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Molecular Biology and Biotechnology of Quinolizidine Alkaloid Biosynthesis in Leguminosae Plants

  • Somnuk Bunsupa
  • Kazuki SaitoEmail author
  • Mami Yamazaki
Chapter

Abstract

Quinolizidine alkaloids (QAs) are an important class of plant secondary metabolites which are mainly distributed in the genus Lupinus. QAs are important for mankind as sources of drug and are assumed to play an important role for the survival of plant as defense compounds against pathogenic organisms or predators. However, the molecular mechanism underlying QA biosynthesis is poorly understood. Over the past decade, several molecular biotechnology techniques, such as amplified fragment length polymorphism, random amplified polymorphic DNA, and PCR-selected subtraction have been employed to identify the genes involved in QA biosynthesis. Nevertheless, only the genes that are involved in the formation of QA-ester in Lupinus plant and related genes have been identified. Alkaloid-free cultivar of Lupinus plants has gained attention not only as feed supplement but also as ingredient for human food. Various genetic mapping and cross-comparison of genome models in each of agronomical and economically important traits in Lupinus plants have been reported which would be valuable information for molecular breeding and evolutionary study of Leguminous plants. This review outlines an overview of QAs, such as the occurrences, chemistry, biochemistry, and chemotaxonomy and recent studies focusing on molecular biology and biotechnology of QA biosynthesis in Leguminosae plants.

