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United States Department of Agriculture

Agricultural Research Service

Research Project: THE TOXICITY OF PYRROLIZIDINE ALKALOID-CONTAINING PLANTS AND OTHER HEPATOTOXIC AND NEUROTOXIC PLANTS

Location: Poisonous Plant Research

Title: Separation and Measurement of Plant Alkaloid Enantiomers by RP-HPLC Analysis of their Fmoc-Alanine Analogs

Authors
item Lee, Stephen
item Gardner, Dale
item Chang, Cheng-Wei - USU
item Panter, Kip
item Molyneux, Russell

Submitted to: Phytochemical Analysis
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 17, 2008
Publication Date: April 25, 2008
Repository URL: http://www.pprl.ars.usda.gov
Citation: Lee, S.T., Gardner, D.R., Chang, C.T., Panter, K.E., Molyneux, R.J. 2008. Separation and Measurement of Plant Alkaloid Enantiomers by RP-HPLC Analysis of their Fmoc-Alanine Analogs. Phytochemical Analysis, 19:395-402. DOI: 10.1002/pca.1064.

Interpretive Summary: Plants often make chemicals that are enantiomers (non-super-imposable mirror images of each other). Enantiomers can cause very different physiological responses. Ammodendrine and anabasine can cause birth defects in livestock. Enantiomeric forms of each have been found in Lupinus and Nicotiana plants, respectively. Simple and economical separation methods were developed to determine the enantiomeric ratios of these chemicals in plants. We show that the enantiomeric ratio of ammodendrine in L. formosus and L. sulphureus can vary between location and species and that we can measure the enantiomeric ratio of anabasine from N. glauca. When this information is linked with toxicity and birth defect information for the isolated enantiomers this method becomes important in discriminating between plants that are toxic and plants and plant communities that are quality livestock forage.

Technical Abstract: Plants often synthesize secondary metabolites that are enantiomers. Enantiomers can cause very different physiological responses. Ammodendrine (1) and anabasine (2) are teratogens that can cause congenital malformations in livestock and enantiomeric forms of each have been found in Lupinus spp. and Nicotiana spp., respectively. Nornicotine (4) an enantiomeric alkaloid found in Nicotiana tabacum has been shown to induce malformations in chick embryos. Simple and economical analytical reversed phase HPLC methods were developed to determine the enantiomeric ratios based on the formation of diastereomers after the reaction of Fmoc-L-Ala-OH with ammodendrine and anabasine from small samples of plant material. We show that the enantiomeric ratio of ammodendrine in L. formosus and L. sulphureus can vary between location and species and that we can measure the enantiomeric ratio of anabasine from N. glauca. We demonstrate that we can measure the enantiomeric ratio of nornicotine. When this information is linked with toxicological and teratogenic data for the isolated enantiomers this method becomes important in discriminating between plants that are toxic or teratogenic and plants and plant communities that are quality livestock forage.

Last Modified: 7/31/2014
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