20 results on '"Leitão, Suzana Guimarães"'
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2. Qualitative chemical characterization of salva-de-marajó (Lippia origanoides, Verbenaceae) preparations
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da Cruz Albino, Rayane, Toledo e Silva, Marcos Vinicius, Ferreira, Victor Paulo, Pierucci, Anna Paola Trindade Rocha, Bizzo, Humberto Ribeiro, Gama, Paola Ervatti, da Silva, Nina Claudia Barboza, de Paula Freitas, Mariana Cunha, Leitão, Suzana Guimarães, and de Oliveira, Danilo Ribeiro more...
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- 2025
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Catalog
3. In silico screening of phenylethanoid glycosides, a class of pharmacologically active compounds as natural inhibitors of SARS-CoV-2 proteases
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Cheohen, Caio Felipe de Araujo Ribas, Esteves, Maria Eduarda Alves, da Fonseca, Thamirys Silva, Leal, Carla Monteiro, Assis, Fernanda de Lemos Fernandes, Campos, Mariana Freire, Rebelo, Raianne Soares, Allonso, Diego, Leitão, Gilda Guimarães, da Silva, Manuela Leal, and Leitão, Suzana Guimarães more...
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- 2023
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4. Counter-current chromatography with off-line detection by ultra high performance liquid chromatography/high resolution mass spectrometry in the study of the phenolic profile of Lippia origanoides
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Leitão, Suzana Guimaraes, Leitão, Gilda Guimarães, Vicco, Douglas K.T., Pereira, João Paulo Barreto, de Morais Simão, Gustavo, Oliveira, Danilo R., Celano, Rita, Campone, Luca, Piccinelli, Anna Lisa, and Rastrelli, Luca more...
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- 2017
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5. Hederifolic acids A-D, hepta and hexasaccharides from the resin glycosides of Ipomoea hederifolia.
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Castañeda-Gómez, Jhon F., Leitão, Suzana Guimarães, and Pereda-Miranda, Rogelio
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IPOMOEA , *GLYCOSIDES , *ACID derivatives , *LIQUID chromatography , *ACIDS , *GLYCOLIPIDS - Abstract
Scarlet morning glory, Ipomoea hederifolia L. (Convolvulaceae), is an ornamental vine native to the Americas with oxytocic, cytotoxic, antipsychotic, anti-inflammatory, antioxidant, and antimicrobial properties. A chemical study of the glycosidic acids from the resin glycosides contained in the aerial parts was carried out, through their isolation as peracetylated derivatives, by recycling preparative liquid chromatography. Structure elucidation was performed by HR-MS in accordance with NMR. Four peracetylated derivatives of glycosidic acids, named hederifolic acids A-D, were identified as heptaglycosides and hexaglycosides linked to 3 S ,12 S -dihydroxyheptadecanoic acid or 12 S-hydroxyheptadecanoic acid. Consequently, hederifolic acids B and D were found to be dehydroxylated homologs at C-3 of the fatty acid aglycones of hederifolic acids A and C, respectively. Saponification-peracetylation was an excellent approach for the purification of hepta- and hexaglycosides of 3 S ,12 S -dihydroxy or 12 S-hydroxyheptadecanoic acids by recycling HPLC. [Display omitted] • Four glycosidic acids, as peracetylated derivatives, were isolated from Scarlett morning glory. • Reversed-phase C 18 preparative recycling preparative liquid chromatograph was used for purification. • Hederifolic acids A-D were heptaglycosides and hexaglycosides of 3 S ,12 S -dihydroxy or 12 S-hydroxyheptadecanoic acids. • Peracetylayed glycosidic acids are an excellent approach for the purification of glycolipids. [ABSTRACT FROM AUTHOR] more...
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- 2023
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6. Bufadienolides from parotoid gland secretions of Cuban toad Peltophryne fustiger (Bufonidae): Inhibition of human kidney Na+/K+-ATPase activity.
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Perera Córdova, Wilmer H., Leitão, Suzana Guimarães, Cunha-Filho, Geraldino, Bosch, Roberto Alonso, Alonso, Isel Pascual, Pereda-Miranda, Rogelio, Gervou, Rodrigo, Touza, Natália Araújo, Quintas, Luis Eduardo M., and Noël, François more...
