Analysis of taxol and related taxanes from <i>taxus canadensis</i> using liquid chromatography combined with mass spectrometry or tandem mass spectrometry

Blay, P. K. S.; Thibault, Pierre; Thiberge, N.; Kiecken, B.; Lebrun, A.; Mercure, C.

doi:10.1002/rcm.1290070715

Cited by 21 publications

(12 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the past decade, liquid chromatography/mass spectrometry (LC/MS) has been recognized as the most appropriate analytical technique for qualitative analysis or pharmacokinetic studies of taxane analogues from realistic samples due to its high sensitivity, specificity and structure characterization ability 12–24. Among these reports, electrospray ionization (ESI) was preferred due to its high‐efficiency ionization 18–24.…”

Section: Methodsmentioning

confidence: 99%

Stereochemical differentiation of C‐7 hydroxyltaxane isomers by electrospray ionization mass spectrometry

Zhang

et al. 2009

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

In this study, different electrospray ionization mass spectrometric (ESI-MS) methods were utilized to analyze several pairs of taxane stereoisomers including paclitaxel and 7-epi-paclitaxel. Both ESI-MS and tandem mass spectrometry (MS/MS) techniques provided stereochemically dependent mass spectra in negative-ion mode, and all studied stereoisomers could be easily distinguished based on their characteristic ions or distinct fragmentation patterns. MS/MS experiments for several taxane analogues at various collision energies were performed to elucidate potential dissociation pathways. The gas-phase deprotonation potentials were also calculated to estimate the most thermodynamically favorable deprotonation site using DFT B3LYP/6-31G(d). The results of the theoretical studies agreed well with the fragmentation patterns of paclitaxel and 7-epi-paclitaxel observed from MS/MS experiments. In addition, it was found that liquid chromatography (LC)/ESI-MS was a useful and sensitive technique for assignment of C-7 taxane stereoisomers from realistic samples.

show abstract

Section: Methodsmentioning

confidence: 99%

Stereochemical differentiation of C‐7 hydroxyltaxane isomers by electrospray ionization mass spectrometry

Zhang

et al. 2009

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…This technique permits the determination of intact alkaloids [22] and was successfully applied to determine Taxus ingredients as well as Taxus pseudoalkaloids itself [14,[23][24][25]. One method provided semiquantitative data in reference to the whole taxine fraction [9].…”

Section: Introductionmentioning

confidence: 99%

Quantitative determination of taxine B in body fluids by LC–MS–MS

Frommherz

Kintz²,

Kijewski³

et al. 2006

Int J Legal Med

View full text Add to dashboard Cite

A new specific and sensitive LC-MS-MS method for the detection of taxine B and isotaxine B, the main toxic pseudo-alkaloids from yew (Taxus sp.), in biological samples (blood, urine, gastric content) was developed. Biological samples were prepared for LC-MS-MS by means of solid-phase extraction (SPE) procedure and yielded a recovery of 86%. Chromatographic separation was achieved using an RP(18) column. Detection of taxine B and isotaxine B was performed using multiple reaction monitoring with m/z 584.2 as precursor ion, i.e. [M+H](+), of both isomers and m/z 194.3 and m/z 107.1 as product ions after collision-induced dissociation. Docetaxel was applied as internal standard. The method was fully validated for the analysis of blood samples. Linearity was proven in the range from 0.1-500 ng/g. The limit of detection and the limit of quantitation are 0.4 and 2 ng/g, respectively. The method was applied to the determination of taxine B and isotaxine B in four fatal cases (two humans, two horses) with suspected yew intoxication. Blood levels were 105, 168, 174 and 212 ng/g.

show abstract

“…[14,15,16,17] as well as to clarify the cause of death, even if rare or recently developed substances are involved [18]. A direct determination of Taxus alkaloids by LC-MS has been reported to analyse the stomach content of horses which were suspected of having been poisoned [19].…”

Section: Introductionmentioning

confidence: 99%

LC-MS determination of Taxus alkaloids in biological specimens

Beike

Karger

Meiners

et al. 2003

International Journal of Legal Medicine

View full text Add to dashboard Cite

A semi-quantitative LC-MS method was developed for the detection of the pseudo alkaloids of Taxus baccata (yew) from human body fluids and tissue samples. This method was used to examine the cause of death of a 43-year-old man who died several hours after he drank a decoction of taxus leaves. Autopsy and histology demonstrated early signs of myocardial hypoxia. Since investigation of the stomach content did not yield evidence of taxus ingestion, the taxus alkaloids were determined in blood, stomach content and tissue samples of the deceased by LC-MS. The samples were prepared by solid phase extraction on RP-18 columns. Chromatographic separation was achieved by HPLC on a RP-8 column, coupled to an ion trap mass spectrometer (Finnigan LCQ). An atmospheric pressure electrospray ionisation was performed. Spectra of the alkaloids were recorded in the single MS mode and in the MS-MS mode and compared with reference spectra obtained from an extract of yew leaves. In the stomach content, the kidneys, the liver and a heart blood sample of the deceased, alkaloids of Taxus baccata, predominantly taxine B and iso-taxine B, were identified. The semi-quantitative evaluation of the heart blood revealed a taxine concentration of 11 µg taxine/g. As far as we know this is the first case in which a semi-quantitative analysis of taxine alkaloids has been performed.

show abstract

Analysis of taxol and related taxanes from taxus canadensis using liquid chromatography combined with mass spectrometry or tandem mass spectrometry

Cited by 21 publications

References 22 publications

Stereochemical differentiation of C‐7 hydroxyltaxane isomers by electrospray ionization mass spectrometry

Stereochemical differentiation of C‐7 hydroxyltaxane isomers by electrospray ionization mass spectrometry

Quantitative determination of taxine B in body fluids by LC–MS–MS

LC-MS determination of Taxus alkaloids in biological specimens

Contact Info

Product

Resources

About