A furantaxane with an unusual 6/8/6/5 ring system and potent tumor MDR reversal activity obtained via microbial transformation

Xiao Liu; Dan Xie; Ridao Chen; Mei Mei; Jianhua Zou; Xiaoguang Chen; Jungui Dai

doi:10.1021/ol301755n

A furantaxane with an unusual 6/8/6/5 ring system and potent tumor MDR reversal activity obtained via microbial transformation

Org Lett. 2012 Aug 17;14(16):4106-9. doi: 10.1021/ol301755n. Epub 2012 Aug 1.

Authors

Xiao Liu¹, Dan Xie, Ridao Chen, Mei Mei, Jianhua Zou, Xiaoguang Chen, Jungui Dai

Affiliation

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, PR China.

PMID: 22852759
DOI: 10.1021/ol301755n

Abstract

A furantaxane (4) with an unusual 6/8/6/5 ring system and two hydroxylated products (2, 3) were isolated following the biotransformation of a taxane (1) by Streptomyces griseus. The structures of the isolates were elucidated by spectroscopic analysis. The absolute configuration of 4, which exhibited potent reversal activity in the A549/taxol MDR tumor cell line, was unambiguously deduced by single-crystal X-ray diffraction.

Publication types

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

MeSH terms

Biotransformation
Bridged-Ring Compounds / chemistry*
Bridged-Ring Compounds / isolation & purification*
Bridged-Ring Compounds / pharmacology*
Crystallography, X-Ray
Drug Resistance, Multiple / drug effects*
Molecular Conformation
Molecular Structure
Streptomyces griseus / chemistry
Streptomyces griseus / metabolism*
Taxoids / chemistry*
Taxoids / isolation & purification*
Taxoids / pharmacology*

Substances

10alpha,18-epoxy-10beta-hydroxy-9-oxo-2alpha,5alpha,14beta-triacetoxytaxa-4(20),11(12)-diene
Bridged-Ring Compounds
Taxoids
taxane