Structure-Activity Relationship of Condensed Tannins and Synergism with trans-Cinnamaldehyde against Caenorhabditis elegans

J Agric Food Chem. 2016 Nov 23;64(46):8795-8805. doi: 10.1021/acs.jafc.6b03842. Epub 2016 Nov 14.

Abstract

Parasitic gastrointestinal nematodes (GIN) of livestock are increasingly developing resistance to synthetic nematocidal drugs. Moreover, the use of nematocides can induce ecotoxicity by affecting free-living nematodes. Condensed tannins (CT) are a structurally diverse group of bioactive plant compounds possessing anthelmintic activity against GIN. We investigated the relationship between the chemical structure of contrasting, purified CT and nematocidal effects using Caenorhabditis elegans. We also explored whether the nematocidal activity of CT could synergize with trans-cinnamaldehyde (CIN). A nonsignificant correlation was evident between the ability of CT fractions to inhibit C. elegans motility and the molar proportion of prodelphinidin subunits in purified CT samples. Synergistic inhibition of motility was achieved by combinations of CT and CIN. Galloylation of procyanidins was also a key factor for synergy. To increase the nematocidal effect of CT, plant sources containing CT with specific structural features could be selected and combined with compounds acting in synergy.

Keywords: Caenorhabditis elegans; cinnamaldehyde; condensed tannins; nematode; proanthocyanidins; procyanidins; prodelphinidins; scanning electron microscopy.

MeSH terms

  • Acrolein / analogs & derivatives*
  • Acrolein / chemistry
  • Acrolein / pharmacology
  • Animals
  • Anthelmintics / chemistry
  • Anthelmintics / pharmacology*
  • Caenorhabditis elegans / drug effects*
  • Caenorhabditis elegans / growth & development
  • Drug Synergism
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plants / chemistry
  • Proanthocyanidins / chemistry
  • Proanthocyanidins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anthelmintics
  • Plant Extracts
  • Proanthocyanidins
  • Acrolein
  • cinnamaldehyde