Resumo em Inglês:

Abstract Myrciaria glomerata O. Berg., Myrtaceae, popularly known as "cabeludinha", has high content of ascorbic acid and anti-inflammatory property and is used in folk medicine. The objectives of this study were the morphological, anatomical and histochemical characterization of the leaves. Leaf studies were made with optical, scanning electron and confocal microscopy. The collection of botanical material was held at the Tijuca Forest, Rio de Janeiro, RJ. Histochemical tests aimed the identification of lipids, starch grains, phenolic compounds and crystals. The leaves are simple, opposite, lanceolate, pinnate, hairy, with involute margins, hypostomatic and dorsiventral. The stomata are anomocytic. The epidermis presents simple trichomes. Epidermal cells show uneven thickening of their periclinal outer walls, mainly on the adaxial side of the leaf. Secretory cavities of essential oils are subepidermal and exceed, in height, the palisade parenchyma, formed by one cell layer. Four to five cellular layers, rich in phenolic compounds and lipids form the spongy parenchyma. The bundles are collateral and there are many crystals of calcium oxalate spread throughout the mesophyll. In the midrib and petiole the bundles are bicollateral. Analysis by scanning electron revealed epicuticular wax rod-shaped and as grains. In confocal microscopy, the adaxial epidermis, the fibers and the secretory epithelium of the cavities show autofluorescence. The data obtained are important in quality control exams of samples of this species.

Resumo em Inglês:

Abstract A new iridoid glycoside, barlupulin C methyl ester (1), together with two known phenylethanoid glycosides (2 and 3) and three known simple phenolic glycosides (4-6) were isolated from the aerial parts of Barleria lupulina Lindl., Acanthaceae. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data, and HR-ESIMS. Interestingly, compound (1) has a formate group attached to the C-6 hydroxy group of the glucose unit. Compounds 2-6 were identified as poliumoside (2), decaffeoylacteoside (3), protocatechuic acid 4-O-β-glucoside (4), vanillic acid 4-O-β-glucoside (5), and leonuriside A (6) on the basis of NMR spectroscopic data analyses and comparison with those reported in the literature. Compounds 3-6 were isolated from B. lupulina for the first time.

Resumo em Inglês:

Abstract Currently Streptomyces is one of the most important antibiotic producing microorganisms against several diseases. In the present study Streptomyces olivochromogenes ERINLG-261 was isolated from the soil samples of the Mudumalai hills, Western Ghats, India. Morphological, physiological, biochemical and 16S rRNA studies strongly suggested that this isolate belonged to the genus Streptomyces. ERINLG-261 showed good antimicrobial activity against different bacteria and fungi in Micromonospora fermentation medium. The active ethyl acetate extract was packed in column chromatography over silica gel which led to the isolation of 2-hydroxy-9,10-anthraquinone as the active principle. The isolated compound showed good antimicrobial activity against tested bacteria and fungi in minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) studies. The compound showed moderate in vitro antiproliferative activity against A549 and COLO320 cells. The compound was subjected to molecular docking studies for the inhibition of Topoisomerase, TtgR and Beta-lactamase enzymes which are targets for antimicrobials. Docking results of the compound showed low docking energy with these enzymes indicating its usefulness as antimicrobial agent. This is the first report of antimicrobial and antiproliferative activity of 2-hydroxy-9,10-anthraquinone isolated from Streptomyces olivochromogenes along with molecular docking studies.

Resumo em Inglês:

