Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Crotonates”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 127 records · Page 7Linked to original sources

Biosynthesis of beta-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units.

A green callus culture of Croton sublyratus Kurz established from the leaf explants appeared to actively synthesize two well-known phytosterols, beta-sitosterol and stigmasterol. The phytosterol biosynthesis was highly active during the linear phase of the culture. Feeding of [1-13C]glucose into the callus culture at this growth phase showed that the label from glucose was highly incorporated into both phytosterols. Isolation of the labeled products followed by 13C NMR analysis revealed that the phytosterols had their 13C-labeling patterns consistent with the acquisition of isoprene units via both the mevalonate pathway and the deoxyxylulose pathway with relatively equal contribution. Since the biosynthesis of phytosterol has so far been reported to be mainly from the classical mevalonate pathway, this study provides a new evidence on the biosynthesis of phytosterols via the novel deoxyxylulose pathway.

Butadienes↗

A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi.

Aerial parts of Croton hieronymi furnished in addition to a large number of plant sterols and triterpenes the C-25 analog of trans-phytol, the squalene derivatives all-trans-2,6,15,19,23-pentamethyltetracosa-2,6,10,(28),14,22,28-hexaene-11-ol and all-trans-10-methylene-2,6,10,14,18,22-pentamethyltetracosa-1,6,10,14,18,22-hexaen-3-ol, the sesquiterpenes epicubenol and T-cadinol, the acetophenone derivative xanthoxylin and the peptide derivatives aurentiamide acetate and N-benzoylphenylalanyl-N-benzoylphenylalaninate.

Croton↗

Cis-4-amino-crotonic acid activates alpha 6 subunit-containing GABA(A) but not GABA(C) receptors in granule cells of adult rat cerebellar slices.

The expression of GABA(C) receptors in granule cells of adult rat cerebellar slices was investigated. The GABA(C) receptor agonist cis-4-amino-crotonic acid (CACA) evoked currents in granule cells. However, CACA-evoked currents were not blocked by the GABA(C) receptor antagonist (1,2,5,6-tetrahydropyridine-4-yl)methylphosphinic acid (TPMPA), but were blocked by the GABA(A) receptor antagonist bicuculline. CACA activated alpha6 subunit-containing GABA receptors as CACA-evoked currents were reduced by furosemide and CACA activated alpha6beta2gamma2s receptors expressed in HEK 293 cells. The channels opened by CACA had conductances which were larger than those described for GABA(C) receptors but were similar to those described for GABA(A) receptors. GABAergic synaptic currents were blocked by low concentrations of bicuculline, but not by TPMPA. Thus, cerebellar granule cells express functional GABA(A) but not GABA(C) receptors.

Animals↗

Sangre de grado Croton palanostigma induces apoptosis in human gastrointestinal cancer cells.

Sangre de grado is an ethnomedicinal red tree sap obtained from Croton spp. that is used to treat gastrointestinal ulcers, cancer and to promote wound healing. To evaluate the potential role of sangre de grado (SdG) in cancer we examined its effects on human cancer cells, AGS (stomach), HT29 and T84 (colon). Viability of cells treated with SdG (10-200 microg/ml) decreased (P<0.01) in a dose dependent manner measured over a 24-h period. Cell proliferation at 48 h decreased (P<0.01) in all cells treated with SdG (>100 microg/ml). When cells in suspension were treated with SdG (100 microg/ml) cell adherence was severely compromised (>85%). Cells treated with SdG (100 microg/ml) underwent apoptosis as detected by nucleus condensation and DNA fragmentation determined by ELISA, and flow cytometry. Morphological changes as assessed by acridine orange. These effects were similar to that observed with Taxol (30 microM). A significant alteration of microtubular architecture was equally observed in both stomach and colon cancer cells exposed to SdG (100 microg/ml). The induction of apoptosis and microtubule damage in AGS, HT29 and T84 cells suggest that sangre de grado should be evaluated further as a potential source of anti-cancer agents.

