Taxanes from rooted cuttings of Taxus canadensis.
A 3,11-cyclotaxane (1), a new epoxytaxane (2), an abeo-taxane (3), and 26 known taxanes were isolated in rooted cuttings of the Canadian yew (Taxus canadensis) for the first time. Their chemical structures were characterized as 1 beta,2 alpha,9 alpha-trihydroxy-10 beta-acetoxy-5 alpha-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one (1), 2 alpha,9 alpha,10 beta-triacetoxy-11,12-epoxy-20-hydroxytaxa-4-en-13-one (2), and 7 beta,9 alpha,10 beta,13 alpha-tetraacetoxy-11(15-->1)abeo-taxa-4(20),11-diene-5 alpha,15-diol (3). Metabolite 2 is a new taxane, metabolite 1 has been reported previously in the needles of Taxus baccata, and metabolite 3 was previously discovered as a biotransformation product but is now reported as a natural product for the first time.
Petzke
Tracy L
TL
Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Québec, Canada H7V 1B7.
Shi
Qing Wen
QW
Sauriol
Françoise
F
Mamer
Orval
O
Zamir
Lolita O
LO
D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000302:isolation & purification*; D002170:Canada; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D043823:Taxoids / Q000737:chemistry / Q000302:isolation & purification*; D020946:Taxus / Q000737:chemistry*
D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane