Highly Oxygenated Triterpenoids and Rare Tetraterpenoids from Abies chensiensis and Their Antibacterial Activity

J Nat Prod. 2019 Oct 25;82(10):2859-2869. doi: 10.1021/acs.jnatprod.9b00616. Epub 2019 Sep 26.

Abstract

Nine new cycloartane triterpenoids (1, 2, 4, 7, 8, 12, 15, 17, and 18) and two new rare tetraterpenoids (24 and 25) formed via a [4 + 2] Diels-Alder cycloaddition between a lanostane triterpenoid and a monoterpenoid, along with 14 previously known triterpenoids, were isolated from the bark of the branches of Abies chensiensis. The structures and absolute configurations of new compounds were elucidated based on spectroscopic data, X-ray diffraction analysis, and electronic circular dichroism. Some of the isolates were evaluated for their antibacterial activity by determining their minimum inhibitory concentrations and growth inhibition curves and examining for morphological alterations. Among the compounds tested, the new cycloartane triterpenoid 8 was the most active against Bacillus subtilis. Thus, morphological alterations of B. subtilis on treatment with 8 were observed by scanning electron microscopy, showing that the cells were irregular, wrinkled, and disrupted.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abies / chemistry*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Carotenoids / chemistry
  • Carotenoids / isolation & purification*
  • Carotenoids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Triterpenes
  • Carotenoids