Article

Alkaloid variation during germination in different Lupin Species

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  • Instituto Nacional de Investigación y Tecnología Agraria y Alimentaria-CSIC
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Abstract

Quinolizidine alkaloids, occurring in lupins, are the largest single group of legume alkaloids with clear ecological functions in the defence of the plant. During germination, some degree of transformation of alkaloids to other more bioactive compounds, such as esters, occurs. The aim of this work was to investigate the transformations of alkaloids during germination, in Lupinus albus, L. angustifolius and L. campestris. Total quinolizidine alkaloid contents in raw seeds were 1.51 g/100 g (L. angustifolius), 2.36 g/100 g (L. albus) and 2.45 g/100 g (L. campestris). During germination in L. albus, lupanine increased and albine and 13-hydroxylupanine decreased substantially. In L. angustifolius, 13-hydroxylupanine also decreased. In L. campestris, hydroxyaphylline and hydroxyaphyllidine increased while epihydroxyaphylline and dehydroepihydroxyaphylline decreased. The ester 13-tigloyloxylupanine increased progressively during the germination of L. angustifolius (from 0 to 0.044 g/100 g) and L. albus (from 0.001 to 0.022 g/100 g). Germination of lupin seeds for 3 days, maximum, could be desirable in order to minimize the presence of alkaloids, as well as to avoid the formation of the quinolizidine alkaloid esters.

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... QAs are constitutive metabolites and their presence and abundance can vary during growth stage and depend on plant organ [1,28,29]. Seed alkaloids concentration may fluctuate depending both on genotype and environment and important variations in alkaloid content between different lots of lupin can be unpredictable [15,30]. This variability is a potential hindrance to the wider use of lupin for human consumption and a toxicological topic for consumers safety. ...
... Germination involves a great number of physiological changes, including synthesis, degradation, and transformation of different compounds. This process can reduce the presence of antinutrients such as a-galactosides or phytic acid in legume seeds, but also alkaloid content [29]. ...
... On the contrary, in L. albus, lupanine content is very high with less transformation into its derivatives [29]. ...
Chapter
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.
... One of the main reasons limiting their wide utilization is the presence in lupin seeds of quinolizidine alkaloids and the raffinose family oligosaccharides, that are considered as antinutritional factors. Among many methods used for removing these compounds (Ciesio³ka et al. 2005), the germination of seeds seems to be the best, leading to their degradation and obtaining high quality products in human and animal nutrition (Snauwaert and Markakis 1976;Wojtaszek 1992;Vidal-Valverde and Frias 1992;Frias et al. 1995;Prodanov et al. 1997;Sierra and Vidal-Valverde 1999;de Cortes Sanchez et al. 2005). Hence, the choice of germination as the processing method was not accidental but well-grounded. ...
... For that reason, many studies on decrease of alkaloid content in lupin were carried out (Gulewicz 1988). Among many technological methods used for decrease of alkaloid content in lupin seeds germination has been recently considered as particularly promising (Trugo 1993;Cunha-Queda and Beirao da Costa 1994;de Cortes Sanchez et al. 2005). The results of our paper show that during germination in controlled conditions the total of lupin alkaloids are clearly reduced. ...
... In case of Lupinus luteus, in the third day of germination at 15 and 24°C gramina appeared. These results are in full agreement with other studies (de Cortes Sanchez et al. 2005). ...
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The objective of our studies were seeds of two lupin species Lupinus luteus L. and Lupinus angustifolius L. cvs. Lord and Graf respectively. Lupin seeds were germinated at 15 and 24°C and during two, three and four days. In the lupin sprouts antinutritional factors: alkaloids and raffinose family oligosaccharides (RFOs) and five nitrogen fractions: non protein (Nnp), albumin (A), globulin (G), glutelin and prolamin (Gt+P) and nitrogen residue fraction (Nr) were determined. The level of these compounds was compared with the proper ones of initial material (not germinated seeds). These studies showed that the germination process clearly affects the decrease of antinutritional factors: RFOs and alkaloids. The decrease level of these compounds depended on such factors like, lupin species and used germination conditions. It was found on the base of nitrogen analysis of particular protein fractions that the germination process of lupin seeds causes deep quantitative and qualitative changes in fractional composition of lupin proteins. It especially concerns the decrease of globulin and residual fraction content and distinct increase of Nnp fraction. The changes in other fractions were not so unequivocal in comparison with the mentioned above and depended on lupin species, temperature and time of germination. Qualitative changes of A, G and Gt+P fractions caused by germination were confirmed by gel electrophoresis (SDS-PAGE). The amino acid analysis of seeds and sprouts of Nnp fractions showed an increased content of Asp, Ser, Ala, Pro - non essential amino acids (NEAA), and Val, Met, iLeu, Leu, Thr - essential amino acids (EAA). Simultaneously a decrease of Glu, Arg (NEAA), Phe, Lis, Cys (EAA) contents was observed. Generally the germination process causes the decrease of total NEAA and an increase of total EAA in Nnp fractions of both lupin species.
... In general, grain legumes are good sources of vegetable protein, among which Lupinus albus is known to have seeds with high protein content, like soybean [15,24]. Based on this fact, L. albus seeds have been employed as a protein source for animal and human nutrition in various parts of the world [17,25]. ...
... On the other hand, for humans and animals, the QAs have received much attention, because they have a strong bitter taste and may be toxic in high doses [34]. QAs display similar agonistic activities as the alkaloid nicotine, i.e., they also affect Na + and K + channels, inducing gastrointestinal, nervous and respiratory symptoms [17,25]. General toxic symptoms caused by quinolizidine alkaloids may include malaise, nausea, respiratory arrest, visual disturbances, ataxia, liver damage, progressive weakness and coma [4,36]. ...
Article
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Lupinus albus L. (lupine) is a legume whose grain/seed has gained increasing interest. Its recognized nutritional properties, namely a high content of protein, dietary fiber and its low fat content, make lupine a suitable alternative not only for animal protein, but also as a substitute for more processed and less balanced flours from a nutritional point of view, used in the preparation of bread, cakes and cookies, among others. In addition, its nutritional and bioactive compounds have potential benefits for human health in the prevention and treatment of some diseases. However, the existence of some anti-nutritional compounds and contaminants reveal some concern, requiring effective methods for their detection and eventual removal. This review intends to address the potential of lupine (L. albus) in food and human health and to balance the pros and cons. Nutritional and anti-nutritional components of L. albus seeds and possible contaminants of lupine seeds are examined. The potential health benefits of lupine (seeds), including energy metabolism, cardiovascular diseases, hypertension, glucose and insulin metabolism, bower function and anticonvulsant action, are discussed based on scientific evidence (both clinical trials and studies performed with animal models).
... QAs are transported from their place of synthesis to the whole plant via the phloem and stored in epidermal tissues and seeds, the latter as both a defense mechanism and as a source of nitrogen for the growth of the nascent plant [22]. During seed germination, QAs are metabolized and mobilized from cotyledons to the roots [22,23]. De novo biosynthesis of QAs activates during the early development of plantlets in a species-specific manner [22]. ...
... QA content decreased during germination of L. aschenbornii, L. montanus, and L. bilineatus seeds; for the latter, the decrease extended to the hypocotyl elongation stage. This phenomenon may be explained by the fact that QAs are used as sources of nitrogen by the nascent plant [22,23]. QAs are an example of the promiscuous use of secondary metabolites by plants for their survival, which maximize the gains from producing molecules of high energetic cost. ...
Article
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Quinolizidine alkaloids (QAs) are synthesized by the genus Lupinus as a defense against herbivores. Synthesis of QAs in lupins is species- and organ-specific. Knowledge about their biosynthesis and their corresponding pathways are still fragmentary, in part because lupins of commercial importance were mainly investigated, representing a small sample of the chemodiversity of the genus. Here, we explore the use of three Mexican lupins: Lupinus aschenbornii, Lupinus montanus, and Lupinus bilineatus as a model to study the physiology of QA biosynthesis. The corresponding QA patterns cover widely and narrowly distributed tetracyclic QAs. Quinolizidine alkaloid patterns of seeds and plantlets at different developmental stages were determined by GLC–MS and compared to identify the onset of de novo QA synthesis and to gain insight into specific and common biosynthesis trends. Onset of de novo QA biosynthesis occurred after the metabolization of seed QA during germination and was species-specific, as expected. A common QA pattern, from which the diversity of QA observed in these species is generated, was not found; however, lupanine and 3β-lupanine were found in the three specieswhile sparteine was not found in Lupinus bilineatus, suggesting that this simplest tetracyclic QA is not the precursor of more complex QAs. Similar patterns of metabolization and biosynthesis of structurally related QAs were observed, suggesting a common regulation.
... When using domestic legumes in compound feeds for monogastric animals it seems advisable to monitor the health condition of the animals. This is because these feed materials contain various anti-nutrient substances which may have a negative impact on animals, manifested as disturbances of homeostasis and a reduction in production results [2,3,5,15]. ...
... Juśkiewicz et al. [4] report that the alkaloids contained in lupine seeds reduce feed intake and stimulate metabolism in the gastrointestinal tract of rats and piglets. In high concentrations they can have a negative effect on production results and on animal health [2,5]. ...
Article
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Thirty crossbred pigs [♀ (Landrace x Yorkshire) x ♂ Duroc] were fattened in a three-stage fattening period. Soybean extraction meal (Group K) or soybean extraction meal with seeds of yellow lupine in the amount of 7.5% (Group D1) or 15% (Group D2) were used as a source of protein in their diet. The animals were slaughtered after reaching a body weight of about 117.5 kg. Blood samples were collected from all pigs at this time. Activity of ALP, AST and ALT and the level of TP, GLU, CHOL, HDL, TG, CREA, UREA, Ca, P, Mg, and Fe were determined in order to assess the impact of the dietary factor on the homeostasis and health of the animals. The values of all biochemical and mineral blood indicators were lower in the experimental groups (D1 and D2) than in the control. Most of these differences were statistically significant (P≤0.05 and P≤0.01). The values of the characteristics were within the reference limits for the species. The dietary factor had no negative effect on homeostasis in the animals.
... Its seeds are employed as a protein source for animal and human nutrition in various parts of the world, not only for their nutritional value, but also for their adaptability to marginal soils and climates. Human consumption of lupins has increased in recent years (De Cortes Sánchez et al. 2005). ...
... Lupin flour is widely considered an excellent raw material for supplementing different food products owing to its high protein content (Pollard et al. 2002;De Cortes Sánchez et al. 2005; and is largely used as eggs substitute, for example in cakes, pancakes, biscuits, or brioche (Tronc 1999), and has been added to spaghetti (Rayas-Duarte et al. 1996), pasta, crisps (Lampart-Szczapa et al. 1997), and bread (Dervas et al. 1999;Papavergou et al. 1999). It has been also used as a butter substitute in cake, brioche, and croissant (Tronc 1999). ...
Article
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Legume seeds are an abundant source of proteins and, among them, lupin is one of the richest. Lupin seed deserves great interest due to its chemical composition and augmented availability in many countries in recent years. The review reports on the current knowledge about nutritional characteristics (proteins, amino acids, starch, sugars, fiber, lipids, fatty acids, vitamins, antinutritional compounds) and potential use of different lupin seed products (flour, kernel fiber, protein isolates and concentrates) for baking applications. The influence of lupin addition on the rheological properties of dough and quality of final products are also described. A separate part of the article is focused on the foaming and emulsifying properties of lupin proteins.