Keywords

Anthracnose Resistance Lupinus Species Quinolizidine Alkaloid Lupinus Plant Sophora Flavescens 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. Ansorge WJ (2009) Next-generation DNA sequencing techniques. Nat Biotechnol 25:195–203Google Scholar
  2. Babaoglu M, Davey MR (2004) Transformed roots of Lupinus mutabilis: induction, culture and isoflavone biosynthesis. Plant Cell Tiss Org 78:29–36CrossRefGoogle Scholar
  3. Babaoglu M, McCabe MS, Power JB, Davey MR (2000) Agrobacterium-mediated transformation of Lupinus mutabilis L. using shoot apical explants. Acta Physiol Plant 22:111–119CrossRefGoogle Scholar
  4. Berlin J, Fecker LF, Rugenhagen C, Sator C, Strack D, Witte L, Wray V (1991) Isoflavone glycoside formation in transformed and non-transformed suspension and hairy cultures of L. polyphyllus and L. hartwegii. Z Naturforsch 46c:725–734Google Scholar
  5. Boersma JG, Pallotta M, Li C, Buirchell BJ, Sivasithamparam K, Yang H (2005) Construction of a genetic linkage map using MFLP and identification of molecular markers linked to domestication genes in narrow-leafed lupin (Lupinus angustifolius L.). Cell Mol Biol Lett 10:331–344PubMedGoogle Scholar
  6. Bourguad F, Gravot A, Milesi S, Gontier E (2001) Production of plant secondary metabolites: a historical perspective. Plant Sci 161:839–851CrossRefGoogle Scholar
  7. Bunsupa S, Okada T, Saito K, Yamazaki M (2011) An acyltransferase-like gene obtained by differential gene expression profiles of quinolizidine alkaloid-producing and nonproducing cultivars of Lupinus angustifolius. Plant Biotechnol 28:89–94CrossRefGoogle Scholar
  8. D’Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9:331–340PubMedCrossRefGoogle Scholar
  9. Delseny M, Han B, Hsing YL (2010) High throughput DNA sequencing: the new sequencing revolution. Plant Sci 179:407–422PubMedCrossRefGoogle Scholar
  10. Facchini JP (2001) Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular regulation, and metabolic engineering application. Annu Rev Plant Physiol Plant Mol Biol 52:29–66PubMedCrossRefGoogle Scholar
  11. Facchini PJ, Bird DA, St-Pierre B (2004) Can Arabidopsis make complex alkaloids? Trends Plant Sci 9:116–122PubMedCrossRefGoogle Scholar
  12. 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):35–38PubMedCrossRefGoogle Scholar
  13. Hirai MY, Suzuki H, Yamazaki M, Saito K (2000) Biochemical and partial molecular characterization of bitter and sweet forms of Lupinus angustifolius, an experimental model for study of molecular regulation of quinolizidine alkaloid biosynthesis. Chem Pharm Bull (Tokyo) 48:1458–1461CrossRefGoogle Scholar
  14. Joseph PM (2008) Indolizidine and quinolizidine alkaloids. Nat Prod Rep 25:139–165CrossRefGoogle Scholar
  15. Lee MJ, Pate JS, Harris DJ, Atkins CA (2007) Synthesis, transport and accumulation of quinolizidine alkaloids in Lupinus albus L. and L. angustifolius L. J Exp Bot 58:935–946PubMedCrossRefGoogle Scholar
  16. Li H, Wylie SJ, Jones MGK (2000) Transgenic yellow lupin (Lupinus luteus). Plant Cell Rep 19:634–637CrossRefGoogle Scholar
  17. Luo J, Fuell C, Parr A, Hill L, Bailey P, Elliott K, Fairhurst SA, Martin C, Michael AJ (2009) A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 21:318–333PubMedCrossRefGoogle Scholar
  18. Molvig L, Tabe LM, Eggum BO, Moore AE, Craig S, Spencer D, Higgins TJ (1997) Enhanced methionine levels and increased nutritive value of seeds of transgenic lupins (Lupinus angustifolius L.) expressing a sunflower seed albumin gene. Proc Natl Acad Sci U S A 94:8393–8398PubMedCrossRefGoogle Scholar
  19. Mugnier J (1988) Establishment of new axenic hairy root lines by inoculation with Agrobacterium rhizogenes. Plant Cell Rep 7:9–12CrossRefGoogle Scholar
  20. Muzquiz M, Cuadrado C, Ayet G, de la Cuadra C, Burbano C, Osagie A (1994) Variation of alkaloid components of lupin seeds in 49 genotypes of Lupinis albus L. from different countries and locations. J Aric Food Chem 42:1447–1450CrossRefGoogle Scholar
  21. Nelson MN, Phan HT, Ellwood SR, Moolhuijzen PM, Hane J, Williams A, O’Lone CE, Fosu-Nyarko J, Scobie M, Cakir M, Jones MG, Bellgard M, Ksiazkiewicz M, Wolko B, Barker SJ, Oliver RP, Cowling WA (2006) The first gene-based map of Lupinus angustifolius L.-location of domestication genes and conserved synteny with Medicago truncatula. Theor Appl Genet 113:225–238PubMedCrossRefGoogle Scholar
  22. Ohmiya S, Saito K, Murakoshi I (1995) Lupine alkaloids. In: Cordell GA (ed) The Alkaloids. Academic Press, LondonGoogle Scholar
  23. 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 46:233–244PubMedCrossRefGoogle Scholar
  24. Oram RN (1983) Selection for higher seed yield in the presence of the Deleterious low alkaloid allele Iucundus in Lupinus angustifolius L. Field Crops Res 7:169–180CrossRefGoogle Scholar
  25. Phan HTT, Ellwood SR, Ford R, Thomas S, Oliver R (2006) Differences in syntenic complexity between Medicago truncatula with Lens culinaris and Lupinus albus. Funct Plant Biol 33:775–782CrossRefGoogle Scholar
