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Optical rotation of quinolizidine alkaloids: An important variable in chemosystematic studies ofFabaceae
Authors:B. -E. van Wyk  G. H. Verdoorn
Affiliation:(1) Department of Botany, Rand Afrikaans University, Auckland Park 2006, P.O. Box 524, Johannesburg, Republic of South Africa;(2) Department of Chemistry & Biochemistry, Rand Afrikaans University, Auckland Park 2006, P.O. Box 524, Johannesburg, Republic of South Africa
Abstract:
The anomalous distribution of (+)-lupanine and (–)-lupanine inPodalyria species provides circumstantial evidence that hydroxylation and subsequent esterification of lupanine is only possible when (–)-sparteine and (+)-lupanine are the precursors. The optical rotation of lupanine and/or sparteine isolated from different genera, in combination with literature data, provide evidence of a separate biosynthetic pathway which leads to lupanine-type esters rather than agr-pyridones. The occurrence of this pathway can be predicted from the optical rotation of sparteine and/or lupanine, even in the absence of end products. Enantiomers-specificity is thus an important variable for establishing homology in comparative studies.
Keywords:Fabaceae  Papilionoideae  Biochemical pathways  chemosystematics  enantiomers  optical rotation  lupanine  sparteine  quinolizidine alkaloids
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