Abstract
Quinolizidine alkaloids (QAs) are usually known as lupin alkaloids because they mainly occur in lupin species and other plants of the Genisteae tribe. They are secondary metabolites synthesized by plants from lysine, for defense against pathogens and other predators. QAs are biosynthesized in green tissues of the plant, transported via phloem and stored in all organs of the plant, including seeds. QAs content depends on genotype, presence of pathogens, and pedo-climatic conditions such as environmental effects and soil characteristics. More than 170 QAs have been identified in different Lupinus species, being the alkaloid pattern highly variable among species; sparteine and lupanine are the most common ones. QAs show neurotoxicity and for this reason Food Authorities of some countries have fixed a limit of 200 mg kg−1 of total QAs in lupin seeds and foods. The level of QAs in lupin seeds can be reduced by debittering processes involving soaking or washing with water; moreover, some lupin varieties producing low levels of QAs have been selected and bred.
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Abbreviations
- BW:
-
Body weight
- DM:
-
Dry matter
- FID:
-
Flame ionization detector
- GC-MS:
-
Gas chromatography–mass spectrometry
- NACE:
-
Nonaqueous capillary electrophoresis
- NOEL:
-
No observed effect level
- LD:
-
Lethal dose
- MOS:
-
Margin of safety
- MRL:
-
Minimal risk level
- QA:
-
Quinolizidine alkaloid
- SPE:
-
Solid phase extraction
- TDI:
-
Tolerable daily intake
- TLC:
-
Thin-layer chromatography
References
Wink M (1992) The role of quinolizidine alkaloids in plant insects interaction. In: Beranys EA (ed) Insect-plant interactions, vol 4. CRC Press, Boca Raton, pp 131–166
Wink M (1993) Allelochemical properties or the raison d’etre of alkaloids. In: Brossi A (ed) The alkaloids, vol 43. Academic, New York, pp 1–118
Wink M (1998) Chemical ecology of alkaloid. In: Roberts MF, Wink M (eds) Alkaloid: biochemistry, ecology, and medicinal application. Plenum Press, New York, pp 265–300
Aniszewski T, Ciesiolka D, Gulewicz K (2001) Equilibrium between basic nitrogen compounds in lupin seeds with differentiated alkaloid content. Phytochemistry 57:43–50
Wink M, Witte L (1985) Quinolizidine alkaloids as nitrogen source for lupin seedlings and cell suspension cultures. Z Naturforsch 40:767–775
Wink M, Gamal IAM (2003) Evolution of chemical defense traits in Leguminoseae: mapping on distribution patterns of secondary metabolites on a molecular phylogeny inferred from the nucleotide sequences of rbcL gene. Biosyst Ecol 31:897–917
Wink M (1987) Quinolizidine alkaloids: biochemistry, metabolism, and function in plants and cell suspension cultures (review). Planta Med 53:509–514
Wink M, Meißner C, Witte L (1995) Patterns of quinolizidine alkaloids in 56 species of the genus lupines. Phytochem 38:139–153
Wink M (1993) Quinolizidine alkaloids. In: Waterman P (ed) Methods in plant biochemistry, vol 8. Academic, London, pp 197–239
Wink M, Carey DB (1994) Variability of quinolizidine alkaloid profiles of Lupinus argenteus (Fabaceae) from North America. Biochem Syst E 22:663–669
Wang SF, Liu AY, Ridsdill-Smith TJ, Ghisalberti EL (2000) Role of alkaloids in resistance of yellow lupin to red-legged earth mite Halotydeus destructor. J Chem Ecol 26:429–441
Hatzold T, Elmadfa I, Gross R, Wink M, Hartmann T, Witte L (1983) Quinolizidine alkaloids in seeds of Lupinus mutabilis. J Agric Food Chem 31:934–938
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 28:89–94
Von Baer D, Perez I (1991) Quality standard propositions for commercial grain of white lupin (Lupinus albus). In: Proceeding of the 6th International Lupin Conference, Temuco-Pucon, Chile, 1991, pp 158–167
Boschin G, Annicchiarico P, Resta D, D’Agostina A, Arnoldi A (2008) Quinolizidine alkaloids in seeds of lupin genotypes of different origin. J Agric Food Chem 56:3657–3663
Culvenor CJ, Petterson DS (1986) Lupin toxins-alkaloids and phomopsin. In: Proceedings 4th International lupin conference, Geraldton Australia, pp 188–198
Australia New Zealand Food Authority (2001) Lupin alkaloids in food. A toxicological review and risk assessment, Techn. Rep. Series 3. pp 1–21. http://www.foodstandards.gov.au/_srcfiles/TR3.pdf
Bulletin Officiel n° 98/27 du Conseil superieur d’hygiene publique de France, 1998.
