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Chemical composition and antimicrobial activity of Croton urucurana Baillon (Euphorbiaceae)

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Abstract

In the methanolic extract of Croton urucurana Baillon (Euphorbiaceae) a number of known compounds, such as acetyl aleuritolic acid, stigmasterol, beta-sitosterol, campesterol, beta-sitosterol-O-glucoside, sonderianin, catechin and gallocatechin were isolated and identified by MS and NMR spectroscopy, HRGC and data from literature. The antibacterial activity of the aqueous-EtOH extract, some fractions of the methanolic extract and some of the isolated compounds, were tested against Staphylococcus aureus and Salmonella typhimurium. Acetyl aleuritolic acid exhibits the best minimum inhibitory concentration (MIC) against both Staphylococcus aureus and Salmonella typhimurium.

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... Extratos de Croton urucurana foram descritivos por apresentarem atividades antibacterianas contra Staphylococcus aureus e Salmonella typhimurium (PERES et al., 1997), antifúgica contra fungos causadores de micoses de peles (GURGEL 2005), antimicrobiana e antioxidante (SIMIONATTO, 2007);anti-hemorrágica (ESMERALDINO, 2005) e analgésica (PERES et al., 1998b). OLIVEIRA et al 2008 relatam ações antibacteriana em uma triagem in vitro do látex e extratos de Croton urucurana. ...
... OLIVEIRA et al 2008 relatam ações antibacteriana em uma triagem in vitro do látex e extratos de Croton urucurana. As ações farmacológicas de C. urucucana, devem-se a presença de compostos bioativos presentes em seus extratos e em suas frações, como por exemplo, o ácido acetilaleuritólico, esteróis (sitosterol, estigmasterol e campesterol), diterpenos (sonderianina), campesterol, β-sitosterol, stigmasterol, ácido acetil aleurítico, catequina, gallocatequina e glicosídeo de sitosterol (PERES et al., 1997), alcaloides, flavonoides e terpenoides (RANDAU et al., 2004). ...
... As cascas de C. urucurana, descrevem a presença de ácido acetilaleuritólico; dos flavonóides catequina e galocatequina; dos diterpenos clerodanos sonderianino, 12-epi-metilbarsbacoato e 15,16-epoxy-3,13(16)-clerodatrieno-2-ona; e dos esteróis: campesterol, stigmasterol, sitosterol e seu glicosídeo (PERES et al., 1997;PERES et al., 1998a;PERES et al., 1998b). A atividade antitumoral de vários flavonóides está atribuída a sua eficiência em inibir as enzimas topoisomerases I e II (SUKAR-DIMAN et al., 2000), diminuir a proliferação celular como consequência de sua ligação ao receptor de estrógeno (PRIMIANO et al., 2001), apresentar atividade inibidora de proteínas quinases (GAMETPAYRASTRE et al., 1999), e/ou induzir apoptose e liberação do citocromo c (LU et al., 2010). ...
Article
Leukemias are malignant neoplasms that affect blood cells and originate in bone marrow. These are cancers of high incidence and are difficult to treat and there is a constant search for more efficient therapies. The present work investigated the cytotoxic action of the hydroalcoholic extract of Croton urucurana in human leukemia cells U937 and THP-1. The U937 and THP-1 cell lines were plated in a 100 μL/well volume (1x106 cells/mL) in 96-well plates, treated with extracts at final concentrations of 50 μg/mL, 100 μg/mL, 200 μg/mL and 400 μg/mL and 800 μg/mL for cell viability tests with MTT(-3- (4.5-dimethyl-2-thiazole) 2.5-diphenyl-2H-tetrazolium bromide). After 48h, viability was assessed by MTT and the supernatant was used for determination of the Lactate Dehydrogenase (LD) enzyme. Fluorescence microscopy was used to evaluate apoptosis. The extract was able to reduce cell viability by the MTT assay, increase LD release and induce apoptosis in both cell lines tested at concentrations of 400 and 800 μg/ mL (p≤0.05). The C. urucurana extract presented cytotoxic activity against human leukemic cell lines U937 and THP-1, presenting itself as promising in the search for new antineoplastic agents.
... By gas chromatography, Peres et al. (1997) evaluated the methanol extract from the leaves of C. urucurana, and observed the presence of acetyl aleuritolic acid, β-sitosterol and sonderianin diterpene, and identified the presence of the steroids stigmasterol, β-sitosterol and campesterol. In phytochemical studies on the species C. macrostachyus performed with the ethanolic extract of roots showed the presence of fatty acids, β-sitosterol, stigmasterol, lupeol, betulin and cyclohexene diepoxide. ...
... Peres et al. (1997) evaluated the hydroethanolic extract and four fractions of the methanol extract of the stem bark of Croton urucurana Baillon, against Staphylococcus aureus and Salmonella typhimurium strains, the results suggested that the hydroethanolic extract and the hexane and hexane-dichloromethane fractions exhibited better activity against S. aureus when compared to Salmonella typhimurium, being the hexane-dichloromethane fraction with greater inhibitory effect against S. aureus (0.8 mg/mL). ...
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The genus Croton, belonging to the Euphorbiaceae family, is a plant with shrubby characteristics, with the ability to regrow in times of rain, develops wildly, especially in deforestation areas, being reported mainly in the Caatinga and Forest region. One of the main characteristics of this genus is that several species are rich in chemical constituents of importance for medicine. In this way, this review of the literature, has an objective that findings regarding the biological activities and chemical composition of Croton species. This study is a literature review, carried out in the following databases: SciELO, BVS, MEDLINE, LILACS, PubMed and ScienceDirect, with a time frame between 1997 and 2020. The articles studied have shown different activities for Croton species, such as anti-inflammatory, antihypertensive, antifungal, antimicrobial, antidiabetic, antioxidant, antinociceptive and anti-tumor. Regarding toxicological aspects, the findings suggest caution in the use of Croton species, as some are toxic. While, regarding the chemical composition, in most species the presence of several secondary metabolites is observed, such as alkaloids, terpenoids, flavonoids and other phenolic compounds. Therefore, the results described in this article suggest that the therapeutic application of Croton species is supported by the literature, however we point out that caution is required in the use of Croton species, some present due to toxicity.
... e leaves and bark of C. urucurana are popularly used to treat various conditions, including rheumatism, wounds, gastric ulcers, liver disorders, diarrhea, cancer, and cardiovascular diseases [6,7]. e main active constituents of C. urucurana are tannins, lignans, and alkaloids [8]. Preclinical studies have shown that C. urucurana has antifungal [9], antibacterial [8], anti-inflammatory [10], antinociceptive [6,11], antitumoral [12,13], wound healing [12,14], antiulcerogenic [15,16], antidiarrheal [17,18], and antihemorrhagic [19] effects. ...
... e main active constituents of C. urucurana are tannins, lignans, and alkaloids [8]. Preclinical studies have shown that C. urucurana has antifungal [9], antibacterial [8], anti-inflammatory [10], antinociceptive [6,11], antitumoral [12,13], wound healing [12,14], antiulcerogenic [15,16], antidiarrheal [17,18], and antihemorrhagic [19] effects. Toxicological studies reported that C. urucurana is potentially nontoxic, with an oral lethal dose 50 (LD50) above 5 g/kg in mice [9]. ...
