Camellianols A-G, Barrigenol-like Triterpenoids with PTP1B Inhibitory Effects from the Endangered Ornamental Plant Camellia crapnelliana

J Nat Prod. 2017 Nov 22;80(11):2874-2882. doi: 10.1021/acs.jnatprod.7b00241. Epub 2017 Oct 24.

Abstract

Seven new naturally occurring barrigenol-like compounds, camellianols A-G (1-7), and 10 known triterpenoids were isolated from the twigs and leaves of the cultivated endangered ornamental plant Camellia crapnelliana. According to the ECD octant rule for saturated cyclohexanones, the absolute configurations of camellianols D (4) and E (5) were defined. The backbones of the remaining new isolates are assumed to have the same absolute configuration as compounds 4, 5, and harpullone (12). Compounds 2, 3, 9, 10, 13, and 16 exhibited inhibitory effects on the protein tyrosine phosphatase 1B (PTP1B) enzyme, with IC50 values less than 10 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Camellia / chemistry*
  • Cyclohexanones / chemistry
  • Cyclohexanones / isolation & purification
  • Cyclohexanones / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Components, Aerial / chemistry*
  • Plant Leaves
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Cyclohexanones
  • Drugs, Chinese Herbal
  • Triterpenes
  • PTPN1 protein, human
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1