Psidials A-C, three unusual meroterpenoids from the leaves of Psidium guajava L

Org Lett. 2010 Feb 19;12(4):656-9. doi: 10.1021/ol9024869.

Abstract

Three novel sesquiterpenoid-based meroterpenoids of psidials A-C (1-3) have been isolated from the leaves of Psidium guajava L. Their complete structures were elucidated by spectral and chemical methods, and that of 1 was confirmed by single-crystal X-ray diffraction analysis. Psidial B (2) and C (3) represented the new skeleton of the 3,5-diformylbenzyl phloroglucinol-coupled sesquiterpenoid. A possible biosynthetic pathway for 2-3 was postulated. 2-3 showed activity to enzyme PTP1B in 10 microM.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Humans
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Psidium / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Drugs, Chinese Herbal
  • Sesquiterpenes
  • psidial A
  • psidial B
  • psidial C
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1