Antineoplastic Agents↗

Suppression of croton oil-induced rabbit corneal edema by sideritis javalambrensis.

This investigation was designed to evaluate the anti-inflammatory activity of the aqueous and hexane extracts of Sideritis javalambrensis, to which pharmacological properties have been attributed in Spanish traditional medicine. The extracts were applied as eye drops in a croton oil-induced corneal edema model in rabbits. Corneal thickness was estimated before the induction of inflammation and 3, 6, 8, 12, 48, 72 and 96 h after induction. Significant inflammation inhibition percentages were shown during both the acute and chronic stages of inflammation by both extracts and by the reference drug dexamethasone, with most therapeutic effect shown during the chronic phase. However, the hexane extract exhibited potent anti-inflammatory activity from 6 to 24 h post-induction, achieving greater percentage inhibition values during this stage than those obtained for dexamethasone.

Animals↗

Croton zehntneri essential oil: effects on behavioral models related to depression and anxiety.

Croton zehntneri (Cz), a popular plant used to treat "nervous disturbance", contains a complex mixture of compounds, including substances exhibiting central nervous system activity. The effects of Cz essential oil administration (p.o.) on the rat's central nervous system were studied in behavioral models used to evaluate anxiety and antidepressive drugs. The results showed that administration of Cz essential oil: 1) increased the immobility duration measured in the forced swimming test as compared to control group (control = 89.8 +/- 45.8; 1 microl = 153.0 +/- 48.7; 3 microl = 157.4 +/- 45.3; 10 microl = 145.3 +/- 51.0); 2) reduced the locomotion frequency observed in the open field (control = 62.5 +/- 22.7; 3 microl = 38.0 +/- 13.5; 10 microl = 39.2 +/- 22.2); 3) had no effect on the experimental group (1 microl) observed in open field; 4) had no effect on animals tested in social interactions, plus-maze and holeboard tests. These data suggest that Cz oil produced central depressor effects in rats without any anxiety alterations. These results may explain the popular use of this plant in Brazilian folk medicine for treating "nervous disturbances".

Animals↗

Minor diterpenoids from cascarilla (Croton eluteria Bennet) and evaluation of the cascarilla extract and cascarillin effects on gastric acid secretion.

Three new diterpenoids belonging to the clerodane (2-3) and halimane (4) structural types have been isolated from the bark of Croton eluteria Bennet, commonly known as cascarilla. Their structures have been fully characterized by spectroscopic means. Cascarilla extract and its major component, cascarillin, were found to significantly increase histamine-induced gastric acid secretion in the mouse stomach. These preliminary results provide the first rationale for the use of cascarilla in bitter preparations aimed at improving digestion.

Animals↗

Pachypodol from Croton ciliatoglanduliferus Ort. as water-splitting enzyme inhibitor on thylakoids.

A bioactivity-guided chemical study of aerial parts of Croton ciliatoglanduliferus Ort. led to the isolation for the first time of the flavonoids retusin (5-hydroxy-3,7,3',4'-tetramethoxyflavone) (1) and pachypodol (5,4'-dihydroxy-3,7,3'-trimethoxyflavone) (2) from the n-hexane extract. Compounds 1 and 2 were separated by preparative thin-layer chromatography. Compound 2 was the most active compound on ATP synthesis inhibition. The I50 value was 51 microM. Pachypodol behaves as a Hill reaction inhibitor. It inhibited the uncoupled electron flow on photosystem II partial reaction from water to dichlorophenol indophenol (DCPIP) and from water to sodium silicomolybdate. However, the uncoupled partial reaction from diphenylcarbazide to DCPIP and the uncoupled photosystem I from DCPIPred to MV were not inhibited by 2. These results were corroborated by fluorescence decay data. Therefore, pachypodol inhibits the water-splitting enzyme activity. Compound 1 with a 4'-methoxy group was a weak inhibitor, indicating that the 4' free -OH group is important for strong inhibition.