Abstract Recent publications have highlighted the numerous biological activities attributed to the lignan (-)-cubebin (1), Piper cubeba L. f., Piperaceae, and ongoing studies have focused on its structural optimization, in order to obtain derivatives with greater pharmacological potential. The aim of this study was the obtainment of (1), its semisynthetic derivatives and evaluation of antibacterial activity. The extract of the seeds of P. cubeba was chromatographed, subjected to recrystallization and was analyzed by HPLC and spectrometric techniques. It was used for the synthesis of: (-)-O-methylcubebin (2), (-)-O-benzylcubebin (3), (-)-O-acetylcubebin (4), (-)-O-(N, N-dimethylamino-ethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6.6'-dinitrohinokinin (7). The evaluation of the antibacterial activity has been done by broth microdilution technique for determination of the minimum inhibitory concentration and the minimum bactericidal concentration against Porphyromonas gingivalis, Prevotella nigrescens, Actinomyces naeslundii, Bacteroides fragilis and Fusobacterium nucleatum. It was possible to make an analysis regarding the relationship between structure and antimicrobial activity of derivatives against microorganisms that cause endodontic infections. The most promising were minimum inhibitory concentration =50 µg/ml against P. gingivalis by (2) and (3), and minimum inhibitory concentration =100 µg/ml against B. fragilis by (6). Cytotoxicity assays demonstrated that (1) and its derivatives do not display toxicity.

Resumo em Inglês:

Abstract Spondias mombin L., Anacardiaceae, is a plant native of Brazil, where it is known as "cajá". In order to find a potential application for this native species, the anti-inflammatory and antioxidant effects were investigated. The anti-inflammatory activity was evaluated using the in vivo model carrageenan-induced peritonitis in mice. The in vitro antioxidant potential as well the cytotoxicity against 3T3 fibroblast cells also were evaluated. Through High Performance Liquid Chromatography-diode array detector analysis, an analytic method was developed and validated. It allowed the identification and quantification of ellagic acid and chlorogenic acid in hydroethanolic extract of S. mombin leaves. This extract showed anti-inflammatory effect at 100, 200, 300 and 500 mg/kg, however, the ethyl acetate fraction, at 200 mg/kg, showed the highlighted results. Ellagic acid and chlorogenic acid (2.5, 5 and 10 mg/kg) also inhibited the leukocyte migration to the site of inflammation. The extract, fractions and compounds showed significant antioxidant potential when evaluated in different assays. The results shown in this work suggest the anti-inflammatory potential of the leaf extract of S. mombim on peritonitis model induced by carrageenan, it was also observed antioxidant properties associated with an absence of cytotoxicity in cell culture. Further in vivo studies are required to confirm the anti-inflammatories action of S. mombin and its possible anti-inflammatory mechanisms of action.

Resumo em Inglês:

Abstract The leaves of Garcinia gracilis Pierre, Clusiaceae, have been used as flavouring materials in food, with no previous reports of their biological activities and chemical constituents. In this study, the methanolic extract of G. gracilis afforded three compounds namely apigenin-8-C-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1), 5-hydroxymethyl-2-furaldehyde, and vanillic acid. All of the isolates were initially evaluated for superoxide anion radical scavenging activity and α-glucosidase inhibitory effects. Compound 1, which was the major component, showed the most potent activities among these three isolates. Further biological evaluations revealed that compound 1 could prevent the pBR322 plasmid DNA damage induced by the photochemical reaction of riboflavin and protect P19-derived neurons from the oxidative stress condition induced by serum deprivation. It was concluded that the potent biological activities of G. gracilis could be attributed to the synergistic effect of compound 1 with other constituents found in the plant.

Resumo em Inglês:

Abstract The aim of the current study is to evaluate the effect of Acmella oleracea (L.) R.K. Jansen, Asteraceae, methanolic extract, hexane (84.28% spilanthol) and dichloromethane (approximately 100% spilanthol) fractions on the tyrosinase enzyme. The dehydrated jambu extract was obtained through maceration using methanol. The extract residue was solubilized in MeOH/H2O (8:2) and subjected to liq.–liq. partition in organic solvents. Both the extraction and the partition procedures were conducted with three replicates. The analyses were performed using GC–MS, 1H and 13C NMR. The hexane fraction provided samples containing 84.28, 82.91 and 62.83% spilanthol in repetitions 1, 2 and 3, respectively. The dichloromethane fraction showed 88.55% spilanthol in repetition 1, and approximately 100% spilanthol in repetitions 2 and 3. The jambu extract as well as the hexane fraction (84.28% spilanthol) were able to activate the oxidizing activity of the tyrosinase enzyme for L-DOPA. The dichloromethane fraction (approximately 100% spilanthol) showed stronger inhibition effect on the tyrosinase enzyme in the first 10 min. The results raise the interest in study in spilanthol formulations for topical use, since it may prevent and/or slow skin hyperpigmentation or depigmentation processes. Furthermore, spilanthol may be used to control the enzymatic browning in fruits and vegetables.

