Emmanoel Costa

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Papers by Emmanoel Costa

Duguetia pycnastera Sandwith (Annonaceae) Leaf Essential Oil Inhibits HepG2 Cell Growth In Vitro and In Vivo

Molecules

Duguetia pycnastera Sandwith (Annonaceae) is a tropical tree that can be found in the Guyanas, Bo... more Duguetia pycnastera Sandwith (Annonaceae) is a tropical tree that can be found in the Guyanas, Bolivia, Venezuela, and Brazil. In Brazil, it is popularly known as “ata”, “envira”, “envira-preta”, and “envira-surucucu”. In the present work, we investigated the in vitro and in vivo HepG2 cell growth inhibition capacity of D. pycnastera leaf essential oil (EO). The chemical composition of the EO was determined by GC–MS and GC–FID analyses. The alamar blue assay was used to examine the in vitro cytotoxicity of EO in cancer cell lines and non-cancerous cells. In EO-treated HepG2 cells, DNA fragmentation was measured by flow cytometry. The in vivo antitumor activity of the EO was assessed in C.B-17 SCID mice xenografted with HepG2 cells treated with the EO at a dosage of 40 mg/kg. Chemical composition analysis displayed the sesquiterpenes α-gurjunene (26.83%), bicyclogermacrene (24.90%), germacrene D (15.35%), and spathulenol (12.97%) as the main EO constituents. The EO exhibited cytotoxi...

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Antitumor Effect of Guatteria olivacea R. E. Fr. (Annonaceae) Leaf Essential Oil in Liver Cancer

Molecules

Guatteria olivacea R. E. Fries (synonym Guatteria punctata (Aubl.) R.A. Howard) is a tree of 10–2... more Guatteria olivacea R. E. Fries (synonym Guatteria punctata (Aubl.) R.A. Howard) is a tree of 10–27 m tall popularly known as “envira-bobó”, “envira-fofa”, “envireira”, “embira”, “embira-branca”, “embira-preta”, envira-branca”, and “envira-preta”, which can be found in the Brazilian Amazon biome. In this study, we evaluated the cytotoxic and antitumor effects of the essential oil (EO) obtained from the leaves of G. olivacea against liver cancer using HepG2 cells as a model. EO was obtained using a hydrodistillation Clevenger-type apparatus and was qualitatively and quantitatively characterized using GC–MS and GC–FID, respectively. The alamar blue assay was used to assess the cytotoxic potential of EO in a panel of human cancer cell lines and human non-cancerous cells. In HepG2 cells treated with EO, YO-PRO-1/propidium iodide staining, cell cycle distribution, and reactive oxygen species (ROS) were examined. In C.B-17 SCID mice with HepG2 cell xenografts, the efficacy of the EO (20 an...

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A Pyrimidine-β-carboline and Other Alkaloids from Annona foetida with Antileishmanial Activity

Journal of Natural Products, 2006

Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmania... more Bioassay-guided fractionation of the bark extract of Annona foetida afforded a new antileishmanial pyrimidine-carboline alkaloid, N-hydroxyannomontine (1), together with the previously reported annomontine (2), O-methylmoschatoline (3), and liriodenine (4). The structure of compound 1 was established on the basis of extensive 1D and 2D NMR and MS analyses. This is the third reported pyrimidine-carboline-type alkaloid and is particularly important for Annona genus chemotaxonomy. In addition, all compounds exhibit in vitro antileishmanial activity against promastigote forms of Leishmania braziliensis. Compounds 2 and 4 showed better activity than compounds 1 and 3 against L. braziliensis. Compound 2 was not active against L. guyanensis.

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ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

Química Nova, 2018

The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatter... more The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (−)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC 50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC 50 values of 3.41 an 8.50 µmol L-1 , respectively.

