Identification of Minor Benzoylated 4-Phenylcoumarins from a Mammea neurophylla Bark Extract

Molecules. 2015 Sep 25;20(10):17735-46. doi: 10.3390/molecules201017735.

Abstract

Through dereplication analysis, seven known Mammea coumarins were identified in a fraction obtained from Mammea neurophylla dichloromethane bark extract selected for its ability to prevent advanced glycation end-product (AGE) formation. Among them, a careful examination of the NMR dataset of pedilanthocoumarin B led to a structural revision. Inspection of LC-DAD-MS(n) chromatograms allowed us to predict the presence of four new compounds, which were further isolated. Using spectroscopic methods (¹H-, (13)C- and 2D-NMR, HRMS, UV), these compounds were identified as new benzoyl substituted 4-phenylcoumarins (iso-pedilanthocoumarin B and neurophyllol C) and 4-(1-acetoxypropyl)coumarins cyclo F (ochrocarpins H and I).

Keywords: 4-(1-acetoxypropyl)coumarins; 4-phenylcoumarins; Calophyllaceae; benzoylcoumarins; dereplication analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemistry*
  • Mammea / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry*

Substances

  • Coumarins
  • Plant Extracts
  • 4-phenylcoumarin