Resumo em Inglês:

Abstract Angiogenesis plays a key role in tumor growth, invasion and metastasis of cancer diseases and therefore, the inhibition of angiogenesis can provide an important therapeutic approach in cancer diseases. This study was designed to compare the anti-angiogenic activities of the ethanolic extract of Artemisia sieberi Besser, Asteraceae, and its active substance, artemisinin in both in vitro and in vivo models. To compare cytotoxicity level of ethanolic extract of A. sieberi with artemisinin, different concentrations (1–100 µg/ml) were tested using MTT assay on human umbilical vein endothelial cells. The anti-angiogenic properties of serial concentrations of ethanolic extract of A. sieberi and artemisinin were examined on human umbilical vein endothelial cells using a three-dimensional angiogenesis assay (in vitro model) and in the chick chorioallantoic membrane assay as in vivo model. The effects of ethanolic extract of A. sieberi and artemisinin were also tested on the expression of VEGFR-1, VEGFR-2 and CD34 genes using real-time PCR. Ethanolic extract of A. sieberi and artemisinin significantly (p < 0.001) inhibited the angiogenesis in the human umbilical vein endothelial cells culture whilst the ethanolic extract of A. sieberi showed higher effect in a concentration-dependent fashion (p < 0.001). The chick chorioallantoic membrane angiogenesis was also completely inhibited by ethanolic extract of A. sieberi at concentration of 33 ng/100 µl/egg. The gene expression analysis showed that the ethanolic extract of A. sieberi and artemisinin reduced the transcription of VEGFR-1, VEGFR-2 and CD34 genes in a concentration-dependent manner. This study demonstrated that the ethanolic extract of A. sieberi is strongly able to inhibit the angiogenesis in human umbilical vein endothelial cells and chick chorioallantoic membrane models compared to the artemisinin.

Resumo em Inglês:

Abstract Schistosomiasis, a chronic disease that affects million people worldwide, is caused by trematode flukes of the genus Schistosoma. The lack of an anti-schistosomiasis vaccine and massive monotherapy with praziquantel reinforces the need for search and development of new therapeutic drugs. Recently, we demonstrated that the essential oil of Piper cubeba L., Piperaceae, and their derivative dibenzylbutyrolactolic (-)-6,6'-dinitrohinokinin, presents in vitro and in vivo activities against Schistosoma mansoni. Here, we identified changes in the protein expression after exposure to dibenzylbutyrolactolic (-)-6,6'-dinitrohinokinin. We applied two-dimensional gel electrophoresis (2-DE) to S. mansoni soluble protein extracts and observed at least 38 spots to be affected by dibenzylbutyrolactolic (-)-6,6'-dinitrohinokinin. We further identified 25 differentially expressed proteins by mass spectrometry. Enrichment for biological processes and predictive analyses of protein-protein interactions suggest that dibenzylbutyrolactolic (-)-6,6'-dinitrohinokinin targets proteins involved mainly in metabolic processes, especially carbohydrate metabolism. In summary, this study provides an interesting approach to understand the anti-parasitic activity of semi-synthetic (-)-6,6'-dinitrohinokinin a derivative compound from lignan and for the development of new therapy strategies.

