RESUMO: Amburana cearensis A. C. Smith (Fabaceae) é uma planta comum na Caatinga cearense, onde é popularmente conhecida como cumaru. Vários compostos têm sido isolados de A. cearensis, incluindo ácido protocatecúico, taninos, cumarina, flavonóides e heterosídeos fenólicos, como por exemplo os amburosídeos A e B. O objetivo desse estudo foi avaliar o potencial antimicrobiano e caracterizar o perfil químico do decocto da casca do caule de A. cearensis, visando a sua possível utilização na conservação de alimentos. A caracterização dos compostos químicos foi realizada pelas análises de RMN uni e bidimensionais de 1H e 13C, e cromatografia líquida acoplada à espectrometria de massa. Foram identificados a cumarina, os amburosídeos A e B, e o ácido (Z)-o-cumárico glicosilado. A atividade antimicrobiana foi realizada pela metodologia de microdiluição em placa sobre Escherichia coli, Salmonella Enteritidis, Pseudomonas aeruginosa, Staphylococcus aureus e Listeria monocytogenes. O decocto mostrou atividade antimicrobiana sobre bactérias Gram-positivas. Antimicrobianos naturais podem oferecer vantagens para a produção de alimentos, inibindo microorganismos patogênicos e melhorando a qualidade higiênico-sanitária.

ABSTRACT: The plant, Amburana cearensis A. C. Smith (Fabaceae), commonly called cumaru, is widespread in the Caatinga cearense, a less known ecosystem in Brazil. A. cearensis is rich in several compounds like protocatechuic acid, tannins, coumarin, flavonoids and phenolic heterosides, such as amburosides A and B, that have been isolated. The aim of this study was to determine the antimicrobial potential and draw the chemical profile of the distinct characteristics of A. cearensis stem bark decoction, for its possible potential as a food conservation agent. The chemical compounds were characterized by one- and two-dimensional 1H and 13C NMR analyses and Liquid Chromatography-Mass Spectrometry (LCMS). The compounds of coumarin, amburosides A and B, and glycosylated (Z)-o-coumaric acid. Using the plaque microdilution technique, the antimicrobial action was tested on Escherichia coli, Salmonella Enteritidis, Pseudomonas aeruginosa, Staphylococcus aureus and Listeria monocytogenes. The decoction demonstrated antimicrobial activity on Gram-positive bacteria. This was encouraging because natural antimicrobials are beneficial for food production, as they can inhibit the pathogenic microorganisms and boost the quality of hygiene and cleanliness.

Myracrodruon urundeuva Fr. Allem. (Anacardiaceae) is the scientific designation of "aroeira-do-sertão", a tree well dispersed through the "Caatinga", the characteristic northeastern Brazil flora. Its trunk bark decoction is used to treat cutaneous affections, urinary and respiratory diseases and as a postpartum aseptic bath. This work reports the analyses of the essential oils from leaves of 62 specimens of "aroeira-do-sertão". Analyses by 1H nuclear magnetic resonance (NMR) and gas chromatography coupled to mass spectrometry (GC-MS) of all oil samples permitted the characterization of all major components and, in consequence, the characterization of six different chemotypes of M. urundeuva, represented by the chemomarkers: myrcene, α-pinene, limonene, Δ3-carene, (Z) and (E)-β-ocimene.

AbstractLeishmaniasis and fungal infection treatment efficacy is limited by toxicity and ever increasing resistance to available drugs, requiring development of alternative compounds. The richness of Cerrado plant antimicrobial secondary metabolites justifies screening of Fabaceae species extracts: Enterolobium ellipticum Benth., Sclerolobium aureum (Tul.) Baill. and Vatairea macrocarpa(Benth.) Ducke, against Leishmania(Leishmania) amazonensis, yeasts and dermatophytes. Among the 26 extracts tested, more than 50% of the total demonstrated significant antifungal activity in comparison to the drug controls (minimal inhibitory concentration 0.12 to ≤31.25 µg/ml). Six extracts capable of complete parasitic growth inhibition had the inhibitory concentration index for 50% values from 9.23 to 78.65 µg/ml. The results led to the selection of the V. macrocarpa ethyl acetate root bark extract for chemical fractionation. This plant, traditionally referred to as angelim-do-cerrado or maleiteira, is used to treat superficial mycoses in Amazonia. A previously unreported pterocarpan vatacarpan together with the known compound musizin was isolated. Vatacarpan demonstrated a minimal inhibitory concentration value of 0.98 µg/ml against Candida albicans ATCC 10231, and thus comparable or superior to fluconazole and amphotericin B. The results add to literature's information the ability of pterocarpans to act as antimicrobial agents.

Eight compounds, including terpenoids (jatrophone, hydroxyjatrophone, 6-hydroxycyperene, cabraleadiol monoacetyl, and cabraleadiol) and coumarins (fraxetin, fraxidin, and isofraxidin), were isolated from Jatropha ribifolia (Euphorbiaceae). Their structures were established by 1D and 2D NMR (COSY, HSQC, and HMBC) spectra, HRESIMS and comparison with published data.

A new trachylobane diterpene ent-trachyloban-18,19-diol (1) was isolated from root bark of Croton floribundus, along with known diterpenes ent-trachyloban-19-oic acid (2), 15b-hydroxy-ent-trachyloban-19-oic acid (3), ent-trachyloban-19-ol (4), ent-kaur-16-en-19-oic acid (5), ent-kaur-16-ene-6a,19-diol (6) and ent-16a-hydroxykaur-11-en-19-oic acid (7). ent-trachyloban-18,19-diol (1) was submitted to derivatization reactions affording four new compounds (8-11). Cytotoxic activity of diterpenes 1, 3, 4, 7-11 against three human cancer cell lines was evaluated. No compounds showed cytotoxic potential with IC50 values greater than 25 mg/mL. Compound 6 was evaluated against five human cancer cell lines, showing moderate effect against three cancer cell lines, MDA-MB-435, HCT-8 and HCT-116, with IC50 values of 14.32, 13.47 and 12.1 mg/mL, respectively.