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BUFADIENOLIDES , *BUFONIDAE , *ADENOSINE triphosphatase , *KIDNEY physiology , *NUCLEAR magnetic resonance spectroscopy - Abstract
Parotoid gland secretions of toad species are a vast reservoir of bioactive molecules with a wide range of biological properties. Herein, for the first time, it is described the isolation by preparative reversed-phase HPLC and the structure elucidation by NMR spectroscopy and/or mass spectrometry of nine major bufadienolides from parotoid gland secretions of the Cuban endemic toad Peltophryne fustiger : ψ-bufarenogin, gamabufotalin, bufarenogin, arenobufagin, 3-( N -suberoylargininyl) marinobufagin, bufotalinin, telocinobufagin, marinobufagin and bufalin. In addition, the secretion was analyzed by UPLC-MS/MS which also allowed the identification of azelayl arginine. The effect of arenobufagin, bufalin and ψ-bufarenogin on Na + /K + -ATPase activity in a human kidney preparation was evaluated. These bufadienolides fully inhibited the Na + /K + -ATPase in a concentration-dependent manner, although arenobufagin (IC 50 = 28.3 nM) and bufalin (IC 50 = 28.7 nM) were 100 times more potent than ψ-bufarenogin (IC 50 = 3020 nM). These results provided evidence about the importance of the hydroxylation at position C-14 in the bufadienolide skeleton for the inhibitory activity on the Na + /K + -ATPase. [ABSTRACT FROM AUTHOR] more...
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- 2016
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7. Flavones and phenylpropanoids from a sedative extract of Lantana trifolia L.
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Julião, Lisieux de Santana, Leitão, Suzana Guimarães, Lotti, Cinzia, Picinelli, Anna Lisa, Rastrelli, Luca, Fernandes, Patricia D., Noël, François, Thibaut, Jean-Pierre Barros, and Leitão, Gilda Guimarães more...
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FLAVONOIDS , *LANTANA , *GLYCOSIDES , *VERBENACEAE , *BENZODIAZEPINE receptors , *NUCLEAR magnetic resonance spectroscopy - Abstract
Abstract: The flavone glycosides, named scutellarein-7-O-β-d-apiofuranoside and apigenin-7-O-β-d-apiofuranosyl-(1→2)-β-d-apiofuranoside, and the flavone celtidifoline (5,6,4′,5′-tetrahydroxy-7,3′-dimethoxyflavone), along with other 11 known compounds, were isolated from leaves of the ethyl acetate extract of Lantana trifolia L. using step gradient High Speed Countercurrent Chromatography (HSCCC) and High Performance Liquid Chromatography (HPLC), respectively. Their structures were elucidated by spectroscopic methods, including 2D NMR and mass spectrometry (ESI-MS) techniques. The ethanolic and ethyl acetate extracts produced an intense sedative effect in mice, one hour after oral administration of 1mg/kg. This effect was neither due to a benzodiazepine-like effect of the three flavone derivatives neither of the phenylpropanoids, betonyoside F and verbascoside, that were tested for their affinity for the [3H] flunitrazepam binding sites. [Copyright &y& Elsevier] more...
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- 2010
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8. Structure reassignment and absolute configuration of 9-epi-presilphiperfolan-1-ol
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Joseph-Nathan, Pedro, Leitão, Suzana Guimarães, Pinto, Shaft Corrêa, Leitão, Gilda Guimarães, Bizzo, Humberto Ribeiro, Costa, Fabio Luiz Paranhos, Amorim, Mauro Barbosa de, Martinez, Natalia, Dellacassa, Eduardo, Hernández-Barragán, Angelina, and Pérez-Hernández, Nury more...
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TERPENES , *MOLECULAR structure , *NUCLEAR magnetic resonance spectroscopy , *X-ray diffraction , *HYDROCARBONS - Abstract
Abstract: Reevaluation of 13C NMR data in combination with X-ray diffraction and VCD studies led us to reassign the structure of (−)-epi-presilphiperfolan-1-ol (1), isolated from Anemia tomentosa var. anthriscifolia, to (−)-9-epi-presilphiperfolan-1-ol (2) and to establish its absolute configuration as 1S,4S,7R,8R,9S. [Copyright &y& Elsevier] more...
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- 2010
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9. Homeopathic medicine of Melissa officinalis combined or not with Phytolacca decandra in the treatment of possible sleep bruxism in children: A crossover randomized triple-blinded controlled clinical trial.
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Tavares-Silva, Cláudia, Holandino, Carla, Homsani, Fortune, Luiz, Ronir Raggio, Prodestino, Jessica, Farah, Adriana, Lima, Juliana de Paula, Simas, Rosineide Costa, Castilho, Caroline Vianna V., Leitão, Suzana Guimarães, Maia, Lucianne Cople, and Fonseca-Gonçalves, Andréa more...
