Simultaneous determination of main taxoids in <i>Taxus</i> needles extracts by solid‐phase extraction‐high‐performance liquid chromatography with pentafluorophenyl column

Fu, Yujie; Sun, Rui; Zu, Yuangang; Liu, Wei; Efferth, Thomas; Gu, Cheng‐Bo; Lin, Zhihong; Luo, Hao

doi:10.1002/bmc.1085

Cited by 19 publications

(15 citation statements)

References 36 publications

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“…Its content in yew trees is as much as 0.5% (dry weight of the bark)18. XDT content is even higher than that of Taxol in nursery cultivated yew trees1920. This analogue is usually discarded during Taxol extraction, causing both resource waste and potential environmental pollution.…”

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confidence: 99%

Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production

Wang

Gong

et al. 2017

Nat Commun

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The natural concentration of the anticancer drug Taxol is about 0.02% in yew trees, whereas that of its analogue 7-β-xylosyl-10-deacetyltaxol is up to 0.5%. While this compound is not an intermediate in Taxol biosynthetic route, it can be converted into Taxol by de-glycosylation and acetylation. Here, we improve the catalytic efficiency of 10-deacetylbaccatin III-10-O-acetyltransferase (DBAT) of Taxus towards 10-deacetyltaxol, a de-glycosylated derivative of 7-β-xylosyl-10-deacetyltaxol to generate Taxol using mutagenesis. We generate a three-dimensional structure of DBAT and identify its active site using alanine scanning and design a double DBAT mutant (DBATG38R/F301V) with a catalytic efficiency approximately six times higher than that of the wild-type. We combine this mutant with a β-xylosidase to obtain an in vitro one-pot conversion of 7-β-xylosyl-10-deacetyltaxol to Taxol yielding 0.64 mg ml−1 Taxol in 50 ml at 15 h. This approach represents a promising environmentally friendly alternative for Taxol production from an abundant analogue.

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confidence: 99%

Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production

Wang

Gong

et al. 2017

Nat Commun

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“…In contrast, the extraction yields of seven taxanes decreased with high water content of 50–100%. Interestingly, when compared with 80% ethanol usually used for the extraction of taxanes [4,5], the 80% water content in the natural aqueous DES showed a similar extraction efficiency for the 10‐DAB III and higher extraction efficiency for the other six taxanes. Considering that 80% water content of the prepared aqueous DES has the characteristics of less solvent consumption, better extraction efficiency, and is eco‐friendly, we chose the menthol‐based aqueous DES with 80% water volume and only 20% menthol/1‐propanol for sample preparation of taxanes.…”

Section: Resultsmentioning

confidence: 99%

“…Paclitaxel, a natural diterpenoid alkaloid with distinct chemical structure, was initially isolated from the bark of Taxus brevifolia [1,2] and considered as a natural anticancer drug used to cure malignant tumors such as breast, ovarian, lung, and non‐small cell lung cancer [3–6]. After a period of clinical application, it has been found that as an active ingredient of a medicinal plant, there were a series of problems in the development of paclitaxel drugs, such as paclitaxel production is still very far away to meet the needs for clinical applications.…”

Section: Introductionmentioning

confidence: 99%

A simple and efficient sample preparation for taxanes in Taxus chinensis needles with natural menthol‐based aqueous deep eutectic solvent

Fan

Chang

Wang

et al. 2020

J of Separation Science

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Taxanes are natural anticancer constituents, and the sample preparation from matrix normally depends on organochlorine solvents. In this study, green and natural menthol-based aqueous deep eutectic solvent was synthesized and used for sample preparation for taxanes. Five key parameters were optimized and the optimal preparation conditions were as follows: menthol/1-propanol ratio 1:1 (mol/mol), solid-liquid ratio 1:30 g/mL, extraction time 30 min, ultrasonic power 250 W, and water content 80%. Under the above conditions, the total extraction efficiency of seven main taxanes was 1.25-to 1.44-fold to the conventional methods. In addition, a high-performance liquid chromatography method with C 18 column was established for quantitation of seven main taxanes in <25 min, which had excellent linearity (R 2 > 0.9986), precision (relative standard deviation < 3.00%), repeatability (relative standard deviation < 3.69%), and recovery (90.26-109.00%). This method performed the extraction, and enrichment processes simultaneously, and it had advantages such as high extraction efficiency, simple operation, low cost, and eco-friendliness. This work indicated that the natural menthol-based deep eutectic solvent aqueous could be an excellent alternative to the sample preparation from Taxus or other plants. K E Y W O R D S aqueous deep eutectic

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“…The mobile phase consisted of ACN (A) and water (B). Based on previous research [50], baseline separation of paclitaxel and other taxoids was achieved with a gradient elution program as follows: 25% A at the first 17 min, and then ramped to 37% A at 18 min, held until 58 min. The UV detector was set at the wavelength of 234 nm.…”

Section: Hplc Analysis Of Four Taxoidsmentioning

confidence: 99%

Preparative separation and enrichment of four taxoids from Taxus chinensis needles extracts by macroporous resin column chromatography

Sun

et al. 2009

J of Separation Science

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Preparative separation and enrichment of four taxoids from Taxus chinensis needles extracts by macroporous resin column chromatography An environment-friendly method was established for the preparative separation and enrichment of four taxoids, namely 10-deacetylbaccatin III (10-DAB III), 7-xylosyl-10-deacetyltaxol (7-xyl-10-DAT), cephalomannine and paclitaxel from Taxus chinensis needles extracts. Characteristics of seven widely used macroporous resins for four taxoids were compared, AB-8 resin offered better adsorption and desorption capacities than others. AB-8 resin column chromatography was used to study the desorption process for four taxoids. The optimum parameters for desorption were 30% ethanol 5 RV for removing impurities, following 15 RV for 10-DAB III, after the desorption of impurities with 35% ethanol 10 RV, 45% ethanol 30 RV for 7-xyl-10-DAT, then 65% ethanol 10 RV for cephalomannine and paclitaxel, the flow rate was 6 RV/ h. After separation on AB-8 resin column chromatography, the contents of 10-DAB III, 7-xyl-10-DAT, cephalomannine and paclitaxel in the product reached 4.58, 13.17, 1.36 and 3.08%, respectively, which were 7.63-, 3.68-, 6.18-and 6.55-fold to those in T. chinensis needles extracts. The recovery yields were 94.96, 77.32, 88.09 and 95.25%. In general, the AB-8 resin column chromatography has the advantages of lower cost, high efficiency and simple procedure. Therefore, it may provide scientific references for the preparative separation and enrichment of taxoids from other T. species.

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Simultaneous determination of main taxoids in Taxus needles extracts by solid‐phase extraction‐high‐performance liquid chromatography with pentafluorophenyl column

Cited by 19 publications

References 36 publications

Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production

Improving 10-deacetylbaccatin III-10-β-O-acetyltransferase catalytic fitness for Taxol production

A simple and efficient sample preparation for taxanes in Taxus chinensis needles with natural menthol‐based aqueous deep eutectic solvent

Preparative separation and enrichment of four taxoids from Taxus chinensis needles extracts by macroporous resin column chromatography

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