated guinea pig trachea and in silico molecular docking/dynamics simulations. In vitro experiments showed that in the presence of aminophylline, FSK and LBD had their relaxant effect potentiated (EC50 from 1.4 ± 0.2 × 10-5 M to 1.5 ± 0.3 × 10-6 M for LBD and from 2.0 ± 0.2 × 10-7 M to 6.4 ± 0.4 × 10-8 M for FSK) while in the presence of Rp-cAMPS this effect was attenuated (EC50 from 1.4 ± 0.2 × 10-5 M to 3 × 10-4 M for LBD and from 2.0 ± 0.2 × 10-7 to 3.1 ± 1.0 × 10-6 M for FSK). Additionally, in silico simulations evidenced that the lipophilic character of LBD is probably responsible for its stability on AC binding site. LBD presented two preferential orientations, where the double bonds of the isoprene moiety as well as the unique polar group (carboxylic acid) in this compound form important anchoring points. In this sense, we consider that the LBD can interact stabilizing the catalytic dimmer of AC as the FSK, although less efficiently.
- Published
- 2020
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