Chemotaxonomic Study of Medicinal Taxus Species with Fingerprint and Multivariate Analysis

Abstract

Species delimitation in Taxus has been controversial and it is very difficult to distinguish yew materials by their morphological characters. In this paper, a valid HPLC fingerprinting method coupled with multivariate analysis was used to define a framework for Taxus species identification and classification. Fingerprint-based similarity was employed for a chemotaxonomic study by hierarchical clustering analysis (HCA) and principal component analysis (PCA). Based on the PCA loadings, twelve chemical constituents were selected as chemotaxonomic markers which can be used to establish a more practical classification. Finally, eight studied species could be divided into six well-supported groups and most samples can be assigned to the correct species. Additionally, twelve markers were tentatively identified by LC/MS.

Abbreviations

10-DAB: 10-deacetylbaccatin III

10-DAP: 10-deacetylpaclitaxel

10-DAXP: 10-deacetyl-7-xylosylpaclitaxel

9-DHB: 9-dihydro-13-acetylbaccatin III

HCA: hierarchical clustering analysis

ITS: internal transcribed spacer

PCA: principal component analysis

Key words

Taxus - Taxaceae - Chemotaxonomy - Fingerprinting - Multivariate Analysis - Taxanes

References

• 1 Baloglu E, Kingston D GI. The taxane diterpenoids.  J Nat Prod. 1999;  62 1448-72
• 2 Appendino G. The phytochemistry of the yew tree.  Nat Prod Rep. 1995;  121 349-60
• 3 Denis J N, Greene A E, Guénard D, Guéritte-Vorgrlrin F, Mangatal L, Potier P. A highly efficient, practical approach to natural taxol.  J Am Chem Soc. 1988;  110 5917-9
• 4 van Rozendaal E, Lelyveld G, van Beek T. Screening of the needles of different yew species and cultivars for paclitaxel and related taxoids.  Phytochemistry. 2000;  53 383-9
• 5 Navia-Osorio A, Garden H, Cusidó R M, Palazón J, Alfermann A W, Piñol M T. Production of paclitaxel and baccatin III in a 20-L airlift bioreactor by a cell suspension of Taxus wallichiana.  Planta Med. 2002;  68 336-40
• 6 Poupat C, Hook I, Guéritte F, Ahond A, Guénard D, Adeline M T. et al . Neutral and basic taxoid contents in the needles of Taxus species.  Planta Med. 2000;  66 580-4
• 7 Khan I A. Issues related to botanicals.  Life Sci. 2006;  78 2033-8
• 8 Li J, Davis C C, Tredici P D, Donoghue M J. Phylogeny and biogeography of Taxus (Taxaceae) inferred from sequences of the internal transcribed spacer region of nuclear ribosomal DNA.  Harvard Papers Bot. 2001;  6 267-74
• 9 Collins D, Mill R R, Moller M. Species separation of Taxus baccata, T. canadensis, and T. cuspidate (Taxaceae) and origins of their reputed hybrids inferred from RAPD and cpDNA data.  Am J Bot. 2003;  90 175-82
• 10 Madhusudanan K P, Chattopadhyay S K, Tripathi V, Sashidhara K V, Kumar S. MS/MS profiling of taxoids from the needles of Taxus wallichiana.  Phytochem Anal. 2002;  13 18-30
• 11 Kerns E H, Volk K J, Whitney J L, Rourick R A, Lee M S. Chemical identification of botanical components using liquid chromatography & mass spectrometry.  Drug Inf J. 1998;  32 471-85
• 12 Parmar V S, Jha A, Bisht K S, Taneja P, Singh S K, Kumar A. et al . Constituents of the yew trees.  Phytochemistry. 1999;  50 1267-304
• 13 Lu G H, Chan K, Liang Y Z, Leung K, Chan C L, Jiang Z H. et al . Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related Umbelliferae herbs.  J Chromatogr A. 2005;  1073 383-92
• 14 Xie P, Chen S, Liang Y, Wang X, Tian R, Upton R. Chromatographic fingerprint analysis - a rational approach for quality assessment of traditional Chinese herbal medicine.  J Chromatogr A. 2006;  1112 171-80
• 15 Zou P, Hong Y, Koh H L. Chemical fingerprinting of Isatis indigotica root by RP-HPLC and hierarchical clustering analysis.  J Pharm Biomed Anal. 2005;  38 514-20
• 16 Becerra J X. Synchronous coadaptation in an ancient case of herbivory.  Proc Natl Acad Sci USA. 2003;  100 12 804-7
• 17 Grayer R J, Chase M W, Simmonds M SJ. A comparison between chemical and molecular characters for the determination of phylogenetic relationships among plant families: an appreciation of Hegnauer's ”Chemotaxonomie der Pflanzen”.  Biochem Syst Ecol. 1999;  27 369-93
• 18 Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective.  Phytochemistry. 2003;  64 3-19
• 19 Vieira R F, Grayer R J, Paton A J. Chemical profiling of Ocimum americanum using external flavonoids.  Phytochemistry. 2003;  63 555-67
• 20 Theodoridis G, Laskaris G, de Jong C F, Hofte A JP, Verpoorte R. Determination of paclitaxel and related diterpenoids in plant extracts by high-performance liquid chromatography with UV detection in high-performance liquid chromatography-mass spectrometry.  J Chromatogr A. 1998;  802 297-305
• 21 Mukherjee S, Ghosh B, Jha T B, Jha S. Variation in content of taxol and related taxanes in Eastern Himalayan populations of Taxus wallichiana.  Planta Med. 2002;  68 757-9
• 22 Massart B, Guo Q, Questier F, Massart D L, Boucon C, deJong S. Data structures and data transformations for clustering chemical data.  Trends Anal Chem. 2001;  20 35-41
• 23 Aruga R. Multivariate classification of constrained data: problems and alternatives.  Anal Chim Acta. 2004;  527 45-51
• 24 Berman E, Kulp K, Knize M, Wu L, Nelson E, Nelson D. et al . Distinguishing monosaccharide stereo- and structural isomers with TOF-SIMS and multivariate statistical analysis.  Anal Chem. 2006;  78 6497-503
• 25 Bailey N, Sampson J, Hylands P J, Nicholson J K, Holmes E. Multi-component metabolic classification of commercial feverfew preparation via high-field ¹H-NMR spectroscopy and chemometrics.  Planta Med. 2002;  68 734-8
• 26 Smith R M, Burford M D. Comparision of flavanoids in feverfew varieties and related species by principal components analysis.  Chemometrics Intelligent Lab Syst. 1993;  18 285-91
• 27 Máximo P, Lourenço A, Tei A, Wink M. Chemotaxonomy of Portuguese Ulex: Quinolizidine alkaloids as taxonomical markers.  Phytochemistry. 2006;  67 1943-9
• 28 Nyman T, Julkunen-Tiitto R. Chemical variation within and among six northern willow species.  Phytochemistry. 2005;  66 2836-43