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Essential Oils of Duguetia Species A. St. Hill (Annonaceae): Chemical Diversity and Pharmacological Potential

Biomolecules

Duguetia A. St. Hill (Annonaceae) is recognized as one of the major genera with approximately 100... more Duguetia A. St. Hill (Annonaceae) is recognized as one of the major genera with approximately 100 species, 67 of which are found in Brazil (29 of those are endemic). They are arboreal species with edible fruits known as “pindaíba”, “pindaíva” “pinha”, and “envira” in Brazil. Many Duguetia species, in particular, have been used in traditional medicine to treat renal colic, stomachache, rheumatism, cough, toothache, muscle pain, fever, gastrointestinal pain, and breathing difficulties. In this study, we reviewed the chemical constituents and pharmacological properties of essential oils (EOs) from Duguetia species. A total of 12 species were found, along with their EO chemical constituents and bioactivities. Bicyclogermacrene, humulene epoxide II, spathulenol, germacrene D, caryophyllene oxide, viridiflorene, α-pinene, β-caryophyllene, and β-pinene were the main chemical constituents reported. The pharmacological effects of Duguetia species EOs included anti-inflammatory, antinocicepti...

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Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Molecules, 2021

Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae fami... more Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximin...

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Chemical composition of the essential oils of Annona pickelii and Annona salzmannii (Annonaceae), and their antitumour and trypanocidal activities

Natural Product Research, 2012

The essential oils from the leaves of Annona pickelii and Annona salzmannii (Annonaceae) were obt... more The essential oils from the leaves of Annona pickelii and Annona salzmannii (Annonaceae) were obtained by hydrodistillation using a Clevenger apparatus, and analysed by GC-MS and GC-FID. A total of 21 compounds were identified in the essential oil of A. pickelii and 23 in that of A. salzmannii; sesquiterpenes predominated in both essential oils. Bicyclogermacrene (38.0%), (E)-caryophyllene (27.8%), α-copaene (6.9%)

Mutagenic and cytostatic activities of the Xylopia laevigata essential oil in human lymphocytes

Natural Product Research

LC-HRMS and acetylcholinesterase affinity assay as a workflow for profiling alkaloids in Annona salzmannii extract

Journal of Chromatography B

Antifungal Polyketides and Other Compounds from Amazonian Endophytic Talaromyces Fungi

Journal of the Brazilian Chemical Society

The continuous search for biologically active compound candidates pushes the pursuit of new subst... more The continuous search for biologically active compound candidates pushes the pursuit of new substances produced by diverse organisms. Endophytic fungi are known as a promising source of metabolites with several biological activities. Based on the rich Amazonian biodiversity and the chemical potential of microbial sources, three Talaromyces strains, all major endophytes from their respective host plants, were studied aiming at the isolation of biologically active secondary metabolites. Through classical chromatographic approaches, 13 compounds were isolated from the antimicrobial extracts of the studied strains. From these, polyketides, steroids, anhydrides, and phenolic compounds were identified. Among them, two previously undescribed compounds were elucidated based on spectroscopic and spectrometric methods, a homodimer chromanone and a maleic anhydride methyl ester. The antimicrobial activity against a panel of pathogenic microorganisms from extracts, fractions, and isolated compounds was evaluated.

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Essential oil from leaves of Conobea scoparioides (Cham. Schltdl.) Benth. (Plantaginaceae) causes cell death in HepG2 cells and inhibits tumor development in a xenograft model

Biomedicine & Pharmacotherapy

ASARONE-DERIVED PHENYLPROPANOIDS AND ISOQUINOLINE-DERIVED ALKALOIDS FROM THE BARK OF Duguetia pycnastera (Annonaceae) AND THEIR CYTOTOXICITIES

