Berchemiosides A-C, 2-Acetoxy-ω-phenylpentaene Fatty Acid Triglycosides from the Unripe Fruits of Berchemia berchemiifolia

J Nat Prod. 2017 Oct 27;80(10):2778-2786. doi: 10.1021/acs.jnatprod.7b00602. Epub 2017 Oct 3.

Abstract

Three compounds in a new class of 2-acetoxy-ω-phenylpentaene fatty acid triglycosides, berchemiosides A-C (1-3), and a biosynthetically related phenolic glycoside (4) were isolated from the unripe fruits of Berchemia berchemiifolia, along with three flavonoid 5-O-diglycosides (5-7) and three known flavonoids (8-10). Their chemical structures including absolute configurations were determined by spectroscopic analysis in combination with chemical derivatization. The pentaene group of 1 was found to have (6E,8E,10Z,12Z,14E)-geometry, whereas those of 2 and 3 exhibited all-E geometries. The isolated compounds were examined for their cytotoxicity and xanthine oxidase (XO) inhibitory activity; only compound 7 showed weak XO inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / isolation & purification*
  • Fatty Acids, Unsaturated / pharmacology
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Fruit / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhamnaceae / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Xanthine Oxidase / antagonists & inhibitors

Substances

  • Fatty Acids, Unsaturated
  • Flavonoids
  • Glycosides
  • berchemioside A
  • berchemioside B
  • berchemioside C
  • Xanthine Oxidase