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

doi:10.1021/np900765y

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

J Nat Prod. 2010 Jun 25;73(6):1049-52. doi: 10.1021/np900765y.

Authors

Alberto Arnone¹, Adriana Bava, Giovanni Fronza, Luciana Malpezzi, Gianluca Nasini

Affiliation

¹ CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, I-20123, Milano, Italy.

PMID: 20527910
DOI: 10.1021/np900765y

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ascomycota / chemistry*
Biotransformation
Drug Screening Assays, Antitumor
Models, Molecular
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Taxoids / chemistry*
Taxoids / isolation & purification*

Substances

Taxoids
wallifoliol
10-deacetylbaccatine III