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Croton urucurana Baill. is a native Brazilian tree, popularly known as “sangra-d’água” or “sangue-de-dragão,” based on the red resinous sap of the trunk. Its use has been transmitted through generations based on popular tradition that attributes analgesic, anti-inflammatory, and cardioprotective properties to the tree. However, its cardioprotective effects have not yet been scientifically investigated. Thus, the present study investigated the pharmacological response to an ethanol-soluble fraction from the leaves of C. urucurana in Wistar rats exposed to smoking and dyslipidemia, two important cardiovascular risk factors. The extract was evaluated by high-performance liquid chromatography. Wistar rats received a 0.5% cholesterol-enriched diet and were exposed to cigarette smoke (9 cigarettes/day for 10 weeks). During the last 5 weeks, the animals were orally treated with vehicle (negative control group), C. urucurana extract (30, 100, and 300 mg/kg), or simvastatin (2.5 mg/kg) + enalapril (15 mg/kg). One group of rats that was not exposed to these risk factors was also evaluated (basal group). Electrocardiograms and systolic, diastolic, and mean blood pressure were measured. Blood was collected to measure total cholesterol, triglycerides, urea, and creatinine. The heart and kidneys were collected and processed for oxidative status and histopathological evaluation. The phytochemical analysis revealed different classes of flavonoids and condensed tannins. The model induced dyslipidemia and cardiac and renal oxidative stress and increased levels of urea and creatinine in the negative control group. Treatment with the C. urucurana extract (300 mg/kg) and simvastatin + enalapril decreased cholesterol and triglyceride levels. In contrast to simvastatin + enalapril treatment, the C. urucurana extract exerted cardiac and renal antioxidant effects. No alterations of electrocardiograms, blood pressure, or histopathology were observed between groups. These findings indicate that C. urucurana exerts lipid-lowering, renal, and cardioprotective effects against oxidative stress in a preclinical model of multiple risk factors for heart disease. 1. Introduction Because of the high risk of morbidity and mortality associated with cardiovascular disease, finding ways to mitigate such risk has become paramount in public healthcare. The presence of classic risk factors, such as hypertension, dyslipidemia, obesity, sedentary lifestyle, smoking, diabetes, and family history, increases the risk of developing cardiovascular disease. Dyslipidemia is an important cardiovascular risk factor. Low-density lipoprotein cholesterol (LDL-c) is the most relevant modifiable risk factor for coronary artery disease [1]. Ample evidence indicates that low LDL-c levels are associated with a proportional reduction of cardiovascular outcomes, including myocardial infarction, stroke, and cardiovascular-related death [2]. Another cardiovascular risk factor is smoking, a disease that is caused by nicotine addiction. An estimated 1.25 billion smokers worldwide are at risk of early death from smoking [3]. The health consequences of smoking are disastrous, given long-term exposure of the body to harmful components in cigarettes. The long-term continued use of tobacco and its derivatives leads to the appearance of cardiovascular, oncological, and respiratory diseases, making it one of the main causes of preventable death worldwide [4]. Despite the high morbidity and mortality of cardiovascular disease, animal models that combine its main risk factors are scarce. Despite the existence of effective and low-cost pharmacological therapies, some new drugs that are recommended by recent guidelines are expensive or unavailable in public healthcare systems [5]. Thus, the search for new therapeutic agents that are less expensive and safe and act effectively for the management of cardiovascular risk factors is essential. Plants remain an important source of potential medicines and the development of new therapies. One important native tree in Brazil is Croton urucurana Baill. (Euphorbiaceae), popularly known as “sangra-d’água” or “sangue-de-dragão.” This species is widely used by the Brazilian native population as a natural source of medicines. The leaves and bark of C. urucurana are popularly used to treat various conditions, including rheumatism, wounds, gastric ulcers, liver disorders, diarrhea, cancer, and cardiovascular diseases [6, 7]. The main active constituents of C. urucurana are tannins, lignans, and alkaloids [8]. Preclinical studies have shown that C. urucurana has antifungal [9], antibacterial [8], anti-inflammatory [10], antinociceptive [6, 11], antitumoral [12, 13], wound healing [12, 14], antiulcerogenic [15, 16], antidiarrheal [17, 18], and antihemorrhagic [19] effects. Toxicological studies reported that C. urucurana is potentially nontoxic, with an oral lethal dose 50 (LD50) above 5 g/kg in mice [9]. However, despite the popular use of C. urucurana for the treatment of cardiovascular diseases [7], the cardioprotective actions of this species have not yet been pharmacologically investigated. Thus, the present study investigated the lipid-lowering and antioxidant effects of an ethanol-soluble fraction obtained from leaves of C. urucurana in Wistar rats in a model of a combination of risk factors (exposure to tobacco smoke and dyslipidemia) for heart disease. 2. Material and Methods 2.1. Drugs Bovine serum albumin, 5,5′-dithiobis(2-nitrobenzoic acid), reduced glutathione (GSH), xylenol orange, K2HPO4, KH2PO4, 1 M Tris, 5 mM ethylenediaminetetraacetic acid, Tris HCl (all from Sigma, St. Louis, MO, USA), pyrogallol, absolute ethanol, absolute methanol, ferrous ammonium sulfate, trichloroacetic acid, formaldehyde (all from Vetec, Rio de Janeiro, Brazil), and ultra-pure water from a Milli-Q system were used for eluent preparation. 2.2. Extract Preparation and Phytochemical Profile Leaves of Croton urucurana Baill. were collected in May 2020 at Dourados, Mato Grosso do Sul (″22°20.9299′ south, 54°83.7713 west), and a voucher specimen (no. 5536) was deposited in the Herbarium of the Federal University of Grande Dourados. The plant was dried in an oven at 50°C for 5 days and pulverized. The extract was prepared by infusion using the methodology of Barbosa et al. [20], in which the pulverized material (100 g) was subjected to the extraction process by infusion with 1 L of boiling water. The resulting infusion was kept in an amber flask for 5 h, filtered, and then treated with 95% ethanol (1 : 3, v/v) to precipitate proteins and polysaccharides, giving rise to the heterogeneous phase that was removed by filtration. The ethanol-soluble fraction was concentrated on a rotary evaporator and lyophilized. The final yield of the dried extract of C. urucurana was 11.31%. Phytochemical characterization was performed using high-performance liquid chromatography (HPLC) with a diode-array detector (DAD; Shimadzu, Prominence LC-20A). Chromatography was conducted in the reverse-phase on a C18-PCP column (Ascentis Express; 150 × 4.6 mm, 2.7 μm particle size) using mobile phases that were composed of (A) 0.1% formic acid in water and (B) 0.05% formic acid in acetonitrile. The separation was obtained by a gradient of B that increased from 5% to 30% in 15 min then to 80% in 20 min, with a return to 5% in 21 min and then 5 min at the initial condition for solvent reequilibration. The flow rate was 0.5 ml/min. The column temperature was held at 40°C. Compound detection was accompanied by ultraviolet (UV) light at 190–400 nm. 2.3. Animals Wistar rats, weighing 150–200 g, were obtained from the central vivarium of the Federal University of Grande Dourados. The animals were housed in the vivarium of the Laboratory for Pre-Clinical Research of Natural Products, Paranaense University, with free access to food and water. The animals were housed under controlled environmental conditions (20° ± 2°C temperature, 50% ± 10% relative humidity, and 12 h/12 h light/dark cycle) with environmental enrichment. The total number of animals in the experiment was 48 (n = 8/group). The animals were weighed weekly on an analytical balance. The experimental protocol was approved by the Ethics Committee on the Use of Animals of Paranaense University (protocol no. 1000/2020). All national and international guidelines on animal welfare were followed. The reporting of animal investigations conformed to Animal Research Reporting of In Vivo Experiments (ARRIVE) guidelines [21]. 2.4. Experimental Design The choice of the animal species, sample size, and extract doses was based on Mendes et al. [22]. For 10 weeks, the animals received standard commercial food that was enriched with 0.5% cholesterol ad libitum. They were exposed to smoke from nine commercial cigarettes (0.8 mg nicotine, 10 mg tar, and 10 mg carbon monoxide) for 1 h daily, 5 days weekly, for 10 weeks, as proposed by Mendes et al. [22]. During the last 5 weeks of the experiment, the animals were treated orally by gavage with vehicle (0.1 ml of filtered water/100 g body weight; negative control [C−] group), the ethanol-soluble fraction of Croton urucurana (30, 100, and 300 mg/kg), or enalapril (15 mg/kg) + simvastatin (2.5 mg/kg) once daily. Nondyslipidemic and nonsmoke-exposed Wistar rats were treated with vehicle (filtered water) and served as the basal group (n = 8). The final groups were the following: (1) basal (rats not exposed to any risk factor and treated with vehicle), (2) negative control (C−; dyslipidemic rats exposed to cigarette smoke and treated for 5 weeks with vehicle), (3) C. urucurana 30 (dyslipidemic rats exposed to cigarette smoke and treated with 30 mg/kg C. urucurana extract for 5 weeks), (4) C. urucurana 100 (dyslipidemic rats exposed to cigarette smoke and treated with 100 mg/kg C. urucurana extract for 5 weeks), (5) C. urucurana 300 (dyslipidemic rats exposed to cigarette smoke and treated with 300 mg/kg C. urucurana extract for 5 weeks), and (6) simvastatin + enalapril (dyslipidemic rats exposed to cigarette smoke and treated with 2.5 mg/kg simvastatin plus 15 mg/kg enalapril for 5 weeks). 2.5. Electrocardiography and Heart Rate and Blood Pressure Measurements On the last day of the experiment, the rats were intramuscularly anesthetized with ketamine (100 mg/kg) + xylazine (20 mg/kg). A bolus injection of heparin (15 IU) was administered subcutaneously. Electrocardiography (ECG) was recorded using a 12-lead ECG recorder (WinCardio, Micromed, Brasília, Brazil) according to Romão et al. [23]. Electrocardiographic waves were recorded for 5 min. After ECG, the left carotid artery was isolated, cannulated, and connected to a pressure transducer that was coupled to a PowerLab recording system. Chart 4.1 software (ADI Instruments, Castle Hill, Australia) was used to record heart rate, systolic blood pressure (SBP), diastolic blood pressure (DBP), and mean arterial pressure (MAP). After 15 min of stabilization, changes in heart rate and blood pressure were recorded for 5 min. 2.6. Blood Collection and Biochemical Analysis Blood samples were collected from the left carotid artery using heparinized syringes. Plasma was separated by centrifugation at 1,500 × g for 10 min and stored at −80°C for biochemical analyses. Total cholesterol, triglyceride, creatinine, and urea levels were measured using commercial kits and an automated analyzer (Quick Lab). 2.7. Euthanasia and Organ Collection The rats were euthanized by puncture of the diaphragm while under anesthesia. The heart and left kidney were removed, carefully dissected, and weighed on an analytical balance. The weights of the heart and kidney were multiplied by 100 and divided by the animal’s body weight before euthanasia to obtain the relative organ weight (%). A sample of the heart and kidney was rapidly separated and frozen in liquid nitrogen to evaluate oxidative stress. Other organ samples were stored in a 10% formalin solution for further histological analysis. 2.8. Tissue Redox Status To investigate the tissue antioxidant system, the heart and kidney samples were homogenized in a 1 : 10 dilution of potassium phosphate buffer (0.1 M, pH 6.5). Afterward, 100 μl was separated, suspended in 80 μl of trichloroacetic acid (12.5%), vortexed, and centrifuged at 6000 × g for 15 min at 4°C. Reduced glutathione levels were measured according to Sedlak and Lindsay [24]. The remaining homogenate was centrifuged at 9000 × g for 20 min at 4°C for the determination of superoxide dismutase (SOD) activity and lipoperoxidation (LPO) levels according to Gao et al. [25] and Jiang et al. [26], respectively. 2.9. Histopathological Analysis Samples of the heart and kidney were fixed in buffered 10% formalin solution (distilled water, 35–40% formaldehyde, and monobasic and dibasic sodium phosphate), dehydrated with alcohol and xylene, embedded in paraffin, sectioned at 6 μm, and stained with hematoxylin/eosin. The slides were analyzed by optical microscopy (Leica DM 2500) to evaluate cellular alterations. 2.10. Statistical Analysis The data were analyzed for homogeneity of variance and a normal distribution. Differences between means were determined by one-way analysis of variance (ANOVA) followed by the Newman–Keuls post hoc test. The level of significance was set at 95% . The data are expressed as the mean ± standard error of the mean (SEM). 3. Results 3.1. Phytochemical Profile The phytochemicals in the ethanol-soluble fraction from the leaf extract of Croton urucurana are described in Table 1. C. urucurana was previously investigated for the chemical composition of its leaves and stem bark. Different compounds were reported in this plant, including flavan-3-ols, proanthocyanidins (condensed tannins), flavonols, O-glycosides, hydroxyflavones, C-glycosides [14, 27], alkaloids, terpenes, and phenolic acids [10], which were obtained with different extraction solvents. In the present study, comparisons with authentic standards identified some main compounds in the extract of the leaves of C. urucurana, despite the lack of information to confirm the identification of some low-abundance peaks (e.g., 1, 2, 3, and 4). Other compounds were tentatively identified based on UV spectra, supported by previous reports, but some compounds were not observed in the current extract. Alves et al. [27] performed a more comprehensive phytochemical analysis of the leaves of C. urucurana. They identified different classes of flavonoids, such as condensed tannins (e.g., proanthocyanidins). In the current extract, we identified peaks 5, 6, and 7 with UV spectra which were consistent with these compounds, with λmax at 277–279 nm. Condensed tannins have been reported in all investigated parts of C. urucurana [10, 14, 27]. Peak Rt UV λmax Tentative identification Reference 1 2.58 264 n.i. — 2 2.81 200, 280 n.i. — 3 3.31 261 n.i. — 4 3.45 254, 278 (Sh) n.i. — 5 8.06 277 Condensed tannin [27] 6 9.07 279 Condensed tannin [27] 7 9.66 278 Condensed tannin [27] 8 10.26 279 Condensed tannin [27] 9 11.39 221, 268, 301 n.i. — 10 14.36 255, 353 Flavonol-O-glycoside [27] 11 14.51 255, 353 Rutin Std. [27] 12 14.75 269, 337 Apigenin-C-glycoside [27] 13 14.83 269, 337 Apigenin-C-glycoside [27] 14 15.13 255, 353 Isoquercitrin Std. [27] 15 15.33 265, 346 Flavone C-glycoside [27] 16 15.81 265, 346 Flavone C-glycoside [27] 17 16.46 245, 333 (Sh), 348 n.i. — 18 20.35 229, 266, 316 n.i. — 19 20.53 229, 266, 316 n.i. — 20 20.87 254, 366 Quercetin Std. 21 22.06 254, 366 Kaempferol Std. n.i.: not identified; Std.: compound confirmed by a comparison with authentic standard.
... Concerning AAA biological importance, this compound proved to possess antibiotic (Addae-Mensah et al., 1992) and antibacterial (Peres et al., 1997) activities and also presented anti-inflammatory and gastrointestinal effects in mice , as briefly described below. AAA showed lack of efficacy on both antitumoral in vivo assays (Grynberg et al., 1999) and gastric mucosa damage (GMD). ...
... Other C. cajucara leaf constituents such as b-sitosterol, stigmasterol and sitosterol-3,O-b-glucoside proved to be bioactive. These compounds showed biological effects against snake venom (Mors, 1991;Bilia et al., 1996;Peres et al., 1997). The bioactivy clerodane CJCR was also isolated from this part of C. cajucara . ...
... Pertenece a la familia de las Euphorbiaceaes, es conocido comúnmente como sangre de drago, y siendo utilizado para los tratamientos empíricos de muchas enfermedades en las medicinas tradicionales o ancestrales de América Latina (2, 20). Es así que los nativos de la Amazonia utilizan las partes del árbol Crotón Lechleri, para el tratamiento de varias enfermedades como son las ulceras gástricas, diarrea, artritis, contra picaduras de insectos, infecciones microbianas, cicatrización de heridas y procesos cancerígenos (10,20). ...
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Objetivo. El objetivo de la investigación fue evaluar el efecto antibacteriano de la sangre de drago (Crotón lechleri) en cultivos in vitro de cepas bacterianas ATCC; Staphylococcus aureus ATCC 25923 y Escherichia coli ATCC 25922, a diferentes concentraciones 1%, 2%, 4%, 6%, 8%, 16%, 80%, 90% y 100%. Materiales y métodos. Se realizó un total 54 cultivos, de los cuales 27 cultivos corresponden al análisis de extracto Sangre de drago (Crotón lechleri) en distintas concentraciones frente a Staphylococcus aureus ATCC 25923 y 27 cultivos al análisis del extracto Sangre de drago (Crotón lechleri) frente a la bacteria Escherichia coli ATCC 25922, donde se aplicó 3 repeticiones para cada tratamiento. Resultados. En los resultados no se observó ningún halo de inhibición de los discos de sensibilidad preparados en diferentes concentraciones por lo que se consideran las cepas bacterianas ATCC; Staphylococcus aureus 25923 y Escherichia coli 25922, no presentan sensibilidad a la sangre de drago (Crotón lechleri). Conclusiones. De los resultados obtenidos podemos concluir que la sangre de drago (Crotón lechleri) no presenta actividad antibacteriana para las cepas de cepas bacterianas ATCC; Staphylococcus aureus 25923 y Escherichia coli 25922.
... Generally, the results were comparable to the standard streptomycin sulfate, and the most susceptible strain was M. smegmatis (McChesney et al., 1991). C. urucurana extracts in ethanol, n-hexane, and n-hexane/ dichloromethane have greater antibacterial action against S. aureus than S. typhimurium (Peres et al., 1997). ...
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Croton contains a wide range of constituents, including phorbol esters, alkaloids, di and triterpenoids such as clerodane, uphold derivatives, and flavonoids and their glycosides, all of which have medicinal value.In addition, several Croton species have a red sap, which contains proanthocyaninsand/or alkaloids in some species.Some species are aromatic because they contain volatile oil. The current review summarizesthe most important biological activities of Croton species for future research as potential medicines. It isimportant to note that the presence of secondary metabolite classes in Croton is a point worth considering because it could lead to the discovery of pharmacologically active substances.
... These alkaloids may be in the form of taspine or some of the several benzylisoquinoline-like compounds. Some of these compounds present in Croton species have been shown to have antibacterial properties (Peres et al., 1997;Abo et al., 1999). Evidence from in vitro studies point to the use of essential oils as antibacterial agents for wide range of pathogenic bacteria strains such as Listeria monocytogenes, Listeria innocua, Salmonella typhimurium, E. coli, Shigella | 235 dysenteria, Bacillus cereus, Staphylococcus aureus and Salmonella typhimurium (Burt, 2004, Nguefack et al., 2004, Schmidt et al., 2005. ...
... These alkaloids may be in the form of taspine or some of the several benzylisoquinoline-like compounds. Some of these compounds present in Croton species have been shown to have antibacterial properties (Peres et al., 1997;Abo et al., 1999). Evidence from in vitro studies point to the use of essential oils as antibacterial agents for wide range of pathogenic bacteria strains such as Listeria monocytogenes, Listeria innocua, Salmonella typhimurium, E. coli, Shigella | 235 dysenteria, Bacillus cereus, Staphylococcus aureus and Salmonella typhimurium (Burt, 2004, Nguefack et al., 2004, Schmidt et al., 2005. ...
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Medicinal plant preparations are chemically complex and may contain one or many structurally related active compounds that produce a combined effect. Phytochemical studies help in standardizing the herbal preparations so as to get the optimal concentrations of these active constituents, as well as in preserving their activities. Croton tiglium (Linn) is a commonly occurring plant in garden of NorthEastern , U.P, India belonging to family euphorbiaceae. In view of extensive medicinal importance of this plant in review is an effect to compile all the information reported on its phytochemical and pharmacological activities as there information will be helpful in scientific use of the plant and formulation development. The present work is an extensive review of the phytochemical and pharmacological reports of Croton tiglium to give comprehensive information in an attempt to provide direction of further research.
... Duas atividades principais se caracterizama desinfecção e a cicatrização -mas o alívio da dor mediante atividades analgésica e antiinflamatória também contribui. Entre os produtos usados figura o óleo de 'andiroba', mais importante como antiinflamatório, uma atividade associada à presença de princípios amargos da classe das meliacinas (PENIDO et al. 2005; (PERES et al. 1997;GURGEL et al. 2001;. A 'andiroba' já alcançou o mercado mundial mas, embora alguns derivados de valor agregado sejam fabricados no país, este beneficiamento ocorre normalmente fora da região amazônica. ...
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A Amazônia é freqüentemente citada como uma fonte de produtos naturais, cuja industrialização e venda no mercado mundial poderia trazer benefícios significantes à região. Neste trabalho alguns produtos específicos são apresentados nas classes de medicamentos, óleos e gorduras, inseticidas e repelentes de insetos. Outras classes como gomas, corantes, óleos essenciais e princípios amargos são abordados de maneira breve. Destaque é dado à importância de qualidade, quantidade, fornecimento regular e estabilidade de preço.