... Oligosaccharides of the raffinose family are recognized as the main compounds causing flatulence, non-starch polysaccharides reduce energy utilization by animals, alkaloids usually reduce palatability and feed intake because of their bitter taste and are characterized as com-pounds with toxic effects (Pastuszewska et al., 2001;Kim et al., 2007). Germination can modify the type and quantity of nutrients in seeds, which can influence the digestibility of protein and amino acids in animals (Sanchez et al., 2005;Sangronis and Machado, 2007). Previous research has revealed an increase in the content of protein and decrease the concentrations of anti-nutritional factors in the sprouts of yellow and blue lupin compared with raw seeds, however, germination negatively influenced standardized ileal digestibility of lysine and methionine ABSTRACT. ...
... Yellow and blue lupin seeds differ significantly in the content of particular alkaloids both before and after germination (Chilomer et al., 2012). Alkaloids during germination are degraded and used as a nitrogen source in the biosynthesis of new, more bioactive compounds, such as other alkaloid types and esters (Sanchez et al., 2005). In the previous part of this study performed by Chilomer et al. (2010Chilomer et al. ( , 2012, higher levels of angustifoline and 3OH-lupanine and the appearance of 13α-tigloxylupanine in germinated blue lupin seeds were noted, whereas in germinated yellow lupin seeds, higher concentrations of lupinine and appearance of gramine were observed. ...
Article
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Two 33-day experiments were conducted. In each experiment, fifty male pigs about 9 kg body weight were divided into five groups and fed ad libitum a mixture containing soya bean meal in the control group (SBM), whereas in the experimental diets, 50% (experiment I) or 75% (experiment II) of the soya protein was replaced by the protein of raw or germinated seeds of yellow (RYL and GYL, respectively) or blue (RBL and GBL) lupin. The species of lupin had a significant effect (p < 0.05) on feed conversion ratio (FCR) in experiment I, whereas diet and germination significantly affected feed intake in experiment II. In experiment I feed utilization per kg body weight gain was worse (p < 0.05) in animals fed on the GYL diet than on GBL diet. In experiment II, intake of the GBL diet was significantly lower (p < 0.05) than of the SBM and RYL diets. Consumption of diet GBL was also significantly lower than of diet RBL. The alkaline phosphatase (AP) concentration was significantly lower (p < 0.05) in the blood of animals fed the diets with germinated lupin than those containing raw lupin seeds. The concentration of AP in the blood of animals fed the RYL diet was significantly higher (p < 0.05) compared with the other diets. The replacement of 50% or 75% of soya bean meal protein by raw or germinated yellow and blue lupin seeds did not significantly affect performance, but the higher level of germinated blue lupin seeds negatively affected feed intake by the pigs.
... Seeds of L. albus have been utilized for both animal and human nutrition [42]. It is well known that L. albus seeds are a high protein source as soybean seeds [7,43]. ...
Article
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Lupins are an important source of protein that could replace soybeans in the diet of ruminants and monogastrics, without reducing their performance. Lupinus albus (L. albus) is the main species of the genus Lupinus that is cultivated in the Mediterranean region. The aim of the present research was to study commercial cultivars and advanced breeding lines of L. albus by using phenotypical, molecular and biochemical data, in order to be used in breeding projects. Seven commercial cultivars (Estoril, Fas Sweet, Multitalia, Magnus, Orus, Ulysse Sulimo and Figaro) and three advanced lines from the company AGROLAND (LKML, LKAP and LKAU) were used. Eleven morphological traits were described using UPOV Guidelines (International Union for the Protection of New Varieties of Plants). Additionally, agronomical traits and yield components were measured. Regarding the nutritional value, grain samples were analyzed for N and the crude protein (CP), neutral detergent fiber (NDF), acid detergent fiber (ADF), acid detergent lignin (ADL), total alkaloids (TA), total phenolic content (TP), total tannins content (TT) and condensed tannins (CT) were calculated. Genetic diversity among genetic materials was assessed by SSRs molecular markers. The metabolomic analysis for four selected cultivars (Figaro, Magnus, Multitalia and Sulimo) was performed on the seeds with the GC/EI/MS technique. According to the results, the advanced lines were most productive but also with higher content of total alkaloids than the commercial cultivars. The only exception was the cultivar Multitalia that was characterized by a high content of alkaloids. Based on the SSRs, the cultivars Magnus, Orus and Estoril were grouped together while the breeding lines LKAP, LICML and LKAU were grouped with Multitalia. Regarding the metabolomic profile, the cultivars Multitalia and Magnus were together, while Sulimo was grouped with Figaro. Finally, the content of several beneficial metabolites for human and animal nutrition was significantly increased in Sulimo and Figaro, compared to Magnus and Multitalia. Both commercial varieties and lines have characteristics that can be exploited and used in breeding programs. Citation: Mavromatis, A.; Nianiou-Obeidat, I.; Polidoros, A.; Parissi, Z.; Tani, E.; Irakli, M.; Aliferis, K.A.; Zafeiriou, I.; Mylona, P.V.; Sarri, E.; et al. Characterization of Lupin Cultivars Based on Phenotypical, Molecular and Metabolomic Analyses. Agronomy 2023, 13, 370. https://doi.
... Germination process was realized as described by de Cortes Sánchez, et al. [46]. Seeds were selected according to their size, color, and absence of damage. ...
Article
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The common bean is an important caloric-protein food source. However, its nutritional value may be affected by the presence of non-nutritional compounds, which decrease the assimilation of some nutrients; however, at low concentrations, they show a beneficial effect. Germination and treatment by controlled pressure-drop (DIC, French acronym of Détente Instantanée Contrôlée) are methods that modify the concentration of these components. The objective of this work was to evaluate the change in the non-nutritional composition of bean seeds and sprouts by DIC treatment. The results show that with the germination, the concentration of phenolic and tannin compounds increased 99% and 73%, respectively, as well as the quantity of saponins (65.7%), while phytates and trypsin inhibitors decreased 26% and 42%, respectively. When applying the DIC treatment, the content of phytates (23-29%), saponins (44%) and oligosaccharides increased in bean sprouts and decreased phenolic compounds (4-14%), tannins (23% to 72%), and trypsin inhibitors (95.5%), according to the pressure and time conditions applied. This technology opens the way to new perspectives, especially to more effective use of legumes as a source of vegetable protein or bioactive compounds.
... The presence of non-nutritional compounds is considered a limiting factor for lupin consumption. The main non-nutritional substances found in lupin seeds are various alkaloids of the quinolizidine group [De Cortes Sánchez et al., 2005;Estivi et al., 2022;Sujak et al., 2006]. Such alkaloids are usually removed by either selecting genotypes with a low content of these components or through post-harvest treatments including germinating, cooking, soaking, fermentation and extraction [Estivi et al., 2022;Prusinski, 2017]. ...
... To shorten processing times and save water, several improved debittering methods have been proposed. Generally, they include longer boiling times (Jiménez-Martínez et al., 2001), post-cooking washing with warm water (Fontanari et al., 2012), different rinsing solutions (Jiménez-Martínez et al., 2001;Mohammed et al., 2016;Villacrés et al., 2020), germination (Cortes Sánchez et al., 2005;Mohammed et al., 2016), fermentation (Jiménez-Martínez et al., 2007) or their combination (Erbaş, 2010;Jiménez-Martínez et al., 2010). Recently, low frequency ultrasound (US) has been tested with promising results on lupin seeds hydration and debittering (Miano et al., 2019;Yaver and Bilgiçli, 2021). ...
Article
Lupin seeds are rich in proteins, lipids and bioactive compounds, but before consumption must be debittered to remove toxic alkaloids. Traditionally, debittering is a water-intensive and protracted process, lasting up to six days. To develop a more efficient procedure, different washing solutions (0.5% and 1% NaCl or citric acid), with or without the use of ultrasound, were applied on Lupinus albus seeds and compared to two control methods, the first with water and the second with a sodium chloride solution. The sonication did not accelerate debittering, while the sodium chloride and citric acid solutions significantly shortened debittering time, reduced water consumption and decreased alkaloid content to commercial values (0.31-1.03 g/kg dry matter). Debittering with a 1% citric acid solution saved 88 h and 65 L water/kg dry lupin compared to the water control method, and 13 h and 31 L water/kg dry lupin compared to the salt solution control method. The electronic tongue grouped the experimental and commercial samples in well-defined clusters; bitter and umami tastes were the main factors, well correlated with alkaloid content. The proposed procedure, either with citric acid or sodium chloride, could be easily adopted by the industry to reduce time and costs of lupin debittering.
... In a recent comprehensive study issued by the EU, a total alkaloid concentration of 10−50 mg/kg bodyweight was mentioned as critical value while children might be more sensitive to lupine alkaloids and even 10 mg/kg bodyweight might be lethal (Schrenk et al., 2019). Regarding the individual quinolizidine alkaloids, multiflorine and cytisine are named as connected to the "crooked calf syndrome" (de Cortes Sánchez et al., 2005;Schrenk et al., 2019) and spartein as being the most toxic lupine-borne alkaloid (Schrenk et al., 2019). To conclude, the total amount of alkaloids in a commercial product should not exceed 200 mg/kg and, in addition, critical individual quinolizidine alkaloids like sparteine, multiflorine, or cytisine ought to be monitored. ...
Article
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Lupines and faba beans are promising ingredients for the beverage industry. They contain high amounts of protein and can be grown in different climate zones and agricultural areas. Therefore, these legumes appear as ideal raw material for vegan, functional, and sustainable beverages. Nevertheless, the sensory characteristic of legumes is generally not accepted in beverages. Therefore, the market contribution of legume‐based beverages is currently only marginal. This review highlights known major flavor aspects of lupines and faba beans and the possibilities to improve these by germination, heat treatment, enzymatic treatment, and subsequent lactic acid fermentation. First, the main aroma and taste compounds are described. Thereby, the “beany” aroma is identified as the most relevant off‐flavor. Second, the nutrients and antinutrients of these legumes regarding to their use as food and as substrate for lactic acid fermentation are reviewed, and possibilities to modulate the substrate are summarized. Finally, the modification of the sensory profile by lactic acid fermentation is outlined. To conclude, it seems likely that the nutritional and flavor attributes in legume‐based beverages can be improved by a combined process of substrate modulation and fermentation. In a first step, antinutrients should be decomposed and proteins solubilized while transforming the solid grains into a liquid substrate. Due to such substrate modulation, a broader variety of strains could be employed and the fermentation could be based exclusively on their impact on the flavor. By applying the concept of combining a substrate modulation with a subsequent fermentation, the use of legumes in beverages could be facilitated and new products like vegan, protein‐rich, refreshing beverages could be marketed.
... [42] On the other hand, in lupines, which are considered as the legumes with the highest level of oligosaccharides, they are significantly reduced even up to not detectable levels after sprouting. [45,58,114,122] Finally, other less studied antinutrients are amylase, trypsin, and chymotrypsin inhibitors. Their decrease in sprouted grains of A. caudatus and A. cruentus was informed. ...
