Biotransformation of 4(20),11-taxadienes by cell suspension cultures of Platycodon grandiflorum

J Asian Nat Prod Res. 2003 Mar;5(1):5-10. doi: 10.1080/1028602031000080397.

Abstract

Platycodon grandiflorum cell suspension cultures were employed to biotransform the taxane diterpenoids 2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (1) and 9alpha-hydroxy-2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (2). One product, 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (3) was obtained from 1 and two products, 9alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (4) and 10beta-hydroxy-2alpha,5alpha,9alpha,14beta-tetraacetoxy-4(20),11-taxadiene (5) were obtained from 2 incubated with Platycodon cultured cells respectively, among which 5 is characterized as a new taxoid compound. The effects of the addition stage for 1 and 2 on the biotransformation were investigated and the results revealed that: (1) the optimal addition stage for 1 was in the early logarithmic phase (6th day) of the cell growth period, in which 78% of 1 was converted and the yield for 3 reached 75%; (2) the optimal addition stage for 2 was on the mid-logarithmic phase (12th day) of the cell growth period, in which 25.3% of 2 was converted and the yields for 4 and 5 reached 18.9 and 14.5%, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / administration & dosage
  • Alkenes / chemistry
  • Alkenes / pharmacokinetics*
  • Biotransformation
  • Cells, Cultured / metabolism
  • Diterpenes / administration & dosage
  • Diterpenes / chemistry
  • Diterpenes / pharmacokinetics*
  • Humans
  • Phytotherapy*
  • Platycodon / metabolism*
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Taxus*

Substances

  • Alkenes
  • Diterpenes
  • taxa-4(5),11(12)diene