Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: transbenzoylation, transacetylation, and opening of the oxetane ring

Alberto Arnone; Adriana Bava; Giovanni Fronza; Gianluca Nasini

doi:10.1021/np900368u

Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: transbenzoylation, transacetylation, and opening of the oxetane ring

J Nat Prod. 2009 Nov;72(11):2000-4. doi: 10.1021/np900368u.

Authors

Alberto Arnone¹, Adriana Bava, Giovanni Fronza, Gianluca Nasini

Affiliation

¹ CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, 20131, Milano, Italy.

PMID: 19845390
DOI: 10.1021/np900368u

Abstract

The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation of a C-9/C13 hemiacetal, epimerization at C-10, and migration of the endocyclic double bond to an exocyclic location. In compound 3, an acetate-assisted opening of the oxetane ring was also observed.

Publication types

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

MeSH terms

Ascomycota / metabolism*
Biotransformation
Bridged-Ring Compounds / chemistry*
Ethers, Cyclic / chemistry*
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Taxoids / chemistry*

Substances

Bridged-Ring Compounds
Ethers, Cyclic
Taxoids
taxane
10-deacetylbaccatine III
oxetane