Article
The Andean grains such as quinoa (Chenopodium quinoa), kiwicha (Amaranthus caudatus), kañiwa (Chenopodium pallidicaule), and tarwi (Lupinus mutabilis) are known for their exceptional nutritional properties. However, germination appears as an economical option to modify and even improve the nutritional qualities of grains. This work presents a literature review about the impact of germination on the content of nutrients, bioactive compounds, and antinutrients of Andean grains and their homologues. In addition, the use of sprouted Andean grains to develop cereal-based healthy products is described. Thus, this work provides an updated reference framework of this growing area of study.
... L. montanus contiene 1.2 g 100 g 1 en hojas más tallos y L. campestris 1.4 g 100 g 1 (Pablo-Pérez et al., 2015). Aunque el perfil de alcaloides es diferente entre estas especies, L. montanus contiene esparteína como alcaloide mayoritario y en bajos niveles angustifolina que también posee actividad bioplaguicida y farmacológica (Ruiz-López et al., 2010) y L. campestris presenta como alcaloide mayoritario a hidroxiaphilidina (Cortes et al., 2005). Extractos de otras especies vegetales han demostrado inhibir el crecimiento micelial de M. roreri, entre ellas los aceites esenciales de hojas y tallos de especies de Lippia en concentraciones de 800 y 1000 g mL 1 (Lozada et al., 2012). ...
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Libertad. 86400 Huimanguillo, Tabasco. 2 Posgrado en Producción Agroalimentaria en el Trópico. Colegio de Postgraduados, Campus Tabasco, LGAC-2: Sistemas Sustentables de Producción Agrí-cola y Pecuaria. Periférico Carlos A. Molinas s/n, 86500 H. Cárdenas, Tabasco, México. *Autor de correspondencia: cfortiz@colpos.mx RESUMEN Se realizó una evaluación de la actividad antifúngica in vitro de extractos acuoso y alcaloideo de semillas, hojas y tallos de L. campestris (Lc) y L. montanus (Lm) sobre la inhibición del crecimiento micelial y esporulación de M. roreri. El menor crecimiento micelial (p0.05) de M. roreri fue registrado al 25% del extracto acuoso de semillas de Lm. De forma similar los extractos alcaloideo totales de semillas y hojas más tallos de Lc y Lm inhibieron el crecimiento miceliar de M. roreri, registrando una inhibición total en todas las concentraciones hasta seis días de evaluación, después de los cuales el crecimiento del hongo se activó, pero sin alcanzar al del testigo. La esporulación sólo fue afectada por el extracto de alcaloides de semillas. La concentración de 10 mg mL 1 presentó la mayor inhibición de la esporulación (83.6%) en semillas de Lm. Los niveles de inhibición del crecimiento micelial con extractos de semillas de Lm fueron de 84.8% a 93.6% (acuoso) y 73.4% a 85.2% (alcaloideo); y los extractos de alcaloides de hojas más tallos de Lm fue de 61.3% a 79.7% y para Lc, 57.9% a 72.1%. ABSTRACT An evaluation of the in vitro antifungal activity of aqueous and alkaloid extracts of seeds, leaves and stems of L. campestris (Lc) and L. montanus (Lm) on the inhibition of the mycelial growth and sporulation of M. roreri was performed. The lower mycelial growth (p0.05) of M. roreri was recorded at 25 % of the aqueous extract of Lm seeds. Similarly, the total alkaloid extracts from seeds and leaves plus stems of Lc and Lm inhibited the mycelial growth of M. roreri, showing a total inhibition in all the concentrations up to six days of evaluation, after which the fungus growth was activated, although without reaching the control. Sporulation was only affected by the extract of alkaloids from seeds. The concentration of 10 mg mL 1 presented the highest sporulation inhibition (83.6 %) in Lm seeds. The levels of inhibition of mycelial growth with Lm seed extracts were 84.8 % to 93.6 % (aqueous) and 73.4% to 85.2% (alkaloid); and the extracts of alkaloids from Lm leaves plus stems were 61.3% to 79.7%, and for Lc, 57.9% to 72.1%.
... By using different methods such as germination ones, the antinutritional compounds can be reduced. More along the improvement of the nutritional profile of lupine grains, toxic alkaloids can be eliminated from the grains [17,18]. In addition to the fact that germination improves the nutritional profile of lupine, in this process, the enzymes present in legumes are activated, which results in an increase in the digestibility of the constituent compounds. ...
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This study focuses on the possibility of using germinated lupine flour (GLF) in the breadmaking process in order to improve dough rheology and bread characteristics. For this purpose, different levels (0%, 5%, 10%, 15% and 20%) of germinated lupine flour were used, and the influence of its addition in wheat flour was analyzed. On empirical dough rheological properties, GLF addition in wheat flour has the effect of decreasing the water absorption capacity, dough consistency, baking strength, extensibility, tolerance for mixing and of increasing total gas production and falling number value. On fundamental dough rheological properties, GLF addition in wheat flour increased the tan δ and decreased the G′ and G″ modules with the increased dough temperature. The microscopic distribution of starch and gluten in the dough system was changed by GLF addition in wheat flour by an increase of the protein area and a decrease of the starch one. Regarding the bread characteristics, the GLF addition improved the specific volume, porosity and elasticity up to 15% GLF addition in wheat flour and decreased the textural properties gumminess and resilience. Regarding the color parameters of the bread, the GLF addition in the dough recipe had a darkening effect on the crumb and bread crust. The sensory data show that the bread samples up to 15% GLF addition in wheat flour were better appreciated than the control sample. According to our data, it is recommended to use a maximum level of 15% of the addition of germinated lupine flour in the dough recipe for making white wheat bread.
... Its seeds are employed as a protein source for animal and human nutrition in various parts worldwide, not only for their nutritional value, but also for their adaptability to marginal soils and climates. Human consumption of lupins has increasable used (De Cortes-Sanchez et al, 2005). Lupinus is a diverse genus, though only four species have been domesticated and are agriculturally significant: L. angustifolius (NLL), L. albus (white lupin), L. luteus (yellow lupin), and L. mutabilis (pearl lupin) (Petterson et al, 1998). ...
... Various researchers have investigated the use of lupine in a substitution role in a variety of cereal-based products (Pollards et al., 2002;Sanchez et al., 2005). Lupine flour is widely considered an excellent raw material for supplementing different food products owing to its high protein content and high fibre content with a good sensory acceptability (Sironi et al., 2005). ...
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There is currently an emerging problem of protein malnutrition in Ethiopia. This food formulation was done to increase the accessibility of nutrient-rich food products for the consumers. Lupine is a legume crop, which is an excellent source of protein. This study aimed to investigate the effect of tef, lupine varieties and blending ratio on the chemical composition of injera and sensory acceptability of Ethiopians staple food. The effect of blending ratio and lupine varieties (Australian sweet lupine and Dibettered lupine seed) were studied. The formulations were generated by using mixture design software. Lupine variety and blending proportion had significant (P
... For instance, soaking in saltwater can remove the bitter alkaloid compounds. [146] de Cortes Sánchez et al. [147] reported that germination can lower the quinolizidine alkaloids content in lupin seeds by fermentation; however, prolonged germination resulted in the formation of other bioactive compounds such as quinolizidine alkaloid esters, which are undesirable. Therefore, the authors recommended germination of lupin seeds of up to 3 days could reduce quinolizidine alkaloids levels and prevent the formation of the quinolizidine alkaloid esters. ...
Article
Over the last decade, plant-based beverages have gained popularity amongst consumers who are seeking alternative and environmentally sustainable options to traditional dairy drinks. Whilst these days there is a variety of cereal-based beverages in the market, the legumebased beverage segment is dominated by soy milk products. There is an opportunity to broaden and diversify this segment into other legumes which may offer better functionality and nutrition than soy. However, little is known about the processability, functionality, health benefits and associated health risks of legume-based milk substitutes. Therefore, this review provides an overview of the current knowledge on fundamental processing steps to convert legumes into milk-alternative beverages, what are processing challenges for different legume varieties, how to overcome these challenges and potential quality deficiencies, and what are the opportunities to maximise textural, nutritional and sensory aspects of legume-based beverages. Special attention is given to chickpea and faba beans, a legume segment largely untouched by industry so far.
... Traditional debittering processes include a hydration phase followed by cooking to inactivate the germination capacity of the grain and increase the permeability of cell wall, thereby facilitating leaching of these compounds through successive washes (Carvajal-Larenas et al., 2013;Awad-Allah & Elkatry, 2013). Other techniques for the elimination of alkaloids include hydro-agitation (Carvajal-Larenas et al., 2013) or biological processes such as germination (De Cortes et al., 2005;Khan et al., 2018). Varieties with low alkaloid contents have been developed, but their adaptation to different environmental conditions is difficult, and these varieties undergo changes over time that may result in the restoration of the bitter attribute (Awad-Allah & Elkatry, 2013). ...
Article
There is a growing interest in vegetable‐based sources of proteins. Despite its high nutrient content, lupine has been rarely exploited as a protein source due to the presence of high levels of non‐nutritive compounds such as alkaloids, which impart a bitter taste. Here, we evaluated the effect of debittering and solid‐state fermentation on the nutritional contents of three lupine varieties (Lupinus mutabilis Sweet). These processes induced significant changes (P < 0.05) in the nutritional composition of the three lupine varieties (INIAP‐450, INIAP‐451, and Criollo) and increased the protein levels to 644.55 g⋅kg−1 (Criollo variety) and the levels of several constituent amino acids such as valine (54.62 g⋅kg−1), methionine (42.47 g⋅kg−1), isoleucine (59.27 g⋅kg−1), and leucine (76.32 g⋅kg−1). The ether extract of INIAP‐450 showed increased levels (up to 244.03 g⋅kg−1); especially, of monounsaturated fatty acids (559.78 g⋅kg−1) and polyunsaturated fatty acids (293.17 g⋅kg−1) were observed. The omega‐6/omega‐3 ratio in the debittered grain oil reached the minimum requirement established for good‐quality oils (5/1). However, the levels of other components decreased, showing levels up to 13.04 g⋅kg−1 (total starch) in the Criollo variety, 22.62 g⋅kg−1 (resistant starch) in INIAP‐450, 6.53 g⋅kg−1 (potassium) in INIAP‐451, 46 g⋅kg−1 (iron) in INIAP‐451, and 29.75 g⋅kg−1 (zinc) in INIAP‐450.
... De Cortes S anchez et al. (2005) studied the change in QA concentration during the germination of seeds from a wild variety of L. campestris from Mexico as well as bitter seeds from L. albus L. (LO-3,923) and L. angustifolius (1,413) from Spain. Samples were taken each day until day 9 of the germination. ...
