Potential of Plant Cell Culture for Taxane Production*

Gibson, Donna M.; Ketchum, Raymond E.B.; Hirasuna, Thomas J.; Shuler, Michael L.

doi:10.1201/9780138737361-6

Cited by 3 publications

(1 citation statement)

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“…The situation is exacerbated by its low content across all the species of Taxus. All these issues triggered the exploration of alternative sources such as semi‐synthesis [13], total synthesis [14], endophyte [15], and cell culture [16]. 10‐Deacetyl baccatin III (10‐DAB III) is a natural precursor of Taxol that is usually present in higher concentrations in the needles of Taxus spp .…”

Section: Introductionmentioning

confidence: 99%

Purification and characterization of Taxol and 10‐Deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high‐performance liquid chromatography, ultra‐high‐performance liquid chromatography‐mass spectrometry, and nuclear magnetic resonance

Nurullah

Usmani

Ahmad

et al. 2023

J of Separation Science

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Taxol and 10‐Deacetyl baccatin III are major taxanes in the bark, needles, and endophytes of Taxus baccata. The current study aimed to develop a process for their separation from different matrices. Crude taxoid was prepared by extraction of samples with methanol, followed by partitioning with dichloromethane and precipitation with hexane. Analytical high‐performance liquid chromatography involved isocratic elution on C18 column (4.6 × 250 mm, 5 μm) with methanol‐water (70:30 v/v) at a flow rate of 1 ml/min. Injection volume was 20 μl and detection was carried out at 227 nm. The content of Taxol and 10‐Deacetyl baccatin III in bark, needles and endophytic culture broth was 11.19 and 1.75 μg/mg; 11.19 and 1.75 μg/mg; and 2.80 and 0.22 μg/L, respectively. Preparative high‐performance liquid chromatography was done on C18 column (10 × 250 mm, 5 μm) at a flow rate of 10 ml/min. About 20 g crude taxoid was processed in < 3 h with a recovery of about 90% for both the analytes. The purity of recovered Taxol and 10‐Deacetyl baccatin III determined by ultra‐high‐performance liquid chromatography‐mass spectrometry was found to be 95.78 ± 3.63% and 99.72 ± 0.18%, respectively. The structure of recovered Taxol was confirmed by nuclear magnetic resonance. The method can find use in biotransformation studies.

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Section: Introductionmentioning

confidence: 99%

Purification and characterization of Taxol and 10‐Deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high‐performance liquid chromatography, ultra‐high‐performance liquid chromatography‐mass spectrometry, and nuclear magnetic resonance

Nurullah

Usmani

Ahmad

et al. 2023

J of Separation Science

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Kinetics of two-liquid-phase Taxus cuspidata cell culture for production of Taxol

Wu¹,

Yang²,

Ma³

et al. 2000

Biochemical Engineering Journal

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TOUR DE PACLITAXEL: Biocatalysis for Semisynthesis

Patel

1998

Annu. Rev. Microbiol.

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In collaboration with the National Cancer Institute, Bristol-Myers Squibb has developed paclitaxel for treatment of various cancers; it has been approved by the Food and Drug Administration for the treatment of ovarian and metastatic breast cancer. Originally paclitaxel was isolated and purified from the bark of Pacific yew trees. This source of paclitaxel was considered to be economically and ecologically unsuitable as it required the destruction of the yew trees. This review article describes alternate methods for the production of paclitaxel, specifically, a semisynthetic approach and the application of biocatalysis in enabling the semisynthesis of paclitaxel. Three novel enzymes were discovered in our laboratory that converted the variety of taxanes to a single molecule, namely 10-deacetylbaccatin III (paclitaxel without C-13 side chain and C-10 acetate), a precursor for paclitaxel semisynthesis. These enzymes are C-13 taxolase (catalyzes the cleavage of C-13 side chain of various taxanes), C-10 deacetylase (catalyzes the cleavage of C-10 acetate of various taxanes), and C-7 xylosidase (catalyzes the cleavage of C-7 xylose from various xylosyltaxanes). Using a biocatalytic approach, paclitaxel and a variety of taxane in extracts of a variety of Taxus cultivars were converted to a 10-deacetylbaccatin III. The concentration of 10-deacetylbaccatin III was increased by 5.5- to 24-fold in the extracts treated with the enzymes, depending upon the type of Taxus cultivars used. Biocatalytic processes have also been described for the preparation of C-13 paclitaxel side chain synthons. The chemical coupling of 10-deacetylbaccatin III or baccatin III to C-13 paclitaxel side chain has been summarized to prepare paclitaxel by semisynthesis.

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Potential of Plant Cell Culture for Taxane Production*

Cited by 3 publications

References 0 publications

Purification and characterization of Taxol and 10‐Deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high‐performance liquid chromatography, ultra‐high‐performance liquid chromatography‐mass spectrometry, and nuclear magnetic resonance

Purification and characterization of Taxol and 10‐Deacetyl baccatin III from the bark, needles, and endophytes of Taxus baccata by preparative high‐performance liquid chromatography, ultra‐high‐performance liquid chromatography‐mass spectrometry, and nuclear magnetic resonance

Kinetics of two-liquid-phase Taxus cuspidata cell culture for production of Taxol

TOUR DE PACLITAXEL: Biocatalysis for Semisynthesis

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