Síntese e estudo de ortossilicatos de zinco luminescentes com aplicação da técnica sol-gel

Usually, the concepts of the Sol-Gel technique are not applied in experimental chemistry courses. This work presents a feasible experiment for chemistry instruction, which involves the synthesis of luminescent materials - Zn2SiO4, with and without Mn2+ as a dopant - by the Sol-Gel technique. The obtained materials were analyzed by scanning electron microscopy, X-Ray diffraction, IR spectroscopy and luminescence measures by UV-vis spectroscopy. The results allow the students to confirm the luminescent properties of the zinc orthosilicate luminophores as well as the structural features expected from literature data.

Constituintes químicos e atividade antioxidante de extratos das folhas de Terminalia fagifolia Mart. et Zucc

Phytochemical investigation of ethanolic leaves extracts of T. fagifolia led to the isolation of (+)-catechin, sitosterol-3-O-β-D-glucopyranoside, α- and β-tocopherol, a mixture of lupeol, α- and β-amyrin, sitosterol and a mixture of glicosid flavonoids (CP-13). The structures of these compounds were identified by ¹H and 13C NMR spectral analysis and comparison with literature data. Absolute configuration of the catechin was determinate by circular dichroism. Antioxidant activity (EC50), evaluated by 2,2-diphenyl-1-picrylhidrazyl (DPPH) assay system, decreased in the order: (+)-catechin > hydroalcoholic fraction > CP-13 > aqueous fraction > EtOH extract.

Constituintes químicos e atividade inseticida dos extratos de frutos de Trichilia elegans E T. catigua (Meliaceae)

Phytochemical investigation of the fruits extracts of Trichilia elegans and Trichilia catigua (Meliaceae) has led to the identification of the limonoids 11β-acetoxyobacunone, cedrelone, methylangolensate and epimeric mixture of photogedunin besides known coumarins (scoparone, scopoletin, umbeliferone) and the steroids stigmasterol, β-sitosterol, sitostenone and campesterol. The structures of the compounds were proposed by spectroscopic analysis and comparison with literature data. An evaluation of the insecticidal activity of the fruits extracts of Trichilia ssp. was carried out and the extracts of T. elegans revealed to have strong insecticidal activity and the extracts of T. catigua showed moderate larval mortality on Spodoptera frugiperda.

Estudo fitoquímico de espécimens cultivados de cumaru (Amburana cearensis A. C. Smith)

Due to the threat of extinction of Amburana cearensis, a tree of medicinal importance for the Northeastern Brazil, a phytochemical analysis was performed with specimens obtained by seed germination. Ten compounds were isolated and identified by spectroscopic methods and comparison with literature data. p-Hydroxybenzoic acid, ayapin, (E/Z)-melilotosides are being reported for the first time for the genus, besides coumarin, isokaempferide, vanillic acid, protocatechuic acid, amburosides A and B which have already been found in the trunk bark. Based on physical and NMR spectroscopy evidences the structures of several melilotosides already described in the literature have been suggested to be revised.

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

Sidastrum paniculatum (L.) Fryxell belongs to the family Malvaceae and is popularly known as "malva roxa" or "malvavisco". The phytochemical study of the hexane, CHCl3 and EtOAc phases from the crude ethanol extract of S. paniculatum led to the isolation of six compounds: a mixture of β-sitosterol and stigmasterol, 4-methoxy-3-hydroxybenzoic acid, 4-methoxy-3-hydroxybenzaldehyde, N-trans-feruloyltyramine and kaempferol-3-O-β-D-(6''-E-p -coumaroyl) glucoside. The structural identification of the compounds was made on the basis of spectroscopic methods such as IR, ¹H and 13C NMR with the aid of including two-dimensional techniques, besides comparison with literature data. The β-sitosterol and stigmasterol mixture showed a significant anti-inflammatory activity.

Chemical constituents of the wood from Zanthoxylum quinduense Tul. (Rutaceae)

Phytochemical investigation of the wood from Zanthoxylum quinduense Tul. allowed the isolation and identification of norchelerythrine, decarine, 6-acetonyldihydrochelerythrine, syringaresinol, evofilin C, p-hydroxybenzaldehyde, vanillic acid, a mixture of β-sitosterol, stigmasterol and campesterol and a mixture of saturated and unsaturated fatty acids, and their esters derivatives. The structures of the isolated compounds were elucidated by spectroscopic techniques and comparison with literature data and the mixture of sterols and fatty acids were identified by GC/MS. The antifungal activity of the ethanolic extract, fractions and pure compounds against Fusarium oxysporum f. sp. lycopersici was determined by bioautography. Evofilin C and nochelerytrine were the only substances that present antifungal activity.