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Abstract The European Commission asked EFSA for a scientific opinion on the risks for animal and human health related to the presence of quinolizidine alkaloids (QAs) in feed and food. This risk assessment is limited to QAs occurring in Lupinus species/varieties relevant for animal and human consumption in Europe (i.e. Lupinus albus L., Lupinus angustifolius L., Lupinus luteus L. and Lupinus mutabilis Sweet). Information on the toxicity of QAs in animals and humans is limited. Following acute exposure to sparteine (reference compound), anticholinergic effects and changes in cardiac electric conductivity are considered to be critical for human hazard characterisation. The CONTAM Panel used a margin of exposure (MOE) approach identifying a lowest single oral effective dose of 0.16 mg sparteine/kg body weight as reference point to characterise the risk following acute exposure. No reference point could be identified to characterise the risk of chronic exposure. Because of similar modes of action for QAs, the CONTAM Panel used a group approach assuming dose additivity. For food, the highest mean concentration of Total QAs (TotQAs) (i.e. the 6 most abundant QAs) was found in lupin seed samples classified as ‘Lupins (dry) and similar‐’. Due to the limited data on occurrence and consumption, dietary exposure was calculated for some specific scenarios and no full human health risk characterisation was possible. The calculated margin of exposures (MOEs) may indicate a risk for some consumers. For example, when lupin seeds are consumed without a debittering step, or as debittered lupin seeds high in QA content and when ‘lupin‐based meat imitates’ are consumed. For horses, companion and farm animals, other than salmonids, the available database on adverse effects was too limited to identify no‐observed‐adverse‐effect levels and/or lowest‐observed‐adverse‐effect levels and no risk characterisation was possible. For salmonids, the CONTAM Panel considers the risk for adverse effects to be low.
... The tough outer cuticle and lignified cell walls of cereal grasses (Bernays 1994) may prevent feeding by O. moreletii but not A. vulgare, given isopods are known to be able to feed on some tough sources of organic material, such as hard seeds (Saska 2008), while millipedes have been found to be limited in their ability to feed on tougher detritus Mendonça 1990, Ashwini andSridhar 2005). In the case of canola and lupin, commercial breeding programs have selectively removed deterrent chemicals such as glucosinolates, erucic acid, and alkaloids due to taste preference of humans (de Cortes Sánchez et al. 2005, Elahi et al. 2016. These crop types have likely become more palatable to a wide range of arthropod species. ...
Article
The isopod, Armadillidium vulgare (Latreille) (Isopoda: Armadillidiidae), and the millipede, Ommatoiulus moreletii (Lucas) (Diplopoda: Iulidae), are increasingly being reported as pests of emerging broadacre crop seedlings in southern Australia. This is thought to be due to the increased adoption of stubble retention practices, leading to increased abundance of these soil-dwelling organisms. Here, we evaluate the propensity of A. vulgare and O. moreletii to damage a range of crop seedlings. Through the combined analysis of a controlled feeding trial and field reports, we show A. vulgare is able to feed on and damage a range of pulses, legumes, cereals, and oilseeds, as emerging seedlings. O. moreletii had a more restricted range of feeding, being limited to lupin, lucerne, and canola in the feeding trial. These results are discussed in the context of developing pest management guidelines for these species.
... In parallel with the processing methods, plant breeders have been trying to develop sweet lupine containing low level of alkaloids. These varieties have advantages of having low alkaloid content but they are also less resistant to disease and herbivore attack (Sanchez et al., 2005). ...
Article
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Lupine seeds (Lupinus albus L.) growing in two different agro-ecological zones of Ethiopia (Dangla and Chagni) were traditionally processed to evaluate the changes in their nutritional status and anti-nutritional factors. The traditional processing methods included roasting followed by soaking; boiling followed by soaking and germination. In all the methods, the whole seed and the kernel were compared. Moisture, crude protein, crude fat, crude fiber, crude ash, utilizable carbohydrates and gross energy for raw seeds which were obtained from Dangla were 6.94%, 37.87%, 9.34%, 11.08%, 2.80%, 38.92% and 391.19 Kcal/100 gm, respectively. The values for seeds from Chagni were 8.04%, 39.71%, 8.79%, 11.07%, 2.90%, 37.56% and 388.12 Kcal/100 gm, respectively. The total alkaloid and phytate contents of the Dangla seeds were 2.46% and 144.33 mg/100 gm and 2.26% and 143.96 mg/100 gm, respectively for Chagni seeds. In roasted and soaked seeds, the alkaloid level was significantly (p<0.05) reduced and de-hulling reduced the anti-nutritional factors effectively. Phytate was significantly reduced during germination and generally the levels of protein, fat, and total energy were found to increase.
... In contrast to soybean lupin can be grown in more temperate or cool climates and it can be considered as the strongest poten- (Dueñas, et al., 2009). Lupin seeds are used as a source of protein for animal and human nutrition in various parts of the world (De Cortes Sanchez, et al., 2005). The large size of soybean and lupin seeds make them vulnerable to mechanical damage during harvest, which can influence their quality. ...
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The aim of the study was to determine the effect of mechanical harvest on the seed quality of yellow lupin. Two effects were studied: the cultivar of yellow lupin (the indeterminate cultivar - Mister and the determinate cultivar - Perkoz) and harvest methods: hand-picked plants with manual shelling of seeds as a control and mechanical shelling with a plot harvester. In comparison with manual shelling of seeds, the mechanical harvest reduced the seed germination and increased the number of abnormal seeds both cultivars. Determinate cultivar was more sensitive, because the loss of its quality was higher (germination of 10%) than indeterminate cultivar (6%). Perkoz had also higher electrical conductivity, with the mean value of 34.3 μS × cm
... angustifolius L., L. luteus L., L. albus L., L. mutabilis Sweet) are used in agriculture on larger scale (Reinhard et al. 2006;Mülayim et al. 2002Mülayim et al. , Ś więcicki et al. 2015. Consumption of lupin seeds has increased in recent years (De Cortes-Sanchez et al. 2005;Ś więcicki et al. 2015) as alkaloids were removed from seeds by debittering or breeding sweet cultivars with highly valuable seed protein and dietary fibre (Cowling et al. 1998;Gladstones 1998;Petterson 1998;El-Adawy et al. 2001;Ś więcicki et al. 2015) as well as low level of antinutritional factors such as phytases, protease inhibitors and lectins (Cowling et al. 1998). ...
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The paper assess the variability of fat content and fatty acids profiles in seeds of a white lupin (Lupinus albus L.) domestic collection. The initial material comprised 371 accessions originated from 30 countries of Europe, Asia, Africa, North- and South America and Australia. According to data given by accession donors the material is divided into four classes of origin: wild lines, landraces, lines created by man and cultivars. Variability of fat content and fatty acids composition were estimated in seeds of each accession. The average fat content for analyzed collection is 9.81%. The broadest range of fat content was noticed for landraces and cultivars as compared to narrowest represented by lines created by man. Fat content ranged from 6.9% (induced mutant Wt 95497) to 14.1% (Polish cultivar Wt 95420 and the landrace Wt 95212 from Jordan). From a dietetic point of view, oil quality is more important than oil quantity in lupin seeds. On average the fatty acid (FA) in examined accessions ranked in following order of abundance: oleic acid (C18:1) > linoleic acid (C18:2) > linolenic acid (C18:3) > palmitic acid (C16:0) > eicosenoic acid (C20:1) > stearic acid (C18:0) ≈ erucic acid (C22:1). In respect to unsaturated fatty acid (UFA), monounsaturated oleic acid in each of estimated classes of accessions was predominant and most abundant (55.7%) in broad range of minimum–maximum values from 41.2 to 66.2%. The second examined monounsaturated fatty acid was erucic acid (1.74%) found in seeds of almost all studied accessions. An exception were four accessions defined similarly to rapeseeds as “zero erucic” forms. In seeds of few accessions a content of erucic acid exceeded 3%. Among polyunsaturated fatty acids linoleic FA (ω−6) dominated followed by linolenic FA (ω−3). Both FA were in the range 13.7–33.2% and 5.6–12.8% with mean values on the level 19.6 and 10.1%, respectively. As a consequence, the examined white lupin seeds showed a very favourable ω−3/ω−6 FA ratio (0.51), ranging from 0.21 to 0.87, much higher than that of most vegetable oils. Fat content was positively correlated with stearic and oleic fatty acids and negatively with palmitic, linoleic, linolenic and erucic acid.
... The micellar protein isolate (ES-PD) showed the lowest protein yield among all protein isolates, while the protein yield of the isoelectric protein isolate (EA-PI) was particularly high. The results agree with the significantly higher protein recovery for isoelectric lupin protein isolate (ILP, corresponding to EA-PI: 60%) reported by Rodriguez-Ambriz, Martinez-Ayala, Millan, and Davila-Ortiz (2005), compared to the micellar lupin protein isolate (MLP, corresponding to ES-PD: 30%). However, the yield difference of 30% between both protein isolates was higher than determined for the protein isolates in the present study (9%). ...
Article
Differences in the protein distribution of various protein isolates from Lupinus angustifolius L. Vitabor were identified as affected by the isolation procedure (alkaline and/or salt-induced extraction followed by isoelectric and/or dilutive precipitation). Protein isolates extracted in alkaline solution showed higher protein yields (26.4–31.7%) compared to salt-induced extraction (19.8–30.0%) or combined alkaline and salt-induced extraction (23.3–25.6%). Chemical variations among the protein isolates especially occurred within the albumins. Protein isolates precipitated isoelectrically showed the highest contents, whereas protein isolates precipitated by dilutive showed the lowest contents of conglutin δ. Furthermore, the alkaline subunits of conglutin α and conglutin γ decreased during alkaline extraction compared to salt-induced extraction. A decrease in protein-bound polar and basic amino acids was shown after protein isolation. In contrast, the amounts of nonpolar, aliphatic, aromatic, hydroxylated and sulfur-rich amino acids were higher in the lupin protein isolates compared to the lupin flakes. However, the functional side chains could not be related to the specific molecular arrangements of the protein isolates, as a similar amino acid composition was found among the protein isolates.
... At the same time, there are reductions in some antinutritional compounds (Muzquiz et al., 1996;Haj os & Osagie, 2004;Jim enez-Martinez et al., 2004). Among the traditional processing techniques that have been described in literature are (i) non-heat processing such as imbibition, germination, dehulling or fermentation; and (ii) heat processing, such as cooking at atmospheric pressure, autoclaving or roasting Egounlety & Aworth, 2003;Mart ın-Cabrejas et al., 2004;Rehman & Shah, 2005;S anchez et al., 2005). Most antinutritional factors are heat-labile, such as protease inhibitors and lectins, so cooking would remove any potential ill effects from consumption (Rochfort & Panozzo, 2007). ...
Article
Protein-energy malnutrition (PEM) is a problem in Africa and other developing nations of the world. Food Agriculture Organization's statistics reveal that in Africa, more than one in four people are undernourished. Cereals are a major staple in many African homes contributing significant amounts of energy, protein, but limiting in essential amino acid lysine, legumes on the other hand are protein and amino acid rich foods, but also lacking in sulphur-containing amino acids. Hence, a combination of cereals with legumes would improve the protein and nutrient density of the subsequent food products. Probably due to their high nutritional values, these food products are susceptible to deterioration and fungal contamination, accompanied by the production of mycotoxins. This review therefore, appraises various works in literature on the use of these crops to produce composite food products and their potential to address the obstinate problem of PEM, including, the problems that could arise during processing and storage of these protein-rich fractions.
