A reinvestigation of the taxol content of himalayan taxus wallichiana zucc. and a revision of the structure of brevifoliol.

Georg, Gunda I.; Gollapudi, Rao; Grunewald, Gary L.; Gunn, Christopher W.; Himes, Richard H.; Rao, Bhattiprolu Kesava; Liang, Xiao Zhong; Mirhom, Youssef Wissa; Mitscher, Lester A.; Velde, au David G. Vander; Ye, Qing Mei

doi:10.1016/s0960-894x(00)80345-5

Cited by 28 publications

(16 citation statements)

References 17 publications

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“…(1994) [42] sinharine Hofer et al (1992) [41] chemical synthesis Johnson et al (1994) [42] NMR UV IR MS degradation no calyculaglycoside A Rodríguez et al (1997) [43] isolation of related compounds, biogenetic considerations, and degradation [44] NMR UV IR CD MS no harrisonin Nakanishi et al (1976) [45] [47] isolation of related compounds and reevaluation Rodríguez and Crews (1994) [48] NMR IR MS no brevifoliol Tachibana et al (1991) [49] reisolation and reexamination Georg et al (1993) [50] NMR EA UV IR derivatization Hubbs and Heathcock (1999) [53] isoschizogamine Renner and Fritz (1965) [51] reisolation and 2D NMR spectroscopy Hµjícek et al (1998) [52] NMR EA IR derivatization no FR900148 Kuroda et al (1980) [54] reisolation and reexamination Yasuda and Sakane (1991) [55] NMR IR MS derivatization Corey and Kania (1998) [58] palominol Rodríguez et al (1990) [56] isolation of related compounds and comparison of spectra Shin and Fenical (1991) [57] NMR UV IR CD MS derivatization Trost and Harrington (2004) [60] (+)-amphidinolide A Kobayashi et al (1991) [59] chemical synthesis Trost and Harrington (2004) [60] NMR UV IR MS Grossman and Rasne (2001) …”

Section: The State Of Modern Structure Elucidationmentioning

confidence: 99%

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

2005

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Over the course of the past half century, the structural elucidation of unknown natural products has undergone a tremendous revolution. Before World War II, a chemist would have relied almost exclusively on the art of chemical synthesis, primarily in the form of degradation and derivatization reactions, to develop and test structural hypotheses in a process that often took years to complete when grams of material were available. Today, a battery of advanced spectroscopic methods, such as multidimensional NMR spectroscopy and high-resolution mass spectrometry, not to mention X-ray crystallography, exist for the expeditious assignment of structures to highly complex molecules isolated from nature in milligram or sub-milligram quantities. In fact, it could be argued that the characterization of natural products has become a routine task, one which no longer even requires a reaction flask! This Review makes the case that imaginative detective work and chemical synthesis still have important roles to play in the process of solving nature's most intriguing molecular puzzles.

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Section: The State Of Modern Structure Elucidationmentioning

confidence: 99%

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

2005

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“…Paclitaxel acts through a new and unique mechanism of promoting the formation and hyperstabilization of microtubules [2]. Although much research has been done on the effects of different factors on paclitaxel content in different species of Taxus [3] since its first isolation from stem bark of Taxus brevifolia Nutt.[4], information regarding potential sources of variation in paclitaxel content in the Himalayan yew is scarce [5], [6]. This species is widely distributed throughout the Himalayan range from Western to Eastern Himalayas.…”

mentioning

confidence: 99%

“…[4], information regarding potential sources of variation in paclitaxel content in the Himalayan yew is scarce [5], [6]. This species is widely distributed throughout the Himalayan range from Western to Eastern Himalayas.…”

mentioning

confidence: 99%

Variation in Content of Taxol and Related Taxanes in Eastern Himalayan Populations of Taxus wallichiana

Mukherjee

Ghosh²,

Jha³

et al. 2002

Planta med

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Extraction and analysis of paclitaxel and other taxanes in bark, needle leaves and stem segments of male and female plants of Taxus wallichiana, representing several populations, indicate that significant variation in taxane content exists within the population. Bark accumulated maximum amount of paclitaxel in almost all plants. Populations located at higher altitude tended to accumulate more paclitaxel than lower altitude plants. Seasons in which samples were collected and plant age have also been shown to affect paclitaxel accumulation. No effects of plant sex on paclitaxel content of the plants analyzed were observed. Significant differences in baccatin-III and 10-deacetylbaccatin III content were found to exist in the trees analyzed in this study.

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“…The structure elucidation of taxcultine [4] was simplified by direct comparison of its esms/ms and nmr spectra with those of 1. The high-resolution mass spectrum of 4 showed a protonated molecular ion at mlz 820.3559, which indicated the composition C44H54NOm.…”

Section: Resultsmentioning

confidence: 99%

“…Although various species of Taxus have been reported to contain taxol, large quantities of taxol for clinical trials were originally isolated from the bark of the Pacific yew. The needles of some Taxus species may become the preferred source (4,5). Semi-synthesis from natural taxoids and total synthesis are also being actively pursued (6).…”

mentioning

confidence: 99%

New Bioactive Taxoids from Cell Cultures of Taxus baccata

Gl²,

Ga³

et al. 1994

J. Nat. Prod.

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Four new taxoids were isolated from cell cultures of Taxus baccata. Their structures were elucidated by spectroscopic analyses. Two were the aglycones corresponding to previously isolated 7-O-xylosides of taxol C [1] and 10-deacetyltaxol C [2]. The third [3] had an N-methylated side-chain, while the fourth, named taxcultine [4], contained an n-propyl group on the side-chain. All four compounds actively promoted tubulin assembly. Taxol C [1] showed potent and selective cytotoxicity in the NCI human cell line screen.

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A reinvestigation of the taxol content of himalayan taxus wallichiana zucc. and a revision of the structure of brevifoliol.

Cited by 28 publications

References 17 publications

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

Variation in Content of Taxol and Related Taxanes in Eastern Himalayan Populations of Taxus wallichiana

New Bioactive Taxoids from Cell Cultures of Taxus baccata

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