2,6-Dichloroindophenol↗

Antifungal activity of 4-substituted crotonic acid esters.

Twenty-three 4-substituted crotonic acid esters were tested for antifungal activity against Candida albicans, Aspergillus niger, Mucor mucedo, and Trichophyton mentagrophytes. For the analogues of the methyl ester containing substituents in the 4 position, the following order of fungitoxicity was observed: I greater than Br greater than Cl greater than CH3S greater than CH3O greater than F=H. Of the homologues of the esters of the 4-iodo and 4-bromo compounds which included methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl, ethyl 4-iodocrotonate was most toxic to the four fungi at pH 7.0 in the presence of 10% beef serum (C. albicans, 18mug/ml, A. niger, 40 mug/ml, M. mucedo, 5 mug/ml, T. mentagrophytes, 4 mug/ml). It is believed that the mechanism of fungitoxicity is due, in part, to a nucleophilic reaction involving SH-containing compounds. This is based on the correlation of fungitoxicity with the order of leaving groups in the nucleophilic reaction and the protection against the toxicity of the test compounds to the fungi by cysteine and glutathione.

Antifungal Agents↗

Geographic distribution of three alkaloid chemotypes of Croton lechleri.

Three known alkaloids, isoboldine (2), norisoboldine (1), and magnoflorine (8), have been isolated for the first time from Croton lechleri, a source of the wound healing latex "sangre de grado". An HPLC system was developed, and a large number of latex and leaf samples of C. lechleri from 22 sites in northern Peru and Ecuador were analyzed to gain an understanding of the natural variation in alkaloid content for the species. Up to six alkaloids were found to occur in the leaves including, in addition to those listed above, thaliporphine (3), glaucine (4), and taspine (9), whereas the latex contained only 9. Taspine (9) is the component that has been previously found to be responsible for the wound healing activity of C. lechleri latex, and its mean concentration throughout the range examined was found to be 9% of the latex by dry weight. In addition, three chemotypes are defined based on the alkaloid content of the leaves, and the geographic distribution of these chemotypes is discussed along with a quantitative analysis of the alkaloid content as a function of chemotype.

Alkaloids↗

Neoclerodane diterpenoids from Croton eluteria.

Five new neoclerodane diterpenoids, rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4-dihydroxy-20-methoxyneocleroda-13(16),14-diene (1), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-15,16,12,20-diepoxy-3,4,20-trihydroxyneocleroda-13(16),14-diene (2), rel-(3R,4S,5S,6R,7S,8S, 9R,10S,12R,20S)-6,7-diacetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (3), rel-(3R,4S,5R,7R,8S,9R,10S,12R,20S)-7-acetoxy-3,4,15,16,12,20-triepoxy-20-hydroxyneocleroda-13(16),14-diene (4), and rel-(3R,4S,5R,7R,8S,9R,10S,12R,20R)-7,20-diacetoxy-3,4,15,16,12,20-triepoxyneocleroda-13(16),14-diene (5), have been isolated from the bark of Croton eluteria. The structures of the compounds 1-5 (cascarillins E-I) were determined by spectroscopic data interpretation.

Chromatography, High Pressure Liquid↗

ent-Kaurane diterpenoids from croton tonkinensis inhibit LPS-induced NF-kappaB activation and NO production.

Four ent-kaurane diterpenoids including two known, ent-7alpha,14beta-dihydroxykaur-16-en-15-one (1) and ent-18-acetoxy-7alpha-hydroxykaur-16-en-5-one (2), and two new, ent-1beta-acetoxy-7alpha,14beta-dihydroxykaur-16-en-15-one (3) and ent-18-acetoxy-7alpha,14beta-dihydroxykaur-16-en-15-one (4), were isolated from the leaves of Croton tonkinensis in a search for inhibitors of NF-kappaB activation and nitric oxide production. These ent-kauranoids inhibited LPS-induced NF-kappaB activation in murine macrophage RAW264.7 cells at IC50 values between 0.07 and 0.42 microM. Consistently, the ent-kauranoids markedly reduced LPS-induced NO production in a comparable concentration-dependent manner.

