Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla

Sci Rep. 2017 Mar 2:7:43646. doi: 10.1038/srep43646.

Abstract

A novel triterpenoid, holophyllane A (1), featuring a B-nor-3,4-seco-17,14-friedo-lanostane, along with its putative precursor, compound 2 were isolated from the methanol extract of the trunks of Abies holophylla. The 2D structure and relative configuration of 1 were initially determined via analysis of 1D and 2D NMR spectroscopic data and the assignment was confirmed by quantum mechanics-based NMR chemical shift calculations. The absolute configuration was established by comparison of the experimental and simulated ECD data generated at different theory levels. Compounds 1 and 2 exhibited moderate to weak cytotoxicity and significant inhibitory activity against nitric oxide (NO) production.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abies / chemistry*
  • Abies / metabolism
  • Biosynthetic Pathways
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / genetics
  • Nitric Oxide Synthase Type II / metabolism
  • Plant Extracts / chemistry*
  • Triterpenes / chemistry*
  • Triterpenes / metabolism

Substances

  • Plant Extracts
  • Triterpenes
  • Nitric Oxide
  • Nitric Oxide Synthase Type II