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Purpose: The present randomized controlled clinical trial evaluated the efficacy of homeopathic medicines of Melissa officinalis (MO), Phytolacca decandra (PD), and the combination of both in the treatment of possible sleep bruxism (SB) in children.Study Design: Patients (n = 52) (6.62 ± 1.79 years old) were selected based on the parents report of SB. The study comprised a crossover design that included 4 phases of 30-day treatment (Placebo; MO 12c; PD 12c; and MO 12c + PD 12c), with a wash-out period of 15 days between treatments.Methods: At baseline and after each phase, the Visual Analogic Scale (VAS) was used as the primary outcome measure to evaluate the influence of treatments on the reduction of SB. The following additional outcome measures were used: a children's sleep diary with parent's/guardian's perceptions of their children's sleep quality, the trait of anxiety scale (TAS) to identify changes in children's anxiety profile, and side effects reports. Data were analyzed by ANOVA with repeated measures followed by Post Hoc LSD test.Results: Significant reduction of SB was observed in VAS after the use of Placebo (-1.72 ± 0.29), MO (-2.36 ± 0.36), PD (-1.44 ± 0.28) and MO + PD (-2.21 ± 0.30) compared to baseline (4.91 ± 1.87). MO showed better results compared to PD (p = 0.018) and Placebo (p = 0.050), and similar result compared to MO+PD (p = 0.724). The sleep diary results and TAS results were not influenced by any of the treatments. No side effects were observed after treatments.Conclusion: MO showed promising results in the treatment of possible sleep bruxism in children, while the association of PD did not improve MO results. [ABSTRACT FROM AUTHOR] more...- Published
- 2019
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10. Contributors to Volume XXXVIII
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Berthod, Alain, Billardello, Béatrice, Brown, Les, Chen, Yu Chuan, Foucault, Alain P., Franco, Pilar, Han, Shi-Jun, Harris, Guy H., Intes, Olivier, Ito, Yoishiro, Jin, Yu-Ren, Legrand, Jack, Leitão, Gilda Guimarães, Leitão, Suzana Guimarães, Maciuk, Alexandre, Marchal, Luc, Minguillón, Cristina, Nuzillard, Jean-Marc, Oliveiros, Laureano, Patissier, Gerard, Renault, Jean-Hugues, Rosant, Jean-Michel, Sutherland, Ian A., Yu, Tiing, Zhang, Li-Xing, Zhang, Lian-Zhong, and Zhang, Tianyou more...
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- 2002
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11. Alkaloids from Siparuna (Siparunaceae) are predicted as the inhibitors of proteolysis and plasma coagulation caused by snake venom and potentially counteract phospholipase A2 activity of Bothrops jararaca.
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Fernandes, Diégina Araújo, Gomes, Brendo Araujo, Mendonça, Simony Carvalho, Pinheiro, Camila de Castro, Sanchez, Eladio Oswaldo Flores, Leitão, Suzana Guimarães, Fuly, André Lopes, and Leitão, Gilda Guimarães more...
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IN vitro studies , *TRADITIONAL medicine , *PHENOMENOLOGICAL biology , *ALKALOIDS , *LIQUID chromatography-mass spectrometry , *SNAKEBITES , *ANTIVENINS , *ENZYME inhibitors , *SNAKE venom , *BIOCHEMISTRY , *PHYTOCHEMICALS , *MULTIVARIATE analysis , *DESCRIPTIVE statistics , *PLANT extracts , *ESTERASES , *ELECTROSPRAY ionization mass spectrometry , *BLOOD coagulation , *DATA analysis software , *ANTITOXINS , *DISEASE complications ,THERAPEUTIC use of alkaloids - Abstract
Snakebite envenomation (SBE) is the world's most lethal neglected tropical disease. Bothrops jararaca is the species that causes the greatest number of SBEs in the South and Southeastern of Brazil. The main symptoms are local (inflammation, edema, hemorrhage, and myonecrosis) and systemic (hemorrhage, hemostatic alterations with consumptive coagulopathy, and death) effects. Species of the genus Siparuna , Siparunaceae, are used in folk and traditional medicine to treat SBE. However, limited information is available concerning Brazilian Siparuna species against SBE. To investigate the correlation between the compounds present in the extracts of five Siparuna species as potential agents against proteolytic activity, plasma coagulation, and phospholipase A 2 (PLA 2) activity caused by B. jararaca venom, using data obtained by UHPLC-MS/MS, biological activity, and multivariate statistics. The ethanol extracts from leaves of S. ficoides , S. decipiens , S. glycycarpa , S. reginae, and S. cymosa were fractionated by liquid-liquid extraction using different solvents of increasing polarity (hexane, dichloromethane, ethyl acetate, and n -butanol), affording their respective extracts, totaling 25 samples that were assayed through in vitro plasma coagulation and proteolytic activity assays. Moreover, the