Enantiomeric pairs of meroterpenoids from Rhododendron fastigiatum

Chin J Nat Med. 2019 Dec;17(12):963-969. doi: 10.1016/S1875-5364(19)30119-0.

Abstract

Five pairs of optically pure meroterpenoid enantiomers (1a/1b-5a/5b) and two known compounds (6 and 7) were isolated from Rhododendron fastigiatum. Compounds 1a/1b-5a/5b were resolved from naturally scalemic mixtures by chiral HPLC. Their structures were elucidated by spectroscopic methods, X-ray crystallographic experiments, and ECD analyses. Compounds 1a/1b, 2a/2b, 3b, 4a/4b, and 5a/5b were new meroterpenoids with different polycyclic systems. Two enantiomeric pairs (2a/2b and 3a/3b), 6, and 7 exhibited inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) in vitro.

Keywords: Meroterpenoid enantiomers; Protein tyrosine phosphatase 1B; Rhododendron fastigiatum.

MeSH terms

  • China
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Rhododendron / chemistry*
  • Terpenes / chemistry*
  • Terpenes / isolation & purification*

Substances

  • Terpenes
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1