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Eryngial (trans-2-dodecenal), a bioactive compound from Eryngium foetidum: its identification, chemical isolation, characterization and comparison with ivermectin in vitro

Published online by Cambridge University Press:  21 October 2013

W. M. FORBES ,
W. A. GALLIMORE ,
A. MANSINGH ,
P. B. REESE  and
R. D. ROBINSON
W. M. FORBES*
Affiliation:
Department of Life Sciences, The University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies
W. A. GALLIMORE
Affiliation:
Department of Chemistry, The University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies
A. MANSINGH
Affiliation:
Department of Life Sciences, The University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies
P. B. REESE
Affiliation:
Department of Chemistry, The University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies
R. D. ROBINSON
Affiliation:
Department of Life Sciences, The University of the West Indies, Mona Campus, Kingston 7, Jamaica, West Indies
*
*Corresponding author: Department of Biology, College of Health, Environment and Science, Slippery Rock University of Pennsylvania, 1 Morrow Way, Slippery Rock, PA 16057, USA. E-mail: wayne.forbes@sru.edu
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Summary

Methanol-water (4:1, v/v) crude extracts (50 mg mL−1) of 25 Jamaican medicinal plants were screened in vitro for anthelmintic activity using infective third-stage larvae of Strongyloides stercoralis. The most effective extract was further chemically scrutinized to isolate and identify the source of the bioactivity, and the efficacy of this compound was compared with ivermectin. Eosin exclusion (0·1 mg mL−1) served as the indicator of mortality in all bioassays. A crude extract of Eryngium foetidum (Apiaceae) was significantly (Probit Analysis, P<0·05) more potent than the other plant extracts, taking 18·9 h to kill 50% (LT50) of the larvae. Further, the petrol extract of E. foetidum was significantly more effective (Probit Analysis, P<0·05) at killing the larvae (LT50, 4·7 h) than either its methanol–water or dichloromethane extract. The latter two effected less than 1% larval mortality after 120 h. With bioassay-driven column chromatography of the petrol extract, trans-2-dodecenal (eryngial) was identified and chemically isolated as the main anthelmintic compound in E. foetidum. There was a significant difference between the 24 h LD50 values (mm) of trans-2-dodecenal (0·461) and ivermectin (2·251) but there was none between the 48 h LD50 values (mm): trans-2-dodecenal (0·411) and ivermectin (0·499) in vitro.

Keywords

Medicinal plantstrans-2-dodecenalivermectinbioassayStrongyloides stercoralis
Type
Research Article
Information
Parasitology , Volume 141 , Issue 2 , February 2014 , pp. 269 - 278
Copyright
Copyright © Cambridge University Press 2013 

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