... For (iso)flavonoid profiling of the lupine, the dried extracts were re-solubilized in 80% (vol/vol) aqueous methanol to a concentration of 5 mg/mL and subjected to LC-MS/MS analysis. Prior to the estrogenic activity assay, alkaloids were removed from the dried extracts by solid phase extraction (SPE), because lupine is known to contain alkaloids of the quinolizidine group that showed in vivo estrogenic activity in rats (De Cortes Sánchez et al., 2005;Elghamry and Shihata, 1964). The SPE was performed on a cation-exchange column (Supelclean LC-SCX, 500 mg, Sigma-Aldrich) according to a procedure described elsewhere (Aniszewski et al., 2001), with the exception that the extract was solubilized in 0.05 M HCl instead of water. ...
Article
The effects of germination and elicitation on (iso)flavonoid composition of extracts from three edible lupine species (Lupinus luteus, Lupinus albus, Lupinus angustifolius) were determined by RP-UHPLC-MS(n). The total (iso)flavonoid content of lupine increased over 10-fold upon germination, with the total content and composition of isoflavonoids more affected than those of flavonoids. Glycosylated isoflavones were the most predominant compounds found in lupine seedlings. Lesser amounts of isoflavone aglycones, including prenylated ones, were also accumulated. Elicitation with Rhizopus oryzae, in addition to germination, raised the content of isoflavonoids further: the total content of 2'-hydroxygenistein derivatives was increased considerably, without increasing that of genistein derivatives. Elicitation by fungus triggered prenylation of isoflavonoids, especially of the 2'-hydroxygenistein derivatives. The preferred positions of prenylation differed among the three lupine species. The change in isoflavone composition increased the agonistic activity of the extracts towards the human estrogen receptors, whereas no antagonistic activity was observed.
... FIO have been analysed using Dionex anion exchange chromatography of ethanolic extracts with pulsed amperometric detection, where 100 mM sodium hydroxide, including a 0-37.5 mM sodium actetate gradient was used as the mobile phase and a Carbopac PA1 column as the stationary phase. Total lupin alkaloids have been measured according to Cortez Sanchez et al (2005) and are the sum of angustifoline, ( iso) d-lupanine, lupanine, 11,12-dehydrolupanine and 13-OH-Lupanine. ...
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Van 25 augustus 2005 tot 1 januari 2012 zijn biologische boeren verplicht om het aandeel biologisch geproduceerd voer in het totaal aan diervoer te verhogen van 85 naar 100%. In dit Engelstalige rapport worden de karakteristieken en mogelijkheden van biologisch geproduceerde eiwithoudende gewassen beschreven
... In parallel with the processing methods, plant breeders have been trying to develop sweet lupine containing low level of alkaloids. These varieties have advantages of having low alkaloid content but they are also less resistant to disease and herbivore attack (Sanchez et al., 2005). ...
Article
Full-text available
Lupine seeds (Lupinus albus L.) growing in two different agro-ecological zones of Ethiopia (Dangla and Chagni) were traditionally processed to evaluate the changes in their nutritional status and anti-nutritional factors. The traditional processing methods included roasting followed by soaking; boiling followed by soaking and germination. In all the methods, the whole seed and the kernel were compared. Moisture, crude protein, crude fat, crude fiber, crude ash, utilizable carbohydrates and gross energy for raw seeds which were obtained from Dangla were 6.94%, 37.87%, 9.34%, 11.08%, 2.80%, 38.92% and 391.19 Kcal/100 gm, respectively. The values for seeds from Chagni were 8.04%, 39.71%, 8.79%, 11.07%, 2.90%, 37.56% and 388.12 Kcal/100 gm, respectively. The total alkaloid and phytate contents of the Dangla seeds were 2.46% and 144.33 mg/100 gm and 2.26% and 143.96 mg/100 gm, respectively for Chagni seeds. In roasted and soaked seeds, the alkaloid level was significantly (p<0.05) reduced and de-hulling reduced the anti-nutritional factors effectively. Phytate was significantly reduced during germination and generally the levels of protein, fat, and total energy were found to increase.
... However, their optimal dietary inclusion levels have not been defined to date. The concentrations of alkaloids, the antinutritional factors found in lupine seeds, have been considerably reduced through breeding programs, yet they can still pose a potential threat to animal health (De Cortes-Sánchez et al. 2005;Maknickiene et al. 2013). ...
Article
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The objective of this study was to determine the effect of alkaloids present in blue lupine (Lupinus angustifolius) seeds on the growth rate, selected indicators of carbohydrate and lipid metabolism, and liver morphology in rats. The experimental material comprised 32 Wistar rats at around 3 weeks of age, with an initial body weight of 81 g. During a 28-day feeding trial, the rats were fed diets containing the seeds of three blue lupine cultivars, Baron, Zeus and Wersal, with different alkaloid concentrations (0.36, 0.41, 0.56 mg/kg, respectively). Diets containing the seeds of three blue lupine cultivars reduced the feed intake and significantly limited the growth rate of experimental rats, compared to the control group. Lupine alkaloids had no effect on the serum concentrations of glucose and total cholesterol in rats, whereas elevated triglyceride concentrations were noted in experimental groups, relative to the control group. Diets containing the seeds of blue lupine cultivars Zeus and Wersal induced changes in alanine transaminase activity. A histopathological analysis of the liver revealed parenchymatous degeneration, which was more advanced in rats fed diets with the seeds of blue lupine cultivars Zeus and Wersal than in the control group, and congestion of portal vessels, which was more severe in rats fed the seeds of blue lupine cultivars Baron and Zeus. © 2015, University of Veterinary and Pharmaceutical Sciences. All rights reserved.
... Although this method is very effective, is expensive, because hard work to extract substances cause damage at seed besides the strong environmental impact by toxicity of leachates. Other methods have also been tested to detoxify such as soaking with addition of chemicals, heat treatments [7], germination [8], among others. It has also been proven genetic selection being preferred seed for sowing which have fewer alkaloids [9]. ...
Article
Lupin cotyledons are good source of nutrients such as proteins and lipids and around of 3.8% of toxic quinolizidine alkaloids difficult to extract. Previously It had reported by Tempeh fabrication was possible to achieve 90% of detoxification. Never before had been reported the incidence of variables of fermentation in the detoxification that could be useful for industrial scale up of process. In this investigation we studied the influence of moisture and particle size in elimination of alkaloids in a process of solid state fermentation with Rhizopus oligosporus. Wet material was fermented without forced aeration during 48 h testing two particle sizes, whole (W) and broken (B) particles. Moreover three moisture levels were evaluated at 40% (H-40), 50% (H-50) and 60% (H-60). Results showed maximum detoxification of 70.55% and 67.71% in broken cotyledons for H-60 and H-50 respectively. In whole cotyledons were achieved 64.26% and 61.08% for same moisture levels. In H-40 lower levels of degradation were showed with 47% and 52% for whole and broken particles respectively although water activity was over 0.9. Moisture over 50% did not cause a proportional increase in removal of alkaloids. Both factors, moisture and particle size influenced degradation; however less size had major incidence than moisture when water content was over 50%. Fermentation process could be useful as partial way to eliminate main toxins of Lupin.
... In this regard, Iannacone and Lamas (2003) and Guzzo et al. (2006) state that the extracts obtained with organic solvents exhibit more activity than the respective aqueous extracts. Additionally, the content of the active components in the plants is variable due to environmental factors, the stage of development and storage, among other factors (Sánchez et al., 2005;Muñoz et al., 2007;Chludil et al., 2009). ...
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A. superciliosus (Coleoptera: Curculionidae), known as "cabrito del maitén" (CM) among other names, is an important pest affecting fruit-bearing bushes in southern and central southern Chile. One means of control is the use of organically synthesized insecticides that target the adult, the application of which generally is disadvantageous because these insecticides have long-lasting residual effects and because spraying coincides with flowering and the harvest of the fruit. To complement other pesticides that are more degradable and selective and less harmful to the environment, this work studied the effect of an infusion of canelo buds (Drimys winteri) with leaves and stems of bitter lupin (Lupinus albus) on CM adults. The research evaluated mortality, anti-feeding effect and the percentage of eggs hatched with four treatments using these plants at concentrations of 10, 20, 40 and 100% infusion, plus a control with no application. Each treatment was replicated ten times. The infusions obtained at a proportion of 1:1 (w/v) exhibited no effect on the variables studied at a significance of 5%, with the exception of its effect on egg hatching, which exhibited an apparent direct relation with the canelo infusion and an inverse relation with the aqueous extract of lupin. The results indicate that the lupin infusion may have an insectistatic effect on the reproduction of CM.
Article
Legume-derived proteins present an opportunity to replace existing animal-source protein in various applications. Those proteins are abundant, relatively lowcost, sustainable, not highly allergenic, and widely acceptable by consumers. In this paper, it was found that legume-derived protein's techno-functional properties (e.g. gelation, emulsification and foaming) are being investigated, in order to assess their ability to substitute for animal-derived proteins in food systems and applications. This paper reviewed the functional attributes of legume-derived proteins, their possible applications in food systems, and their potential in the food industry.The techno-functional properties of the proteins vary among different legumes, and while some proteins properties are sufficient for industrial uses, other may need to be modified. It was concluded that legume-derived proteins could replace some existing animal-derived protein based food systems.
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Covering: up to 2022Quinolizidine alkaloids (QAs) are a class of alkaloids that accumulate in a variety of leguminous plants and have applications in the agricultural, pharmaceutical and chemical industries. QAs are notoriously present in cultivated lupins (Lupinus spp.) where they complicate the use of the valuable, high-protein beans due to their toxic properties and bitter taste. Compared to many other alkaloid classes, the biosynthesis of QAs is poorly understood, with only the two first pathway enzymes having been discovered so far. In this article, we review the different biosynthetic hypotheses that have been put forth in the literature (1988-2009) and highlight one particular hypothesis (1988) that agrees with the often ignored precursor feeding studies (1964-1994). Our focus is on the biosynthesis of the simple tetracyclic QA (-)-sparteine, from which many of the QAs found in lupins derive. We examine every pathway step on the way to (-)-sparteine and discuss plausible mechanisms, altogether proposing the involvement of 6-9 enzymes. Together with the new resources for gene discovery developed for lupins in the past few years, this review will contribute to the full elucidation of the QA pathway, including the identification and characterization of the missing pathway enzymes.
Article
This study was carried out to investigate the effect of different levels (0, 2, 4, 6 and 8% w/v) of sweet lupine powder (SLP) and Bifidobacterium longum ATCC 15707 on physiochemical, textural, microbiological and sensory properties of low‐fat bio‐Labneh samples during storage for 21 days at 5 ± 1°C. The results showed that the textural properties of low‐fat bio‐Labneh with a higher level of SLP (8%) were harder than those made without adding SLP. Overall acceptability of sample processed by using 2% of SLP indicated that it is more acceptable compared with other treatments. The total cell count of B. longum ATCC 15707 gradually increased until the 14th day of the storage period after that decreased till the end of the storage period. Furthermore, the number of viable cells of B. longum ATCC15707 remained >7 log cfu/g at the end of the storage period in the treated samples. Sweet lupine powder had a positive impact on the quality characteristics of low‐fat bio‐Labneh and enhanced the growth of B. longum ATCC 15707 in the Labneh matrix that resulted in a wider spectrum of health benefits of Labneh cheese to the consumers. The Labneh that was supplemented with 2% sweet lupine powder was the most acceptable treatment.