The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6"-O-p-coumaroyl-β-galactopyranosyl- kaempferol, 6"-O-p-coumaroyl-β-glucopyranosyl-3"-methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric methods, including HR-ESI-MS, 1D and 2D NMR experiments, and by comparison with previously-described physical and spectral data.

The new iridoid glucoside 10-O-vanilloyl-geniposidic acid has been isolated from the aerial parts of Alibertia myrciifolia along with hydroxyhopanone, 3α,22-dihydroxyhopane, ursolic acid, luteolin-3´,4´-dimethyl ether, caffeic acid and geniposidic acid. The structures of the isolated compounds were determined by means of mass spectrometry and nuclear magnetic resonance spectral analyses. The antifungal activities of the iridoids 10-O-vanilloyl-geniposidic acid and geniposidic acid were evaluated against the phytopathogenic fungi strains Colletotrichum gloeosporioides, Fusarium solani and Aspergillus niger.

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.

Dois α-aminoácidos lipídicos 1a e 1b foram isolados do zoantídeo Protopalythoa variabilis através de fracionamento guiado pela atividade citotóxica. As estruturas foram determinadas por diferentes métodos espectroscópicos, tais como, RMN (ressonância magnética nuclear) ¹H e 13C, IV (infravermelho) e espectrometria de massa de alta resolução (modo positivo). A atividade citotóxica dos extratos, das frações e 1a/1b foi avaliada in vitro através do teste do MTT contra quatro linhagens de células tumorais. Este achado tem implicações biológicas e químicas importantes para essa classe de compostos. Este é o primeiro relato de α-aminoácidos lipídicos a partir de uma fonte natural, bem como de sua atividade citotóxica.

Two lipidic α-amino acids 1a and 1b were isolated from the zoanthid Protopalythoa variabilis using a bioguided fractionation for cytotoxic activity. The structures of the metabolites were determined by spectroscopic methods, including NMR (nuclear magnetic resonance) ¹H e 13C, IR (infrared) and high resolution mass spectrometry (positive mode). The cytotoxic activity of the crude extract, as well as of the mixture of 1a and 1b were measured in vitro using the MTT assay for four human tumor cell lines. This finding has important biological and chemical implications for this type of compound. This is the first report of lipidic α-amino acids from natural sources, as well as of their cytotoxic activity.

Phytochemical investigation of the hexane extract of fruit shells of Copaifera langsdorffii Desf. (Caesalpinioideae) afforded ent-kaur-16-en-19-oic acid, polyalthic acid, nivenolide and the mixture of caryophyllene oxide and ent-kaur-16-en-19-oic acid. The chloroform extract of unripe seeds led to the isolation of coumarin and the GC/MS analysis of the extract allowed the identification of 81.8% of the fatty acid composition after hydrolysis followed by methylation. The main fatty acid identified was oleic acid (33.1%). The isolation of all secondary metabolites was accomplished by modern chromatographic methods and the structure determination was accomplished by spectrometric methods (IR, MS, NMR ¹H and 13C).

The phytochemical analysis of the ethanol extract trunk bark of Amburana cearensis allowed the isolation and identification of twelve constituents: coumarin, sucrose, two phenol acids (vanillic acid and protocatechuic acid), five flavonoids (afrormosin, isokaempferide, kaempferol, quercetin and 4'-methoxy-fisetin), a phenol glucoside (amburoside A) and a mixture of glucosilated b-sitosterol and stigmasterol. Their structures were elucidated by spectroscopic methods such as IR, MS, ¹H and 13C NMR, including uni and bidimensional techniques, in addition to comparison with literature data.

The essential oils from leaves, root bark and root wood of Cochlospermum vitifolium were investigated for the first time. The oils were obtained by hydrodistillation and analyzed by GC/MS. The main volatile constituents were beta-caryophyllene (8.2 - 46.5%), beta-bisabolene (11.5 - 29.3%), gamma-muurolene (28.4%), alpha-humulene (26.0%), 1-hydroxy-3-hexadecanone (16.2 - 19.5%) and beta-pinene (10.6%). Phytochemical analysis of the root bark and root wood extracts yielded excelsin, pinoresinol, narigenin, aromadendrin, galic acid and a triacylbenzene, along with beta-sitosterol and stigmasterol and their D-glucosides. The structures of all compounds were determined by analyses of the spectroscopic data (NMR and MS), and comparison with the literature.

Estudos anteriores mostraram que óleos essenciais voláteis obtidos de plantas potenciam o tempo de sono induzido por pentobarbital e álcool em camundongos. Cetamina é um anestésico muito utilizado em crianças, sendo conhecida por causar uma anestesia dissociativa. Seus efeitos alucinógenos podem ser reduzidos quando administrada em associação a benzodiazepínicos. O objetivo deste estudo foi determinar a influência dos óleos de Psidium guyanensis (Araçá azedo), Psidium pohlianum (Araçá doce), Psidium guajava (Araçá goiaba), Rosmarinus officinalis (Alecrim) e Lippia alba (Cidreira) no tempo de sono induzido por cetamina em camundongos. Os resultados indicam que o tempo de sono induzido por cetamina foi prolongado pelos óleos essenciais de Psidium guyanensis, Psidium pohlianum, Psidium guajava e Lippia Alba mostrando novas possibilidades de associação com a cetamina a fim de prolongar o seu efeito sedativo, proporcionando uma anestesia mais adequada.