Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the Leaves of Uvaria cherrevensis

J Nat Prod. 2019 Jan 25;82(1):101-110. doi: 10.1021/acs.jnatprod.8b00794. Epub 2019 Jan 4.

Abstract

The chemical study of leaf extracts from Uvaria cherrevensis resulted in the identification of 11 new polyoxygenated cyclohexenes, cherrevenols A-K (1-11), and a new seco-cyclohexene derivative, cherrevenol L (12). Nine known compounds (13-21) were also isolated. Three of the isolated compounds are chlorinated polyoxygenated cyclohexenes. The structures of these compounds were determined using spectroscopic methods and, in some cases (compounds 2, 6, 8, and 10), single-crystal X-ray crystallographic structural analysis or chemical correlation (compounds 6 and 7). Compounds 6 and 7 were both isolated as scalemic mixtures (ee 23-24%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chlorocebus aethiops
  • Cyclohexenes / chemistry
  • Cyclohexenes / isolation & purification*
  • Cyclohexenes / pharmacology
  • Humans
  • KB Cells
  • Magnetic Resonance Spectroscopy
  • Plant Extracts / analysis
  • Uvaria / chemistry*
  • Vero Cells

Substances

  • Cyclohexenes
  • Plant Extracts