... Interaction of aleuritolic acid (L12). Aleuritolic acid (L12) is a pentacyclic triterpenoid isolated from the stem bark of C. megalocarpus, 44 C. dichogamus, C. psudopulchellus and C. oligandrus, 10 C. urucurana 45 and Jatropha isabellei. 46 Previous studies have proven anti-inflammatory, 47 antifilarial, 48 51 Seal et al. 52 Aleuritolic acid forms two hydrogen bonds with LYS353 with an interatomic distance of 2.77 Å and 3.62 Å. ...
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The human immunodeficiency virus (HIV) infection and the associated acquired immune deficiency syndrome (AIDS) remain global challenges even after decades of successful treatment, with eastern and southern Africa still bearing the highest burden of disease. Following a thorough computational study, we report top 10 phytochemicals isolated from Croton dichogamus as potent reverse transcriptase inhibitors. The pentacyclic triterpenoid, aleuritolic acid (L12) has displayed best docking pose with binding energy of -8.48 kcal/mol and Ki of 0.61 μM making it superior in binding efficiency when compared to all docked compounds including the FDA-approved drugs. Other phytochemicals such as crotoxide A, crothalimene A, crotodichogamoin B and crotonolide E have also displayed strong binding energies. These compounds could further be investigated as potential antiretroviral medication.
... All these mechanisms inhibit the bacteria growth (Álvarez-Martínez et al. 2020). Catechol, it's a compound from phenol/polyphenol classification, and this compound act similar Makarewicz et al. (2021) describe in previous sentence, catechol act promotes the substrate deprivation to bacteria (Peres et al. 1997). Another study made by Carvalho et al. (2016) with Guarana seeds evaluated its antimicrobial, antineoplastic, and immunomodulatory effect in different presentations, such as seed crude extract and ethyl-acetate fraction. ...
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Brazilian Amazon contains over 30,000 plant species and foods rich in bioactive compounds such as terpenes, phenolic acids, alkaloids, and flavonoids, of potential health benefits (antioxidant, antimicrobial, antiparasitic, anticancer, gastroprotection, prebiotic effects, among others). The existence of residues from non-edible parts of plants (leaves, roots, stems, branches, barks) or fruit wastes (peel, bagasse, seeds) in the agri-food industry and its supply chain is an important challenge in food loss and waste management. In this critical review several Amazon species, focusing on extracts/essential oils from nonedible parts or wastes, were analyzed in terms of phytochemicals, biological activity, and underlying mechanisms. We hope this review emphasizes the importance of Amazon’s sustainability initiatives on population health due to the potential shown against cancer, infectious diseases, and prevention of oral diseases. It is urgent to think about the conversion of amazon food wastes and co-products into high-added-value raw materials to develop novel drugs, food packaging systems, or nutraceutical foods. For free reading, please access our print link of 50 free online copies : https://www.tandfonline.com/eprint/PUP8YV6UIDXSX5XIFKMQ/full?target=10.1080/10408398.2022.2101983
... Excess lipids are a precipitating factor for the development of MAFLD, which generates hepatic disorders that are also prevented by the hepatoprotective action of Croton urucurana in its popular hepatoprotective use. The main constituents of C. urucurana are tannins, lignans, and alkaloids (Peres et al., 1997). Toxicological studies found that C. urucurana is potentially nontoxic, with an oral lethal dose 50 (LD50) > 5 g/kg in mice (Gurgel et al., 2005). ...
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Background: Metabolic associated fatty liver disease (MAFLD) affects a quarter of the worldwide population, but no drug therapies have yet been developed. Croton urucurana Baill. (Euphorbiaceae) is a medicinal species, that is, widely distributed in Brazil. It is used in popular medicine to treat gastrointestinal, cardiovascular, and endocrine system diseases. However, its hepatoprotective and lipid-lowering effects have not yet been scientifically investigated. Aim of the study: The present study investigated the effects of an extract of C. urucurana in a rat model of MAFLD that was associated with multiple risk factors, including hypertension, smoking, and dyslipidemia. Material and Methods: The phytochemical composition of C. urucurana was evaluated by liquid chromatography-mass spectrometry. Spontaneously hypertensive rats received a 0.5% cholesterol-enriched diet and were exposed to cigarette smoke (9 cigarettes/day for 10 weeks). During the last 5 weeks, the animals were orally treated with vehicle (negative control [C-] group), C. urucurana extract (30, 100, and 300 mg/kg), or simvastatin + enalapril (two standard reference drugs that are commonly used to treat dyslipidemia and hypertension, respectively). One group of rats that were not exposed to these risk factors was also evaluated (basal group). Blood was collected for the analysis of cholesterol, triglyceride, alanine aminotransferase (ALT), and aspartate aminotransferase (AST) levels. The liver and feces were collected for lipid quantification. The liver was also processed for antioxidant and histopathological analysis. Results: The main constituents of the C. urucurana extract were flavonoids, glycosides, and alkaloids. The model successfully induced MAFLD, reflected by increases in AST and ALT levels, and induced oxidative stress in the C- group. Treatment with the C. urucurana extract (300 mg/kg) and simvastatin + enalapril decreased plasma and hepatic lipid levels. In contrast to simvastatin + enalapril treatment, C. urucurana reduced AST and ALT levels. Massive lesions were observed in the liver in the C- group, which were reversed by treatment with the C. urucurana extract (300 mg/kg). Conclusion: C. urucurana extract exerted promising hepatoprotective and lipid-lowering effects in a preclinical rat model of MAFLD.
... Rich variety of phytochemical compounds is produced by the plants that equip them with antimicrobial properties. Major classes of antimicrobial compounds found in plant extracts include phenolics (simple phenols, phenolic acid, quinones, flavonoids, flavones, tannins, coumarins, stilbenes) (Brownlee et al., 1990;Toda et al., 1992;Kubo et al., 1993;Perrett et al, 1995;Fernandez et al., 1996;Peres et al., 1997;Tako et al., 2020), terpenoids (Cichewicz and Thorpe, 1996), alkaloids, lectins and polypeptides, polyacetylenes (Table 3). However, in order to utilize the natural plant extracts in extending shelf-life or vase life and maintenance of quality, antimicrobial action of these plants extracts need to be thoroughly understood. ...
Article
Post harvest handling of flower crops is a vast sector witnessing the unprecedented load of chemicals being applied on flower commodities to retain their freshness and display quality. Concerns about unregulated use of synthetic chemicals are often not raised as the commodities in question are not consumed as eatables. Several studies from leading flower markets of Europe, Africa and other countries have highlighted the ill-effects of excessive chemical use on environment and health of flower workers. Nowadays, there is a growing concern to reduce the use of harmful chemicals in food crops and to divert towards organic production, and same also applies to the ornamental plant sector. Use of harmful chemicals such as Silverthiosulphate (STS), Silver nitrate (AgNO3), Aluminium and Cobalt compounds, Hydroxy quinoline, and Thiabendazole (TBZ) during post harvest handling of flower crops should be minimised to avoid associated health consequences. Safe and effective natural alternatives need to be explored for use in vases to replace these chemicals. This review summarizes role of different chemicals in extending longevity of cut flowers and also associated risks. Various studies on cut flower handling with use of herbal extracts reveal their potential to reduce the use of chemicals.
... Purification with petroleum ether of the hexane fraction, obtained from the ethanolic extract of the stem bark of Croton argyrodaphne Baill, resulted in the isolation of triterpenoid 1. The DEPT Q spectroscopic data of 1 was in agreement with those reported for acetyl aleuritolic acid (3β-acetoxy taraxer-14-en-28-oic acid) [4,5] reported to exhibit antimicrobial activity against S.aureus and S. typhimuriu, previously isolated from Croton urucurana, Croton macrostachys, Croton megalocarpus [6][7][8]. Compound 2 was obtained as white powder. The structure of 2 is similar of penduliflaworosin previously isolated from Croton Croton penduliflorus, Croton crassifolius [22,23] . ...
... In this way, several compounds can be found, being of high or low polarity. In Croton urucurana the composition was predominantly acetyl aleuritolic acid, stigmasterol, βsitosterol, campesterol, β-sitosterol-O-glucoside, sonderianin, catechin, and gallocatechin [39]. In Croton stellulifer, the major components were α-phellandrene, p-cymene, linalool, and α-pinene [40]. ...
Article
Background Croton species are widely spread around the world, and present a varied chemical composition distributed in many classes of secondary metabolites, such as terpenoides, alkaloids, phenolic compounds and phenylpropanoids. These compounds can be obtained by different extraction methods, and more recently, with supercritical fluids. The crude and isolated extracts may have applications due to their biological activities in animals and humans. Methods The text was written based on literature data from 1996 onwards. Results The research showed in a concise way the botanical and taxonomic aspects of Croton and the success of its application is in studies related to the biological activities of the plant parts. It was also related to the chemical composition of its extracts and isolated compounds, obtained by many methods. Conclusion In summary, the review feature studies reported the use of extracts and isolated Croton compounds due to their biological effects with antioxidant, antimicrobial, anti-inflammatory, neuroprotective, antitumor, anticancer, cytotoxic, insecticidal and allelopathic activities, with potential application in food, cosmetics, pharmaceuticals, and agrochemicals products.
... Extratos vegetais e substâncias isoladas apresentam resultados significativos na inibição ou erradicação do biofilme de Staphylococcuss (Freire et al. 2009, Gomes 2010, Oliveira 2011, Cobrado et al. 2012, Saising et al. 2011. O Brasil é um país megabiodiverso e dentre a imensa riqueza da flora, o gênero Croton se destaca por apresentar espécies como C. nepetaefolius que produz oditerpeno casbano, com acentuada atividade frente S. aureus em biofilme (Carneiro et al. 2011) e C. urucurana, popularmente conhecida como Sangue de dragão, cujo extrato e compostos isolados possuem ação antibacteriana in vitro frente S. aureus livre (Peres et al. 1997, Simionatto et al. 2007, Silva Junior et al. 2009, Zuchinalli 2009 ...
