A preliminary study of the taxane chemistry and natural history of the Mexican yew, Taxus globosa Schltdl (original) (raw)

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.

Sex influences the taxanes content in Taxus baccata

Acta Physiologiae Plantarum, 2012

Like other species of the genus Taxus, European yew trees contain taxanes, including paclitaxel (T) and its precursor 10-deacetylbaccatin III (10-DAB). Taxanes are one of the most effective anticancer drugs. This study was undertaken to describe the levels and patterns of taxane variation in the Sudetian region (SW Poland). Paclitaxel (T) and 10-deacetylbaccatin III (10-DAB) concentrations were analysed in five populations. Needles and twigs were analysed from 60 individuals (30 males and 30 females) in each population. In addition, morphometric measurements were taken in the populations to obtain light intensity coefficients (specific leaf area, SLA). High variability in the taxane contents at both intra and interpopulational levels was found. Nevertheless, females had a significantly higher taxane content compared to males. Because taxanes are carbon-based secondary metabolites, females have higher rate of gas exchange of females compared to males. This was probably an adaptation to greater reproductive effort incurred by females. In this regard, female individuals seem to be better for selecting elite cultivars with a higher taxane production. The relationship between light intensity and taxane content was not significant. Shading, important for optimizing crop production, should not reduce the concentration of taxanes. Keywords Taxus baccata Á Taxanes Á Sex Á Dioecy Á Light intensity Abbreviations 10-DAB 10-deacetylbaccatin III T Paclitaxel SLA Specific leaf area SPE Solid phase extraction Communicated by J. V. Jorrin-Novo.

Chemical Composition of Taxus baccata L. Leaves and Male Cones Water:Methanol Extracts

Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 2020

The yew tree (Taxus baccata) is an ancient species in the world that has both toxic and medicinal properties. Identifying the chemical components of different parts of this tree can be useful in the better understanding of the toxicity and medicinal effect of this plant. Therefore, the chemical composition of water: methanol extracts of T. baccata L. leaf and male cones obtained from endemic species of Iran were characterized using GC-MS analysis. Twenty two components were identified for leaves including oleic acid (20.87%) and octadeca-9,12-dien-1-ol (17.77%) as the most abundant components, and seventeen components were identified for male cones which were 3-O-methyl-d-glucose (64.00%) and oleic acid (13.32%) as the most abundant components. Furthermore, the potential applications of some of the characterized components are discussed into the depths.

Taxoids from the Roots of Taxus × media cv. Hicksii

Journal of Natural Products, 1994

A%mm.-The roots of TaxusXmpdia cy. Hicksii gave two new pseudoalkaloidal taxoids, identified as N-debenzoyl-N-butanoyl taxol [l] and 7/3-acetoxy-9-acetylspicataxine [2a]. A new baccatin IV derivative Val and the lignans hydroxymatairesinol [SI and (-)-epinomachelogenin E91 were also isolated. The epoxidation of Aqz0)''' taxadienes was investigated, disclosing an unusual reactivity of the bridgehead double-bond towards peracids. Regiochemically and stereochemically unnatural epoxides of taxoids were obtained. Nmr data for these compounds were compared with literature values on the natural epoxides. No significant correlation between the configuration of the 4(20)-oxirane ring and the chemical shift of H-5 was found. The stem bark and the needles of several species of yew have been thoroughly investigated (2), but very few studies have been done on the constituents of the roots (3,4). As part of a study aimed at assessing the availability of taxol and taxol-equivalent diterpenoids from cultivated yew species, we investigated the constituents of the roots of T. Xmediu Rehd. cv. Hicksii (5). This yew was developed for ornamental purposes and is popular as landscape material. Extensive cultivations exist in nurseries, and the needles have been studied as a potential source of taxol(6). A previous study has shown the presence of taxol and two novel analogs in the roots (7). We report here the isolation of three new taxoids El, 2a, 7a7 and of a lignan not previously described as a natural product E97. RESULTS AND DISCUSSION ' Compound 1 has the molecular formula C44H53N0,4 (cims). Its 'H-nmr spectrum was similar to that of taxol C (N-debenzoyl-N-hexanoyl taxol) (7). The only significant difference was the absence of the w-2 and w-3 methylene protons of the N-acyl residue. The 13C-nmr spectrum was almost superimposable on that of taxol C (7) except for the absence of the 0-2 and 0-3 carbons. These data suggested that 1 differs from taxol C by 'Part 14 in the series "The Chemistry and Occurrence of Taxane Derivatives." For part 13, see Appendino et al. (1).

Seasonal variations in the content of taxanes in the bark of Taxus baccata L

Phytochemical Analysis, 1999

Analytical determination by HPLC of five taxanes-paclitaxel, cephalomannine, 10-deacetylpaclitaxel, 10deacetylcephalomannine and taxcultine-in extracts from the bark of Taxus baccata indicates that taxane concentrations vary seasonally. The highest concentration was found in October and the lowest in January for all taxanes examined.

Sample preparation for taxol and cephalomannine determination in various organs of Taxus sp

Journal of Pharmaceutical and Biomedical Analysis, 1996

Solid-phase extraction and preparative thin-layer chromatography were applied as sample preparation techniques for the purification of crude extracts from twigs and needles of various Taxus species as well as for the isolation of taxol and cephalomannine for further reversed phase high performance liquid chromatography analysis. Significant differences in the contents of taxanes examined were found. The preparative chromatographic methods used were compared and evaluated as routine and reproducible procedures for the rapid isolation and determination of taxol and cephalomannine in plant extracts.