MetaCyc Pathway: lupanine biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: lupanine biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisNitrogen-Containing Secondary Compounds BiosynthesisAlkaloids BiosynthesisQuinolizidine Alkaloids Biosynthesis

Some taxa known to possess this pathway include : Lupinus albus, Lupinus polyphyllus

Expected Taxonomic Range: Fabaceae

Lupanine is a tetracyclic quinolizidine alkaloid. Quinolizidine alkaloids are mainly distributed in the family Leguminosae. In some leguminous species, the final products of their biosynthesis as well as the storage forms are the ester alkaloids, usually as the esters of acetic acid, tiglic acid, p-coumaric acid, and ferulic acid. The tigloyl esters of quinolizidine alkaloids are found as the major forms among ester alkaloids in some Lupinus plants including L. termis, L. albus, and L. polyphyllus. Quinolizidine alkaloids were shown to have inhibitory activities against insects.

The pathway occurs in the chloroplast [Hartmann80, Wink82].

Citations: [Suzuki94]

Created 31-Jan-2007 by Zhang P, TAIR


Hartmann80: Hartmann T, Schoofs G, Wink M (1980). "A chloroplast-localized lysine decarboxylase of Lupinus polyphyllus: the first enzyme in the biosynthetic pathway of quinolizidine alkaloids." FEBS Lett 115(1);35-8. PMID: 7389917

Suzuki94: Suzuki H, Murakoshi I, Saito K (1994). "A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants." J Biol Chem 269(22);15853-60. PMID: 8195240

Wink82: Wink M, Hartmann T (1982). "Localization of the Enzymes of Quinolizidine Alkaloid Biosynthesis in Leaf Chloroplasts of Lupinus polyphyllus." Plant Physiol 70(1);74-77. PMID: 16662483

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

BaronaGomez04: Barona-Gomez F, Wong U, Giannakopulos AE, Derrick PJ, Challis GL (2004). "Identification of a cluster of genes that directs desferrioxamine biosynthesis in Streptomyces coelicolor M145." J Am Chem Soc 126(50);16282-3. PMID: 15600304

Boeker83: Boeker EA, Fischer EH (1983). "Lysine decarboxylase (Escherichia coli B)." Methods Enzymol 94;180-4. PMID: 6353151

BRENDA14: BRENDA team (2014). Imported from BRENDA version existing on Aug 2014.

Fothergill77: Fothergill JC, Guest JR (1977). "Catabolism of L-lysine by Pseudomonas aeruginosa." J Gen Microbiol 99(1);139-55. PMID: 405455

Goldemberg80: Goldemberg SH (1980). "Lysine decarboxylase mutants of Escherichia coli: evidence for two enzyme forms." J Bacteriol 141(3);1428-31. PMID: 6767710

Kamio83: Kamio Y, Terawaki Y (1983). "Purification and properties of Selenomonas ruminantium lysine decarboxylase." J Bacteriol 153(2);658-64. PMID: 6401702

Kanjee11: Kanjee U, Gutsche I, Alexopoulos E, Zhao B, El Bakkouri M, Thibault G, Liu K, Ramachandran S, Snider J, Pai EF, Houry WA (2011). "Linkage between the bacterial acid stress and stringent responses: the structure of the inducible lysine decarboxylase." EMBO J 30(5);931-44. PMID: 21278708

Kanjee11a: Kanjee U, Gutsche I, Ramachandran S, Houry WA (2011). "The enzymatic activities of the Escherichia coli basic aliphatic amino acid decarboxylases exhibit a pH zone of inhibition." Biochemistry 50(43);9388-98. PMID: 21957966

Kikuchi97: Kikuchi Y, Kojima H, Tanaka T, Takatsuka Y, Kamio Y (1997). "Characterization of a second lysine decarboxylase isolated from Escherichia coli." J Bacteriol 1997;179(14);4486-92. PMID: 9226257

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lemonnier98: Lemonnier M, Lane D (1998). "Expression of the second lysine decarboxylase gene of Escherichia coli." Microbiology 1998;144 ( Pt 3);751-60. PMID: 9534244

Moreau07: Moreau PL (2007). "The lysine decarboxylase CadA protects Escherichia coli starved of phosphate against fermentation acids." J Bacteriol 189(6);2249-61. PMID: 17209032

Okada05: Okada T, Hirai MY, Suzuki H, Yamazaki M, Saito K (2005). "Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants." Plant Cell Physiol 46(1);233-44. PMID: 15659437

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216

Sabo74: Sabo DL, Boeker EA, Byers B, Waron H, Fischer EH (1974). "Purification and physical properties of inducible Escherichia coli lysine decarboxylase." Biochemistry 1974;13(4);662-70. PMID: 4590109

Sabo74a: Sabo DL, Fischer EH (1974). "Chemical properties of Escherichia coli lysine decarboxylase including a segment of its pyridoxal 5'-phosphate binding site." Biochemistry 13(4);670-6. PMID: 4204273

Schupp87: Schupp, T., Waldmeier, U., Divers, M. (1987). "Biosynthesis of desferrioxamine B in Streptomyces pilosus: evidence for the involvement of lysine decarboxylase." FEMS Microbiol. Let. 42: 135-139.

SHER54: SHER IH, MALLETTE MF (1954). "The adaptive nature of the formation of lysine decarboxylase in Escherichia coli B." Arch Biochem Biophys 52(2);331-9. PMID: 13208257

SHER54a: SHER IH, MALLETTE MF (1954). "Purification and study of L-lysine decarboxylase from Escherichia coli B." Arch Biochem Biophys 53(2);354-69. PMID: 13218704

Takatsuka99: Takatsuka Y, Onoda M, Sugiyama T, Muramoto K, Tomita T, Kamio Y (1999). "Novel characteristics of Selenomonas ruminantium lysine decarboxylase capable of decarboxylating both L-lysine and L-ornithine." Biosci Biotechnol Biochem 63(6);1063-9. PMID: 10427692

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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