A simplified method for the determination of taxanes in yew needles by reversed‐phase (C18) high pressure liquid chromatography (original) (raw)
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Phytochemical Analysis, 1999
Clippings of Taxus canadensis were collected and divided into needles, twigs and whole clippings samples. The biomass was extracted and analysed for taxanes using high performance liquid chromatography. The addition of n-octylbenzamide as an internal standard was found to reduce the standard deviation of calculated yields by a third. Paclitaxel was found to be highest in needles (0.0434% dry wt). The presence of paclitaxel was confirmed by photodiode array spectra. Impurities were found to co-elute with other taxanes. A compound was tentatively identified as 9-dihydro-13-acetylbaccatin III based on residence time and UV spectra. The effect of storage on paclitaxel content was investigated and it was found that paclitaxel was stable in dried needles stored at room temperature for at least 1 year.
Natural Taxanes: From Plant Composition to Human Pharmacology and Toxicity
International Journal of Molecular Sciences
Biologically active taxanes, present in small- to medium-sized evergreen conifers of various Taxus species, are widely used for their antioxidant, antimicrobial and anti-inflammatory effects, but mostly for their antitumour effects used in the treatment of solid tumours of the breast, ovary, lung, bladder, prostate, oesophagus and melanoma. More of the substances found in Taxus plant extracts have medical potential. Therefore, at the beginning of this review, we describe the methods of isolation, identification and determination of taxanes in different plant parts. One of the most important taxanes is paclitaxel, for which we summarize the pharmacokinetic parameters of its different formulations. We also describe toxicological risks during clinical therapy such as hypersensitivity, neurotoxicity, gastrointestinal, cardiovascular, haematological, skin and renal toxicity and toxicity to the respiratory system. Since the effect of the drug-form PTX is enhanced by various Taxus spp. ext...
Screening of the needles of different yew species and cultivars for paclitaxel and related taxoids
Phytochemistry, 2000
The needles of several yew species and cultivars were analysed by high-pressure liquid chromatography for paclitaxel, 10deacetylpaclitaxel, cephalomannine, baccatin III, 10-deacetylbaccatin III and brevifoliol. About 750 samples were collected from ®ve dierent locations in the Netherlands and the UK. The results of this screening show a large variation in taxane content between the dierent species and cultivars. The content of paclitaxel and 10-deacetylbaccatin III varied from 0 to 500 mg/g and 0 to 4800 mg/g dried needles, respectively. Brevifoliol was found in a very high concentration in Taxus brevifolia. 10-Deacetylpaclitaxel, cephalomannine and baccatin III were found in concentrations ranging from 0 to 500 mg/g dried needles. #
Journal of Liquid Chromatography & Related Technologies, 2009
Four types of solvent extraction methods (ultrasound and microwave assisted extraction, pressurized liquid extraction, and extraction in the Soxhlet apparatus) for paclitaxel, cephalomannine and 10-deacetylbaccatin, taxoids recovered from common yew twigs, were compared. By use of pressurised liquid extraction the most effective extractant of taxoids was determined. HPLC was used for the analysis of extracts. Comparison of the obtained results revealed differences in the extraction power of the applied methods. The greatest yields were obtained by multiple PLE, which can be recommended as the best sample preparation method for taxoids analysis in yew twigs.