Resumo em Inglês:

Abstract In hybrid cultivated form, Dendranthema grandiflorum (Ramat.) Kitam., Asteraceae, flowers (Chrysanthemum morifolium Ramat.) were utilized in the production of extracts, which were analyzed for larvicidal activity against Aedes aegypti third instar larvae. Methanol and dichloromethane extracts showed LC50 values of 5.02 and 5.93 ppm, respectively. Using GC–MS, phytochemical analyses of the dichloromethane extract showed the presence of triterpenoids and fatty acids, while flavonoids and caffeoylquinic acids were shown to occur in the methanol extract by ESI Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (ESI-FT-ICR-MS). Triterpenoids and fatty acids are well known insecticidal compounds. From this study, it can be concluded that D. grandiflorum grown for floriculture, as an agribusiness, can have additional applications as raw material for the production of insecticidal products.

Resumo em Inglês:

Abstract Doxorubicin is a chemotherapy drug but its clinical using is limited because of its cardiotoxicity. Reactive oxygen species play an important role in the pathological process. The aim of this study is to evaluate the protective effect of Rheum turkestanicum Janisch., Polygonaceae, against doxorubicin-induced apoptosis and death in H9c2 cells. The cells were incubated with different concentrations of R. turkestanicum extract and N-acetylcysteine as positive control for 2 h, followed by incubation with 5 µM doxorubicin for 24 h. Cell viability and apoptotic induction were determined by using MTT and PI assays, respectively. The level of reactive oxygen species and lipid peroxidation was measured by fluorimetric methods. Doxorubicin significantly decreased cell viability which was accompanied by an increase in ROS production and lipid peroxidation. Pretreatment with R. turkestanicum increased the viability of cardiomyocytes and could decrease lipid peroxidation and reactive oxygen species generation. Also, R. turkestanicum attenuated apoptotic induction. N-acetylcysteine at 100 µM reduced the levels of reactive oxygen species and lipid peroxidation. But, treating H9c2 cells with N-acetylcysteine did little to protect H9c2 cells from doxorubicin-induced cell death. R. turkestanicum exerts protective effect against oxidative stress-induced cardiomyocytes damage. Our findings showed that R. turkestanicum could exert the cardioprotective effects against doxorubicin-induced toxicity partly by anti-apoptotic activity. Also, N-acetylcysteine prevented oxidative stress via reduction of reactive oxygen species and lipid peroxidation. N-acetylcysteine induced less protective effects than R. turkestanicum extract against doxorubicin-induced cytotoxicity.

Resumo em Inglês:

Abstract Genus Aloe, Xanthorrhoeaceae, is well distributed all over Egypt, and many species have been used as medicinal plants; mainly reported to prevent cardiovascular diseases, cancer and diabetes. This study attempts to analyze the secondary metabolites in the methanol extract of the leaves of eight Aloe species; A. vera (L.) Burm. f., A. arborescens Mill., A. eru A. Berger, A. grandidentata Salm-Dyck, A. perfoliata L., A. brevifolia Mill., A. saponaria Haw. and A. ferox Mill. growing in Egypt. For this aim HPLC–DAD–MS/MS in negative ion mode was used. Although belonging to the same genus, the composition of each species presented different particularities. Seventy one compounds were identified in the investigated Aloe species, of which cis-p-coumaric acid derivaties, 3,4-O-(E) caffeoylferuloylquinic acid and caffeoyl quinic acid hexoside were the most common phenolic acids identified. Aloeresin E and isoaloeresin D, 2'-O-feruloylaloesin were the common anthraquinones identified. Lucenin II, vicenin II, and orientin were the common identified flavonoids in the investigated Aloe species. 6'-Malonylnataloin, aloe-emodin-8-O-glucoside, flavone-6,8-di-C-glucosides could be considered as chemotaxonomic markers for the investigated Aloe species. The eight Aloe species had significant anti-inflammatory activity, in addition to the significant acceleration of diabetic wound healing in rats following topical application of the methanol extracts of their leaves. This is the first simultaneous characterization and qualitative determination of multiple phenolic compounds in Aloe species from locally grown cultivars in Egypt using HPLC–DAD–MS/MS, which can be applied to standardize the quality of different Aloe species and the future design of nutraceuticals and cosmetic preparations.