ACNFP Report on seeds from narrow leafed lupin, Appendix IX, MAFF Publications, London, GB, 1996, p 107
Saito K, Koike Y, Suzuki H, Murakoshi I (1993) Biogenetic implication of lupin alkaloid biosynthesis in bitter and sweet forms of Lupinus luteus and Lupinus albus. Phytochemistry 34:1041–1044
Wink M, Hartmann T (1982) Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA:13-hydroxylupanine O-tigloyltransferase from Lupinus albus L. Planta 156:560–565
Wink M, Roberts M (1998) Compartmentation of alkaloid synthesis, transport and storage. In: Roberts MF, Wink M (eds) Alkaloids: biochemistry, ecology and medicinal applications. Plenum, New York, pp 239–262
Bunsupa S, Katayama K, Ikeura E, Oikawa A, Toyooka K, Saito K, Yamazaki M (2012) Lysine decarboxylase catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production in leguminosae. Plant Cell 24:1202–1216
Facchini PJ (2001) Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu Rev Plant Physiol Plant Mol Biol 52:29–66
Wink M, Hartmann T (1985) Enzymology of quinolizidine alkaloid biosynthesis. In: Zalewski RI, Skolik JJ (eds) Natural products chemistry. Elsevier, Amsterdam, pp 511–520
Wink M, Hartmann T (1981) Sites of enzyme synthesis of quinolizidine alkaloids and their accumulation in Lupinus polyphyllus. J Plant Physiol 102:337–344
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 58:935–946
Zamora-Natera F, García-López P, Ruiz-López M, Rodríguez-Macías R, Salcedo-Pérez E (2009) Composición y concentración de alcaloides en Lupinus exaltatus Zucc. durante su crecimiento y desarrollo. Interciencia 34:672–676
De Cortes SM, Altares P, Pedrosa MM, Burbano C, Cuadrado C, Goyoaga C, Muzquiz M, Jimenez-Martinez C, Davila-Ortiz G (2005) Alkaloid variation during germination in different lupin species. Food Chem 90:347–355
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 Lupinus albus L. from different countries and locations. J Agric Food Chem 42:1447–1450
Cowling WA, Tarr A (2004) Effect of genotype and environment on seed quality in sweet narrow-leafed lupin (Lupinus angustifolius L.). Aust J Agric Res 55:745–751
Christiansen JL, Jornsgard B, Buskov S, Olsen CE (1997) Effect of drought stress on content and composition of seed alkaloids in narrow-leafed lupin, Lupinus angustifolius L. Eur J Agron 7:307–314
Gremigni P, Wong MTF, Edwards LK, Harris DJ, Hambiln J (2001) Potassium nutrition effects on seed alkaloid concentrations, yield and mineral content of lupins (Lupinus angustifolius). Plant Soil 234:131–142
Ciesiolka D, Muzquiz M, Burbano C, Altares P, Pedrosa MM, Wysocki W, Folkman W, Popenda M, Gulewicz K (2005) An effect of various nitrogen forms used as fertilizer on Lupinus albus L. yield and protein, alkaloid and α-galactosides content. J Agron Crop Sci 191:458–463
Gremigni P, Hambiln J, Harris DJ, Cowling WA (2003) The interaction of phosphorus and potassium with seed alkaloid concentrations, yield and mineral content in narrow-leafed lupin (Lupinus angustifolius). Plant Soil 253:413–427
Michael JP (2007) Indolizidine and quinolizidine alkaloids. Nat Prod Rep 24:191–222
Stobiecki M, Wojtaszek P, Gulewicz K (1997) Application of solid phase extraction for profiling quinolizidine alkaloids and phenolic compounds in Lupinus albus. Phytochem Anal 8:153–158
Chludil HD, Del Vilarino MP, Franco ML, Leica SR (2009) Changes in Lupinus albus and Lupinus angustifolius alkaloid profiles in response to mechanical damage. J Agric Food Chem 57:6107–6113
Yovo K, Huguet F, Pothier J, Durand M, Breteau M, Narcisse G (1984) Comparative pharmacological study of sparteine and its ketonic derivative lupanine from seeds of Lupinus albus. Planta Med 50:420–424
Petterson DS, Ellis ZI, Harris DJ, Spadek ZE (1987) Acute toxicity of major alkaloids of cultivated Lupinus angustifolius seed to rats. J Appl Toxicol 7:51–53
Stobiecki M, Blaszczyk B, Kowalczyk-Bronisz SH, Gulewicz K (1993) The toxicity of seed extracts and their fractions from Lupinus angustifolius and L. albus. J Appl Toxicol 13:347–352
Petterson DS, Greirson BN, Allen DG, Harris DJ, Power BM, Dusi LJ, Ilett KF (1994) Disposition of lupanine and 13-hydroxylupanine in man. Xenobiotica 24:933–941
Ballester D, Yanez E, Garcia R, Erazo S, Lopez F, Haardt E, Cornejo S, Lopez A, Pikniak J, Chichester CO (1980) Chemical composition, nutritive value, and toxicological evaluation of two species of sweet lupine (Lupinus albus and L. luteus). J Agric Food Chem 28:402–405
