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PubMed2002

Characterization of a fucoarabinogalactan, the main polysaccharide from the gum exudate of Croton urucurana.

A fucoarabinogalactan (CU-1), the main component of the gum exudate of the medicinal plant Croton urucurana, has been isolated by precipitation and subsequent dialysis and finally purified by ion-exchange chromatography. The estimated average molecular weight of CU-1 by gel permeation chromatography was approximately 2.48 x 10(6) Da. CU-1 was found to contain 1.0% proteins and 93.7% total sugars, mainly fucose, arabinose, and galactose (molar ratio: 7.8, 8.1, 19.0), and minor quantities of mannose, xylose, glucose, and uronic acids (molar ratio: 2.2, 1.0, 0.3, 3.0). Among the uronic acids, glucuronic acid was identified and the presence of mannuronic acid could be also presumed. Methylation analysis of this polysaccharide revealed high proportions of 1,3-linked, 1,2,3-linked, and 1,2,3,6-linked galactose, 1-linked fucose, and 1-linked arabinose. This suggests that CU-1 is constituted by a principal skeleton of (1-->3)-linked galactopyranose units, with some of these galactose units branched at the 2-position or at both the 2- and 6-positions, and with mainly terminal fucopyranosyl and arabinofuranosyl residues in the side chains. This is the first report on the polysaccharide constitution of a gum exudate from a Croton species.

Amino Acids↗

PubMed2003

New antimycobacterial and antimalarial 8,9-secokaurane diterpenes from Croton kongensis.

Two new 8,9-secokaurane diterpenes, ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione (1) and ent-8,9-seco-8,14-epoxy-7alpha-hydroxy-11beta-acetoxy-16-kauren-9,15-dione (2), together with two known compounds, ent-8,9-seco-7alpha-hydroxy-11beta-acetoxykaura-8(14),16-dien-9,15-dione (3) and ent-7beta-hydroxy-15-oxokaur-16-en-18-yl acetate, were isolated from Croton kongensis. This is the first report on the presence of 8,9-secokauranes in the plant genus Croton. Diterpenes 1-3 exhibited antimycobacterial activity with minimum inhibitory concentrations (MICs) of 25.0, 6.25, and 6.25 microg/mL, respectively, and possessed antimalarial activity with IC(50) ranges of 1.0-2.8 microg/mL. They also demonstrated comparable cytotoxicity toward the Vero (IC(50) ranged from 0.9 to 3.2 microg/mL), KB (IC(50) from 1.2 to 13.8 microg/mL), and BC cell lines (IC(50) from 1.1 to 2.2 microg/mL, except for compound 1, which was inactive against BC cells).

Animals↗

PubMed2001

Pathological findings in cumulative irritation induced by SLS and croton oil in hairless mice.

It is known that the pathological features of acute irritant contact dermatitis are specific according to the irritant. However, in chronic irritant contact dermatitis, it is not clear whether specific patterns exist. To investigate whether the specific pathology of acute irritant contact dermatitis is sustained in chronic irritant contact dermatitis, sodium lauryl sulfate (SLS) and croton oil were applied 3x a week for 2 weeks on the dorsal skin of hairless mice using Finn Chambers. The pathologic changes induced by irritants at various concentrations were evaluated using H&E and Luna's staining, as well as immunohistochemistry for 5-bromo-2-deoxyuridine (BrdU), keratin 6 and loricrin. Our results showed that epidermal hyperplasia and inflammatory infiltration were relatively marked in the groups treated with higher concentrations of irritants. These features were more prominent in the 1% croton oil treated group than in the 0.25% SLS treated group. However, lower concentrations of irritants resulted in very similar histological changes, characterized by epidermal hyperplasia with minimal inflammatory infiltration, irrespective of the chemical. Our results suggest that the histological responses to irritants vary with concentration in cumulative irritation, as in acute irritation, but repetitive mild irritation may evoke common histological changes, characterized by epidermal hyperplasia with minimal inflammatory infiltration, irrespective of the chemical used.

Animals↗

PubMed2003

Immunomodulatory activity and chemical characterisation of sangre de drago (dragon's blood) from Croton lechleri.

The immunomodulatory activity of the latex from Croton lechleri (sangre de drago) was determined by in vitro assays. Classical (CP) and alternative (AP) complement pathways activities were determined in human serum. Intracellular generation of reactive oxygen species (ROS) by human polymorphonuclear leukocytes (PMNs) and monocytes, and phagocytosis of opsonised fluorescent microspheres were measured by flow cytometry. Free radical scavenging activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Activity on proliferation of murine lymphocytes was also investigated. In addition, anti-inflammatory activity was assayed in vivo by carrageenan-induced rat paw oedema test. Some of the activities were compared with those of the isolated alkaloid taspine. Sangre de drago from Croton lechleri showed immunomodulatory activity. It exhibited a potent inhibitory activity on CP and AP of complement system and inhibited the proliferation of activated T-cells. The latex showed free radical scavenging capacity. Depending on the concentration, it showed antioxidant or prooxidant properties, and stimulated or inhibited the phagocytosis. Moreover, the latex has strong anti-inflammatory activity when administered i. p. Taspine cannot be considered the main responsible for these activities, and other constituents, probably proanthocyanidins, should be also involved.

Adjuvants, Immunologic↗

PubMed2003

Anti-inflammatory and antioxidant effects of Croton celtidifolius bark.

Croton celtidifolius Baill commonly known as "sangue-de-adave" is a tree found in the Atlantic Forest of south of Brazil, mainly in Santa Catarina. The bark and leaf infusions of this medicinal plant have been popularly used for the treatment of inflammatory diseases. In this study we evaluated the anti-inflammatory and antioxidant properties of crude extract (CE), aqueous fraction (AqF), ethyl acetate fraction (EAF), butanolic fraction (BuF) and catechin, gallocatechin and sub-fractions, 19SF, 35SF and 63SF that contained a mixture of proanthocyanidins and were derived from the EAF fraction. The CE, AqF, EAF, BuF, catechin and sub-fractions 35SF and 63SF reduced paw edema induced by carrageenan. The CE, fractions, sub-fractions and isolated compounds showed antioxidant properties in vitro, all were able to scavenge superoxide anions at a concentration of 100 microg ml(-1). The EAF, catechin and gallocatechin were most effective in the deoxyribose assay, IC50 0.69 (0.44-1.06), 0.20 (0.11-0.39), 0.55 (0.28-1.08) microg x ml(-1) respectively. The CE and other fractions and sub-fractions inhibited deoxyribose degradation up to 1 microg x ml(-1). In the hydrophobic system only AqF did not show lipid peroxidation inhibition. The CE, other fractions, sub-fractions and isolated compounds inhibited lipidid peroxidation only at a concentration of 100 microg x ml(-1). In summary, this study demonstrates that Croton celtidifolius bark has significant anti-inflammatory and antioxidant activity.

Animals↗

PubMed2001

Crotoflavol, a new phenanthrene from Croton flavens.

Phytochemical investigations of the leaves of Croton flavens L. var. balsamiferus (Jacq.) Muell. Arg. has led to the isolation of the novel 2,5-dihydroxy-3,6-dimethoxyphenanthrene crotoflavol. The structure was elucidated on the basis of spectroscopic evidence. This is the first report on the isolation of a phenanthrene from a Croton species.

Croton↗

PubMed1990

Assignment of Clostridium bryantii to Syntrophospora bryantii gen. nov., comb. nov. on the basis of a 16S rRNA sequence analysis of its crotonate-grown pure culture.

The Clostridium bryantii-Methanospirillum hungatei syntrophic coculture, grown on caproate, was adapted to grow on crotonate. Then, C. bryantii was isolated in pure culture from crotonate bottle plates. A 16S rRNA sequence analysis of the pure subculture revealed that, as a member of the gram-positive phylum, it was not closely related to any of the Clostridium species with which it was compared or to any of the other clusters in the gram-positive phylum with which it was compared. However, it was closely related to another syntrophic fatty acid-degrading bacterium, Syntrophomonas wolfei. On the basis of its phylogeny, physiology, and cell wall ultrastructure, we propose assignment of C. bryantii to Syntrophospora bryantii gen. nov., nov. comb.

Bacteriological Techniques↗

PubMed2002

Anaerobaculum mobile sp. nov., a novel anaerobic, moderately thermophilic, peptide-fermenting bacterium that uses crotonate as an electron acceptor, and emended description of the genus Anaerobaculum.

