Chlorabietols A-C, Phloroglucinol-Diterpene Adducts from the Chloranthaceae Plant Chloranthus oldhamii

J Org Chem. 2015 Nov 6;80(21):11080-5. doi: 10.1021/acs.joc.5b01658. Epub 2015 Oct 14.

Abstract

Three unprecedented phloroglucinol-diterpene adducts, chlorabietols A-C (1-3), were isolated from the roots of the rare Chloranthaceae plant Chloranthus oldhamii. They represent a new class of compounds, featuring an abietane-type diterpenoid coupled with different alkenyl phloroglucinol units by forming a 2,3-dihydrofuran ring. Their structures were elucidated by detailed spectroscopic analysis, molecular modeling studies, and electronic circular dichroism calculations. Compounds 1-3 showed inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 12.6, 5.3, and 4.9 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Furans / chemistry*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Phloroglucinol / chemistry*
  • Phloroglucinol / isolation & purification
  • Plant Roots
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / pharmacology*

Substances

  • Diterpenes
  • Furans
  • chlorabietol A
  • chlorabietol B
  • chlorabietol C
  • 2,3-dihydrofuran
  • Phloroglucinol
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1