Química Nova

The phytochemical investigation of the hexane and methanol extracts from the bark of Duguetia pyc... more The phytochemical investigation of the hexane and methanol extracts from the bark of Duguetia pycnastera Sandwith (Annonaceae) afforded seven known compounds, two asarone-derived phenylpropanoids and five isoquinoline-derived alkaloids. The asarones, γ-asarone (1-allyl-2,4,5-trimethoxybenzene) and 2,4,5-trimethoxy-styrene were isolated of the hexane extract while the aporphine alkaloids, O-methylmoschatoline, lysicamine, nornuciferidine, and guatterine N-oxide, and the benzyltetrahydroisoquinoline alkaloid, (S)-reticuline were isolated of the alkaloid fraction of the methanol extract. This is the first report of these compounds in D. pycnastera. γ-Asarone is being reported for the first time in the Annonaceae. Nornuciferidine is described for the second time in the Annonaceae while guatterine N-oxide is the third register. The structures of the isolated compounds were established by extensive analyses using 1D and 2D NMR spectroscopy in combination with MS. The cytotoxic activity of the isolated compounds (except for nornuciferidine) was evaluated against cancer and non-cancerous cell lines, in which lysicamine was the most active compound, mainly against HL-60, HepG2, and K562 with IC 50 values of 24.40, 28.86 and 38.75 µmol L-1 , respectively.

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In vitro and in vivo growth inhibition of human acute promyelocytic leukemia HL-60 cells by Guatteria megalophylla Diels (Annonaceae) leaf essential oil

Biomedicine & Pharmacotherapy

Chalcone-based molecules: Experimental and theoretical studies on the two-photon absorption and molecular first hyperpolarizability

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

Evaluation of (–)-borneol derivatives against the Zika vector, Aedes aegypti and a non-target species, Artemia sp

Environmental Science and Pollution Research

Integrative Approach Based on Leaf Spray Mass Spectrometry, HPLC‑DAD‑MS/MS, and NMR for Comprehensive Characterization of Isoquinoline-Derived Alkaloids in Leaves of Onychopetalum amazonicum R. E. Fr

Journal of the Brazilian Chemical Society

Onychopetalum is an Amazonian botanical genus close-related with Bocageopsis and Unonopsis, whose... more Onychopetalum is an Amazonian botanical genus close-related with Bocageopsis and Unonopsis, whose species are used in traditional medicine. Although these genera are widely investigated from the phytochemical viewpoint, the knowledge about Onychopetalum remains almost unexplored. In order to perform a comprehensive characterization of isoquinoline-derived alkaloids from Onychopetalum amazonicum, an integrative approach based on the alkaloid profile analysis by leaf spray mass spectrometry (LS-MS), followed by a robust dereplication through highperformance liquid chromatography coupled with diode array detector and atmospheric pressure chemical ionization tandem mass spectrometry, (HPLC-DAD-APCI-MS/MS) and nuclear magnetic resonance (NMR) analysis was adopted. LS-MS allowed the tentative identification of reticuline, norjuziphine, nornuciferine, O-methylisopiline, nuciferine, N-methyl-O-methylisopiline, anonaine, and N-methylanonaine. HPLC-DAD-MS/MS analysis supported the tentative identification of N-methylasimilobine, asimilobine, norushinsunine, N-methylisopiline, isopiline, liriodenine, and lysicamine. Moreover, the integration of MS and NMR data allowed the additional identification of stepholidine and isocorypalmine. The applied integrative approach proposed herein enabled a comprehensive analysis of the alkaloid content from the O. amazonicum, showing to be a useful strategy for the dereplication of isoquinoline-derived alkaloids.

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Antitumor Effect of the Essential Oil from the Leaves of Croton matourensis Aubl. (Euphorbiaceae)

Molecules

Croton matourensis Aubl. (synonym Croton lanjouwensis Jabl.), popularly known as “orelha de burro... more Croton matourensis Aubl. (synonym Croton lanjouwensis Jabl.), popularly known as “orelha de burro”, “maravuvuia”, and/or “sangrad’água”, is a medicinal plant used in Brazilian folk medicine as a depurative and in the treatment of infections, fractures, and colds. In this work, we investigated the chemical composition and in vitro cytotoxic and in vivo antitumor effects of the essential oil (EO) from the leaves of C. matourensis collected from the Amazon rainforest. The EO was obtained by hydrodistillation using a Clevenger-type apparatus and characterized qualitatively and quantitatively by gas chromatography coupled to mass spectrometry (GC–MS) and gas chromatography with flame ionization detection (GC–FID), respectively. In vitro cytotoxicity of the EO was assessed in cancer cell lines (MCF-7, HCT116, HepG2, and HL-60) and the non-cancer cell line (MRC-5) using the Alamar blue assay. Furthermore, annexin V-FITC/PI staining and the cell cycle distribution were evaluated with EO-tre...

