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PubMed2000

Antimicrobial activity and chemical composition of the bark oil of Croton stellulifer, an endemic species from S. Tomé e Príncipe.

The composition and the antimicrobial activity of the bark oil of Croton stellulifer, an endemic and rare species of these islands (S. Tomé and Príncipe) are reported. Analysis was carried out by GC, GC/MS and 13C-NMR. The major constituents were alpha-phellandrene (15.4-18.6%), p-cymene (14.4-17.7%), linalool (12.0-12.6%) and alpha-pinene (8.1-9.1%). Kessane, a sesquiterpenoid oxide, not yet reported in the genus Croton, was identified by NMR. The essential oil of C. stellulifer was active against both bacterial and fungal strains, except Aspergillus niger.

Anti-Infective Agents↗
PubMed2006

Phylogeny and biogeography of Croton alabamensis (Euphorbiaceae), a rare shrub from Texas and Alabama, using DNA sequence and AFLP data.

Croton alabamensis (Euphorbiaceae s.s.) is a rare plant species known from several populations in Texas and Alabama that have been assigned to var. texensis and var. alabamensis, respectively. We performed maximum parsimony, maximum likelihood, and Bayesian analyses of DNA sequences from the nuclear ribosomal internal transcribed spacer (ITS) and 5.8S regions and chloroplast trnL-trnF regions from collections of the two varieties of C. alabamensis and from outgroup taxa. C. alabamensis emerges alone on a long branch that is sister to Croton section Corylocroton and the Cuban endemic genus Moacroton. Molecular clock analysis estimates the split of C. alabamensis from its closest relatives in sect. Corylocroton at 41 million years ago, whereas the split of the two varieties of C. alabamensis occurred sometime in the Quaternary. Amplified fragment length polymorphism (AFLP) analyses were performed using two selective primer pairs on a larger sampling of accessions (22 from Texas, 17 from Alabama) to further discriminate phylogenetic structure and quantify genetic diversity. Using both neighbour joining and minimum evolution, the populations from the Cahaba and Black Warrior watersheds in Alabama form two well-separated groups, and in Texas, geographically distinct populations are recovered from Fort Hood, Balcones Canyonlands, and Pace Bend Park. Most of the molecular variance is accounted for by variance within populations. Approximately equal variance is found among populations within states and between states (varieties). Genetic distance between the Texas populations is significantly less than genetic distance between the Alabama populations. Both sequence and AFLP data support the same relationships between the varieties of C. alabamensis and their outgroup, while the AFLP data provide better resolution among the different geographical regions where C. alabamensis occurs. The conservation implications of these findings are discussed.

Alabama↗
PubMedDate not supplied

Seasonal variation of the chemical constituents from Croton species.

The terpenes, sterols, alkaloid (glaucine) and alpha-tocopherol show seasonal variation for Croton hemiargyreus hemiargyreus and Croton echinocarpus. The amounts of triterpenes are higher during the tropical summer and in most samples the major sesquiterpene was characterized as caryophyllene. The seasonal variation of glaucine showed a maximum between June and October for C. hemiargyreus, and was present only in January and June in C. echinocarpus.

Brazil↗
PubMed1995

[The effects of antitumor agents of croton alkaloids and cisplatin on human red blood cell membranes].

The effects of antitumor drugs of croton alkaloids (CA) extracted from croton, and cisplatin on the structure of human erythrocyte membrane and bovine serum albumin (BSA) were studied with the techniques of circular dichroism, fluorescence spectroscopy and ultraviolet absorption. From measuring circular dichroism between 200-240nm, it was found that the alpha helix of membrane and BSA increased after CA addition. Cisplatin was also found effective in altering membrane alpha helical content. BSA showed a loss of fluorescence intensity and a blue-shift of emission peak after CA addition. The florescence quenching and peak shift may reflect the movement of tryptophan to a more nonpolar environment (the hydrophobic portions of proteins). This is consistent with the increase in helicity of BSA in the presence of CA. From measuring fluorescence polarization of membrane, it was found that membrane fluidity decreased in the presence of CA, but did not change in the presence of cisplatin. The results indicate that both CA and cisplatin lead to alterations in the secondary structure of membrane protein. The conformation change in membrane protein may account for the pharmocological effect of CA and cisplatin.

Alkaloids↗
PubMed1996

Systemic application of cysteine-2:1-crotonal adduct for pharmacokinetic studies of tumor models in rats and mice.

A selective cytostatic effect is demonstrated for systemic application of the Michael adduct of crotonal (CAS 4170-30-3) with cysteine (CAS 52-90-4). As in earlier studies, our initial model was the Ehrlich ascites tumor (EAT) in mouse. Tablets containing 150 mg of the substance were implanted subcutaneously. Substance concentrations were found to be higher in the ascites fluid than in the blood. A better model, the Walker-256 carcinosarcoma (Wa256), was used subsequently. Due to its rapid growth, results are available promptly. The EAT results were confirmed and it was also found that there are higher substance concentrations in the cytoplasma of Wa-256 cells than in cells in neighboring liver tissue. During the period when substance was being liberated from the tablet, substance concentration in the blood was constant, and considerably lower than in ascites fluid or cytoplasma. This confirms that cysteine-2:1-crotonal adduct can be applied systemically from a subcutaneous depot to a model tumor in a cytostatic concentration.

Animals↗
PubMed2005

Antimicrobial activity of Croton cajucara Benth linalool-rich essential oil on artificial biofilms and planktonic microorganisms.

We have previously demonstrated that a linalool-rich essential oil from Croton cajucara Benth presents leishmanicidal activity. In the present study, we demonstrate that this essential oil inhibits the growth of reference samples of Candida albicans, Lactobacillus casei, Staphylococcus aureus, Streptococcus sobrinus, Porphyromonas gingivalis and Streptococcus mutans cell suspensions, all of them associated with oral cavity disease. The purified linalool fraction was only inhibitory for C. albicans. Microbes of saliva specimens from human individuals with fixed orthodontic appliances, as well as the reference strains, were used to construct an artificial biofilm which was exposed to linalool or to the essential oil. As in microbial suspensions, the essential oil was toxic for all the microorganisms, while the purified linalool fraction mainly inhibited the growth of C. albicans. The compounds of the essential oil were separated by thin layer chromatography and exposed to the above-cited microorganisms. In this analysis, the proliferation of the bacterial cells was inhibited by still uncharacterized molecules, and linalool was confirmed as the antifungal component of the essential oil. The effects of linalool on the cell biology of C. albicans were evaluated by electron microscopy, which showed that linalool induced a reduction in cell size and abnormal germination. Neither the crude essential oil nor the purified linalool fraction is toxic to mammalian cells, which suggests that the essential oil or its purified components may be useful to control the microbial population in patients with fixed orthodontic appliances.

Acyclic Monoterpenes↗
PubMed2006

Role of capsaicin-sensitive sensory nerves in mediation of the cardiovascular effects of the essential oil of croton zehntneri leaves in anaesthetized rats.

The essential oil of Croton zehntneri Pax et Hoffm. (EOCZ) contains anethole (42%) and estragole (46%), two isomers that share some chemical structural similarities with capsaicin. The present study investigated the cardiovascular effects of EOCZ and the role of capsaicin-sensitive sensory nerve fibres in the mediation of these effects in anaesthetized rats. 2. Intravenous bolus injection of EOCZ (1-20 mg/kg) elicited dose-dependent hypotension and bradycardia that were immediate and transient. Similar responses were also observed with anethole and estragole (both at 10 mg/kg). After cervical bivagotomy or perineural treatment of both cervical vagus nerves with capsaicin (250 mg/mL) to selectively block the conduction of sensory C-fibres, both cardiovascular responses to EOCZ (10 mg/kg) were abolished. 3. Like capsaicin, an epigastric retrograde intra-arterial injection of EOCZ (10 mg/kg, i.a.) into the femoral artery elicited a monophasic hypotensive response. This reflex response was blocked by either neonatal pretreatment with capsaicin (50 mg/kg, s.c.) or intrathecal injection of the substance P receptor antagonist RP 67580 (7.8 nmol, at the spinal level L5-L6), suggesting that it is mediated exclusively by substance P-containing primary afferent fibres. 4. The cardiovascular responses to EOCZ (10 mg/kg, i.v.) were also significantly reduced by the selective vallinoid TPRV1 receptor antagonist capsazepine (1 mg/kg, i.v.). 5. It is concluded that i.v. administration of EOCZ in anaesthetized rats elicits a capsaicin-like bradycardic and depressor reflex, which appears to be mediated by the activation of vallinoid TPRV1 receptors located on vagal sensory nerves. Like capsaicin, i.a. injection of EOCZ induces a spinally mediated sensory reflex.

