Approach to the biosynthesis of atisine-type diterpenoid alkaloids

J Nat Prod. 2009 Apr;72(4):645-9. doi: 10.1021/np800657j.

Abstract

To determine the biosynthesis pathway of the atisine-type diterpenoid alkaloids spiramines A/B and C/D, feeding experiments in in vitro cultured plantlets and enzymatic transformations in cell-free extracts were performed in combination with LCMS and tandem MS analyses. L-[2-(13)C,(15)N]Serine was used in the feeding experiments and enzymatic transformations, and the diterpene spiraminol was identified as a biosynthetic precursor of spiramine alkaloids. The LCMS and tandem MS spectra of the extracts from these experiments indicated that L-[2-(13)C,(15)N]serine was incorporated into spiramines A/B and C/D. The labeled reaction products show that l-serine is the one possible nitrogen source involved in the biosynthesis of atisine-type DAs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / metabolism*
  • Diterpenes / chemistry
  • Diterpenes / metabolism*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / metabolism*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / metabolism*
  • Molecular Structure
  • Serine / chemistry
  • Serine / metabolism
  • Spiraea / chemistry*

Substances

  • Alkaloids
  • Diterpenes
  • Drugs, Chinese Herbal
  • Heterocyclic Compounds, 4 or More Rings
  • Serine