A novel anaerobic, moderately thermophilic, peptide-fermenting bacterium, strain NGA(T), was isolated from an anaerobic wool-scouring wastewater treatment lagoon. The cells were gram-negative, straight rods of 0.5-1.0 x 2.0-4.0 microm, motile by means of a single flagellum. The DNA G+C content was 51.5 mol%. The optimum pH and temperature range for growth were 6.6-7.3 and 55-60 degrees C, respectively. The optimum NaCl concentration was 0.08 g l(-1). The bacterium fermented organic acids (malate, tartrate, pyruvate, glycerol and fumarate), a few carbohydrates (starch, glucose, fructose and gluconate), Casamino acids, tryptone and yeast extract. Carbohydrates and organic acids were converted to acetate, hydrogen and CO2. The bacterium oxidized leucine to isovalerate with crotonate as an electron acceptor, but not in co-culture with Methanothermobacter thermoautotrophicus DSM 3720T. Thiosulfate, sulfur and cystine were reduced to sulfide and crotonate was reduced to butyrate with glucose and tryptone-yeast extract as electron donors. Phylogenetic analysis of the 16S rRNA gene indicated that strain NGA(T) was related to Anaerobaculum thermoterrenum (98% similarity), the only described species of the genus. The DNA-DNA hybridization value for strain NGA(T) and A. thermoterrenum ACM 5076T was 40.8%. On the basis of these results, strain NGA(T) is proposed as a novel species of the genus Anaerobaculum, namely Anaerobaculum mobile sp. nov. The type strain is NGA(T) (= DSM 13181T =ATCC BAA-54T).

Crotonates↗

PubMed2005

Cytotoxic diterpenoids from Vietnamese medicinal plant Croton tonkinensis GAGNEP.

Six new ent-kaurane-type diterpenoids were isolated from the leaves of the endemic Vietnamese medicinal plant Croton tonkinensis GAGNEP. (Euphorbiaceae) together with three known ent-11alpha-acetoxy-7beta,14alpha-dihydroxykaur-16-en-15-one (1), ent-kaur-16-en-15-one 18-oic acid (5) and ent-18-hydroxykaur-16-ene (7). Their structures were determined by spectroscopic analyses to be ent-7beta-acetoxy-11alpha-hydroxykaur-16-en-15-one (2), ent-18-acetoxy-11alpha-hydroxykaur-16-en-15-one (3), ent-11alpha-acetoxykaur-16-en-18-oic acid (4), ent-15alpha,18-dihydroxykaur-16-ene (6), ent-11alpha,18-diacetoxy-7beta-hydroxykaur-16-en-15-one (8), and ent-(16S)-1alpha,14alpha-diacetoxy-7beta-hydroxy-17-methoxykauran-15-one (14). ent-Kaurane-type diterpenoids from Croton tonkinensis 2-4, 6, and 9-13, were tested for toxicity in the brine shrimp lethality assay. Compounds 9, 10, and 12 demonstrated significant activity, compounds 2, 3, 6, and 11 showed weak activity, and compounds 4 and 13 were inactive.

Animals↗

PubMed1988

[Croton oil-induced hemorrhoid model in rat: comparison of anti-inflammatory activity of diflucortolone valerate with other glucocorticoids].

A hemorrhoid model was prepared by means of application of croton oil onto the recto-anus of rats. Cotton swab soaked with the inducer, which consisted of water, pyridine, diethylether and 6% croton oil in diethylether, was inserted into the anus. The following conditions were found to be optimal for preparing the model: cotton swab containing 0.16 ml of the inducer solution was applied to the anus of a 6 week-old rat (body wt. about 140 g) for 10 sec. The edema developed linearly until 7-8 hr after application, and the severity of the edema was sustained almost constantly for more than 24 hr. Macroscopic observations at 6 hr p. a. revealed homogeneous and consistent inflammation in the recto-anus applied region. Histological observation showed appearance of edema, infiltration of fibrin, inflammatory cells, vasodilation, blood congestion and medium to high degrees of necrosis in the mucosal epithelium. Thus this model was useful for evaluating the effect of anti-hemorrhoidal drugs on intumescence and vasodilatation. The efficacy of diflucortolone valerate, hydrocortisone caproate and hydrocortisone was evaluated in this model. Wet weight and vasopermeability increased by the inducer was suppressed strongly by simultaneous application of the corticoids, and the degree of suppression was parallel with the potency of the glucocorticoid activity. Compared to Scheriproct, Posterisan forte, Posterisan and Borraginol N, Neriproct showed the strongest effects in the protection against and treatment of the experimental hemorrhoid. Scheriproct, which was less active than Neriproct, was also found to have higher efficacy than the others.

Animals↗

PubMed2001

Antinociceptive effects of the essential oil of Croton zehntneri in mice.

