Microbial transformations of the taxan ring of 10-DAB by some strains of the fungus Curvularia lunata: formation of the bis-abeotaxanes wallifoliol and 4-deacylwallifoliol.

Alberto Arnone, Adriana Bava, Giovanni Fronza, Luciana Malpezzi, Gianluca Nasini

CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, I-20123, Milano, Italy.

Journal of natural products 2010 Jun 25

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The fermentation of 10-deacetylbaccatine III (10-DAB) (1) with Curvularia lunata afforded 4-deacylwallifoliol (4) and wallifoliol (5), the only natural taxoid with the unusual 5/6/6/6/4 ring system. The X-ray structure of compound 4 is reported. The skeletal rearrangements induced by the microbial enzymatic systems are also discussed.

Citation

Alberto Arnone, Adriana Bava, Giovanni Fronza, Luciana Malpezzi, Gianluca Nasini. Microbial transformations of the taxan ring of 10-DAB by some strains of the fungus Curvularia lunata: formation of the bis-abeotaxanes wallifoliol and 4-deacylwallifoliol. Journal of natural products. 2010 Jun 25;73(6):1049-52