Showing papers on "Brucine published in 2010"

Simultaneous determination of six alkaloids in blood and urine using a hydrophilic interaction liquid chromatography method coupled with electrospray ionization tandem mass spectrometry.

Abstract: A method was developed for the simultaneous determination of six toxic alkaloids (aconitine, hypaconitine, gelsemine, raceanisodamine, strychnine, brucine) in blood and urine by hydrophilic interaction liquid chromatography (HILIC) coupled with electrospray tandem mass spectrometry. Ephedrine was selected as the internal standard. Samples were extracted and cleaned up by solid-phase extraction (SPE) using Oasis MCX cartridges. Separation parameters such as organic modifier, buffer pH, and concentration of buffer salt were investigated. Gradient separation and analysis were achieved for six alkaloids on a 3-μm Atlantis HILIC column using a mobile phase consisting of 30 mM ammonium formate and acetonitrile at pH 3. Two multiple reaction monitoring (MRM) transitions for each substance were monitored to provide sufficient identification of alkaloid. The retention mechanisms were explored in the method development. Validation included assessment of linearity, limit of quantification, accuracy, and precision. Bias was less than 15.1% and precision was better than 8.3% for both blood and urine samples. A total of 54 clinical samples were examined by this validated method.

The resolution of DL‐4‐oxalysine

Abstract: Both enantiomorphs have been isolated from racemic Nα, Nδ-diphthaloyl-4-oxalysine in optically pure form via brucine salts and converted into (+)-and (-)-4-oxalysine by acid hydrolysis. (-)-4-Oxalysine has a negative Cotton-effect from which we conclude that this stereoisomer possesses the D-configuration. This conclusion is corroborated by the formation of a quasi-racemic compound between (+)-Nα, Nδ-diphthaloyl-4-oxalysine, stereochemically corresponding to (-)-oxalysine, and Nα, Nδ-diphthaloyl-L-4-thialysine.

Crucial factors influencing racemic resolution of N-(4-nitrobenzoyl)-DL-serine by brucine

Abstract: Twelve new crystalline products (1–12) presented in the paper are the result of different or similar recognition of N-(4-nitrobenzoyl)-D- and N-(4-nitrobenzoyl)-L-serine by brucine dependent on the solvent used (methanol or ethanol), as well as how the sample for crystallization was prepared. Depending on the temperature at which the samples for crystallization were prepared, racemic resolution of N-(4-nitrobenzoyl)-DL-serine can be efficient or inefficient (4 and 1).

Simultaneous determination of strychnine and brucine in herbal formulation by UV derivative spectrophotometry.

Abstract: A simple, precise and accurate UV first order derivative spectrophotometric method has been developed and validated for the quantitative determination of strychnine and brucine in herbal formulation. The response of strychnine and brucine was linear over the range of 10-50 mg/mL respectively. The strychnine and brucine in herbal formulation were quantified using the first order derivative spectrum in which strychnine responded at 265.4 nm and brucine responded at 256.4 nm. The developed UV method was validated in terms of precision, accuracy, stability, LOD and LOQ.

Brucine‐Derived Amino Alcohol Catalyzed Asymmetric Henry Reaction: An Orthogonal Enantioselectivity Approach.

Abstract: A new approach to both enantioenriched Henry products is developed by use of different molecularities of metal−ligand complexes generated from Cu(I) and Zn(II) metals with readily available chiral amino alcohol 1.

Study on Bcl-2 and Caspase-3 Expression in Brain Nervous Cell after Brucine Poisoning

Abstract: Objective To observe changes in expression of Bcl-2 and Caspase-3 under different times and dosages after brucine poisoning.Methods20 Wistar rats were taken as the normal control group and 44 Wistar rats as brucine poisoning model group.Changes in expression of Bcl-2 and Caspase-3 in the rat brain cells after brucine poisoning were investigated using immunohistochemistry and computer competitive image analysis system.ResultsIn the different time periods of 1~7 days after low and medium dosages brucine poisoning,the cell numbers of positive expression of Bcl-2 and Caspase-3 were higher than those of the normal control.The differences were statistically significant(P0.05).ConclusionsBcl-2 and Caspase-3 were involved in the pathophysiological process of rat brucine poisoning.

Hydrophilic-Interaction Chromatography with UV Detection for Analysis of Strychnine and Brucine in the Crude Seeds of Strychnos nux-vomica and Their Processed Products

Abstract: An easy and rapid method based on hydrophilic-interaction chromatography has been developed and validated for measurement of two major alkaloids, strychnine and brucine, in Strychnos nux-vomica plant seeds and preparations. The seeds were processed in different ways. Separation was performed at ambient temperature on a carbohydrate column with acetonitrile–water 90:10 (v/v) as mobile phase at a flow rate of 1.0 mL min−1. Detection was at 254 nm. Calibration plots were linear over the range 0.1–200 μg mL−1 for both compounds. Average recoveries of strychnine and brucine from spiked samples were 99.9 and 98.5%, respectively.

