Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Molecules. 2021 May 27;26(11):3224. doi: 10.3390/molecules26113224.

Abstract

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

Keywords: biological activity; bletistrin G; natural products; shancigusin C; total synthesis.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Biological Products / pharmacology*
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Chemistry, Pharmaceutical / methods
  • Dihydrostilbenoids / chemistry
  • Drug Design
  • Drug Resistance, Multiple*
  • Drug Resistance, Neoplasm
  • Humans
  • Leukemia / drug therapy
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Orchidaceae*
  • Plant Extracts / pharmacology*
  • Stereoisomerism
  • Stilbenes / chemistry

Substances

  • Antineoplastic Agents
  • Biological Products
  • Dihydrostilbenoids
  • Plant Extracts
  • Stilbenes