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.
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.
Arnone
Alberto
A
CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, I-20123, Milano, Italy.
Bava
Adriana
A
Fronza
Giovanni
G
Malpezzi
Luciana
L
Nasini
Gianluca
G
D001203:Ascomycota / Q000737:chemistry*; D001711:Biotransformation; D004354:Drug Screening Assays, Antitumor; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D043823:Taxoids / Q000737:chemistry* / Q000302:isolation & purification*
D043823:Taxoids; C089567:wallifoliol; C042213:10-deacetylbaccatine III