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The purpose of this study was to evaluate the use of supercritical fluid extraction with cosolvent (SFE‐co) as an alternative process in the extraction of lupin alkaloids. A sample of crushed Lupinus mutabilis Sweet seeds, with a high content of alkaloids, was treated using aqueous extraction (AQE) and SFE‐co, where the effect of the operating conditions and the solvent in the SFE‐co were evaluated applying a factorial design. Results showed that both methods reduced the content of total alkaloids in the lupin seed, ensuring its safe consumption. SFE‐co got an extraction yield (39.19 ± 0.14 mg/g) comparable with AQE (39.22 ± 0.16 mg/g) at a temperature of 323 K, a pressure of 27 MPa, using as a solvent supercritical carbon dioxide (scCO2) and dilute ethanol solution, but limited to a fraction of the treated sample. SFE‐co, unlike AQE, was able to keep the nutritional value of the lupin seeds, reducing the time process from 235 hr (AQE) to 2.5 hr, assuring the non‐use of an excessive amount of water and hazardous solvents. Moreover, the fractions formed in the extraction vessel by SFE‐co allowed the understanding of the extraction mechanism of different components from a complex matrix related to their chemical polarity. Practical Applications This study shows that it is possible to remove lupin alkaloids with green technology as supercritical fluid extraction with cosolvents, reaching extraction yields comparable with the conventional method (aqueous extraction), keeping the nutritional value of the sample, saving time and resources. However, working with a larger quantity of material than the usual used in a laboratory showed an inhomogeneous extraction of alkaloids from the sample, limiting the optimal extraction yield to one of the fractions formed. This reveals a future problem in the use of this technology at an industrial level, where the characteristics of the extracts are not only important but also the material treated since, in the lupin industry, the debittered seed and the released alkaloids are useful in the food and pharmaceutical industries, respectively.
Article
The oil samples were rich in linoleic acid (mean 45.39%) and then the most common fatty acids were oleic (mean 36.79%), palmitic (mean 8.27%) and stearic acids (mean 5.61%). Calcium 463.80‐4065.50 mg/kg, boron 0.00‐12.26 mg/kg, chromium 0.00‐10.25 mg/kg, copper 3.92‐44.48 mg/kg, iron 0.00‐149.23 mg/kg, magnesium 34.07‐2002.53 mg/kg, potassium 2463.21‐6779.90 mg/kg, sodium 91.69‐8532.82 mg/kg were determined in the chips samples. Glycemic index values of the chips made using whole lupine flour varied between 50.10 and 60.90. In addition to this, the glycemic index values of the whole lupine flour added chips were found lower than the glycemic index values of hulled lupine flour added chips. It was observed that the glycemic index values of the lupine flour added samples were lower than the control group (without lupine flour added). The lowest glycemic index value was found in the sample with the highest ratio of lupine flour.
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otanicals have been main components of prescriptions of Unani physicians in the treatment of diseases since time immemorial. Turmus (Lupinus albus L.) has been used for various therapeutic purposes since ancient time. It has been used as a potent drug in hyperpigmentary skin disorders such as Kalaf (melasma), Barañ (freckles), Til (moles), etc. Unani classical literature describes its actions as Jälé (cleanser/detergent), Qätil-i-Dédän-i-Am'ä' (antihelmintic), Mudirr-i-Bawl (diuretic), Mudirr-i-Ùayò (emmenagogue), Muùallil-i-Awräm (anti-inflammatory), Musakkin-i-Alam (analgesic), Mufattit-i-Ùañäh (lithotriptic), Muqawwi-i-Bañar (eye tonic), Mugharré (nutritive) and Mukhrij-i-Janén (abortifacient). Through this review paper, an attempt has been made to describe morphology, pharmacological actions, ethno-medicinal, traditional and therapeutic uses of Lupinus albus L. and finally provide an ample scope for further researches to explore its therapeutic potential to develop a better medicine for diabetes mellitus type 2, worm infestations, melasma and hyperlipidaemia.
Article
Products of lupin, a leguminous plant belonging to genus Lupinus, have high protein contents and are consumed in Mediterranean and Middle East countries. However, quinolizidine alkaloids (QAs) present in lupin have been reported to be toxic for humans and animals. Therefore, we carried out a quantitative determination of the QAs such as sparteine, angustifoline, lupanine, and 13-hydroxylupanine, which are known to be the major components in lupin and lupin products. The QAs were determined in three lupin products, namely, lupin beans, lupin cookies, and a lupin drink. The analysis was carried out using gas chromatography with a flame ionization detector (GC-FID) and the method was also validated. All of the QAs were eluted in 20 min, and the correlation coefficients were acceptable (R² > 0.99). The limit of quantification in this method was lower than for a previously used capillary electrophoresis–mass spectrometric method. The total QA contents in lupin beans, lupin cookies, and lupin drink were 97.031, 4.786, and 67.887 µg/mL. Based on our results, it was concluded that these products were safe for consumption. It is believed that this method can be effectively used for the determination of QAs as GC-FID is a widely used technique.
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Abstract: A Lupinus campestris milk-like product was obtained with 6.3% protein by using an alkaline thermal treatment. The colour of the suspension showed a greater similarity to cow’s milk than to commercial soymilk. To adjust the carbohydrate concentration and induce fermentation, 3% of sucrose and 1.5% of lactose were added. The product was pasteurized and inoculated with a culture of Streptococcus thermophilus and Lactobacillus delbrueckii ssp bulgaricus. A lupin yogurt-like product with pH 4.02, 0.87% lactic acid, and a lactic acid bacteria count (3.2 × 108 CFU ml−1 ) and viscosity similar to commercial cow’s milk yogurt was obtained. The amino acid composition of the proteins in the lupin milk and yogurt products had a good balance, with the exception, as in other legumes, of the sulphur-containing amino acids. Sensory evaluation indicated that the product was well accepted by consumers. These results offer a good possibility for the utilization of this legume in human nutrition through the elaboration of products that are analogous to others already present in the commercial market.  2003 Society of Chemical Industry Keywords: legumes; Lupinus campestris; lupin milk; yogurt
Article
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Information on food composition including types and contents of nutrients and anti-nutrients is important for food and nutrition research. There is satisfactory information on established nutritive elements for various food groups. However, literature on anti-nutrient component generally scattered and scanty on few major food groups and commonly consumed plant parts. A better understanding of both the positive and negative qualities of vegetable component would help develop better evidence-based promotion and appropriate dietary strategies. This paper reviews seven types of anti-nutrient elements in vegetables: oxalates, phytates, nitrates, tannins, glucosinolates, saponins and alkaloids and their effects, mechanisms, content and processing methods. A total of 360 research papers were systematically identified and 123 were selected with acceptable anti-nutrient data. Vegetable families and plant parts with highest content of each anti-nutrient were identified, with the Leguiminosae family having highest content of phytate, tannins and saponins, and leafy vegetables having high oxalate. The simplest food processing methods to reduce anti-nutrients in vegetables are boiling and removal of certain plant parts. While consumption of vegetables with anti-nutrients do not normally cause adverse effects in the general population, future research to determine nutrient bioavailability based on diets will help increase awareness and improve recommendations on plant food intake.
Article
Information on food composition including types and contents of nutrients and anti-nutrients is important for food and nutrition research. There is satisfactory information on established nutritive elements for various food groups. However, literature on anti-nutrient component generally scattered and scanty on few major food groups and commonly consumed plant parts. A better understanding of both the positive and negative qualities of vegetable component would help develop better evidence-based promotion and appropriate dietary strategies. This paper reviews seven types of anti-nutrient elements in vegetables: oxalates, phytates, nitrates, tannins, glucosinolates, saponins and alkaloids and their effects, mechanisms, content and processing methods. A total of 360 research papers were systematically identified and 123 were selected with acceptable anti-nutrient data. Vegetable families and plant parts with highest content of each anti-nutrient were identified, with the Leguiminosae family having highest content of phytate, tannins and saponins, and leafy vegetables having high oxalate. The simplest food processing methods to reduce anti-nutrients in vegetables are boiling and removal of certain plant parts. While consumption of vegetables with anti-nutrients do not normally cause adverse effects in the general population, future research to determine nutrient bioavailability based on diets will help increase awareness and improve recommendations on plant food intake.
Article
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Quinolizidine alkaloids (QAs) are toxic secondary metabolites found within the genus Lupinus, some species of which are commercially important grain legume crops including Lupinus angustifolius (narrow-leafed lupin, NLL), L. luteus (yellow lupin), L. albus (white lupin), and L. mutabilis (pearl lupin), with NLL grain being the most largely produced of the four species in Australia and worldwide. While QAs offer the plants protection against insect pests, the accumulation of QAs in lupin grain complicates its use for food purposes as QA levels must remain below the industry threshold (0.02%), which is often exceeded. It is not well understood what factors cause grain QA levels to exceed this threshold. Much of the early work on QA biosynthesis began in the 1970– 1980s, with many QA chemical structures well-characterized and lupin cell cultures and enzyme assays employed to identify some biosynthetic enzymes and pathway intermediates. More recently, two genes associated with these enzymes have been characterized, however, the QA biosynthetic pathway remains only partially elucidated. Here, we review the research accomplished thus far concerning QAs in lupin and consider some possibilities for further elucidation and manipulation of the QA pathway in lupin crops, drawing on examples from model alkaloid species. One breeding strategy for lupin is to produce plants with high QAs in vegetative tissues while low in the grain in order to confer insect resistance to plants while keeping grain QA levels within industry regulations. With the knowledge achieved on alkaloid biosynthesis in other plant species in recent years, and the recent development of genomic and transcriptomic resources for NLL, there is considerable scope to facilitate advances in our knowledge of QAs, leading to the production of improved lupin crops.
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Legumes, including lupins, beans, lentil and chickpea, are one of the most important crops in the world because of their nutritional quality. Lupin seeds have been used as human food and animal feed since ancient times. It was known that antioxidant photochemical in foods have many health benefits including prevention of various diseases associated with oxidative stress such as cancer, cardiovascular disease, neuro-degeneration and diabetes. Lupin grains are rich sources of complex carbohydrates, protein, vitamins and minerals. Antioxidants can be found naturally in foods. Total polyphenols content and antioxidant activity were measured in four varieties of lupin, namely in white lupin, blue lupin, yellow lupin and Mutabilis lupin species. A majority of antioxidants naturally present in foods occur in phenolic structures and especially in flavonoid structures. The content of the total polyphenols was determined by using the Folin-Ciocalteu reagent (FCR). Antioxidant activity was measured by using a compound DPPH (2.2-diphenyl-1-picrylhydrazyl). In the present experiment according to the average contents of total polyphenols (TPC) in dry matter of lupin seeds there was the following line: L. Angustifolius (blue) lupin (696.212 mg GAE.100g⁻¹) > L. Albus (white) lupin (614.13 mg GAE.100g⁻¹) > L. Luteus (yellow) lupin (467.78 mg GAE.100g⁻¹) > L. Mutabilis (pearl) lupin (367.36 mg GAE.100g⁻¹). Based on the measured values of total antioxidant capacity (TAC) of lupin samples can be classified as follows: L. Albus (white) lupin (43.44%) >L. Angustifolius (blue) lupin (38.27%) >L. Luteus (yellow) lupin (22.29%) >L. Mutabilis (Pearl) lupin (20.80%). The relationship of antioxidant capacity with total polyphenolic was discussed. According to used statistical analyzes. Correlation between the phenolic contents and antioxidant capacity was significantly positive (r = 0.88). Our results confirmed that legumes can be a good source of bioactive compounds in the human nutrition. The main objective of the present work was to evaluated the content of total polyphenols and an antioxidant capacity of four Lupine species. © 2017 Potravinarstvo Slovak Journal of Food Sciences, License.
