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United States Department of Agriculture

Agricultural Research Service

Title: Separation and Isolation of Teratogenic Piperidine Enantiomers from Nicotiana and Lupinus Species

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

Submitted to: Poisonous Plant Global Research and Solutions
Publication Type: Book / Chapter
Publication Acceptance Date: May 31, 2006
Publication Date: June 20, 2007
Citation: Lee, S.T., Panter, K.E., Molyneux, R.J., Chang, C.T., Gardner, D.R., Pfister, J.A. 2007. Separation and isolation of teratogenic piperidine enantiomers from nicotiana and lupinus species. Poisonous Plant Global Research and Solutions, Chpt. 80, pp. 469 - 475.

Interpretive Summary: Ingestion of Lupinus and Nicotiana species by pregnant livestock at specific gestational periods can result in offspring with cleft palates and deformed front limbs. Ammodendrine and anabasine are teratogens and are found in Lupinus and Nicotiana species, respectively. Both ammodendrine and anabasine are piperidine alkaloids that have chiral centers. Ammodendrine and anabasine were reacted in a peptide coupling reaction with 9-fluorenylmethoxycabonyl-L-alanine to give diastereomers which were separated and isolated by HPLC. Ammodendrine was found to occur as a mixture of enantiomers in several Lupinus species. Anabasine was also found to occur as a mixture of enantiomers in Nicotiana glauca. Ammodendrine and anabasine enantiomers were obtained by Edman Degradation of the ammodendrine and anabasine based diastereomers. Isolation of ammodendrine and anabasine into the D-(+) and L-(-) forms allowed for optical rotation measurements and toxicological characterization of the enantiomers.

Technical Abstract: Ingestion of Lupinus and Nicotiana species by pregnant livestock at specific gestational periods can result in calves, piglets, lambs and kids with cleft palate and front limb contractures. Ammodendrine and anabasine are teratogens and are found in Lupinus and Nicotiana species, respectively. Both ammodendrine and anabasine are piperidine alkaloids that have chiral centers. Ammodendrine and anabasine were reacted in a peptide coupling reaction with 9-fluorenylmethoxycabonyl-L-alanine to give diastereomers which were separated and isolated by HPLC. Ammodendrine was found to occur as a mixture of enantiomers in several Lupinus species. Anabasine was also found to occur as a mixture of enantiomers in Nicotiana glauca. Ammodendrine and anabasine enantiomers were obtained by Edman Degradation of the ammodendrine and anabasine based diastereomers. Isolation of ammodendrine and anabasine into the D-(+) and L-(-) forms allowed for optical rotation measurements and toxicological characterization of the enantiomers.

Last Modified: 12/17/2014
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