Magmenthanes A-H: Eight new meroterpenoids from the bark of Magnolia officinalis var. Biloba

Bioorg Chem. 2019 Jul:88:102948. doi: 10.1016/j.bioorg.2019.102948. Epub 2019 Apr 27.

Abstract

Eight new meroterpenoids with different types of monoterpene units, namely, magmenthanes A-H (1-8), were identified from the bark of Magnolia officinalis var. biloba. Magmenthane A (1) possesses a 1,3-dioxabicyclo [4.3.01,5] nonane skeleton, 1-5 possess five pairs of enantiomers and 6 possesses a 1,1'-diallyl-biphenyl fragment. The structures of 1-8 were elucidated on the basis of 1D and 2D NMR, HRESIMS and electronic circular dichroism (ECD) calculations. Compounds 5 and 8 displayed significant PTP1B inhibitory activities with IC50 values of 4.38 and 3.88 μM, respectively.

Keywords: Magnolia officinalis var. biloba; Meroterpenoid; PTP1B inhibitory.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Glutamic Acid / pharmacology
  • Humans
  • Magnolia / chemistry*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification
  • Neuroprotective Agents / pharmacology*
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
  • Structure-Activity Relationship
  • Terpenes / chemistry
  • Terpenes / isolation & purification
  • Terpenes / pharmacology*

Substances

  • Enzyme Inhibitors
  • Neuroprotective Agents
  • Plant Extracts
  • Terpenes
  • Glutamic Acid
  • PTPN1 protein, human
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1