Atividade inseticida dos frutos de Trichilia claussenii (Meliaceae) sobre Spodoptera frugiperda

An evaluation of the insecticidal activity of the fruits extracts of Trichilia claussenii was carried out and the methanol extract revealed to have strong insecticidal activity. The fractionation of methanol extract of T. claussenii seeds bioassay-guided against Spodoptera frugiperda has led to the identification of the ω-phenylalkyl and alkenyl fatty acids as active compounds in this extract. The structures of the compounds were proposed by spectroscopic analysis and comparison with literature data.

Determinação do coeficiente de atividade em diluição infinita de hidrocarbonetos em furfural a 298,15 K por SPME-GC/FID

In this work a new method (SPME-GC/FID) was developed to analyze the activity of binary liquid mixtures. The purpose is to demonstrate that SPME is capable to be used to determinate activity coefficients at infinite dilution knowing the fiber properties, with a lower cost than the conventional methods encountered in literature such as GLC. The activity coefficients at infinite dilution in furfural for n-hexane, n-heptane and cyclohexane at 298.15 K was determined using SPME and deviations of literature data was about 7%.

Glicoalcaloides antifúngicos, flavonoides e outros constituintes químicos de Solanum asperum

Two glycoalkaloids: solamargine and solasonine; three flavonoids: tiliroside, 7-O-α-L-ramnopyranosyl-kaempferol and 3-O-[ß-D-glucopyranosyl-(1→6)-α-L-ramnopyranosyl]-7- O-α-L-ramnopyranosyl-kaempferol, in addition to the tripeptide Leu-Ile-Val, the aminoacid proline and the eicosanoic acid were isolated from Solanum asperum (Solanaceae). The structures of all compounds were determined by interpretation of their spectra (IR, MS, ¹H and 13C NMR) and comparison with the literature data. All compounds, except the glycoalkaloids, are being reported for the first time for S. asperum. Solasonine showed strong activity (MIC < 0.24 μg/mL) against four filamentous fungi species of the genera Microsporum and Trichophyton.

Bromopyrrole alkaloids from the caribbean sponge Agelas cerebrum

Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source.

Constituintes químicos das folhas de Rollinia leptopetala R. E. Fries

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.

Desreplicação de alcaloides aporfínicos e oxoaporfínicos de Unonopsis guatterioides por ESI-IT-MS

The dereplication of aporphine and oxoaporphine alkaloids by direct infusion in ESI-IT-MSn system was applied for alkaloidal fractions of the Unonopsis guatterioides (Annonaceae). Its main advantage over other dereplication methods is the ability to quickly identify substances in complex mixtures without the use of coupled techniques and expensive databases. By only the fragmentation keys and comparison with literature data the aporphine alkaloids anonaine, asimilobine and nornuciferine were identified. The nornuciferine is being reported for the first time in Unonopsis. The oxoaporphine alkaloids liriodenine and lisycamine were identified in the alkaloidal fractions by comparison with the fragmentations of authentic samples.

Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-β-D-glucopyranoside) and a neolignan glucoside, dehydrodiconiferyl alcohol-4-β-D-glucoside. All compounds were identified by a combination of spectroscopic methods (¹H, 1D, 2D NMR, 13C and UV), ESI-MS and comparison with the literature data. This is the first report of flavonoids in the genus Guarea and of a neolignan glucoside in the Meliaceae family.

Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa

Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents.

Constituintes químicos das folhas de Riedeliella graciliflora Harms (Leguminosae)

A new salicylic acid derivative, pentacosanyl salicylate, was isolated from the leaves of the plant toxic to cattle, Riedeliella graciliflora, in addition to a digalactosyldiacylglycerol (DGDG), 1,2-di-O-α-linolenoyl-3-O-α-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-glycerol, kaempferol-3-O-β-D-glucopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, quercetin-3-O-α-L-rhamnopyranoside, rutin, (+)-catechin and the dimer (+)-catechin-(4β-8)-catechin, glutinol, squalene, β-sitosterol, stigmasterol, phytol, β-carotene, α-tocopherol and ficaprenol-12. Their structures were determined using spectral techniques (MS, IR, and NMR-1D and 2D) and based on literature data.