Butler WH, Ford GP, Creasy DM (1996) A 90 day feeding study of lupin (Lupinus angustifolius) flour spiked with lupin alkaloids in the rat. Food Chem Toxicol 34:531–536
Pothier J, Cheav L, Galand N, Viel C (1998) A comparative study of the effects of sparteine, lupanine and lupin extract on the central nervous system of the mouse. J Pharm Pharmacol 50:949–954
Di Grande A, Paradiso R, Amico S, Fulco G, Fantauzza B, Noto P (2004) Anticholinergic toxicity associated with lupin seed ingestion: case report. Eur J Emerg Med 11:119–120
Litkey J, Dailey MW (2007) Anticholinergic toxicity associated with the ingestion of lupini beans. Case Rep 25:215–216
Marquez LR, Guitierrez-Rave M, Miranda FI (1991) Acute poisoning by lupine seed debittering water. Vet Hum Toxicol 33:265–267
Jimenez-Martinez C, Mora-Escobedo R, Cardador Martinez A, Mercedes M, Martin Pedrosa M, Davila-Ortiz G (2010) Effect of aqueous, acid, and alkaline thermal treatments on antinutritional factors content and protein quality in Lupinus campestris seed flour. J Agric Food Chem 58:1741–1745
Panter KE, James LF, Gardner DR (1999) Lupines, poison hemlock and Nicotiana spp. toxicity and teratogenicity in livestock. J Nat Toxins 8:117–134
Lee ST, Cook D, Panter KE, Gardner DR, Ralps MH, Motteram ES, Pfister JA, Gay CC (2007) Lupine induced “crooked calf disease” in Washington and Oregon: identification of the alkaloid profiles in Lupinus sulphureus, Lupinus leucophyllus, and Lupinus sericeus. J Agric Food Chem 55:10649–10655
Montes Hernandez E, Corona Rangel ML, Encarnacion Corona A, Cantor del Angel JA, Sanchez Lopez JA, Sporer F, Wink M, Bermudez Torres K (2011) Quinolizidine alkaloid composition in different organs of Lupinus aschenbornii. Rev Bras Farmacogn 21:824–828
Wippich C, Wink M (1985) Biological properties of alkaloids. Influence of quinolizidine alkaloids and gramine on the germination and development of powderly mildew, Erysiphe graminis f. sp. hordei. Experientia 41:1477–1479
Garcia-Lopez PM, de la Mora PG, Wysocka W, Maiztegui B, Alzugaray ME, Del Zotto H (2004) Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion. Eur J Pharmacol 504:139–142
Erdemoglu N, Ozkan S, Tosun F (2007) Alkaloid profile and antimicrobial activity of Lupinus angustifolius L. alkaloid extract. Phytochem Rev 6:197–201
Borelli MI (2004) Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion. Eur J Pharmacol 504:139–142
Bermudez Torres K, Martinez Herrera J, Figueroa Brito R, Wink M, Legal L (2009) Activity of quinolizidine alkaloids from three Mexican Lupinus against the lepidopteran crop pest Spodoptera frugiperda. BioControl 54:459–466
Santana FC, Empis J (2001) Bacterial removal of quinolizidine alkaloids from Lupinus albus flours. Eur Food Res Technol 212:217–224
Jimenez-Martinez C, Hernandez-Sanchez H, Alvarez-Manilla G, Robledo-Quintos N, Martinez-Herrera J, Davila-Ortiz G (2001) Effect of aqueous and alkaline thermal treatments on chemical composition and oligosaccaride, alkaloid and tannin contents of Lupinus campestris seeds. J Sci Food Agric 81:421–428
Jimenez-Martinez C, Hernandez-Sanchez H, Davila-Ortiz G (2007) Diminution of quinolizidine alkaloids, olisaccharides and phenolic compounds from two species of Lupinus and soybean seeds by the effect of Rhizopus oligosporus. J Sci Food Agric 87:1315–1322
Reinhard H, Rupp H, Sager F, Streule M, Zoller O (2006) Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food. J Chromatogr A 1112:353–360
Chen X, Yi C, Li M, Lu X, Li Z, Wang X (2002) Determination of sophoridine and related lupin alkaloids using tris(2,2′-bipyridine)ruthenium electrogenerated chemiluminescence. Anal Chim Acta 446:79–86
Ganzera M, Kruger A, Wink M (2010) Determination of quinolizidine alkaloids in different Lupinus species by NACE using UV and MS detection. J Pharm Biomed Anal 53:1231–1235
Resta D, Boschin G, D’Agostina A, Arnoldi A (2008) Evaluation of total quinolizidine alkaloid content in lupin flours, lupin-based ingredients and foods. Mol Nutr Food Res 52:490–495
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Boschin, G., Resta, D. (2013). Alkaloids Derived from Lysine: Quinolizidine (a Focus on Lupin Alkaloids). In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_11
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