extracts were analyzed by UHPLC-MS/MS, using electrospray ionization (ESI) and atmospheric-pressure chemical ionization (APCI) in negative and positive ionization modes. The data was processed in MZmine v. 2.53 and evaluated by multivariate statistical tests (PLS) using the software UnscramblerX v. 10.4. These data were also used to build molecular networks (GNPS), and some ions of interest could be annotated using the library of molecules on the GNPS platform. A total of 19 extracts inhibited B. jararaca -induced plasma coagulation, with emphasis on S. cymosa and S. reginae (800 s). The inhibition of the proteolytic activity was also promising, ranging from 16% (S. glycycarpa) to 99% (S. cymosa, S. decipiens, and S. reginae). In addition, most extracts from S. cymosa and S. reginae inhibited 70–90% of PLA 2 activity. Based on data from positive mode APCI analyses, it was possible to obtain a statistic model with reliable predictive capacity which exhibited an average R2 of 0.95 and a Q2 of 0.88, indicating a robust fit. This process revealed five ions, identified as the alkaloids: coclaurine (1), stepholidine (2) O -methylisopiline (3), nornantenine (4) and laurolitsine (5). This is the first study to evidence the potential antivenom of alkaloids from Siparuna species. Altogether, our results give support to the popular use of Siparuna extracts in SBE accidents, suggesting their potential as an alternative or complementary strategy against envenoming by B. jararaca venom. The predicted ions in the chemometric analysis for the assayed activities can also be correlated with the blocking activity and encourage the continuation of this study for possible isolation and testing of individual compounds on the used models. [Display omitted] • Siparuna spp. are used in folk medicine to counter snakebite envenomation in tropics. • Siparuna extracts inhibited B. jararaca snake venom proteolytic activity (30–96%). • Siparuna extracts inhibit B. jararaca venom-induced plasma coagulation (75–800s). • Siparuna extracts can inhibit up to 90% of PLA 2 of B. jararaca activity. • Five alkaloids in the PLSr model are candidates with potential antivenom activity. [ABSTRACT FROM AUTHOR] more...
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- 2024
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12. Inhibition of multidrug-resistant MCF-7 breast cancer cells with combinations of clinical drugs and resin glycosides from Operculina hamiltonii.
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Moreno-Velasco, Armando, Fragoso-Serrano, Mabel, de Jesús Flores-Tafoya, Pedro, Carrillo-Rojas, Sebastian, Bautista, Elihu, Leitão, Suzana Guimarães, Castañeda-Gómez, Jhon F., and Pereda-Miranda, Rogelio more...
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CANCER cells , *BREAST cancer , *P-glycoprotein , *CYTOTOXINS , *ANTINEOPLASTIC agents , *EPITHELIAL cells , *MACROCYCLIC compounds , *GLYCOSIDES - Abstract
The jalap roots, Operculina hamiltonii D.F. Austin & Staples (Convolvulaceae) , are extensively commercialized as a depurative and laxative remedy in traditional medicine of the north and northeast regions of Brazil. The purification by recycling HPLC and structure elucidation of three new acyl sugars or resin glycosides are described here from a commercial product made of powdered roots. Three macrocyclic structures of a tetrasaccharide of (11 S)-hydroxyhexadecanoic acid, operculinic acid C (1), the undescribed hamiltonins II and III (3 and 4), in addition to the known batatinoside III (5), presented a diastereoisomeric relationship as one residue of n -dodecanoic acid esterified the oligosaccharide core on a different position in each compound. Furthermore, hamiltonin IV (6) was characterized as an ester-type homodimer of acylated operculinic acid C with the same substitution pattern identified in hamiltonins II (3) and III (4) for each of the dimer subunits. All the isolated resin glycosides did not display any intrinsic cytotoxicity (IC 50 > 25 μM). However, a combination of the individual isolated compounds 3 – 6 (1–50 μM) demonstrated an enhancement of cytotoxic effects with sublethal doses of vinblastine and podophyllotoxin (0.003 μM) in multidrug-resistant breast carcinoma epithelial cells (MCF-7/Vin). Combination of resin glycosides demonstrated a potentiation of cytotoxicity with sublethal doses of vinblastine and podophyllotoxin in multidrug-resistant breast carcinoma cells. [Display omitted] • Purification of resin glycoside was performed by recycling HPLC from jalap roots. • Hamiltonin IV was characterized as an ester-type dimer assembled by operculinic acid C. • Non-cytotoxic resin glycosides enhanced the intracellular concentration of drugs. • Resin glycosides inhibited cytotoxic drug efflux and promoted their accumulation. [ABSTRACT FROM AUTHOR] more...
