Palmarumycins BG1-BG7 and preussomerin BG1: establishment of their absolute configurations using theoretical calculations of electronic circular dichroism spectra

J Org Chem. 2011 Mar 18;76(6):1821-30. doi: 10.1021/jo1024877. Epub 2011 Feb 18.

Abstract

Palmarumycins BG1-BG7 (1-7), seven new compounds related to palmarumycins, were isolated from the aerial parts of Bruguiera gymnorrhiza as well as a new preussomerin derivative BG1 (8). The structures of these compounds were determined mainly by the analysis of their NMR and MS data, and their relative configurations were assigned on the basis of their (3)J(H,H) coupling constants. Compounds 4 and 7 have a sulfate group that is unprecedented among members of spirodioxynaphthalene-type natural products. The absolute configurations of 1-8 were determined by TDDFT CD calculations of the solution conformers. Compound 5 displayed inhibitory activity against HL 60 and MCF-7 cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Circular Dichroism
  • Electrons*
  • HL-60 Cells
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Quantum Theory*
  • Spiro Compounds / chemistry*
  • Spiro Compounds / metabolism
  • Spiro Compounds / pharmacology

Substances

  • Antineoplastic Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Spiro Compounds
  • preussomerin BG1