Journal of Chromatography A, 2001
An HPLC method was developed for quick scanning of taxanes from large numbers of plant cell suspension samples. The method was optimized for analysis of a range of taxanes of differing polarity. Identification of a standard mixture of paclitaxel and 12 related taxanes was achieved in less than 15 min using a gradient mode and a Microsorb-MV C column. 8 The method was used to investigate the influence of several factors on stability and recovery of paclitaxel from suspension media and cultures of Taxus cuspidata cv Densiformis. Incubation time had the most significant influence on stability of paclitaxel, contributing 88% to the total variation. Shaking contributed 6% to the total variation. Light contributed only 0.25% to the total variation. Analysis of test samples of suspension cultures of T. cuspidata cv Densiformis over a 4 week period show paclitaxel, 10-deacetylbaccatin III,
Journal of Immunological Methods, 1993
A rapid and sensitive indirect competitive inhibition enzyme immunoassay (CIEIA) method has been developed for quantitating taxanes in extracts of Tuxus breuifoliu Nutt. tissue and in human plasma. High titer rabbit polyclonal antibodies (pAb) were raised against a conjugate of 7-succinyltaxol and keyhole limpet hemocyanin. The presence of taxane analyte competitively inhibited the binding of the rabbit anti-taxane pAbs to a 7-succinyltaxol-bovine serum albumin solid phase coating antigen. The CIEIA detected taxol and cephalomannine in concentrations as low as 0.3 ng/ml (3.5 X lop4 PM), but did not detect baccatin III or lo-deacetylbaccatin III at concentrations below 1000 ng/ml (1.7 PM and 1.8 PM, respectively). This method is useful for estimating the taxane content of T. breuifoliu extracts and may be useful for monitoring the taxol plasma level of taxol-treated patients.
Journal of Chromatography A, 2011
Paclitaxel was purified using high-performance displacement chromatography (HPDC) technique, but not by the mechanism of HPDC. On small scale, paclitaxel was extracted with methanol from dry needles of Taxus canadensis and was enriched by extracting with chloroform after removing water-soluble hydrophilic components and hexane-soluble hydrophobic components. Then, 93-99% purity of paclitaxel was obtained using the HPDC technique. On large scale, taxanes were enriched by solvent partitioning between acetic acid/MeOH/H 2 O and hexane and extracted with CH 2 Cl 2. Taxanes except paclitaxel were further removed by extracting with methanol-water-trifluoroacetic acid (1.0:98.9:0.1, v/v/v). Applying HPDC technique to water-insoluble substances is problematic as this method requires a highly aqueous solvent system. In order to overcome this incompatibility, a system was set up where paclitaxel, although in low concentration, was extracted by methanol-water-trifluoroacetic acid (10.0:89.9:0.1, v/v/v). Recycling the extracting solvent to ensure minimal volume, the extracted paclitaxel was adsorbed on a C 18 trap column. A C 18 column of 4.6 mm internal diameter was then connected to the trap column. The HPDC technique was thus carried out using an isocratic acetonitrile-water-trifluoroacetic acid (30.0:69.9:0.1, v/v/v) mobile phase consisting of a displacer cetylpyridinium trifluoroacetate (3 mg/mL). Paclitaxel was co-eluted with the displacer and spontaneously crystallized. The crystal (114 mg) showed 99.4% purity and only 10% of paclitaxel in the starting crude extract was lost during the enrichment/purification processes. This large scale purification method was successfully applied to purify paclitaxel from Chinese yew in small scale, suggesting general applicability of the method. This is the first report of purifying a water-insoluble natural product using HPDC technique.
A new taxane from Taxus canadensis needles
Chemistry of Natural Compounds, 2012
Paclitaxel (Taxol ® ) [1] by virtue of its complex and densely functionalized, challenging and seductive structure, coupled with its novel mechanism of action, potent antitumor activity, and its clinical use as a powerful anticancer drug used for the treatment of ovarian and breast cancers as well as Kaposics sarcoma and non-small-cell lung cancers, has attracted the attention of many chemists and biological scientists. Indeed, taxol and its analogues continue to stimulate a great deal of interest in the isolation of further taxoids from plants in the genus Taxus. As a result, more than 550 taxane diterpenoids have been isolated and identified . The isolation of new and minor taxanes is important in the context of the plant biosynthesis and metabolism of these compounds .
Analysis of taxol and major taxoids in Himalayan yew, Taxus wallichiana
Journal of Chromatography A, 1999
A reversed-phase column liquid chromatography method for the analysis of taxol, 10-deacetylbaccatin III, baccatin IV, 1-hydroxybaccatin I, 2-acetoxybrevifoliol, brevifoliol, 2′-deacetoxydecinnamoyltaxinine J and 2′-deacetoxytaxinine J in yew needles has been developed using a Nova-Pak Phenyl column and a binary gradient profile. The various aspects of analysis such as extraction efficiency, detection limits, reproducibility and peak purity were validated using UV–Vis as well as photodiode array detection.