Administering Taxus suspension cells with labeled 5alpha-hydroxytaxadiene and 5alpha,10beta-dihydroxytaxadiene, and the corresponding 5alpha-acetate esters, demonstrated that acetylation at C5 of the monool precursor promotes the formation of 14beta-hydroxy taxoids, such as taxuyunnanine C, at the expense of 13alpha-hydroxy taxoids, including Taxol and its congeners, but that the major bifurcation in taxoid biosynthesis, toward 13alpha- or 14beta-hydroxy taxoids, occurs after 10beta-hydroxylation of the taxane core.
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http://dx.doi.org/10.1016/j.phytochem.2006.10.019 | DOI Listing |
Chem Biodivers
October 2005
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan 650204, PR China.
Two new taxoids, 2,20-O-diacetyltaxumairol N (1) and 14beta-hydroxy-10-deacetyl-2-O-debenzoylbacatin III (2), were isolated from the needles and stems of Taxus chinensis. Their structures were determined on the basis of extensive 1D- and 2D-NMR-spectral analysis. Compound 1 showed weak cytotoxicity activity against T-24 (IC50 = 34 microg/ml) and QGY-7701 (IC50 = 22 microg/ml) cancer lines.
View Article and Find Full Text PDFPhytochemistry
February 2007
Institute of Biological Chemistry, Washington State University, 299 Clark Hall, P.O. Box 646340, Pullman, WA 99164-6340, USA.
Administering Taxus suspension cells with labeled 5alpha-hydroxytaxadiene and 5alpha,10beta-dihydroxytaxadiene, and the corresponding 5alpha-acetate esters, demonstrated that acetylation at C5 of the monool precursor promotes the formation of 14beta-hydroxy taxoids, such as taxuyunnanine C, at the expense of 13alpha-hydroxy taxoids, including Taxol and its congeners, but that the major bifurcation in taxoid biosynthesis, toward 13alpha- or 14beta-hydroxy taxoids, occurs after 10beta-hydroxylation of the taxane core.
View Article and Find Full Text PDFBioorg Med Chem Lett
October 2006
Dipartimento di Scienze Chimiche, Università di Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy.
This article describes a new, convenient, improved synthesis of the 2-debenzoyl-2-m-methoxybenzoyl-7-triethylsilyl-13-oxo-14beta-hydroxybaccatin III 1,14-carbonate, the key intermediate in the synthesis of two new second-generation antitumor taxanes.
View Article and Find Full Text PDFIDrugs
June 2004
Akikoa Pharmaceuticals Inc, 303 Gray Street, Arlington, MA 02476, USA.
Bayer Corp, under license from Indena SpA, is developing BAY-59-8862, a taxane synthesized from 14beta-hydroxy-10-deacetylbaccatin III, for the potential treatment of cancer.
View Article and Find Full Text PDFBioorg Chem
August 2003
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xueyuan Road 38#, 100083, Beijing, PR China.
Three C-14 oxygenated taxanes isolated from callus cultures of Taxus spp., 2alpha,5alpha,10beta,14beta-tetra-acetoxy-4(20),11-taxadiene 3, 2alpha,5alpha,10beta-triacetoxy-14beta-propionyloxy-4(20),11-taxadiene 4, 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methylbutyryl)-oxy-4(20),11-taxadiene 5, and three deacetylated derivatives of 3, 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene 6, 14beta-hydroxy-2alpha,5alpha,10beta-triacetoxy-4(20),11-taxadiene 7, 10beta,14beta-dihydroxy-2alpha,5alpha-diacetoxy-4(20),11-taxadiene 8, could all be regio- and stereo-selectively hydroxylated at the 9alpha-position by Ginkgo cell suspension cultures to yield a series of new 9alpha,14beta-dihydroxylated taxoids. The effects of functional groups, especially at C-14 of the substrates, on the biotransformation were also investigated.
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