Allylbenzene Derivatives↗
PubMed2005

HPLC-SPE-NMR hyphenation in natural products research: optimization of analysis of Croton membranaceus extract.

The HPLC-SPE-NMR technique was used for the analysis of a root-bark extract of Croton membranaceus. The components of the extract were separated on an analytical-size reversed-phase HPLC column, the chromatographic peaks were trapped on SPE (solid-phase extraction) cartridges after post-column dilution of the eluate with water and the compounds were eluted from the cartridges with acetonitrile-d(3) into a 30 microl 600 MHz NMR probe in a fully automated procedure. The trapping efficiency of scopoletin (1), the major extract constituent, was much higher on a GP (general phase, a polystyrene-type polymer) SPE phase than on a C18 phase. Thus, under the conditions used, up to 100 microg of scopoletin per cartridge could be accumulated linearly after repeated trappings. The maximum achievable NMR signal-to-noise ratio using the GP cartridges was at least four times higher than that achievable with the C18 cartridges. It was shown that excessively long T(1) relaxation times may compromise experiments in which acetonitrile-d(3) is used as the cartridge eluent. Nevertheless, the sensitivity gain provided by the HPLC-SPE-NMR technique through repeated peak trappings allowed the acquisition of good-quality proton-detected 2D NMR spectra without the need for solvent suppression.

Acetonitriles↗
PubMedDate not supplied

A validated method for the quantification of pimarane and trachylobane diterpenes in the leaves of Croton zambesicus by capillary gas chromatography.

A sensitive and accurate method, combining Soxhlet extraction, solid-phase extraction and capillary gas chromatography, is described for the quantitative determination of four new diterpenes (ent-trachyloban-3beta-ol, ent-18-hydroxy-trachyloban-3-one, ent-trachyloban-3-one and isopimara-7,15-dien-3beta-ol) from the leaves of Croton zambesicus. This is the first method describing the quantification of trachylobane diterpenes in a crude extract. It has been fully validated in order to be able to compare the diterpene composition in other samples of C. zambesicus, which is an important source of trachylobanes.

Chromatography, Gas↗
PubMed2006

Cytotoxic activity of four xanthones from Emericella variecolor, an endophytic fungus isolated from Croton oblongifolius.

Four xanthones were isolated from mycelia of Emericella variecolor, an endophytic fungus isolated from the leaves of Croton oblongifolius. Their structures were elucidated by spectroscopic analysis to be shamixanthone, 14-methoxytajixanthone-25-acetate, tajixanthone methanoate, and tajixanthone hydrate. All compounds were tested for cytotoxic activity against various human tumor cell lines including gastric carcinoma, colon carcinoma, breast carcinoma, human hepatocarcinoma, and lung carcinoma. The antitumor activities of these xanthones were compared with that of doxorubicin hydrochloride, a chemotherapeutic substance. All of them showed moderate activities and were selective against gastric carcinoma, colon carcinoma, and breast carcinoma. Only tajixanthone hydrate exhibited moderate activity against all cancer cell lines. Furthermore, under the test conditions it was found that 14-methoxytajixanthone-25-acetate and tajixanthone hydrate are almost as active as doxorubicin hydrochloride against gastric carcinoma (KATO3) and breast carcinoma (BT474).

Antineoplastic Agents↗
PubMed2003

Diterpenoids from the stem barks of Croton robustus.

