Cipacinoids A-D, Four Limonoids with Spirocyclic Skeletons from Cipadessa cinerascens

Org Lett. 2016 Feb 5;18(3):444-7. doi: 10.1021/acs.orglett.5b03487. Epub 2016 Jan 13.

Abstract

Four limonoids, cipacinoids A-D (1-4), with spirocyclic skeletons were isolated from Cipadessa cinerascens. It is particularly notable that compounds 1-3 had a 17S-configuration for the first time in the limonoid family. Their structures with absolute configurations were assigned by spectroscopic data, X-ray crystallography, and CD analysis. Compound 1 showed moderate protein tyrosine phosphatase 1B (PTP1B) inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Limonins / pharmacology
  • Meliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology

Substances

  • Drugs, Chinese Herbal
  • Limonins
  • Spiro Compounds
  • cipacinoid A
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1