title: A new large-scale process for taxol and related taxanes from Taxus brevifolia.
abstract: OBJECTIVE
  In view of the demonstrated antitumor activity of taxol, ready availability of the drug is important. The current isolation methods starting from the bark of Taxus brevifolia involve multiple manipulations, leading to only taxol and in a yield of 0.01%. A new process consisting of a single reverse phase column is introduced here, and the present purpose is to determine its large scale applicability.
  
  
  METHODS
  The chloroform extractable fraction of the bark of T. brevifolia is applied directly on to a C-18 bonded silica column in 25% acetonitrile/water, with elution using a step gradient: 30-50% acetonitrile/water. On standing, eight different taxanes, including taxol, crystallize out directly from different fractions. The crystals are filtered and purified further by recrystallization. Taxol and four other taxanes are purified this way. The other three require a short silica column. Taxol is freed from cephalomannine by selective ozonolysis.
  
  
  RESULTS
  The large scale process gave taxol (0.04%), 10-deacetylbaccatin III (0.02%), 10-deacetyl taxol-7-xyloside (0.1%), 10-deacetyl taxol-C-7-xyloside (0.04%), 10-deacetyl cephalomannine-7-xyloside (0.006%), taxol-7-xyloside (0.008%), 10-deacetyl taxol (0.008%) and cephalomannine (0.004%). Processing of the needles of T. brevifolia gave brevifoliol (0.17%), and that of the wood, 10-deacetyl taxol-C-7-xyloside (0.01%) and 10-deacetyl taxol-C.
  
  
  CONCLUSIONS
  The reverse phase column process is simpler (one column, direct crystallization), more efficient (eight taxanes obtained simultaneously) and also gives higher yields.
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification*; D001952:Bridged-Ring Compounds / Q000302:isolation & purification*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000302:isolation & purification*; D010865:Pilot Projects; D010946:Plants, Medicinal / Q000737:chemistry*; D043823:Taxoids
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane; D017239:Paclitaxel