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- 2024
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13. Spray-dried extract from the Amazonian adaptogenic plant Ampelozizyphus amazonicus Ducke (Saracura-mirá): Chemical composition and immunomodulatory properties.
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Simen, Tatiana Jotha Mattos, Finotelli, Priscilla Vanessa, Barboza, Fernanda Ferreira, Pereira, MarinaVieira Agostinho, Pierucci, Anna Paola Trindade Rocha, Moura, Mirian Ribeiro Leite, de Oliveira, Danilo Ribeiro, Abraçado, Leida Gomes, Celano, Rita, de Souza Figueiredo, Fabiana, Piccinelli, Anna Lisa, Rastrelli, Luca, Leitão, Gilda Guimarães, Peçanha, Ligia M. Torres, and Leitão, Suzana Guimarães more...
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IMMUNOREGULATION , *IMMUNOLOGICAL adjuvants , *MASS spectrometry , *HIGH performance liquid chromatography , *ANTIBODY formation - Abstract
Ampelozizyphus amazonicus Ducke is a medicinal plant used in the Amazon region to prepare a drink with tonic, immunomodulatory and adaptogenic properties. Due to the growing interest in dietary supplements with these properties and, to provide a new functional ingredient, barks from A. amazonicus were extracted. The extract was spray dried without drying adjuvants, resulting in a powder (SARF), which was characterized by its physico-chemical properties and proximate, mineral and saponin contents. The SARF saponins were characterized by ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry (HPLC-HRMS n ) analysis. The SARF particles tended to have a spherical shape and a unimodal size distribution. The particles also had good rehydration characteristics and high saponin content (33%). The effect of SARF on antibody production was investigated, and we found that SARF increased the basal levels of anti-ovalbumin, anti-LPS and anti-dextran IgM antibodies, and the anti-dextran IgG antibodies in unimmunized mice. No increase in antibody titers was observed after SARF treatment in immunized mice. These results suggest that SARF could be an interesting new functional ingredient for food applications or pharmaceutical products. [ABSTRACT FROM AUTHOR] more...
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- 2016
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14. Amazonian medicinal smokes: Chemical analysis of Burseraceae pitch (breu) oleoresin smokes and insights into their use on headache.
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da Cruz Albino, Rayane, Braz, Marcelle Magalhães, Bizzo, Humberto Ribeiro, Santana da Silva, Raquel Vieira, Leitão, Suzana Guimarães, and Ribeiro de Oliveira, Danilo
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SALES personnel , *ESSENTIAL oils , *ANTI-inflammatory agents , *ANALGESICS , *GUMS & resins , *SMOKE , *HEADACHE , *PHARMACEUTICAL chemistry , *PLANT extracts , *ANALYTICAL chemistry - Abstract
In Latin American Traditional Medicine, the use of Burseraceae oleoresins for headache relief is widespread. In the quilombola (maroon) communities of the municipality of Oriximiná, Pará State, Brazil, Burseraceae oleoresins are burned as incenses to treat headache; an effect attained by inhaling the smokes. This study was designed to investigate the scientific rationale behind the use of Burseraceae pitch oleoresin smokes on headache by identifying its chemical constituents and discussing whether they could be beneficial for headache treatment. Two samples of pitch oleoresins were purchased from Amazonian public markets; one of them marketed as " breu preto " (black pitch), and the other as " breu branco " (white pitch). The smoke headspaces produced upon burning these oleoresins were collected and analysed by GC-MS. For comparative purposes, the triterpenoid fingerprints of the oleoresins' dichloromethane extracts and profiles of the essential oils were also obtained by GC-MS — and GC-FID, in the case of the essential oils. A total of 32 compounds were detected in black and white pitch oleoresin smokes. All smoke headspaces of the pitch oleoresins shared the presence of volatile terpenoids (e.g., α-terpineol) and triterpenoids (e.g., α-amyrin, β-amyrin, α-amyrone, and β-amyrone). These compounds were also present in the crude resins and could potentially be responsible for anti-inflammatory, antinociceptive and analgesic effects on headache. The pharmacological data on the terpenoids detected in the Burseraceae pitch smokes strongly support their traditional use for headache, but their actual effects upon inhalation have yet to be determined. [Display omitted] [ABSTRACT FROM AUTHOR] more...
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- 2021
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15. Distribution of 5,6-dihydro-α-pyrones by electrospray ionization ion trap mass spectrometry in different aerial parts of Hyptis monticola.
