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.
Shi
Qing-Wen
QW
Human Health Research Center, INRS-Institut Armand-Frappier, Université du Québec, 531 Boulevard des Prairies, Laval, Quebec, Canada H7V 1B7.
Lederman
Zel
Z
Sauriol
Francoise
F
McCollum
Robert S
RS
Zamir
Lolita O
LO
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