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RESUMO: A mastite bovina é a enfermidade que causa maior impacto na produção leiteira, sendo o microrganismo Staphylococcus aureus o mais prevalente. Este gênero possui a capacidade de produzir biofilmes que é um importante mecanismo de resistência aos antibióticos. Considerando a capacidade terapêutica das plantas, a espécie Croton urucurana, nativa do Cerrado, foi alvo do presente estudo, que teve como objetivo avaliar a atividade antibiofilme in vitro do extrato vegetal e substâncias isoladas desta espécie, frente Staphylococcus aureus, isolados de leite de vacas com mastite, bem como dos antibióticos gentamicina e vancomicina. A atividade antibiofilme foi avaliada por meio do cristal violeta e da contagem de unidades formadoras de colônia. As imagens foram obtidas por microscopia eletrônica de varredura. O extrato bruto e frações de C. urucurana apresentaram atividade antibiofilme superior à gentamicina e semelhante à vancomicina, enquanto a substância isolada α-Costol foi significativamente mais ativa quando comparada aos demais tratamentos avaliados, reduzindo cerca de 6 ciclos logarítmicos da população bacteriana em biofilme. Conclui-se que os fitocomplexos e a substância α-Costol isolados de Croton urucurana são promissores no combate a um dos principais agentes etiológicos da mastite bovina.
... Due to a series of difficulties in the DBNs isolation from plants, a diversity of methodologies has been developed for the synthesis of DBNs and BNs (benzofuran neolignans, which differ from DBNs by a double bond between C7 and C8) (Ward 2000). Natural and synthetic DBNs have raised much interest over the years because they exhibit several biological activities, such as anti-inflammatory (Cho et al. 2000), antioxidant (Chin et al. 2008Huang et al. 2013), cytotoxic (Huang et al. 2013, antileishmanial (Miert et al. 2005), antitumor (Pieters et al. 1999;Apers et al. 2003), cytoprotective (Chin et al. 2008, antimicrobial (Peres et al. 1997;Koroishi et al. 2008), and trypanocidal (Pelizzaro-Rocha et al. 2011) actions, among other effects. Despite this broad spectrum of biological activities, few studies on the insecticidal activity of NLs have been reported to date (Bernard et al. 1995;Chauret et al. 1996). ...
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Bemisia tabaci (Gennadius) biotype B (Hemiptera: Aleyrodidae) has developed resistance to numerous conventional insecticides, which has led us to investigate the toxicity of ten dihydrobenzofuran- (DBN) and benzofuran-type (BN) neolignans structurally related to conocarpan against second instar B. tabaci nymphs. At concentrations higher than 5 mg/L, most of the tested compounds killed 100% of B. tabaci biotype B nymphs 6 days after spraying. The contact toxicity of compounds 2 ((±)-trans-dehydrodiferulate dimethyl ester), 3 ((±)-4-O-methyl-trans-dehydrodiferulate dimethyl ester), 5 ((±)-4-O-acetyl-trans-dehydrodiferulate dimethyl ester), 6 ((±)-7′,8′-dihydro-trans-dehydrodicoumarate dimethyl ester), 8 ((±)-4-O-methyl-7′,8′-dihydro-trans-dehydrodiferulate dimethyl ester), and 10 ((±)-7′,8′-dihydro-7,8-dehydro-trans-dehydrodicoumarate dimethyl ester) was higher than the contact toxicity of pyriproxyfen at a concentration of 75 mg/L, which was used as positive control. Repellent (compounds 2 and 7 ((±)-7′,8′-dihydro-trans-dehydrodiferulate dimethyl ester) and oviposition deterrent (compounds 2, 3, and 7) effects were observed for adult whiteflies exposed to leaves sprayed with DBNs for 24 and 48 h, respectively. These results suggest that DBNs have potential application in the development of effective pest management compounds.
... The ability of flavonoids to scavenge hydroxyl radicals, superoxide anions and lipid peroxy radicals could be their most important function (Iniaghe et al., 2009) and such property could be harnessed in the food/beverage industry for production of foods/beverages especially now that functional foods are being emphasized and popularized. Flavonoids have been reported to exert multiple biological properties which include antimicrobial activity (Peres et al., 1997), however, the best-described property of flavonoids is their capacity to act as powerful antioxidants which can protect the human body from free radicals which are clearly associated with etiology of cancers and other chronic diseases, and reactive O 2 species, thereby inhibiting oxidative cell damage, provide strong anticancer activity and protect cells against carcinogenesis (Adaramoye et al., 2011, Kuete et al., 2015. Flavonoids in the intestinal tract reduce the risk of heart disease (Okwu, 2005). ...
... Using sterilized micropipettes 25ml of different solvents with selected leaf extract was added into the well. The 17,18,19 and antifungal activity. Several studies have been conducted in the past three decades that demonstrate antimicrobial properties in herbs, and their derivatives such as essential oils and leaf extracts.From this study it can be said that, methanol, ethanol and acetone shade dried extract of Acalypha indica leaf extract showed wide range of Antibacterial and Antifungal activity and can be used and administered in medical practice. ...
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Anti-microbial and anti-fungal activity of different solvent extracts of Acalypha indica (Euphorbeace family) was tested against bacterial pathogens (Pseudomonasaeruginosa, E.Coli, KlebsiellaPneumonia and Staphylococcus aureus) and fungal strains (Candida albicans, Aspergillus niger, Candida tropicalis andCandida kefyr) using the Agar Well diffusion method . It was observed that all the extracts showed positive activity) against bacteria and fungi. Ethanolic extract of Acalypha indica showed more potency against Staphylococcus aureus with an inhibition zone of12.46 (mm) and Methanolic extract exhibited higher activity against E.coli with an inhibition zone of11.26 (mm). Ethanolic extract of Acalypha indica showed prominent antifungal activity against candida albicans with an inhibition diameter of 12.53 (mm) and Aspergillus niger with a diameter of 9.21 (mm) when compared to other solvent extracts. Erythromycin and Ketoconazole were used as positive standards for antimicrobial and anti fungal experiments. In the present study, Ethanol extract showed a varying degree of inhibition to the growth of tested organisms compared to Methanol, Acetone and Chloroform against Bacteria and Fungi. The results confirmed the presence of antibacterial and antifungal compounds in shade dried extracts of Acalypha indica against human pathogenic organisms.
... Other findings have revealed that organic solvents are actually involved in extracting anti-bacterial phytochemical groups from most anti-bacterial plants including Acalypha indica (Maji et al., 2010). In addition, most of the plants in Euphorbiaceae family usually possess anti-bacterial activities for bacteria and fungi (Awoyinka et al., 2007;Falodun et al., 2008;Peres et al., 1997). As a general conclusion, Acalypha indica plant is effective for use as an antibacterial agent. ...
Article
Ethnopharmacological relevance: Acalypha indica is an herbal plant that grows in wet, temperate and tropical region, primarily along the earth's equator line. This plant is considered by most people as a weed and can easily be found in these regions. Although this plant is a weed, Acalypha indica has been acknowledged by local people as a useful source of medicine for several therapeutic treatments. They consume parts of the plant for many therapeutics purposes such as anthelmintic, anti-ulcer, bronchitis, asthma, wound healing, anti-bacterial and other applications. As this review was being conducted, most of the reports related to ethnomedicinal practices were from Asian and African regions. The aim of the review: The aim of this review is to summarize the current studies on ethnomedicinal practices, phytochemistry, pharmacological studies and a potential study of Acalypha indica in different locations around the world. This review updates related information regarding the potential therapeutic treatments and also discusses the toxicity issue of Acalypha indica. Materials and methods: This review was performed through a systematic search related to Acalypha indica including the ethnomedicinal practices, phytochemistry and pharmacological studies around the world. The data was collected from online journals, magazines, and books, all of which were published in English, Malay and Indonesian. Search engine websites such as Google, Google Scholar, PubMed, Science Direct, Researchgate and other online collections were utilized in this review to obtain information. Results: The links between ethnomedicinal practices and scientific studies have been discussed with a fair justification. Several pharmacological properties exhibited certain potentials based on the obtained results that came from different related studies. Based on literature studies, Acalypha indica has the capability to serve as anthelmintic, anti-inflammation, anti-bacterial, anti-cancer, anti-diabetes, anti-hyperlipidemic, anti-obesity, anti-venom, hepatoprotective, hypoxia, and wound healing medicine. For the traditional practices, the authors also mentioned several benefits of consuming the raw plant and decoction. Conclusion: This review summarizes the current studies of Acalypha indica collected from many regions. This review hopefully will provide a useful and basic knowledge platform for anyone interested in gaining information regarding Acalypha indica.
... More than 70% repellency was recorded and the effect of the repellency was able to sustain up to 6 hours. Peres et al. (1997Peres et al. ( , 1998 stated that catechin and gallocatechin found in the methanolic extracts of Croton urucurana Baillon has insecticidal potential. Catechin and gallocatechin are phenolic compounds that give fruits its astringent properties and play an important role in plant defense (Winkel-Shirley, 2001). ...
... However, terpenoids and phenolics are thought to exert inhibitory action against microorganisms by membrane disruption (Cichewick and Thorpe, 1996;Lambert et al., 2001;Schultes, 1978). Simple phenols and flavonoids appear to inhibit growth by binding to biochemicals essential for metabolism (Peres et al., 1997). Both coumarins and alkaloids are thought to inhibit growth of microorganisms at the genetic level (Hoult and Paya, 1996;Rahman and Chaudhary, 1995;Shukla, 2010). ...
Article
Postharvest losses of stored products are enormous due to fungal deteriorations. Although, there are a number of synthetic fungicides available in the market for checking these deteriorations, they have several side effects such as high toxicity, long degradation periods, their residues in food chain, chronic poisoning through the continuous intake of small quantities, development of new races of pathogens, non-biodegradable nature and exhaustible source. Therefore, we must search the new sources of pesticides, which in addition to their efficiency, must be safe and selective to target specific pathogen. Plants are very rich sources of bioactive chemicals such as phenolics, polyphenols, quinones, flavones, flavonoids, flavonols, tannins, cumarins, terpenoids, lectins and polypeptides. Some plants yield fraction of essential oils, which have inhibitory effects on microorganisms. They are highly enriched with terpenoids. They are volatile, biodegradable, eco-friendly and are easily available in local environment. Several studies have been conducted on the use of such botanicals for controlling postharvest diseases, and hence, the present communication reviews the work done on investigating the fungitoxic potential of essential oils and extracts from higher plants in fungal deterioration of stored products.
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Esta obra constituiu-se a partir de um processo colaborativo entre professores, estudantes e pesquisadores que se destacaram e qualificaram as discussões neste espaço formativo. Resulta, também, de movimentos interinstitucionais e de ações de incentivo à pesquisa que congregam pesquisadores das mais diversas áreas do conhecimento e de diferentes Instituições de Educação Superior públicas e privadas de abrangência nacional e internacional. Tem como objetivo integrar ações interinstitucionais nacionais e internacionais com redes de pesquisa que tenham a finalidade de fomentar a formação continuada dos profissionais da educação, por meio da produção e socialização de conhecimentos das diversas áreas dos Saberes. Agradecemos aos autores pelo empenho, disponibilidade e dedicação para o desenvolvimento e conclusão dessa obra. Esperamos também que esta obra sirva de instrumento didático-pedagógico para estudantes, professores dos diversos níveis de ensino em seus trabalhos e demais interessados pela temática.
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Cascabela thevatica leaf part was tested for antibacterial efficacy against Escherichia coli organism using the disc diffusion method. The crude alcoholic extract was found effective against Escherichia coli organism. The antibacterial activity is attributed to the presence of alkaloids, which was confirmed by gas chromatography end positive alkaloid test. The minimum inhibitory concentration (MIC) was determined for the crude extract by paper disc diffusion method. The result were compared with reference antibiotic tetracycline (one unit strength).
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Plants, being the significant and natural source of medication for humankind against several ailments with characteristic substances hidden on them, have been recognized for many centuries. Accessibility of various methodologies for the revelation of therapeutically characteristic items has opened new avenues to redefine plants as the best reservoirs of new structural types. The role of plant metabolites to hinder the development and movement of pathogenic microbes is cherished. Production of extended-spectrum β-lactamases is an amazing tolerance mechanism that hinders the antibacterial treatment of infections caused by Gram-negative bacteria and is a serious problem for the current antimicrobial compounds. The exploration of the invention from sources of plant metabolites gives sustenance against the concern of the development of resistant pathogens. Essential oils are volatile, natural, complex compounds described by a solid odor and are framed by aromatic plants as secondary metabolites. The bioactive properties of essential oils are commonly controlled by the characteristic compounds present in them. They have been commonly utilized for bactericidal, virucidal, fungicidal, antiparasitic, insecticidal, medicinal, and antioxidant applications. Alkaloids are plant secondary metabolites that have appeared to have strong pharmacological properties. The impact of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial development and efflux pump activity was assessed on Pseudomonas aeruginosa. Plant-derived chemicals may have direct antibacterial activity and/or indirect antibacterial activity as antibiotic resistance modifying agents, increasing the efficiency of antibiotics when used in combination. The thorough screening of plant-derived bioactive chemicals as resistance-modifying agents, including those that can act synergistically with antibiotics, is a viable method to overcome bacterial resistance. The synergistic assessment studies with the plant extract/essential oil and the antibiotic compounds is essential with a target for achieving a redesigned model with sustainable effects which are appreciably noticeable in specific sites of the plants compared to the entirety of their individual parts.
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Ethnopharmacological relevance Croton urucurana Baill. (Euphorbiaceae), popularly known as ‘sangue de dragão’ is a Brazilian species widely used in traditional medicine for cardiovascular ailments. Aim To investigate the cardiovascular effects of the C. urucurana extract in spontaneously hypertensive rats (SHRs). Materials and methods Leaves from C. urucurana were collected and morphoanatomically characterized. The ethanol-soluble fraction (ESCU) was obtained and analyzed by LC-DAD-MS. Using female Wistar rats we investigated the acute toxicity of ESCU. Then, SHRs (six months old) received vehicle, hydrochlorothiazide (25 mg/kg), or ESCU (30, 100, 300 mg/kg) for 28 days. At the beginning and at the end of treatments, urine samples were obtained to assess renal function. At the end of the trial period, the blood pressure, mesenteric vascular beds (MVBs) reactivity, and electrocardiographic profile were evaluated. Serum angiotensin-converting enzyme activity, as well as urea, creatinine, sodium, potassium, nitrite, malondialdehyde, nitrotyrosine, and aldosterone levels were determined. Relative organ weights and histopathological analysis were performed. Finally, the cardiac function on a Langendorff system, as well as the molecular mechanisms involved in the vasodilator effects of ESCU in MVBs were also investigated. Results The compounds annotated from ESCU by LC-DAD-MS included mainly phenylpropanoid derivatives, alkaloids, O-glycosylated megastigmanes, glycosylated flavonoids, flavan-3-ols, and others, such as quercetin O-deoxyhexosyl-hexoside, magnoflorine, reticuline, and taspine. None of the animals showed any signs of toxicity. Male SHRs treated only with the vehicle showed important cardiovascular changes, including a reduction in renal function, increase in serum oxidative stress, and hemodynamic, electrocardiographic, and morphological changes typical of hypertensive disease. Moreover, parameters of cardiac function, including left ventricular developed pressure, peak rate of contraction, peak rate of relaxation, and the rate pressure product were significantly altered, showing a significant impairment of ventricular function. All ESCU-doses presented a significant cardioprotective effect in SHRs rats. The 28-day treatment normalized the hemodynamic, electrocardiographic, morphological, and renal impairments, as well as reversed the changes in ventricular function induced by hypertension. In MVBs with an intact endothelium, ESCU (0.1, 0.3, and 1 mg) dose-dependently induced vasodilation. Endothelium removal or the inhibition of nitric oxide synthase prevented the vasodilatory effect of ESCU. Perfusion with a physiological saline solution that contained KCl, tetraethylammonium, or apamin also abolished the vasodilatory effect of ESCU. Conclusion Prolonged ESCU-treatment showed significant cardioprotective effects in SHRs. Moreover, the data showed the role of nitric oxide and calcium-activated small conductance potassium channels in the cardiovascular effects of ESCU.
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At present, the concept of health consciousness in urban and rural people is becoming increasingly popularized. Keeping in mind the health effects of modern medicine, people have been using herbal medicines either alone or in combination with other products to achieve this state of health. There are substantial monetary profits associated with the expansion and use of plants with medicinal importance and their associated products in aboriginal medications in disease treatment, which indicates that the ways are widening for the herbal renaissance. This is evident from reports published by the World Health Organization (WHO) that 70%–80% of the global population fulfills its primary healthcare needs by using different herbs for medicinal purposes. From prehistoric times to present day, about 53,000 species of herbs are exploited in human disease treatment. The controlled accessibility of various agents needs to be considered if plant-based medicinal products are to be developed as chemotherapeutic medicines. Due to this overexploitation, many species are threatened with extinction. For the judicious use of herbal medicines and their products, great care should be kept in mind while using these herbal medicines, and their overexploitation must be controlled. This can only be achieved when we strive hard to implement three major goals of the Convention on Biological Diversity (1992): conservation of biodiversity, sustainable use of biodiversity components, and fair and equitable benefit sharing from genetic resources. Although plants with medicinal and aromatic importance have not been clearly on the program of biodiversity convention conferences, the goals of the Convention on Biological Diversity are wholly related to these resources of plants with medicinal value.
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Flavonoids were isolated by PVPP column chromatography of leaf extracts of Croton floribundus Spreng and C. urucurana Baill. and identified by NMR and co-chromatography with standards. The two species revealed highly distinct flavonoid profiles. C. urucurana, belonging to the phylogenetically basal section Cyclostigma, yielded the flavone C-glycosides vitexin and orientin, quercetin and the O-glycosides quercetin 7-O-rhamnoside, rhamnitrin and rutin, in addition to tiliroside. Instead, C. floribundus, from the more derived section Lasiogyne, yielded no C-glycosides, but a high diversity of classes of flavonols, including kaempferol, three flavonol O-methyl ethers, isoquercitrin, three tri-O-galactosides, in addition to tiliroside and an isorhamnetin-coumaroyl-O-glycoside. The present work is the first report for Croton of two rhamnosides (isolated from C. urucurana). It is also the first report for Euphorbiaceae of two tri-O-glycosides obtained from C. floribundus. The distribution of flavonoids in the two species as determined by HPLC-DAD of extracts of small leaf samples of herbarium specimens is highly similar with the profiles resulting from isolation of compounds from bulky leaf samples. Differences among specimens of the same species were restricted to relative proportions of individual constituents. The results indicate that flavonoid profiles are effective to characterize and distinguish the two species. The present results, combined with literature data, supports the condition of tiliroside as a marker of Croton and the hypothesis of an evolutionary trend in the genus toward the loss of C-glycosides and a progressive complexity of flavonoid profiles.
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The sections in this article are Introduction Induced Local Defence by Means of Phytoalexins Antibacterial and Antifungal Agents of Higher Plants Secondary Metabolites from Higher Plants with Antiviral Properties Conclusions
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The World Organization for Animal Health (OIE) mentions that the inappropriate use of antibiotics has led to the emergence of strains of resistant bacteria to the mechanisms of action of these drugs, due to the scarcity of effective therapies, the development of new treatment options is required for diseases that affect health, in this respect plant extracts or their pure compounds offer an alternative. The aim of the present investigation was to characterize and evaluate the in vitro antibacterial activity of the hydroalcoholic extract of Croton draco on bacteria of sanitary importance. The extract was obtained by hydroalcoholic maceration, a qualitative and chemical characterization of the extract was carried out, and the antibacterial activity was determined by the Minimum Inhibitory Concentration (MIC) and the Minimum Bactericidal Concentration (MBC). The qualitative characterization tests performed on the hydroalcoholic extract of Croton draco indicate the presence of phenolic compounds, terpenes, saponins and alkaloids, by gas chromatography the presence of thymol and carvacrol was determined in concentrations of 0.5340 mg/ml and 0.4206 mg/mL respectively. The bacteria showed different degrees of sensitivity to the hydroalcoholic extract, however, greater activity was determined against Gram positive bacteria such as Listeria monocytogenes, Staphylococcus aureus and Bacillus subtilis.
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Plants have developed effective defence strategies to protect themselves from phytopathogenic microbes and herbivores in their environment. Disease resistance in plants depends on the activation of coordinated, multicomponent defence mechanisms. One mechanism for disease resistance in plants is their ability to accumulate low‐molecular‐weight compounds (secondary metabolites) with high antimicrobial activities, such as alkaloids, coumarins, isoflavonoids, polyacetylenes, quinones, tannins and terpenes. Based on this knowledge, there is every reason to believe that the plant kingdom is an important source of new antimicrobial agents with special biological targets. Thus, in the last two decades, hundreds of different new secondary metabolites were screened for their potential antibacterial, antifungal and antiviral activities. For instance, several secondary metabolites with antiviral properties have exhibited competitive in vitro and in vivo activities with those found for synthetic antiviral drugs. It has been shown that phyto‐antiviral agents interfere with many viral targets, ranging from adsorption of the virus to the host cell via the inhibition of virus‐specific enzymes (e.g. reverse transcriptase, protease) to release virus from the cells. It is generally accepted that bioactive plant‐derived secondary metabolites are useful leads to synthesize new and more active antimicrobial agents as well as substances with new pharmacological effects by repeated structural modification. It is expected that structurally modified natural products will exhibit increased potency, selectivity, duration of action, bioavailability and reduced toxicity.
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Corantes naturais das cascas das árvores Stryphnodendron adstringens (Mart.) Coville e Croton urucurana Baill., nativas do Brasil: extração, tingimento, solidez de cor e caracterização do efluente São Paulo 2018
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It is about the genetically modified organisms, their history and development, their positive and negative impacts on environment and the future perspective
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Plants have been utilized for health and medicinal benefits for hundreds of years due to their multiple beneficial attributes such as anticancer, antitumor, antioxidant, antimicrobial, antibacterial, anti-ulcer, anti-arthritic, etc. It has been estimated that there are altogether 250,000 species of higher plants on Earth and among them 35,000–70,000 species are being used to treat various diseases due to the presence of secondary metabolites (alkaloids, flavonoids, steroids, glycosides, saponins, etc.). Cancer is a worldwide leading cause of morbidity and mortality. To cure this at right time, herbal drugs are more beneficial than synthetic drugs, because the synthetic medicines can cause heavy damage to normal cells while destroying the tumor cells. The present work consists of a review of 149 plant families harboring 667 species reported to possess anticancer property. Moreover, other biological properties of the bioactive compounds are also covered. This work is based on reliable data collected from multifarious databases such as CAB abstract, MEDLINE, EMBASE, J GATE, ERIC, Proquest, INMEDPLAN, NATTS, The Plant List, JSTOR, Google Scholar, Springer, Elsevier, and websites such as www.sciencedirect.com, www.jstor.org, www.eflora.org, and www.pfaf.org. The complete data regarding plant names, synonyms, common names, botanical description, medicinal properties, and bioactive compounds present in the plant parts is compiled. In near future, these bioactive compounds can be deployed singly or in combination with routine chemotherapy and radiotherapy to treat various types of cancers, after proper standardization, dose optimization, and stringent clinical trials.
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Natural dyes have become an alternative option of interest for textile dyeing. The selection of native species as a natural dye can make its use feasible and enhance local biodiversity. In the present study, the extract of Croton urucurana Baill. bark, which is native to Brazil, was investigated as a natural textile dye. The extract showed a reddish-brown color and the presence of tannins. The extract was characterized by physicochemical methods and optimization of the dyeing process was determined by factorial design 2³. The dyed fabrics were evaluated for color fastness to light, wash, rubbing and perspiration. They showed colors between beige and reddish-brown and had good fastness properties. Antibacterial activity assessment was performed on the extract and fabrics and UV protection was evaluated in the fabrics. The wastewater generated from the dyeing process was also characterized. It exhibited high biochemical oxygen demand and chemical oxygen demand, in addition to a large amount of dissolved iron and aluminum, when these metals were used as a mordant in the dyeing process. On balance, the extract of C. urucurana has the potential to be employed as a textile dye.
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The efficacies of 11 plant-derived antimicrobials were evaluated against Escherichia coli in vitro in solution at room temperature. These included lemongrass, cinnamon, and oregano essential oils and their active components (citral, cinnamaldehyde, and carvacrol, respectively). Allspice and clove bud oils and olive, green tea, and grape seed extracts were also studied. The efficacies of the antimicrobials were both concentration- and exposure time-dependent. The essential oils and their active components demonstrated statistically significant >5.0-log10 reductions within 1-10 minutes. The plant extracts were less effective; green tea and grape seed extracts required 24 hours before significant reductions were observed (1.93-log10 and 5.05-log10, respectively). Nevertheless, olive extract exhibited a reduction of ~5-log10 within 30 minutes. Most of these plant-derived compounds exhibited strong bactericidal activity and can potentially be applied as alternatives to chemicals for foods/food contact surfaces since they are Generally Recognized As Safe (GRAS) for human consumption. They may also be useful in applications in which other antimicrobials have reduced efficacy (e.g., in the presence of organics) or used with sensitive populations that are unable to tolerate exposure to harsher chemicals (e.g., elderly care facilities). These compounds could be used alone, in combination, or with fast-acting antimicrobials to provide a long-lasting residual.
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The aim of this study was to screen the antimicrobial and acaricidal activity of 20 endemic or indigenous plants from Reunion Island (Indian Ocean). Plants were chosen on the basis of their traditional uses and their biocidal activities found in the literature. A survey was conducted in the local population to assess and supplement knowledge about the selected plants. The collected information confirmed and/or supplemented the data obtained for nine plants. Seven plants were described for the first time for their traditional uses in medicine and ethnoveterinary practices. To evaluate their biocidal activities, leaves or bark were treated with ethyl acetate using an accelerated solvent extraction method. Six bacteria and five fungi, frequently implicated in infectious diseases, were used to assess the antimicrobial activity of these extracts. A preliminary screening using the paper disk diffusion assay showed an effective antibacterial activity of 16 extracts. The minimum inhibitory concentration (MIC) of active plant extracts was then determined using a microdilution method. The leaf extract from Peperomia borbonensis displayed the widest spectrum of antibacterial activity and was the only one to act as a fungicide. In parallel, acaricidal bioassays were performed on the larvae of the tick Rhipicephalus microplus (Ixodidae), and plant extracts from Peperomia borbonensis and Zanthoxylum heterophyllum were the most effective. The preliminary studies of these plant extracts exhibited biocidal activities that were not described in the literature and that are congruent with traditional uses for some of them. Investigations are currently being conducted to isolate the active compound(s) and evaluate their potential for future developments and applications.
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Bipolaris sorokiniana is a causative organism of spot blotch disease that is well known cereal pathogen of global concern. Amongst the group of fungus B. sorokiniana is regarded as one of the most severe foliar disease constraints causing yield loss. This fungus is most dangerous for crops growing the warmer areas because high temperature and high relative humidity enhanced its activity to flourish the disease. To control the harmful impact of spot blotch disease caused by B. sorokiniana there are various methods have been proposed however, impact of heat shock has been of more interest by researchers. Thus in this chapter the impact of heat shock on B. sorokiniana has been discussed explaining various aspects.
