A yew in Israel, new taxane derivatives.
Five new taxanes, 5alpha,9alpha,10beta,13alpha-tetraacetoxy-14beta-O-(beta-d-glucopyranosyl)taxa-4(20),11-diene (1), 1beta,2alpha,9alpha,10beta-tetrahydroxy-5alpha-cinnamoyoxytaxa-4(20),11-dien-13-one (2), 2alpha,9alpha,10beta-trihydroxy-5alpha-cinnamoyoxytaxa-4(20),11-dien-13-one (3), 9alpha-acetoxy-2alpha,10beta-dihydroxy-5alpha-cinnamoyoxytaxa-4(20),11-dien-13-one (4), and 2alpha,10beta-diacetoxy-1beta,9alpha-dihydroxy-5alpha-cinnamoyoxy-3,11-cyclotaxa-4(20)-dien-13-one (5), have been identified in a Taxus baccata yew grown in Israel from seeds imported from the United States. We have also characterized 40 previously known taxanes from this plant material. The structures of the new taxanes (1-5) were rigorously established with 1D and 2D NMR data and confirmed by high-resolution FAB-mass spectrometry.
Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Quebec, Canada H7V 1B7.
Qing-Wen
QW
Shi
Zel
Z
Lederman
Francoise
F
Sauriol
Robert S
RS
McCollum
Lolita O
LO
Zamir
D001952:Bridged-Ring Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007557:Israel; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D043823:Taxoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020946:Taxus / Q000737:chemistry*
D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane