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Alkaloids Derived from Lysine: Quinolizidine (a Focus on Lupin Alkaloids)

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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

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via Mangiagalli 25, Milan, 20133, Italy

    Dr. Giovanna Boschin

  2. HPF Nutraceutics s.r.l., Via Balzaretti 9, Milan, 20133, Italy

    Donatella Resta

Authors
  1. Dr. Giovanna Boschin
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  2. Donatella Resta
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Correspondence to Giovanna Boschin .

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Editors and Affiliations

  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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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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