From Nicotiana glauca

Figure 2.4 Piperidine teratogens (a) anabasine from Nicotiana glauca, and (b) ammodendrine from Lupinus formosus.

Castorena, J.L. etal. 1987. A tal poisoning from Nicotiana glauca " Jottmal of Toxicology 25(5) 429-435-... 

Derivation (1) Extraction from Anabasis aphylla and Nicotiana glauca, (2) synthetic. 

Chamberlain, W.J. Polar lipid materials in cigarette smoke condensate Tob. Sci. 20 (1976) 168-170. Chedekel, M.R. 1. Aberrant biosynthetic studies in Nicotiana tabacum and Nicotiana glauca. 11. Synthetic studies of the tobacco alkaloids. 1,4-Additions to acyl carbanion equivalents Dissertation Abstr. (1973) 2519. Chen, C.M. and D.K. Meltiz Cytokinin biosynthesis in a cell-free system from cytokinin-autotrophic tobacco tissue cultures FEBS Lett. 107 (1979) 15-20. 

Although amino-acids have been administered to plants on occasions legion in number, rarely has attention been paid to the question of whether there is any selectivity for the D- or L-amino-acid in alkaloid biosynthesis. An exception appears in work on the Amaryllidaceae alkaloids where it was shown that d- and L-tyrosine were equally well utilized in lycorine biosynthesis. The question has now been answered in Nicotiana glauca for the biosynthesis of anabasine (118) and pipecolic acid (113) from lysine. Pipecolic acid was found to be derived preferentially from the D-isomer ( 48 times better), in accord with a similar preference in intact rats and corn seedlings, whereas L-lysine was the more effective precursor ( 30 times) for anabasine. 

Figure 2.6a. Biosynthesis of anabasine, nicotine, and nornicotine from a common substrate, nicotinic acid, in Nicotiana glauca (pathway B) and in N. tabacum (pathway B ).

Figure 2.15. Segregation in Nicotiana glauca x N. tabacum hybrids (Blaim and Berbec 1968). The ability to demethylate nicotine is shown in D—the dominant allele from N. glauca. Plants which bear the D gene produce nornicotine expected—75%, observed—77%. Courtesy of the authors and the journal.

DL-[2- H.6- C]lysine was incorporated into sedamine without loss of tritium, indicating an alternative pathway in plants from lysine to sedamine and other alkaloids. In this connection it is of interest that D-lysine is transformed into pipecolic acid whereas L-lysine is converted into the alkaloid anabasin in Nicotiana glauca. Analogously, in Pseudomonas putida, L-lysine is transformed into S-aminopentanoic acid but D-lysine into pipecolic acid. " The latter transformation has also been observed in corn and ryegrass seedlings. ... 

Leete E, Chedekel MR (1972) The aberrant formation of (-)-iV-methylanabasine from N-methyl-A -piperideinium chloride in Nicotiana tabacum and N. glauca. Phytochemistry 11 2751-2756... 

---