Resumo em Inglês:

Abstract Hedyosmum brasiliense Miq., Chloranthaceae, has been used in Southern Brazil as a sedative, anti-inflammatory, and aphrodisiac. In this study, endothelium-intact and endothelium-denuded rat aortic rings and strips of corpus cavernosum were used to investigate the relaxant effects of an hexane fraction of leaves of H. brasiliense and its sesquiterpene lactones 13-hydroxy-8,9-dehydroshizukanolide, podoandin, and elemanolide 15-acetoxy-isogermafurenolide. The incubation of hexane fraction of leaves of H. brasiliense resulted in significant relaxation of endothelium-intact aortic rings previously contracted by phenylephrine. In addition, 13-hydroxy-8,9-dehydroshizukanolide and podoandin displayed a clear concentration-dependent ability to relax endothelium-intact (∼85 to 90%) and endothelium-denuded (∼45 to 55%) rat aortic rings. A less pronounced vascular relaxation was recorded when 15-hydroxy-isogermafurenolide was tested. Interestingly, in tissues previously incubated with the nitric oxide synthase inhibitor L-NAME (100 µM), both 13-hydroxy-8,9-dehydroshizukanolide and podoandin had their effects in endothelium-intact vessels reduced to the same degree of relaxation observed in endothelium-denuded aortic rings. Podoandin, 13-hydroxy-8,9-dehydroshizukanolide, and 15-acetoxy-isogermafurenolide (100 µM) were also able to relax precontracted corpus cavernosum strips by 49.5 ± 3.9%, 65.9 ± 7.3% and 57.9 ± 5.5%, respectively. Our results demonstrated that 13-hydroxy-8,9-dehydroshizukanolide, podoandin and 15-acetoxy-isogermafurenolide, isolated from H. brasiliense, generate both endothelium-dependent and -independent relaxation of rat aortic rings, as well as being able to induce in vitro relaxation of rat corpus cavernosum. Importantly, the endothelium-dependent effect is fully dependent on nitric oxide production. Considering that penile erection depends on both relaxation of cavernosal smooth muscle and inflow of blood for the cavernous bodies, this is the first study reporting experimental evidence supporting the aphrodisiac properties of H. brasiliense.

Resumo em Inglês:

Abstract To study the hepatoprotective effect of the essential oil of Artemisia capillaris Thunb., Asteraceae, on CCl4-induced liver injury in mice, the levels of serum aspartate aminotransferase and alanine aminotransferase, hepatic levels of reduced glutathione, activity of glutathione peroxidase, and the activities of superoxide dismutase and malondialdehyde were assayed. Administration of the essential oil of A. capillaris at 100 and 50 mg/kg to mice prior to CCl4 injection was shown to confer stronger in vivo protective effects and could observably antagonize the CCl4-induced increase in the serum alanine aminotransferase and aspartate aminotransferase activities and malondialdehyde levels as well as prevent CCl4-induced decrease in the antioxidant superoxide dismutase activity, glutathione level and glutathione peroxidase activity (p < 0.01). The oil mainly contained β-citronellol, 1,8-cineole, camphor, linalool, α-pinene, β-pinene, thymol and myrcene. This finding demonstrates that the essential oil of A. capillaris can protect hepatic function against CCl4-induced liver injury in mice.

Resumo em Inglês:

Abstract Solanum paniculatum L., Solanaceae, locally known as "jurubeba", is widely used in Brazil for culinary purposes, and in folk medicine to treat of diverse disorder including gastric dysfunctions. In this study we investigated the antidiarrheal activity of S. paniculatum roots extract in rats at different concentrations (125, 250 and 500 mg/kg, p.o) using different experimental models such as castor oil-induced diarrhea, enteropooling and gastrointestinal motility, determined by in vivo experimental models. The major compound of root extract was characterized as chlorogenic acid based in the IR, 1D and 2D NMR analysis. All the extract doses achieved antidiarrheal potency, as indicated by reduced weight of feces in castor oil-induced diarrhea, decreased intestinal motility and significantly inhibited castor oil-induced enteropooling compared to the vehicle group. The highest dose (500 mg/kg) produced greater anti-motility effect and better reduction of enteropooling, similar to the reference drug Loperamide (5 mg/kg). Extract from S. paniculatum L. roots had antidiarrheal activity, as shown by the lower weight of the feces as well as decrease in the accumulation of intestinal fluid and slower transit, justifying the traditional use of plant for diarrhea.