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da Silva, Aline Soares, Martínez-Fructuoso, Lucero, Simas, Rosineide Costa, Leitão, Gilda Guimarães, Fragoso-Serrano, Mabel, Barros, Yasmim Santana, de Souza, Diego Ramalho, Pereda-Miranda, Rogelio, and Leitão, Suzana Guimarães more...
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MASS spectrometry , *ION traps , *COUNTERCURRENT chromatography , *HIGH performance liquid chromatography , *ELECTROSPRAY ionization mass spectrometry , *NUCLEAR magnetic resonance , *STEREOCHEMISTRY , *NUCLEAR magnetic resonance spectroscopy - Abstract
Hyptis monticola Mart. ex Benth. (Lamiaceae) is an endemic species of altitude regions of Brazil. From the leaves of this plant, two 5,6-dihydro- α -pyrones, named monticolides A and B, have been reported as cytotoxic agents against different tumor cell lines. The isolation by high-speed countercurrent chromatography in combination with recycling preparative high-performance liquid chromatography of the undescribed monticolides C-F is presented. These compounds corresponded to a series of related monticolide derivatives differing from each other by the number of acyl substituents. Their characterization by mass spectrometry and nuclear magnetic resonance is also presented, in conjunction with an evidence by a simple chemical correlation for their absolute stereochemistry. The distribution of these chemical markers in extracts of flowers, leaves and branches collected in different seasons by electrospray ionization ion trap mass spectrometry in positive mode was analyzed. Multivariate data analyses indicated that seasonality affects monticolide concentrations in different organs of the aerial parts. Monticolides A-F seem to be present as the original markers of the analyzed plant. However, mono-, di- and triacetylated monticolides can undergo acid-catalyzed transesterifications and their natural yields estimated were affected during the isolation procedures. [Display omitted] • Monticolides C-F were isolated as undescribed 6-heptyl-5,6-dihydro-2 H -pyran-2-ones. • Distribution of monticolides A-F in different plant organs were analyzed by UHPLC-ESI- MS/MS. • Multivariate data analyses indicated that seasonality affects monticolide concentrations. • Monticolides A-F seems to be present as original makers of the analyzed plant material. • Mono-, di- and triacetylated montecolides can undergo acid-catalyzed transesterifications. [ABSTRACT FROM AUTHOR] more...
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- 2021
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16. Amazonian Siparuna extracts as potential anti-influenza agents: Metabolic fingerprinting.
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Leal, Carla Monteiro, Simas, Rosineide Costa, Miranda, Milene, Campos, Mariana Freire, Gomes, Brendo Araujo, Siqueira, Marilda M., Vale, Gabrielle do, Gomes de Almeida, Carlos Vitor, Leitão, Suzana Guimarães, and Leitão, Gilda Guimarães more...
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FOLIAR diagnosis , *INFLUENZA prevention , *ALKALOIDS , *ANTIVIRAL agents , *BIOCHEMISTRY , *EPITHELIAL cells , *ETHANOL , *FLAVONOIDS , *GLYCOSIDES , *PHENOMENOLOGY , *MEDICINAL plants , *PLANT extracts , *DESCRIPTIVE statistics - Abstract
Siparuna species are used in Brazilian Folk Medicine for the treatment and prophylaxis of colds, fever, headache, gastrointestinal disorders and rheumatic pain. This study aimed to investigate a possible anti-influenza activity of 25 extracts from leaves of Amazonian S. cristata , S. decipiens , S. glycycarpa , S. reginae and S. sarmentosa based on their folk medicinal uses as well as to investigate their metabolic fingerprinting. The chemical composition of the active extracts was further dereplicated. The chemical composition of the crude EtOH extracts from five Siparuna species were investigated by ESI (±) LC-QTOF-MS2. Organic extracts were obtained by liquid-liquid partition with solvents of increasing polarity, generating 25 extracts which were subjected to a quick DI-ESI (±) IT-MS fingerprint analysis. These extracts were tested against influenza virus replication and cellular toxicity using MDCK cells and influenza A/Michigan/45/2015 (H1N1)pdm09 virus. The compounds in the active BuOH extracts from S. glycycarpa and S. sarmentosa were annotated by ESI (±) LC-QTOF-MS2. Analysis of the EtOH extracts revealed the presence of alkaloids and flavonoids, in the positive and negative ionization modes. Out of the 25 organic extracts screened for their antiviral activity, the BuOH extracts from S. glycycarpa and S. sarmentosa were the most active, inhibiting 96.0 ± 1.3% and 89.5 ± 0.8% of influenza virus replication 24 h post-infection. These inhibitory effects were maintained until 72hpi. Alkaloids, O - and C -flavonoid glycosides, dihydrochalcones and a procyanidin dimer were annotated in these extracts. The inhibitory effect against influenza A(H1N1)pdm09 virus replication shown by Amazonian Siparuna species corroborates the use of these plants in Brazilian Folk Medicine, showing their potential as anti-influenza agents. These promising results stimulate the continuation of this study with the aim of isolating the compound(s) responsible for this bioactivity, thus contributing to a better knowledge of those species and to the research of natural products with potential anti-influenza activity. Image 1 [ABSTRACT FROM AUTHOR] more...