Three compounds were isolated from the stem barks of Croton robustus. Their structures were elucidated as trachyloban-19-oic acid, trachyloban-19-ol and poilaneic acid by spectroscopic analysis. Among them, trachyloban-19-ol and methyl trachyloban-19-oate exhibited weak cytotoxic activity against gastric carcinoma and colon carcinoma with ED50 of 9.2, 9.6 and 8.3, 9.1 microg/mL, respectively.

Cell Line, Tumor↗
PubMed2000

Inhibition of croton oil-induced oedema in mice ear skin by capsular polysaccharides from cyanobacteria.

The anti-inflammatory properties of hydrophilic extracts of the capsular polymers of twelve cyanobacterial strains belonging to the genera Phormidium and Nostoc from marine and terrestrial habitats were tested topically on croton oil-induced oedema in mice ear skin. The screening program identified several strains as producers of anti-inflammatory products (up to 56% inhibition of the oedema). The inhibition response was dose-dependent. The application of trichloroacetic acid-treated extracts reduced the oedema by about 60%. On the other hand, one of the strains enhanced the inflammatory response. Analysis of five of the extracts showed the presence of neutral sugars (from 34.3% to 47.1%, w/w), uronic acids (from 7.1% to 26.7%, w/w) and proteins (from 30.1% to 57.0%, w/w) in the crude polymer. Rhamnose, fucose, arabinose, xylose, mannose, glucose, galactose, galacturonic acid and glucuronic acid were detected as well as sulphate groups (from 9.6% to 21.5%, w/w of sugars). The main components found were glucose and mannose.

Animals↗
PubMed1981

A rapid method for isolating phorbol from croton oil.

The published method for isolating phorbol from croton oil has been improved and made more rapid, mainly by the addition of silica-gel column chromatography. The spectral characteristics are recorded, including the 13C nuclear magnetic resonance (NMR) spectrum.

Chromatography, Gel↗
PubMed1981

Combined effect of the extracts from Croton tiglium, Euphorbia lathyris or Euphorbia tirucalli and n-butyrate on Epstein-Barr virus expression in human lymphoblastoid P3HR-1 and Raji cells.

The combined usage of n-butyrate and 12-O-tetradecanoylphorbol-13-acetate (TPA) or the oily extracts from Croton tiglium, Euphorbia lathyris or Euphorbia tirucalli exerted a marked effect on induction of Epstein-Barr virus (EBV)-associated early (EA) and viral capsid (VCA) antigens in EBV genome-carrying human lymphoblastoid cell lines. In producer P3HR-1 cells, the enhancing effect of the 2 components was additive both for EA and VCA, while in non-producer Raji cells, a synergistic increase of EA was observed. The possible implication of these findings relating to the cause of EBV-associated diseases is discussed.

Antigens, Viral↗
PubMed1989

Effects of the gut-stimulating principle in Croton penduliflorus seed oil on the central nervous system.

The gut-stimulating principle in Croton penduliflorus seed oil isolated as white crystals (CP crystals) significantly reduced pentobarbitone-induced sleeping time in mice at doses of 3 and 6 mg/kg intraperitoneally. Indomethacin (4 mg/kg) and atropine (0.044 mg/kg) significantly reversed the action of CP crystals on pentobarbitone sleeping time with indomethacin having a profound reversal effect. CP crystals significantly reduced the mean onset of convulsions and the mean death time in mice treated with a surely convulsive dose of strychnine. CP crystals significantly reduced the intensity of morphine and pethidine analgesia and prolonged the duration of pethidine analgesia. Most actions of CP crystals suggest that it stimulates the CNS and reduces the intensity of opioids (except codeine) while prolonging their duration of analgesic action.

Analgesia↗
PubMed1995

Croton zehntneri: possible central nervous system effects of the essential oil in rodents.

The effects of essential oil of Croton zehntneri (Euphorbiaceae), orally administered were studied on behavioral parameters using rats and mice. The oil suspension did not modify pentobarbital induced-hypnosis, stereotypic behavior, catalepsy and amphetamine-induced hypermotility. The open-field behaviors were decreased and the minimal convulsant dose of pentylenetetrazole was increased.

Amphetamine↗