Transformation of strictosamide to vincoside lactam by acid catalysis

Chin J Nat Med. 2013 Mar;11(2):188-92. doi: 10.1016/S1875-5364(13)60048-5.

Abstract

Aim: To identify the structure of the acid-catalyzed product of strictosamide and explore the reaction mechanism.

Methods: The acid-catalyzed reaction process of strictosamide was monitored by HPLC, and a macroporous resin was used to purify the reaction solution. The structure of the product was confirmed by MS, NMR, and ROESY spectra.

Results: The acid-catalyzed transformation yield from strictosamide to vincoside lactam was 52%.

Conclusion: The reaction mechanism of the transformation from strictosamide to vincoside lactam may be related to the stability of the three-dimensional configuration of the compound. These results offer a new way to obtain vincoside lactam from the widely distributed indole alkaloid strictosamide by acid-catalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Lactams / chemistry*
  • Molecular Structure
  • Vinca Alkaloids / chemistry*

Substances

  • Acids
  • Lactams
  • Vinca Alkaloids
  • strictosamide