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Chinese dragon's blood, the red resin of Dracaena cochinchinensis, one of the famous traditional medicines, has been used to promote blood circulation, disperse blood stasis, stop bleeding, relieve pain and muscle regeneration for thousands of years. The aims of this study were to evaluate the anti-atherosclerotic effect of Longxuetongluo Capsule (LTC), which made by total phenolic compounds of Chinese dragon's blood, in high cholesterol diet (HCD)-induced atherosclerosis model rats and explore the possible mechanism. Atherosclerosis rats were induced by administration of HCD for 4 weeks and treated with atorvastatin (2.08mg/kg/d) or various concentrations of LTC (81, 162 and 324mg/kg/d) for additional 4 weeks. Body weight (BW), lipid profiles, serum VCAM-1, ICAM-1, MCP-1, AST and ALT were then tested. Histopathological evaluation of aorta and liver were determined by hematoxylin and eosin staining. NF-κB expression in aorta was detected by Immunohistochemical staining. Meanwhile, the inhibition effects of LTC on the migration and proliferation and Intracellular Ca(2+) levels induced by PDGF-BB were also evaluated in rat aortic smooth muscle cells (A7r5). The results demonstrated that LTC produced a significant anti-atherosclerotic activity in terms of reduction in serum lipids and lipoprotein profile, VCAM-1, ICAM-1, MCP-1, AST, ALT levels, and increase in HDL-c level compared to atherosclerotic group. Rats treated with LTC not only attenuated the pathological region and atheroma formation, but also reduced hepatic steatosis and inflammatory cell infiltration. Immunohistochemical analysis showed LTC reduced NF-κB expression in aorta. Furthermore, PDGF-BB induced proliferation and migration of A7r5 and intracellular calcium rise were also abrogated by LTC. The results indicate that LTC prevents atherosclerosis and fatty liver by controlling lipid metabolism, the underlying mechanism may attributed to its anti-inflammation activity, regulation of the vascular smooth muscle function and intracellular calcium signaling.
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Croton urucurana Baillon, espécie conhecida popularmente como “sangria d’água”, pertence à família Euphorbiaceae, possui grande importância na medicina popular, a qual lhe atribui propriedades antibacterianas, anti-inflamatórias, antissépticas, antivirais, antidiarreicas, antissecretória intestinal e cicatrizante. Os objetivos deste estudo foram verificar a presença, nos extratos aquoso, etanólico e hidroalcoólico, de metabolitos secundários (alcaloides, antraquinonas, esteroides/triterpenoides, flavonoides, glicosídeos, saponinas e taninos), analisar a inibição do crescimento das bactérias Staphylococcus aureus ATCC 25923 e Salmonella thyphimurium ATCC 14028, e verificar a atividade antioxidante através do método DPPH. Para o perfil fitoquímico o melhor extrato foi o aquoso, quanto à susceptibilidade bacteriana, houve inibição com o extrato etanólico e o extrato com a maior atividade antioxidante foi o hidroalcóolico, apresentando IC50 1,3 μg/mL. Considerando os resultados obtidos no estudo, foi possível concluir que os extratos da Croton urucurana Baillon apresentam resultados interessantes e que mais investigações devem ser realizadas para a elucidação aprimorada dos seus benefícios.
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Phytochemical investigation of the ethanol extract from the twigs and leaves of Croton tiglium led to the isolation of two new phorbol esters (1-2) and seven known ones (3-9). Their structures were elucidated by the analyses of extensive spectroscopic data (IR, MS, and 1D and 2D NMR) and comparing with related compounds. Meanwhile, compounds 1-9 were determined for their cytotoxic activities on human lung cancer cell line A549. Among them, 1-2 were inactive against the cell line A549 (IC50?>?100??M), but compounds 3 and 7 showed weak activities.
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Cancer is a disease of deregulated cellular behavior. Acquisition of oncogenic attributes, loss of tumor suppressive functions, evasion of physiological tissue architecture and interactions with the cellular microenvironment enable malignant cells to escape the mechanisms of normal cellular homeostasis in an organism. Cancer cells are therefore able to sustain unlimited proliferation, to thrive under conditions that preclude normal cell survival, and to spread to distant sites through the process of metastasis. Natural products are important sources of new anticancer drugs, new drug leads and new chemical entities. The plant based drug discovery resulted mainly in the development of anticancer agents including plants (vincristine, vinblastine, paclitaxel, etoposide, camptothecin, topotecan and irinotecan). Beside this there is numerous agents identified from fruits and vegetables can used in anticancer therapy. The agents include curcumin (turmeric), resveratrol (red grapes, peanuts and berries), genistein (soybean), diallyl sulfide (allium), S-allyl cysteine (allium), allicin (garlic), lycopene (tomato), capsaicin (red chilli), diosgenin (fenugreek), 6-gingerol (ginger), ellagic acid (pomegranate), ursolic acid (apple, pears, prunes), silymarin (milk thistle), anethol (anise, camphor, and fennel), catechins (green tea), eugenol (cloves), indole-3-carbinol (cruciferous vegetables), limonene (citrus fruits), beta carotene (carrots), and dietary fiber. In this review active principle derived from natural products are offering a great opportunity to evaluate not only totally new chemical classes of anticancer agents, but also novel lead compound and potentially relevant mechanisms of action.
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From the heartwood of Croton sonderianus was isolated a new furanoid diterpene, sonderianin. The structure was elucidated by spectral analysis, X-ray studies and chemical evidence.
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Sonderianol (12-hydroxy-3-oxo-cleistanth-8, 11, 13, 15-tetraene) and 3, 4-seco-sonderianol (methyl 12-hydroxy-3, 4-seco-cleistanth-8, 11, 13, 15, 18(4)-penten-3-oate), two new diterpenes with cleistanthane skeletons, were isolated from heartwood of Croton sonderianus.
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Further chemical examination of the constituents in the bark of Croton lechleri led to isolation of two new diterpenoidal compounds, korberin A and korberin B. Their structure was elucidated by 1H and 13C NMR spectroscopic methods, and they were shown to be diterpenoid lactones with the clerodane skeleton. Their antibacterial activity was tested using a direct bioautographic TLC assay.
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(+)-Epicatechin has been isolated from various species of Palmae and (+)-epiafzelechin from Livinstona chinensis. This is the first time that catechins with (+)-epi-configuration have been found in natural sources.
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A novel insecticidal diterpene was isolated from Croton linearis and its structure determined by spectroscopic methods. Its 72 hr LD50 on Cylas formicarius elegantulus (summer) was 0.32 μg insect−1.
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It is shown that 1H-13C shift-correlated two-dimensional spectra obtained for polarization transfer via two-bond and three-bond 13C-1H coupling can, in conjunction with related experiments, be used to assign unambiguously the molecular skeletons of two of the less common triterpenes, moretenone and 3-acetylaleuritolic acid. It is concluded that this is a technique of considerable generality for assigning structures of triterpenes and is more reliable than alternative approaches such as mass spectral fragmentation patterns. It has the additional benefit of simultaneously providing reliable l3C and 1H spectral assignments for these compounds.
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The blood-red sap of Croton lechleri was found to contain proanthocyanidins as major constituents which accounted for up to 90% of the dried weight. In addition to (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin and dimeric procyanidins B-1 and B-4, five novel dimers and trimers were isolated and characterized as catechin-(4α→8)- epigallocatechin, gallocatechin-(4α→8)-epicatechin, gallocatechin-(4α→6)-epigallocatechin, catechin-(4α→8)- gallocatechin-(4α→8)-gallocatechin and gallocatechin-(4α→8)-gallocatechin-(4α→8)-epigallocatechin. Higher oligomers were also obtained. A new procedure combining chemical degradation with 1H NMR spectroscopy has been developed for determination of the composition and molecular size of oligomeric/polymeric proanthocyanidins. The oligomers of the sap were shown to have the mean degree of polymerization of 4,5–6 and 6–7, respectively, and Mr up to 2130. The heterogeneity of the oligomers was clearly indicated by the presence of a variety of flavan-3-ols as extension and terminal units. An exceptionally high content of gallocatechin and epigallocatechin in the oligomers was observed.
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A new bianthraquinone, 5,5′-bi-7-methylphyscion, and a new methylatedent-catechin have been isolated from the roots ofCassia trachypus. The structure of the bianthraquinone was elucidated by detailed NMR investigation while that of the catechin by comparison of molecular rotation and NMR data with those of known catechins.
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Extracts of Euphorbia esula L. and Croton tiglium L., two members of the Euphorbiaceae which have been used widely in folk medicine for treating cancers, showed antileukemic activity against the P-388 lymphocytic leukemia in mice. Systematic fractionation of the extract of Euphorbia esula L. led to characterization of a major antileukemic component as the new diterpenoid diester, ingenol 3,20-dibenzoate. Similar fractionation of Croton oil led to characterization of phorbol 12-tiglate 13-decanoate as an active principle.
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Cajucarinolide and isocajucarinolide, two new clerodane diterpenes, have been isolated from the cortices of Croton cajucara (Euphorbiaceae). These compounds possess anti-inflammatory activity and inhibit bee venom phospholipase A2 in vitro.
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A screening program was devised which enabled the detection of antimicrobial activity in extracts of higher plants. In preliminary studies, a wide variety of pure plant products and plants were shown to have potentially interesting activity against a variety of screening organisms. The rationale for the various component parts of the screening process and the results of the screen are briefly discussed.
Identificaçã de glicosí na Hymanaea martiana Hayne, Arzeik: Estruturas e Ati6idades farmaco-ló. Disssertaçã (Mestrado em Ciê)
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Carneiro, E. (1989) Identificaçã de glicosí na Hymanaea martiana Hayne, Arzeik: Estruturas e Ati6idades farmaco-ló. Disssertaçã (Mestrado em Ciê), Universi-dade Federal de Santa Catarina (Brasil), pp. 211.
A dihidrobenzofuran lignan from Croton erytrochilus
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Pieters, L., Bruyne, T. de, Claeys, M., Vietlinck, A.J. (1993) A dihidrobenzofuran lignan from Croton erytrochilus. Journal of Natural Products 61 (6), 899 – 906.
Identificação de glicosı́deos na Hymanaea martiana Hayne
  • E Carneiro