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Physicochemical characterization and antinociceptive effect of β-cyclodextrin/Lippia pedunculosa essential oil in mice

Current topics in medicinal chemistry, Jan 6, 2018

Some researches have been shown that Lippia pedunculosa essential oil (EOLP) has interesting biol... more Some researches have been shown that Lippia pedunculosa essential oil (EOLP) has interesting biological activities. However, its low water solubility is the main challenge to achieve its therapeutic potential. In this context, cyclodextrins (CDs) have been widely used in order to overcame this problem due to your capability to improve the physicochemical properties of drugs. In this perspective, the main goal of this study was to investigate how the improvement of the physicochemical properties of inclusion complexes (EOLP and β-CD) enhance the antinociceptive effect in mice. To achieve that, we prepared samples by physical mixture (PM), paste complexation (PC) and slurry complexation (SC) methods, followed by their physicochemical characterization. In addition, it was evaluated if the use of β-CD enhances the antinociceptive effect of EOLP in mice. The analysis showed that rotundifolone (72.02%) was the major compound of EOLP and we found out based in DSC results that β-CD protecte...

$Research paper thumbnail of {"__content__"=>"Synthesis and Chemometrics of Thymol and Carvacrol Derivatives as Larvicides against.", "i"=>{"__content__"=>"Aedes aegypti"}}$

{"__content__"=>"Synthesis and Chemometrics of Thymol and Carvacrol Derivatives as Larvicides against.", "i"=>{"__content__"=>"Aedes aegypti"}}

Journal of arthropod-borne diseases, 2017

Thymol and carvacrol have previously demonstrated larvicidal activity against(Diptera: Culicidae)... more Thymol and carvacrol have previously demonstrated larvicidal activity against(Diptera: Culicidae). In view of this fact, it was of our interest to obtain synthetic derivatives and evaluate their larvicidal activity onlarvae. Structural modifications were performed on thymol and carvacrol in an effort to understand the functional groups necessary for modulating their activities and to lead possibly to more effective larvae control agents. The derivatives were further subjected to SAR and computational studies (molecular modeling and chemometric tools (CPCA and PCA)) to extract structural information regarding their larvicidal properties. Field collected and Rockefeller populations ofwere used. Carvacrol and thymol exhibited LCof 51 and 58ppm for field collected larvae, respectively. Carvacrol derivatives exhibited LCranging from 39 to 169ppm, while thymol derivatives exhibited LCranging from 18 to 465ppm. Substitution of the acidic proton of carvacrol by esters, ethers, and acetic ac...

Guaianolide sesquiterpene lactones and aporphine alkaloids from the stem bark of Guatteria friesiana

Phytochemistry, Jan 20, 2017

Three guaianolide sesquiterpenes, denoted guatterfriesols A-C, and four aporphine alkaloid deriva... more Three guaianolide sesquiterpenes, denoted guatterfriesols A-C, and four aporphine alkaloid derivatives were isolated from the stem bark of the Amazonian plant Guatteria friesiana. Thus far, sesquiterpene lactones have not been described in Annonaceae. Structures of the previously undescribed compounds were established by using 1D and 2D NMR spectroscopy in combination with MS. The absolute stereochemistry was assigned via NOE NMR experiments, ECD spectroscopy, and theoretical calculations using the TDDFT approach. Among the isolated compounds, the alkaloid guatterfriesidine showed anti-glycation activity by inhibiting the formation of advanced glycation end-products (AGEs) through the prevention of oxidation in both BSA/methylglyoxal and BSA/fructose systems.

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