Croton zehntneri is an aromatic plant native to Northeastern Brazil, where it is often used in folk medicine. In the present study the antinociceptive effects of the essential oil of Croton zehntneri (EOCz) were evaluated in mice. EOCz administered orally at doses of 100 and 300 mg/kg reduced paw licking time in the second phase of the formalin test from the control value of 41.61 +/- 8.62 to 12.01 +/- 7.97 and 6.57 +/- 3.42 s, respectively. During the first phase of the formalin test only 300 mg/kg induced a significant alteration (from 58.2 +/- 7.02, control, to 28.7 +/- 4.73 s). The number of contortions in response to intraperitoneal injections of acetic acid did not differ significantly between controls (80.6 +/- 9.01) and experimental (300 mg/kg body weight) animals (89.1 +/- 9.53% of the control numbers; P > or =0.05, Student t-test). In the hot-plate test, EOCz at doses > or =100 mg/kg significantly increased the latency time with respect to controls (11.2 +/- 0.80). At 100 and 300 mg/kg this increase persisted for 180 and 240 min, respectively. The data show that EOCz is effective as an antinociceptive agent.

Administration, Oral↗

PubMed2006

Larvicidal activity of essential oils from Brazilian Croton species against Aedes aegypti L.

Aedes aegypti is the major vector of dengue fever, an endemic disease in Brazil. In an effort to find effective and affordable ways of controlling this mosquito, the larvicidal activities of essential oils from Croton species widely found in northeastern Brazil were analyzed. The essential oils were extracted by steam distillation, and their chemical composition was determined by gas liquid-chromatography coupled with mass spectroscopy. The main components were methyleugenol and alpha-copaene for C. nepetaefolius (LC50 of 84 ppm); alpha-pinene and beta-pinene for C. argyrophyloides (LC50 of 102 ppm); and alpha-pinene, beta-phelandrene, and trans-caryophyllene for C. sonderianus (LC50 of 104 ppm). Croton zenhtneri exhibited higher larvicidal activity with LC50 of 28 ppm, and the main active constituent was identified as anethole, a phenylpropanoid compound.

Aedes↗

PubMed1999

Effect of emu oil on auricular inflammation induced with croton oil in mice.

OBJECTIVE: To determine the acute anti-inflammatory effects of topically applied emu oil. ANIMALS: 96 male CD-1 mice assigned randomly to 4 groups, each comprising 24 mice. PROCEDURE: To induce auricular inflammation, 50 microl of a solution comprising 10 microl of croton oil dissolved in 1 ml of acetone was applied to the inner surface of the left auricle (pinna). One hour later, 3 or 5 microl of emu oil (low- and high-dose groups, respectively) or 5 microl of porcine oil (oil-control) was applied to the left pinna. Control mice remained untreated. Six mice per group were euthanatized 3, 6, 12, and 24 hours after induction of inflammation. Specimens of auricular tissue (ear plugs) were obtained, using a 6-mm biopsy punch. Magnitude of swelling was calculated as the weight difference between left (inflamed) and right (noninflamed) ear plugs; degree of edema was determined as the difference between wet and dry weights of the left ear plug. RESULTS: Magnitude of swelling was significantly reduced at 6 and 12 hours in mice treated with emu or porcine oil, compared with controls. The greatest reduction in swelling was detected in the high-dose emu group at 6 hours. Compared with controls, degree of edema was significantly reduced at 6 hours only in the high-dose group, whereas by 12 hours, all groups treated with oils had significantly less edema than controls. At 24 hours, magnitude of swelling and degree of edema did not differ among groups. CONCLUSION: Topically applied emu oil significantly reduced severity of acute auricular inflammation induced by croton oil in mice.

Administration, Topical↗

PubMed1977

[Hodgkin's disease: study of delayed hypersensitivity of 64 non treated patients. Value of epicutaneous test using croton oil].

Cellular immunity in 64 patients with Hodgkin's disease was studied during diagnosis before any treatment. The functional deficiency of the thymodependent lymphocyte was demonstrated in vivo by skin tests and, in vitro, by the test of inhibition of leucocyte migration to phytohemagglutininin and spontaneous rosette formation, to sheep red cells. This deficiency correlates with the clinical spread and the histological severity. The relationship between skin anergy and biological tests was found. The epicutaneous test using croton oil possesses non-specific inflammatory activity. It is negative this test is negative, skin reactivity to specific antigens is reduced. The croton tests help interpretation of skin responses to specific antigens and thus assessment of the immune state.

Adolescent↗

PubMed1984

In vitro binding of butyric acid and crotonic acid by the soluble glutathione S-transferases from rat liver.