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- 2021
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17. (−)-epi-Presilphiperfolan-1-ol, a new triquinane sesquiterpene from the essential oil of Anemia tomentosa var. anthriscifolia (Pteridophyta)
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Pinto, Shaft Corrêa, Leitão, Gilda Guimarães, Bizzo, Humberto Ribeiro, Martinez, Natalia, Dellacassa, Eduardo, dos Santos, Fernando Martins, Costa, Fabio Luiz Paranhos, Amorim, Mauro Barbosa de, and Leitão, Suzana Guimarães more...
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SESQUITERPENES , *ESSENTIAL oils , *ANEMIA , *PTERIDOPHYTA , *CHROMATOGRAPHIC analysis , *NUCLEAR magnetic resonance spectroscopy , *CHIRALITY - Abstract
Abstract: (−)-epi-Presilphiperfolan-1-ol, (1), a new triquinane sesquiterpene, was isolated from the essential oil of Anemia tomentosa var. anthriscifolia by column chromatography. Its structure elucidation was accomplished by extensive 1D- and 2D-NMR analyses, as well as by GC–MS, chiral bidimensional GC, dehydration reactions, and a comparative (GIAO/DFT) theoretical study of the 13C NMR chemical shifts of 1 and its known isomers (presilphiperfolan-1-ol (1a), presilphiperfolan-8-ol (3), and presilphiperfolan-9-ol (4)). [Copyright &y& Elsevier] more...
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- 2009
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18. Dihydro-furanones from Hyptis species: Chemical correlations and DFT-NMR/ECD calculations for stereochemical assignments.
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Martínez-Fructuoso, Lucero, Pereda-Miranda, Rogelio, Fragoso-Serrano, Mabel, da Silva, Aline Soares, and Leitão, Suzana Guimarães
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CHEMICAL species , *CHEMICAL shift (Nuclear magnetic resonance) , *MARINE fungi , *BIOACTIVE compounds , *HYDROXYCINNAMIC acids , *QUANTUM mechanics , *FLAVONOIDS - Abstract
Dihydro-furanones are bioactive compounds isolated from various plants, marine fungi, and sponges. The present investigation describes the isolation by recycling HPLC and structural characterization by NMR of four previously undescribed 2(5 H)-furanones, monticofuranolide A and pectinolides N–P, one phenylpropanoid, rosmarinic acid, and five known flavonoids, in addition to the undescribed natural flavonoid, 2 R ,3 R -dihydrogossipetin or 5,7,8,3′,4′-pentahydroxy flavanonol, from collections of H. monticola Mart. ex Benth and Hyptis pectinata (L.) Poit. Chemical correlations, resembling the biogenetic relationship of the isolated 2(5 H)-furanones with their 5,6-dihydro-2 H -pyran-2-one precursors, were accomplished to confirm their absolute configuration. Density functional theory-NMR/ECD calculations have been used to solve the absolute configuration for this type of compounds. The absolute configuration of 2(5 H)-furanones from Hyptis was secured by chemical correlations with the dihydro-2 H -pyran-2-one precursors and DFT-NMR/ECD calculations. Image 1 • Four undescribed dihydro-furanones were isolated from two Hyptis species. • Correlations with the dihydro-pyranone precursors secured their absolute configurations. • 2 R ,3 R -Dihydrogossipetin was isolated as a natural flavonoid. • 2(5 H)-Furanones were slightly cytotoxic. [ABSTRACT FROM AUTHOR] more...
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- 2020
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19. Differentiation of black and white pitch (Burseraceae) oleoresins: A mass spectrometry-based chemoethnotaxonomic study.
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Albino, Rayane da Cruz, Simas, Rosineide Costa, da Silva Martins, Karine, Bizzo, Humberto Ribeiro, Rodrigues da Silva, Eduardo, Dal Sasso, Marco Aurélio, Santana da Silva, Raquel Vieira, Leitão, Suzana Guimarães, and Oliveira, Danilo Ribeiro de more...