Resumo em Inglês:

Abstract Although the use of exudates in traditional medicine has been commonly observed during ethnopharmacological surveys, few records have been made concerning the scientific merits of these products. The aim of this study was to document ethnopharmacological data and to classify exudates used as medicine by the "caboclos" river-dwellers from the Unini River of Amazonas, Brazil, on chemical analyses basis. Using an ethnographic approach, indicated plants and their respective exudates were collected, identified and incorporated into herbarium of the National Institute of Amazonian Research. To classify these exudates, plant material was extracted using methanol, and obtained extracts were analyzed by Nuclear Magnetic Resonance and mass spectrometry aiming identification of main compounds. Fifteen exudates were indicated by "caboclos" river-dwellers as home remedies; among their therapeutic uses, inflammatory processes, culture-bound syndromes and respiratory diseases are most prominent. Based on their solubility and chemicals classes, fifteen exudates were classified into: latex (7), resins (5), sap (1), gum (1), oleoresin (1); and eleven of them have not been mentioned on pharmacological literature until this moment. The obtained results may contribute to chemical/pharmacological application of exudates from these species, several of which have been classically used in Brazilian folk medicine.

Resumo em Inglês:

Abstract Zingiber zerumbet (L.) Roscoe ex Sm., Zingiberaceae, is a perennial, aromatic and tuberose plant that grows in humid locations. Also known as bitter ginger, Z. zerumbet is traditionally found throughout Asia, where it is widely used in foods, beverages and for ornamental purposes. The viscous juice present in the inflorescence of the plant is rich in surfactants and is also known as "ginger shampoo". The rhizome can be macerated in ethanol and used as a tonic and a stimulant. In Brazil Z. zerumbet is found in the Amazon region, in Taruma-mirim and Puraquequara (rural areas of Manaus, Amazon, Brazil). The main chemical compounds found in Z. zerumbet are terpenes and polyphenols. Zerumbone, a sesquiterpene, is the principal bioactive compound of Z. zerumbet and it is widely studied for its medicinal properties. The extracts and isolated metabolites of Z. zerumbet have exhibited the following properties: anti-inflammatory, antioxidant, antidiabetic, anticancer, antimicrobial, analgesic and antiviral. The National Institute of Amazon Research in Brazil is currently conducting studies using extracts from this plant to obtain compounds active in tumor models. The aim of this review is to provide a overview about the main aspects related with pharmacognosy and pharmacology of Z. zerumbet published in the literature over the last decade.

Resumo em Inglês:

Abstract Eryngium creticum Lam. (E. cyaneum Sibth. & Sm., E. syriacum Lam.), Saniculoideae, Apiaceae is of great importance in the traditional Greco – Arab medicine. This study was carried out in order to contribute to the ethnopharmacological knowledge of this medicinal species. This review describes the botanical characterization and distribution, as well as critically assesses the phytochemical properties and biological activities of E. creticum, a species that has been used in traditional medicine for many decades. Possible trends and perspectives for future research of this plant are discussed, as well. E. creticum has been found to contain several chemical constituents, mostly sesquiterpenes, monoterpenes, aldehydes, coumarins, sitosterols and sugars. Eryngo with its bioactive compounds possesses a wild range of biological activities. It was reported that in traditional medicine E. creticum was applied mainly as the remedy for snake and scorpion bites. Some published studies have shown a broad spectrum of biological and pharmacological activities, including anti-snake and anti-scorpion venom, as well as antibacterial, antifungal and antileishmanial effects. Other have indicated antihyperglycemic, hypoglycemic and antioxidant activities of this species. The in vitro studies and in vivo models have provided a simple bioscientific explanation for its various ethnopharmacological uses.