The in vitro interaction of butyric acid, crotonic acid and n-butylamine with rat liver glutathione S-transferase (GST) was studied, using glutathione (GSH) and 1-chloro-2,4-dinitrobenzene (CDNB) as substrates. Both acids inhibited the GST activity in crude extracts in a dose dependent manner; the amine did not. The GST isoenzymes were inhibited at different degrees. Kinetic studies never revealed competitive inhibition kinetics, with GSH nor with CDNB as the variable substrate. Titration of remaining GSH in appropriate incubation mixtures revealed no GST catalyzed conjugation with GSH. It is concluded that butyric and crotonic acid interact with GST by direct binding to these proteins via their carboxyl group. This binding could have a protective function against these compounds.

Animals↗

PubMed2001

Studies on the antidiarrhoeal effect of dragon's blood from Croton urucurana.

The red sap obtained by slashing the bark of Croton urucurana Baill. (Euphorbiaceae), also known as dragon's blood, was screened for a possible antidiarrhoeal activity on castor oil-induced diarrhoea in rats, cholera toxin-induced intestinal secretion in mice and on small intestinal transit in mice. Dragon's blood at an oral dose of 600 mg/kg caused in marked inhibition of the diarrhoeal response following castor oil administration as well as the intestinal fluid accumulation promoted by cholera toxin. At a similar dose the red sap significantly inhibited the small intestinal transit which was, however, found to be independent of the opioid mechanism. These results suggest a potential usefulness of the red sap from Croton urucurana Baill. in the control of secretory diarrhoea associated pathologies.

Animals↗

PubMed2000

Ethnopharmacology, phytochemistry and pharmacology: a successful combination in the study of Croton cajucara.

Phytochemical and pharmacological studies of Croton cajucara were oriented by traditional medicine. The stem bark of the mature plant is a rich source of clerodane-type diterpenes: trans-dehydrocrotonin (DCTN), trans-crotonin (CTN), cis-cajucarin B, cajucarin A, cajucarinolide and two novel clerodanes, trans-cajucarin B and sacacarin. In young (18-month-old) plants, the triterpene acetyl aleuritolic acid (AAA) was the major stem bark component and in these the diterpene DCTN was not present. The highest concentration of DCTN (1.4% of dry bark) was detected in 4-6 year-old plants, while 3-year-old plants contained only 0.26% of this diterpene. Three steroids (beta-sitosterol, stigmasterol and sitosterol-3-O-beta-glucoside), two flavonoids (kaempferol 3,4', 7-trimethyl ether and 3,7-dimethyl ether) and one diterpene (cajucarinolide) were isolated from the leaves of this Croton. The main pharmacological activity was correlated with DCTN. This clerodane produced anti-inflammatory and antinociceptive effects and a significant hypoglycemia in alloxan-induced diabetic rats. The compound also reduced the index of gastric lesions induced by restraint-in-cold. Dose-related DCTN and CTN inhibited in vivo the basal acid secretion in pylorus-ligature rats and oxyntic glands isolated from rabbit gastric mucosa, DCTN, CTN or AAA decreased in vitro uptake basal acid secretion induced by histamine and measured with the 14C-aminopyrine uptake method. Uniquely DCTN inhibited 14C-AP uptake induced by bethanechol. The terpenoids, DCTN and AAA, and the chloroform extract of 6-month-old plants reduced gastrointestinal transit in mice. The effects of DCTN and CTN on the survival of mice bearing Sarcoma 180 and Ehrlich carcinoma ascitic tumors, on the proliferation of cultured cells and TNFalpha were determined. DCTN was also evaluated for a possible antioestrogenic activity using the immature rat as a model system for bioassay of oestrogen and for an anti-implantation effect in regularly cycling rats. The biological experiments, using the plant extracts and the terpenoids DCTN, CTN and AAA, are herein discussed.

Animals↗

PubMed1976

Studies on the proteins from the seeds of Croton tiglium and of Jatropha curcas. Toxic properties and inhibition of protein synthesis in vitro.

1. Proteins extracted from the seeds of the Euphorbiaceae croton tiglium and Jatropha curcas were separated into three major peaks (I,II,and III) by Sephadex chromatography. 2. The crude protein from both seeds and peaks I and II from Croton and peak I from Jatropha were toxic to mice, to different extents. 3. The crude protein and peak I and peak II from both seeds, inhibited protein synthesis by a reticulocyte lysate; maximum inhibition was exerted by peak II from both seeds. None of these preparations affected protein synthesis in vitro by Ehrlich ascites cells.

Animals↗