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GAS chromatography , *GUMS & resins , *LIQUID chromatography , *MASS spectrometry , *TERPENES - Abstract
In the quilombola communities of the municipality of Oriximiná (Pará State, Brazil), Protium spp. (Burseraceae) oleoresins are distinguished in black and white pitch. White pitch oleoresins may be superior to black pitch in terms of quality, but the criteria used for their differentiation are fairly subjective. This study was designed to provide a scientific rationale for the traditional differentiation of black and white pitch oleoresins based on their non-volatile fraction. Black and white pitch oleoresin samples collected in quilombola territories in Oriximiná were analysed by GC-EI-MS and UPLC-APCI-MS. The feasibility of EI and APCI mass spectrometry-based pattern recognition methods PLS-DA and Random Forest Analysis (RFA) for black and white pitch oleoresins differentiation was demonstrated. The UPLC-APCI-MS method allowed the separation of 43 triterpenoids. Assessment of the triterpenoid fingerprints by GC-EI-MS led to the tentative identification of ursa-9(11),12-dien-3-ol as a potential marker for black pitch oleoresins. PLS-DA and RFA applied to the APCI-MS and EI-MS data gave good models for black and white pitch oleoresins classification. The most important ions for the classifications of black pitch oleoresins by APCI-MS/PLS-DA and APCI-MS/RFA likely represented triterpenoid acids. The triterpenoid pattern differs between black and white pitch oleoresins. The characteristic presence of ursa-9(11),12-dien-3-ol and triterpenoids acids in black pitch oleoresins, along with other field observations, suggest that black pitch oleoresins are actually aged white pitch oleoresins. Image 1 • A new term, "chemoethnotaxonomy", is being proposed. • Analysis of black and white pitch oleoresins by UPLC-APCI-MS and GC-EI-MS. • Construction of PLS-DA and Random Forest Analysis models for pitch classification using MS data. • Identification of ursa-9(11),12-dien-3-ol as a potential chemical marker for black pitch oleoresins. [ABSTRACT FROM AUTHOR] more...
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- 2020
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20. Conformational states of the pig kidney Na+/K+-ATPase differently affect bufadienolides and cardenolides: A directed structure-activity and structure-kinetics study.
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Azalim, Pedro, do Monte, Fernando M., Rendeiro, Mariana Manzano, Liu, Xiaofan, O'Doherty, George A., Fontes, Carlos Frederico, Leitão, Suzana Guimarães, Quintas, Luis Eduardo M., and Noël, François
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CARDIAC glycosides , *CARDENOLIDES , *ADENOSINE triphosphatase , *KIDNEYS , *OCHRATOXINS , *SWINE , *MTOR protein , *CLASS differences - Abstract
There is a renewed interest in the Na+/K+-ATPase (NKA, EC 3.6.3.9) either as a target for new therapeutic uses or for understanding the putative pathophysiological role of its mammalian endogenous ligands. Recent data indicate that bufalin binds to the pig kidney NKA in a way different from ouabain and digoxin, raising the question of a putative class difference between bufadienolides and cardenolides. The purpose of this work was to perform a study of the relationship between structure and both activity and kinetics, focusing mainly on the influence of the lactone ring in C17 (5 vs. 6 membered), the effect of C14-15 cyclization and the carbohydrate moiety in C3. We compared the potency of fourteen related cardiotonic steroids (CTS) for inhibition of the cycling pig kidney NKA in two different concentrations of K+, as well as the affinity for binding to the E2P conformation of the enzyme (Mg-Pi medium) and the potency for inhibiting the E2[2K] conformation of the NKA (K+-pNPPase activity). Cardenolides were clearly sensitive to the antagonistic effect of high K+ concentrations whereas bufadienolides were not or less sensitive. The C14-15 cyclization observed in some bufadienolides, such as resibufogenin and marinobufagin, caused a drastic fall in the affinity for binding to the NKA in the E2P conformation and increased the velocity of K+-pNPPase inhibition. The absence of a carbohydrate moiety in C3 increased the velocity of inhibition. Cardenolides were much more dependent on the E2P conformation for binding than bufadienolides since their ratios of E2[2K] IC 50 to E2P K i were higher than for bufadienolides. Therefore, the present data established the remarkable influence of C14-15 cyclization and of the carbohydrate moiety in C3 on both affinity and kinetics of CTS and indicate that, as a class, bufadienolides would harbor qualitative differences from cardenolides with respect to the NKA conformations to which they can bind. [ABSTRACT FROM AUTHOR] more...
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- 2020
- Full Text
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