Animals↗

New diterpenes from Croton insularis.

Two new diterpenes (1 and 2) have been isolated from the aerial parts of Croton insularis. Their structures have been established by NMR and mass spectral data, and the absolute configuration of 1 and related trachylobane diterpenes was determined through a series of chemical correlations.

Animals↗

Three new sesquiterpenes from Croton arboreous.

Three new sesquiterpenes, 5alpha,7alpha,10betaH-3-patchoulen-2-one (1), 5alpha,7alpha10betaH-4(14)-patchoulen-2alpha-ol (2), and 9alpha,10beta-dihydroxy-2beta,4beta-peroxy-1alpha,5beta,7alphaH-guaiane (3), were isolated from the aerial parts of Croton arboreous along with 14 known compounds. The structures of these compounds were determined on the bases of their spectroscopic data (IR, UV, OR, 1D and 2D NMR, and MS). The anti-inflammatory activity against ear edema in mice produced by 12-O-tetradecanoylphorbol-13-acetate (TPA) was evaluated for all the pure compounds and showed that compounds 4-7 are active.

Animals↗

Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and -2.

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.

Animals↗

Musidunin and musiduol, insect antifeedants from Croton jatrophoides.

Two novel limonoids, musidunin (1) and musiduol (2), were isolated from a methanol extract of Croton jatrophoides by bioassay-guided fractionation. Their structures were established by extensive NMR experiments. Interestingly, A,B-seco limonoid 1 contains a unique acetal annulation of A, A', and B' rings. Both limonoids exhibited antifeedant activities against two pests, Pectinophora gossypiella and Spodoptera frugiperda.

Animals↗

Defensive chemistry of an aposematic bug, Pachycoris stallii Uhler and volatile compounds of its host plant Croton californicus Muell.-Arg.

Volatile components of Pachycoris stallii scent gland secretions and the bug's host plant, Croton californicus, were identified by gas chromatography and mass spectroscopy. The predominant compounds isolated from C. californicus fruit and leaves were beta-myrcene and beta-caryophyllene. Metathoracic gland secretions of P. stallii contained mostly (E)-2-hexenal, (E)-4-oxo-2-hexenal, (E)-2-hexenyl acetate, and n-tridecane. In males, n-tridecane was present throughout the metathoracic gland, but in females this compound was found only in the median reservoir/accessory gland. (E)-2-Hexenal was present throughout the gland of female bugs, but in males was primarily present in the median reservoir/accessory gland. (E)-4-Oxo-2-hexenal and n-dodecane were isolated from the median reservoir/accessory gland of male and female bugs. Metathoracic glands were sexually monomorphic. Data from chemical analyses and anatomical observations suggest that dorsal abdominal glands of adults were apparently obsolescent. In nymphs, dorsal abdominal glands produced (E)-2-hexenal, (E )-4-oxo-2-hexenal, n-dodecane, n-tridecane, and tetradecanal. The proportion of the predominant constituent, (E)-4-oxo-2-hexenal, decreased from 72% in the first instar to 47% in the fourth instar. Proportions of tetradecanal and n-tridecane were greater in the fourth instar than in the first instar. Observations of dissected glands indicated that median and posterior dorsal abdominal glands of all nymphal instars were more developed than anterior dorsal abdominal glands. Scanning electron micrography revealed the presence of polygonal microsculpturing on the integument surrounding the ostioles of metathoracic and dorsal abdominal glands. Chemical, anatomical, and behavioral data indicated that P. stallii has a chemical defense system based on short-chain carbonyl compounds and that this system is directed against arthropods. The abundance of arthropod natural enemies apparently has forced P. stallii to maintain this defense system despite feeding on a toxic host plant.

Acetates↗