title: Structure-Activity Relationship of Condensed Tannins and Synergism with trans-Cinnamaldehyde against Caenorhabditis elegans.
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.
authors: Chemistry and Biochemistry Laboratory, School of Agriculture, Policy and Development, University of Reading , 1 Earley Gate, Reading RG6 6AT, United Kingdom.
authors: Honorata M
authors: HM
authors: Ropiak
authors: Veterinary Parasitology Group, Department of Veterinary Disease Biology, University of Copenhagen , Dyrlægevej 100, 1870 Frederiksberg C, Denmark.
authors: Olivier
authors: O
authors: Desrues
authors: Veterinary Parasitology Group, Department of Veterinary Disease Biology, University of Copenhagen , Dyrlægevej 100, 1870 Frederiksberg C, Denmark.
authors: Andrew R
authors: AR
authors: Williams
authors: Chemistry and Biochemistry Laboratory, School of Agriculture, Policy and Development, University of Reading , 1 Earley Gate, Reading RG6 6AT, United Kingdom.
authors: Aina
authors: A
authors: Ramsay
authors: Chemistry and Biochemistry Laboratory, School of Agriculture, Policy and Development, University of Reading , 1 Earley Gate, Reading RG6 6AT, United Kingdom.
authors: Irene
authors: I
authors: Mueller-Harvey
authors: Veterinary Parasitology Group, Department of Veterinary Disease Biology, University of Copenhagen , Dyrlægevej 100, 1870 Frederiksberg C, Denmark.
authors: Stig M
authors: SM
authors: Thamsborg
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000871:Anthelmintics / Q000737:chemistry / Q000494:pharmacology*; D017173:Caenorhabditis elegans / Q000187:drug effects* / Q000254:growth & development; D004357:Drug Synergism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D010944:Plants / Q000737:chemistry; D044945:Proanthocyanidins / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000871:Anthelmintics; D010936:Plant Extracts; D044945:Proanthocyanidins; D000171:Acrolein; C012843:cinnamaldehyde
keywords: Caenorhabditis elegans; cinnamaldehyde; condensed tannins; nematode; proanthocyanidins; procyanidins; prodelphinidins; scanning electron microscopy