Di- and Triterpenoids from the Leaves of Casearia balansae and Neurite Outgrowth Promoting Effects of PC12 Cells

J Nat Prod. 2016 Jan 22;79(1):170-9. doi: 10.1021/acs.jnatprod.5b00815. Epub 2015 Dec 24.

Abstract

A bioassay-guided phytochemical investigation of the leaves of Casearia balansae led to the isolation of six new cucurbitane-type triterpenoid derivatives (balanterpenes A-F, 1-6) and four new clerdoane-type diterpenoids (balanterpenes G-J, 7-10). The structures of 1-10 were established on the basis of extensive analysis of NMR spectroscopic data, X-ray crystallography, and experimental and calculated electronic circular dichroism spectra. Compound 1 features a ring-expanded triterpenoid skeleton with the C-19 methyl involved in the ring formation, compound 6 possesses a rare hexanortriterpenoid scaffold, and compounds 7-10 may be four new diterpenoid artifacts presumably formed during the extraction and purification processes. Compounds 3 and 7-10 showed promoting effects on neurite outgrowth of PC12 cells with EC50 values in the range 2.9-10.0 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Casearia / chemistry*
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification*
  • Diterpenes, Clerodane / pharmacology*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Molecular Structure
  • Neurites / drug effects*
  • Nuclear Magnetic Resonance, Biomolecular
  • PC12 Cells
  • Plant Leaves / chemistry
  • Rats
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Diterpenes, Clerodane
  • Drugs, Chinese Herbal
  • Triterpenes