Article
One dimeric matrine-type alkaloid, ochrocephalamine A (1), was isolated from the poisonous plant Oxytropis ochrocephala Bunge. Its structure was elucidated by spectroscopic data and single-crystal X-ray diffraction. The insecticidal and cytotoxic activities of 1 were evaluated.
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The effect of three different processing methods on alkaloids, phytate, total phenolics, antioxidant activity and minerals content and extractability of newly developed lupin cultivar (Golo) was investigated. Germination of lupin seeds as well as fermentation (before boiling) significantly (P ≤ 0.05) increased alkaloids content ( > 50%). However, boiling of fermented seeds and debittering process had significantly (P ≤ 0.05) lowered the level of alkaloids, with few exceptions for boiled fermented seeds compared to raw seeds. Regardless of the processing method and compared to raw seeds, phytate level was significantly (P ≤ 0.05) decreased ( ≤ 21.24%) while total phenolics significantly (P ≤ 0.05) increased ( > 50%). Antiradical activity significantly (P ≤ 0.05) increased for germinated seeds and decreased for fermented ones. The increase in antioxidant activity was accompanied by lower values in IC50. All processing methods significantly (P ≤ 0.05) decreased minerals content but significantly (P ≤ 0.05) increased the extractability. Practical Applications Despite the high protein content and antioxidant properties of the newly developed lupin cultivar, it also has high antinutritional factors. The result in this study suggested that through processing (germination, boiling, fermentation), the antinutrients and alkaloids of the lupin can be reduced and the antioxidant properties increased, thereby increasing the utilization potential of the cultivar as functional ingredient in foods.
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A. superciliosus (Coleoptera: Curculionidae), known as "cabrito del maitén" (CM) among other names, is an important pest affecting fruit-bearing bushes in southern and central southern Chile. One means of control is the use of organically synthesized insecticides that target the adult, the application of which generally is disadvantageous because these insecticides have long-lasting residual effects and because spraying coincides with flowering and the harvest of the fruit. To complement other pesticides that are more degradable and selective and less harmful to the environment, this work studied the effect of an infusion of canelo buds (Drimys winteri) with leaves and stems of bitter lupin (Lupinus albus) on CM adults. The research evaluated mortality, anti-feeding effect and the percentage of eggs hatched with four treatments using these plants at concentrations of 10, 20, 40 and 100% infusion, plus a control with no application. Each treatment was replicated ten times. The infusions obtained at a proportion of 1:1 (w/v) exhibited no effect on the variables studied at a significance of 5%, with the exception of its effect on egg hatching, which exhibited an apparent direct relation with the canelo infusion and an inverse relation with the aqueous extract of lupin. The results indicate that the lupin infusion may have an insectistatic effect on the reproduction of CM.
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Lupin is nutritious type of legumes and its nutritional value could be increased by germination. Substitution of wheat flour (WF) with germinated lupin flour (GLF) at levels of 10–50% was investigated for their effects on the physiochemical and organoleptic properties of cookies. Ash, fiber, protein and lipid contents increased in GLF and germinated lupin cookies (GLC) as level of replacement increased. However, carbohydrates in WF and control cookies (CC) were higher than GLF and GLC. Physical analysis for cookies revealed that the spread factor values, weight and thickness increased with decreased in diameter as the levels of WF replacement increased. Organoleptic evaluation revealed that up to 50% substitution of WF with GLF produced acceptable cookies with significant differences between CC and GLC, while the most desirable treatment in overall impression, flavor and texture was GLC30. The study findings could be implicated to develop new healthy food products by using GLF. Practically, it is possible to produce healthy and nutritionally adequate cookies that are rich in proteins to supply certain amino acids such as lysine and tryptophan, with long shelf life, and with good eating quality, by substituting wheat flour with germinated lupin flour to a 30% or even to a 40 or 50% level, with increasing the germination time to reduce the bitter taste, if any. Production of healthy cookies could be used as snack foods that are appropriate and appealing for schoolchildren who need more protein per unit body weight than adults, and could also be used as dieting foods for cancer and burn patients, as the nutritional composition of germinated lupin flour might have significant health benefits so as to consider it as a nutritious food.
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The alkaloid patterns during germination and seedling development of Lupinus polyphyllus, L. angustifolius, L. albus, L. pubescens, Cytisus scoparius, Baptisia australis, Spartium junceum and Laburnum anagyroides were studied by capillary glc and EI-MS and CI-MS. The alkaloid contents were relatively high in the seeds and decreased by 20-100% during germination and the early developmental stages. The plants with fully developed leaves were able to synthesize new alkaloids. The decrease of alkaloid concentrations during germination was interpreted in terms of alkaloid turnover and use of the alkaloidal nitrogen for seedling development. The ability of plants to rely on the alkaloidal nitrogen as a nitrogen source could also be shown in lupin cell cultures which could survive and even grow on media which contained sparteine as the sole nitrogen source.
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The enzymatic sequence responsible for the biosynthesis of tetracyclic quinolizidine alkaloids could be localized in chloroplasts isolated from Lupinus polyphyllus leaves and L. albus seedlings by differential centrifugation. Upon feeding of cadaverine to isolated chloroplasts lupanine is produced as the main alkaloid. Chloroplasts treated with digitonine produce sparteine and 17-oxosparteine instead of lupanine, thus indicating that the biosynthetic sequence is interrupted. The intermediacy of 17-oxosparteine could be confirmed since exogeneous 17-oxosparteine is converted into lupanine by intact chloroplasts. 17-Oxosparteine synthase (see Z. Naturforsch. 34 c, 704 1979) the key enzyme of quinolizidine alkaloid biosynthesis could be solubilized from chloro­ plasts treated with detergents or osmotic shock.
Article
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Quinolizidine alkaloids formed in the leaves of Lupinus albus L. are translocated via the phloem to the other plant organs, especially the maturing fruits. Compared with amino-acid transport in the phloem, the alkaloids contribute about 8% to the overall nitrogen being exported from the leaf. Since it is likely that the alkaloids are subsequently degraded in the target tissues a minor role of quinolizidine alkaloids might be nitrogen transport. A marked diurnal fluctuation of alkaloids was observed in the leaves, the phloem sap, the roots and the fruits with an increase during the day and an amplitude of several hundred percent thus providing evidence for a rapid turnover of endogenous alkaloids.
Article
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The bitter and sweet forms of a plant species differing with alkaloid contents may provide a model system for investigation of alkaloid biosynthesis at a molecular level. The pattern and concentration of quinolizidine alkaloids were determined by capillary GC-MS in bitter and sweet plants of Lupinus angustifolius. Bitter plant contained lupanine, 13alpha-hydroxylupanine, angustifoline, alpha-isolupanine, tetrahydrorhombifoline, and ester-derivatives of 13alpha-hydroxylupanine. In contrast, no alkaloid was detected in sweet plant. The enzymatic activity of acyltransferase for formation of 13alpha-tigloyloxylupanine was similar or even higher in the cell-free extracts of sweet plant than that in bitter plant. These results suggest that the biosynthetic step(s) of ring closure forming the initial cyclic alkaloid, lupanine, from cadaverine is presumably blocked in sweet plant, and that the later steps for modification of the cyclized alkaloids are not altered. We hypothesized that the gene(s) encoding enzyme(s) for ring-closure step might be repressed in sweet plant, and that the expression might take place only in bitter plant. To isolate the genes specifically expressed in bitter plant, cDNA-amplified fragment length polymorphism (cDNA-AFLP) analysis was carried out. However, no bitter-specific gene was isolated, suggesting that alkaloid biosynthesis in sweet plant may be down-regulated at a post-transcriptional level.
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L. hintonii C. P. Smith grows in the Central Highland forests of Mexico at altitudes between 2800 m to 3200 m above see level. Members of the genus Lupinus produce quinolizidine alkaloids as main chemical defensive compounds against herbivores. Surprisingly alkaloid profiles are rather constant within this species, while substantial variation was found when compared to morphologically closely related other taxa. As part of a phytochemical project on Mexican wild lupins, we report on the alkaloid profiles of seeds and leaves of L. hintonii. 19 alkaloids could be identified by capillary GLC-MS. Six major alkaloids occurred in leaves and seeds: 13-hydroxylupanine (28% and 45% respectively), tetrahydrorhombifoline (31% and 23% respectively), angustifoline (2% and 4% respectively), lupanine (7% and 5% respectively), 13alpha-tigloyloxylupanine (19% and 5% respectively) and 4alpha-angeloyl-3beta-hydroxylupanine (9% and 2%). This chemical pattern resembles that of the North American lupin L. floribundus.
Article
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Esters of 13-hydroxylupanine and 4-hydroxylupanine with acetic, propionic, butyric, isobutyric, valeric, isovaleric, tiglic, benzoic, and TRANS-cinnamic acid have been synthesized and characterized by capillary gas-liquid chromatography and mass spectrometry (EI-MS, CI-MS). In LUPINUS POLYPHYLLUS, L. ALBUS, L. ANGUSTIFOLIUS, and L. MUTABILIS we could identify new ester alkaloids (e.g. 13-propyloxylupanine, 13-butyryloxylupanine, 13-isobutyryloxylupanine, and 4-tigloyloxylupanine) besides the known esters, i.e. 13-acetoxylupanine, 13-isovaleroyloxylupanine, 13-angeloyloxylupanine, 13-tigloyloxylupanine, 13-benzoyloxylupanine, 13- CIS-cinnamoyloxylupanine nine, and 13- TRANS-cinnamoyloxylupanine.
Chapter
A characteristic feature of plants is their ability to synthesize a wide range of natural products, the so-called secondary metabolites. Up till now more than 4500 terpenoids, 700 polyketides, 750 polyacetylenes, 500 phenylpropanoids, 1200 flavonoids, 400 non-protein amino acids, 100 glucosinolates, 50 cyanogenic glycosides, 100 amines and over 400 alkaloids have been described. Many of these compounds are used by man as pharmaceuticals, flavours, fragrances, colours, stimulants, hallucinogens, poisons, pesticides or as lead structure for the organic chemists to other more powerful substances and, therefore, plant allelochemicals are often economically important.
Chapter
It may be assumed that plants developed a wide variety of secondary metabolites during hundreds of millions of years of evolution as a means of defending themselves against herbivores, microorganisms, viruses, and other plants (see Chapter 11). Among the more than 50,000 natural products that are known today, over 12,000 are alkaloids.
Article
Crooked calf disease is produced when pregnant cows between the 40th and 70th days of gestation graze certain members of the genus Lupinus that contain the quinolizidine alkaloid anagyrine. Calves born to these cows may have twisted or bowed limbs (arthrogryposis), twisted or bowed spine (scoliosis or kyphosis), twisted neck (torticollis), cleft palate, or a combination of any of these. The concentration of the teratogen anagyrine in these lupines is very high early in growth, decreases to a low level during flowering, rises abruptly in mature seeds, and decreases to a very low level after seeds have dropped. Data collected from 6 ranches for 8- to 25-year periods showed no consistent correlation between incidence of the disease and the free-choice feeding of a variety of mineral supplements. Marked variation in incidence did occur, however, during these periods. The variation was related to the period of gestation at which the cows grazed the lupine and to the stage of growth of the lupine-in other words, the amount of anagyrine ingested. Management programs that prevent pregnant cows from eating highly teratogenic early growth or seed-stage lupine plants between gestation days 40 and 70 will reduce crooked calf disease incidence.
Article
The distribution of the first two enzymes of the biosynthetic pathway of quinolizidine alkaloid biosynthesis, lysine decarboxylase and 17-oxosparteine synthase, was studied in the various organs of a flowering Lupinus polyphyllus plant. Lysine decarboxylase activity is present in all plant parts, whereas the activiy of the key enzyme 17-oxosparteine synthase is only expressed in leaf extracts. This indicates that alkaloid synthesis is bound to the leaves, where both enzyme had been localized in chloroplasts previously. The alkaloid content, alkaloid concentration and the alkaloid composition was quantitatively evaluated for the various organs of two flowering L. polyphyllus plants. The highest alkaloid content was found in the roots (38-45% of total alkaloids) and leaves (27-31%), but alkaloids are virtually present in all parts of a plant. Relatively high alkaloid concentrations were found in leaves, in younger parts of the shoot axis and in mature seeds. The alkaloid content of leaves is reduced during senescence by 90% as compared with young leaves. The alkaloid pattern evaluated quantitatively by capillary gas chromatography for the organs of two plants and seeds includes the following compounds: lupanine, sparteine, angustifoline, N-methylangustifoline, dehydrolupanine, 17-oxolupanine, 13-hydroxylupanine and its esters (13-tigloyl-, 13-angeloyl-, 13-benzoyl- and 13-cis and 13-transcinnamoyl-oxylupanine). A high percentage of ester alkaloids and a low content of 13-hydroxylupanine was found in leaves. Roots and seeds, the main sites of alkaloid accumulation, displayed the opposite pattern, i.e. high concentration of 13-hydroxylupanine and low concentration of ester alkaloids.
Article
The bactericidal effect of lupine alkaloids against Pseudomonas syringae P.V. phaseolicola; Pseudomonas syringae P.V. tomato; Pseudomonas putida; Erwinia carotovora var. carotovora was tested. Crude alkaloids extracts from Lupinus albus (L.) and Lupinus luteus (L.) containing mainly lupanine and lupinine, respectively, were assayed at different concentrations. The individual bactericidal effects of sparteine and gramine were also analyzed. The results indicated that lupinine showed the highest bactericidal effect on the four bacteria studied, as concentrations between 5 and 10 mM are needed to stop the bacteria growth completely. Gramine could be also considered effective in the control of P. phaseolicola and P. tomato. In both cases the growth is completely inhibited by concentrations lower than 10 mM. The possible bactericidal effect of Lupinus alkaloids is discussed.
Article
Forty-nine genotypes of Lupinus albus seeds from different countries have been analyzed for their alkaloid content by thin-layer chromatography and gas chromatography-mass spectrometry. Twenty samples were sweet, while 29 were bitter, and the taste was positively correlated with the alkaloid content. The composition of the-alkaloids showed that lupanine was the main alkaloid present, and variable amounts of albine, alpha-isolupanine, multiflorine, and 13-hydroxylupanine were also detected in the seeds.
Article
The aim of this work was to investigate the effect of germination on the concentrations of some antinutritional factors in Lupinus albus and L luteus seeds. The seeds were germinated for 24, 48, 72 and 96 h. The alkaloid, phytic acid and -galactoside changes were monitored by capillary gas chromatography and HPLC techniques. The rate of seed germination for both lupin species was lower in total darkness than when 8 h of light was supplied. The total alkaloid level was not significantly altered by 96 h germination of the seeds. Albine, -isolupanine, lupanine, multiflorine and 13-OH-lupanine were identified in L albus whereas lupinine, sparteine and lupanine were identified in L luteus. -galactoside levels were drastically reduced during germination of lupin seeds and stachyose was the predominant sugar in both species. The major inositol phosphate (IP6) appeared to be degraded to lower inositol phosphates during lupin seed germination. It is concluded that germination is a useful process to improve the nutritional value of lupin seeds.
Article
The accumulation pattern of quinolizidine alkaloids during development of seedlings and young plants of Lupinus angustifolius and L. luteus are described. The enzymes catalysing the syntheses of the cinnamic acid O-ester of 13-hydroxylupanine and hydroxycinnamic acid O-esters of lupinine (4-coumaroyl- and feruloyllupinine) are characterized and classified as cinnamoyl-CoA: 13-hydroxylupanine O-cinnamoyltransferase (EC 2.3. 1.-) and hydroxycinnamoyl-CoA: lupinine O-hydroxycinnamoyltransferase (EC 2.3. 1.-).
Article
A Lupinus campestris milk-like product was obtained with 6.3% protein by using an alkaline thermal treatment. The colour of the suspension showed a greater similarity to cow's milk than to commercial soymilk. To adjust the carbohydrate concentration and induce fermentation, 3% of sucrose and 1.5% of lactose were added. The product was pasteurized and inoculated with a culture of Streptococcus thermophilus and Lactobacillus delbrueckii ssp bulgaricus. A lupin yogurt-like product with pH 4.02, 0.87% lactic acid, and a lactic acid bacteria count (3.2 × 108 CFU ml−1) and viscosity similar to commercial cow's milk yogurt was obtained. The amino acid composition of the proteins in the lupin milk and yogurt products had a good balance, with the exception, as in other legumes, of the sulphur-containing amino acids. Sensory evaluation indicated that the product was well accepted by consumers. These results offer a good possibility for the utilization of this legume in human nutrition through the elaboration of products that are analogous to others already present in the commercial market. Copyright © 2003 Society of Chemical Industry
Article
 The changes in the quantities of inositol phosphates during the maturation and germination of pea, faba bean and lupin seeds were determined in two consecutive (1993 and 1994) years of differing weather conditions. Irrespective of the year, all seeds accumulated predominantly inositol hexaphosphate (IP6). The weather conditions influenced the accumulation of inositol phosphates in maturing seeds, but they did not influence the total content. Gradual degradation of inositol phosphates occurred during seed germination. After 8 days of germination, IP6 was degraded by some 80% in peas, 78% in faba beans and 42% in lupin seeds. The enzymic hydrolysis of higher forms of inositol phosphates (IP6 and IP5) in germinating seeds was assumed to yield inositol tetraphosphate (IP4) and inositol triphosphate (IP3), because the quantities of these compounds increased during seed germination.
Article
The alkaloid composition of 56 species (90 taxa if all subspecies and chemotypes are included) of the genus Lupinus was studied by capillary gas-liquid chromatography and GLC-mass spectrometry (GC-EIMS). The distribution of 100 alkaloids (quinolizidines, piperidines, dipiperidines and simple indoles) and their relative abundances in leaves and seeds (if available) are recorded.
Article
Two types of protein isolates were prepared from Lupinus angustifolius defatted flour by alkaline extraction, with (Isolate B) and without (Isolate A) sodium sulphite, and acid precipitation of proteins at the isoelectric point (IEP 4.3). Chemical composition, main functional properties and protein composition of L. angustifolius defatted flour and protein isolates were determined. Isolate A and B have 93.9 and 84.6% protein content, respectively, and had a balanced composition of essential amino acids, with respect to the FAO pattern except for lysine. The in vitro protein digestibility ranged between 86.3 and 93.9% for isolate A and B, respectively.
Article
Alkaloidal extracts from teratogenic lupins produced congenital deformities in calves typical of crooked calf disease when the extracts were administered to pregnant cows during the susceptible gestational period. These data and previous epidemiologic studies suggest that one of the four alkaloids in the preparation, anagyrine, is the responsible teratogen. Severity of the malformations was directly related to the level of anagyrine present in the preparations administered.
Article
The seed of modern cultivars of Lupinus angustifolius normally contain less than 0.03% alkaloids. The acute oral LD50 to rats of a pro rata mixture of the alkaloids of L. angustifolius seed was found to be 2279 mg/kg. For lupanine the LD50 by oral administration was 1464 mg/kg and by intraperitoneal injection 177 mg/kg. For 13-hydroxylupanine the LD50 by intraperitoneal injection was 199 mg/kg. Since these two alkaloids comprise about 85% of the total and are known to be rapidly cleared from the body it is suggested that the alkaloids in this species do not pose a health problem for man.
Analysis of quinolizidine alkaloids from North-American lupins by GC-MS
  • C Meibner
  • M Wink
Meibner, C., & Wink, M. (1992). Analysis of quinolizidine alkaloids from North-American lupins by GC-MS. In M. Wink (Ed.), Lupinen 1991-Forschung, Anbau und Verwertung (pp. 91-129). Universit€ at Heidelberg.
International Rules for Seeds Testing Published by The International Seed Testing Association (ISTA), Switzerland Alkaloid profile of leaves and sedes of Lupinus hintonii C.P. Smith
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Anon. (1999). International Rules for Seeds Testing. Published by The International Seed Testing Association (ISTA), Switzerland. Berm udez Torres, K., Robledo Quintos, N., Barrera Necha, L. L., & Wink, M. (2001). Alkaloid profile of leaves and sedes of Lupinus hintonii C.P. Smith. Zeitschrift fur Naturforschung c, 57, 243–247.
Lupin toxins – alkaloids and phomopsins South Perth, Australia: Department of Agriculture A RSM study to the effect of controlled germination in Lupinus luteus alkaloid content
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Culvernor, C. C. J., & Petterson, D. S. (1986). Lupin toxins – alkaloids and phomopsins. In Proceedings of the fourth international lupin conference (pp. 188–198). South Perth, Australia: Department of Agriculture. Cunha-Queda, A. C., & Beirao da Costa, M. L. (1994). A RSM study to the effect of controlled germination in Lupinus luteus alkaloid content. In J. M. Neves-Martins & M. L. Beir~ ao da Costa (Eds.), Advances in lupin research (pp. 521–523). Lisboa: Instituto Superior de Agronom ıa (ISA press).
Effect of germination on nutritive value of lupin seeds
  • L C Trugo
Trugo, L.C. (1993). Effect of germination on nutritive value of lupin seeds. In Abstracts of the VII international lupin conference, Portugal: Evora.
A RSM study to the effect of controlled germination in Lupinus luteus alkaloid content
  • Cunha-Queda
Cunha-Queda, A. C., & Beirao da Costa, M. L. (1994). A RSM study to the effect of controlled germination in Lupinus luteus alkaloid content. In J. M. Neves-Martins & M. L. Beir~ ao da Costa (Eds.), Advances in lupin research (pp. 521-523). Lisboa: Instituto Superior de Agronom ıa (ISA press).
Lupin toxins - alkaloids and phomopsins
  • C C J Culvernor
  • D S Petterson
Culvernor, C. C. J., & Petterson, D. S. (1986). Lupin toxins-alkaloids and phomopsins. In Proceedings of the fourth international lupin conference (pp. 188-198). South Perth, Australia: Department of Agriculture.
Acute toxicity of the major alkaloids of cultivated Lupinus angustifolius seed to rats
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