  26. Phan HT, Ellwood SR, Adhikari K, Nelson MN, Oliver RP (2007) Differences in syntenic complexity between Medicago truncatula with Lens culinaris and Lupinus albus. DNA Res 14:59–70PubMedCrossRefGoogle Scholar
  27. Pigeaire A, Abernethy D, Smith PM, Simpson K, Fletcher N, Lu CY, Atkins CA, Cornish E (1997) Transformation of a grain legume (Lupinus angustifolius L.) via Agrobacterium tumefaciens-mediated gene transfer to shoot apices. Mol Breed 3:341–349CrossRefGoogle Scholar
  28. Roberts MF, Wink M (1998) Chemical ecology of alkaloids. In: Roberts MF, Wink M (ed) Alkaloids biochemistry, ecology, and medicinal applications. Plenum, New YorkGoogle Scholar
  29. Saito K, Murakoshi I (1995) Chemistry, biochemistry and chemotaxonomy of lupin alkaloids in the Leguminosae. In: Rahman AU (ed) Studies in natural products chemistry: structure and chemistry (Part C), vol 15. Elsevier Science Publishers, AmsterdamGoogle Scholar
  30. Saito K, Koike Y, Suzuki H, Murakoshi I (1993a) Biogenic implication of lupin alkaloid biosynthesis in bitter and sweet forms of Lupinus luteus and L. albus. Phytochemistry 34:1041–1044CrossRefGoogle Scholar
  31. Saito K, Suzuki H, Takamatsu S, Murakoshi I (1993b) Acyltransferases for lupin alkaloids in Lupinus hirsutus. Phytochemistry 32:87–91CrossRefGoogle Scholar
  32. Saito K, Yamazaki M, Takamatsu S, Kawaguchi A, Murakoshi I (1989a) Greening induced production of (+)-lupanine in tissue culture of Thermopsis lupinoides. Phytochemistry 28:2341–2344CrossRefGoogle Scholar
  33. Saito K, Yamazaki M, Yamakawa K, Fujisawa S, Takamatsu S, Kawaguchi A, Murakoshi I (1989b) Lupin alkaloids in tissue culture of Sophora flavescens var. angustifolius: greening induced production of matrine. Chem Pharm Bull 37:3001–3004CrossRefGoogle Scholar
  34. Suzuki H, Koike Y, Murakoshi I, Saito K (1996) Subcellular localization of acyltransferases for quinolizidine alkaloid biosynthesis in Lupinus. Phytochemistry 42:1557–1562CrossRefGoogle Scholar
  35. 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 269:15853–15860PubMedGoogle Scholar
  36. Tang W, Eisenbrand G (1992) Chinese drugs of plant origin, chemistry, pharmacology, and use in traditional and modern medicine. Springer, BerlinGoogle Scholar
  37. Wink M (1987a) Quinolizidine alkaloids: biochemistry, metabolism, and function in plants and cell suspension cultures. Planta Med 53(6):509–514PubMedCrossRefGoogle Scholar
  38. Wink M (1987b) Why do lupin cell cultures fail to produce alkaloids in large quantities. Plant Cell Tiss Org 8:103–111CrossRefGoogle Scholar
  39. Wink M (1990) Physiology of secondary product formation in plants. In: Charlwood BV, Rhodes MJC (eds) Secondary products from plant tissue culture. Clarendon Press, OxfordGoogle Scholar
  40. Wink M (1992) The role of quinolizidine alkaloids in plant insect interactions. In: Bernays EA (ed) Insect-plant interactions, Vol IV. CRC Press, Boca RatonGoogle Scholar
  41. Wink M (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64:3–19PubMedCrossRefGoogle Scholar
  42. Wink M, Hartmann T (1979) Cadaverine-pyruvate transamination: the principal step of enzymatic quinolizidine alkaloid biosynthesis in Lupinus polyphyllus cell suspension cultures. FEBS Lett 101:343–346PubMedCrossRefGoogle Scholar
  43. Wink M, Hartmann T (1980) Production of quinolizidine alkaloids by photomixotrophic cell suspension cultures: biochemical and biogenetic aspects. Planta Med 40:149–155CrossRefGoogle Scholar
  44. Wink M, Hartmann T (1982) Localization of the enzymes of quinolizidine alkaloid biosynthesis in leaf chloroplasts of Lupinus polyphyllus. Plant Physiol 70:74–77PubMedCrossRefGoogle Scholar
  45. Wink M, Mende P (1987) Uptake of lupanine by Alkaloid-storing epidermal cells of Lupinus polyphyllus. Planta Med 53:465–469PubMedCrossRefGoogle Scholar
  46. Wink M, Mohamed GIA (2003) Evolution of chemical defense traits in the Leguminosae: mapping of distribution patterns of secondary metabolites on a molecular phylogeny inferred from nucleotide sequences of the rbcL gene. Biochem Syst Ecol 31:897–917CrossRefGoogle Scholar
  47. Wink M, Roberts MF (1998) Compartmentation of alkaloid synthesis, transport, and storage. In: Roberts MF, Wink M (eds) Alkaloids biochemistry, ecology, and medicinal applications. Plenum, New YorkGoogle Scholar
  48. Wink M, Witte L (1985) Quinolizidine alkaloids as nitrogen source for lupin seedlings and cell suspension cultures. Z Naturforsch 40c:767–775Google Scholar
  49. Wink M, Meißner C, Witte L (1995) Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus. Phytochemistry 38:139–153CrossRefGoogle Scholar
  50. Yamazaki M, Shibata M, Nishiyama Y, Springob K, Kitayama M, Shimada N, Aoki T, Ayabe S, Saito K (2008) Differential gene expression profiles of red and green forms of Perilla frutescens leading to comprehensive identification of anthocyanin biosynthetic genes. FEBS J 275:3494–3502PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical Sciences, Department of Molecular Biology and BiotechnologyChiba UniversityChuo-kuJapan

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