Asymmetric Darzens-Type Epoxidationvia Chiral Ammonium Ylides

Abstract: Asymmetric Darzens-type epoxide formation of aryl aldehydes with chiral para-substituted benzylammonium ylides, prepared from brucine and corresponding benzylic chlorides and treated in situ under basic condition, was carried out to afford chiral 2,3-diaryl epoxides with moderate to good ee (84% ee). Brucine was found to be an excellent tertiary amine for a chirality transfer agent.

The reaction of 2-chlorocyclohexanol with brucine

Abstract: 2-Chlorocyclohexanol-1 forms a clathrate compound with brucine. This reaction provides a means of obtaining chlorocyclohexanol - and related compounds - that are partially resolved into optical antipodes.

Characterization Of In Vitro Metabolism of Brucine Using Human Liver Microsomes

Abstract: Background. Brucine, one of the bitter alkaloids isolated from Chinese folk medicine Strychnos nux-vomica L. (Loganiaceae), is known as an effective analgesic and anti- inflammatory agent for relieving arthritic and traumatic pain. However, therapeutic application of brucine is limited by its high incidence of side-effects, such as violent convulsion and even lethal poisoning. Thus, it is imperative to investigate the brucine’s metabolic profile in human which is helpful for understanding the pharmacology and toxicology of brucine. Method. In the present study, characterization of the metabolites and cytochrome P450 isoforms involved in the metabolism of brucine were investigated in vitro incubation systems by using human liver microsomes(HLMs) and recombinant human CYP isoforms (rhCYPs). Results. Two major metabolites (M-1 and M-2) and one minor metabolite (M-3) were detected when brucine was incubated with HLM in the presence of NADPH. M1 and M2 were tentatively identified as mono-oxygenated metabolites and the minor metabolite (M-3) was assigned as demethylated metabolite by using liquid chromatography /mass spectrometry (LC/MS). CYP3A4 was identified as the major CYP isoforms involved in the formation of the two major metabolites(M-1 and M-2) by a series of studies including inhibition with specific P450 inhibitors, metabolism by rhCYP isoforms, and correlation analysis. In human liver microsomes, the Km values were 111.3±3.4 and 94.5±3.9 μM, and the Vmax values were 62.9±0.7 and 117.0±1.6 pmol/min/mg for M-1 and M-2, respectively. Conclusion. This study clarified the metabolite profile and kinetic properties of brucine in human and provided important information relevant to the pharmacology and toxicology of brucine and brucine-containing Chinese Traditional Medicines.

Apoptosis of U266 cells induced by brucine through death-receptor pathway

Abstract: Objective To investigate the mechanism of the apoptotic effect of brucine on human multiple myeloma. Methods MTT, morphology, flow cytometry, and RT-PCR were used to observe the apoptotic pathways of brucine on human multiple myeloma cell line-U266. Results The apoptotic effect of brucine showed a dose and time dependent manner, 48 hour IC50 0.16 mg/ml. The cells treated with brucine showed significant feature associated with apoptosis by Hoechst 33258 at fluorescence microscope.Mitochondrial membrance potential showed no statistical significant difference in different concentration with Rhodamine 123 by flow cytometry (P ＞0.05). The Caspase-3 expression detected by RT-PCR was increased at 12, 24 and 48 hours treated with brucine, and its gray value was (0.2597±-0.020), (0.5488±0.016), (0.6205±0.006), (0.6533±0.009) (P ＞ 0.05), detection of added z-IETD-fmk, z-LEHD-fmk (Caspase-8 and Caspase-9specific inhibitor) the expression of Caspase-3, the gray scale values were (0.7118±0.006), (0.2637±0.003)(P ＜0.01); and (0.7182±0.004) (0.7195±0.003) (P=0.836). Caspase-8 was activated. Conclusion Within the 0.4 mg/ml concentration brucine can induce apoptosis in U266 cells. Brucine induced apoptosis on cell line U266 through Caspase-8 activation by death-receptor pathway. Key words: Brucine; U266 cell line; Apoptosis

Use of (S)-α-Methylbenzylamine in the Resolution of Racemic 2- Octanol and α-Methylbenzyl Alcohol.

Abstract: The title chiral amine can be a convenient substitute for brucine or strychnine in Ingersoll's classical method for the resolution of alcohols via fractional crystallization of their diastereoisomeric phthalate salts.