Elsevier

Phytochemistry

Volume 53, Issue 3, 2 February 2000, Pages 383-389
Phytochemistry

Screening of the needles of different yew species and cultivars for paclitaxel and related taxoids

https://doi.org/10.1016/S0031-9422(99)00094-1Get rights and content

Abstract

The needles of several yew species and cultivars were analysed by high-pressure liquid chromatography for paclitaxel, 10-deacetylpaclitaxel, cephalomannine, baccatin III, 10-deacetylbaccatin III and brevifoliol. About 750 samples were collected from five different locations in the Netherlands and the UK. The results of this screening show a large variation in taxane content between the different species and cultivars. The content of paclitaxel and 10-deacetylbaccatin III varied from 0 to 500 μg/g and 0 to 4800 μg/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 μg/g dried needles.

Introduction

Paclitaxel (Taxol®, Yewtaxan®) (1) is an important anticancer drug which was first isolated from the bark of the Pacific yew (Taxus brevifolia Nutt.) (Wani, Taylor, Wall, Coggon, & McPhail, 1971), a slow growing evergreen from western US and Canada. Because of the lack of a sustainable supply and a growing demand for the drug, various means to increase the supply of paclitaxel have been investigated. Some promising possibilities are semisynthesis from a readily available paclitaxel precursor such as 10-deacetylbaccatin III (5), or isolation of paclitaxel from the needles of more common Taxus species Denis et al., 1988, Witherup et al., 1990, Wiegerinck et al., 1996. Furthermore, a lot of effort is invested in producing or isolating paclitaxel analogues with less toxicity, improved water solubility and/or improved biological activity Deutsch et al., 1989, Kingston, Samanarayake, & Ivey, 1990, Guéritte-Voegelein et al., 1991, Amato, 1993. For these reasons, many Taxus species and cultivars have been screened for their taxane content Witherup et al., 1990, Vidensek, Lim, Campbell, & Carlson, 1990, Mattina & Paiva, 1992, ElSohly et al., 1995. However, most yew samples have only been analysed for paclitaxel. Furthermore, it is known that there is a significant seasonal influence on the taxane content of yew needles Vance, Kelsey, & Sabin, 1994, ElSohly, Croom, Kopycki, Joshi, & McChesney, 1997. Therefore, it is not correct to compare analytical results from yew samples that were collected during different times of the year. We report here the analysis of yew species and cultivars collected during the same time period.

Section snippets

Results and discussion

For the large-scale screening of yew needles for their content of taxanes a labour-efficient and selective clean-up method in combination with an HPLC quantitation on standard C18 columns was developed (van Rozendaal, Lelyveld, & van Beek, 1997). The needles were screened for paclitaxel (1), 10-deacetylpaclitaxel (2), cephalomannine (3), baccatin III (4), 10-deacetylbaccatin III (5) and brevifoliol (6).

About 750 samples of yew needles were collected, belonging to the following species: T.

Plant material

Needles from several Taxaceae species and cultivars were collected between 16 February and 15 March 1996 from two sites of the Research Station for Nursery Stock (Boskoop and Horst, both in The Netherlands) and three botanical gardens (Wageningen Agricultural University Botanical Gardens, The Netherlands; Pinetum Blijdenstein, Hilversum, The Netherlands; Bedgebury National Pinetum, Kent, UK). Herbarium accession numbers are available on request. After being dried for 3 h at 60° in an oven with

Acknowledgements

We are grateful to Pharmachemie BV, Haarlem, The Netherlands, for their financial support of synthetic organic chemical and phytochemical research on paclitaxel and related taxanes at the University of Nijmegen (dr. J.W. Scheeren) and Wageningen Agricultural University. This work is part of this research cooperation. Further, we wish to thank the National Cancer Institute, US, for their kind gift of taxane standards. The authors are also grateful for the cooperation of the following nurseries

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