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Keywords = lupanine

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10 pages, 1862 KiB  
Article
Characterization of a Diaporthe toxica Strain: Growth, Spore Formation, Phomopsin-A, and Alkaloids Production on Lupins
by Francesco Buccioni, Chiara Rossi, Annalisa Serio, Federico Fanti and Antonello Paparella
Toxins 2024, 16(11), 481; https://doi.org/10.3390/toxins16110481 - 7 Nov 2024
Viewed by 1336
Abstract
The growing interest in vegetable proteins, namely those derived from lupins, has raised concerns over potential safety risks associated with these food products. Lupin serves as the main host for the mycotoxin-producing fungus called Diaporthe toxica. This species, which is associated with [...] Read more.
The growing interest in vegetable proteins, namely those derived from lupins, has raised concerns over potential safety risks associated with these food products. Lupin serves as the main host for the mycotoxin-producing fungus called Diaporthe toxica. This species, which is associated with animal diseases, has been scarcely characterized. Recently, phomopsin-A (PHO-A), the main mycotoxin produced by D. toxica, was found to be harmful to humans. Therefore, this study aimed at characterizing D. toxica growth and spore formation both in vitro and on lupin samples. In addition, the production of PHO-A and alkaloids was investigated on lupin beans by using three different inoculation methods. Particularly, growth and spore production were evaluated on different media, while PHO-A and alkaloid production were determined by means of µSPE extraction followed by UHPLC-MS/MS and HPLC-MS/MS, respectively. The results have demonstrated differences in growth on different media, with potato and oat-flakes-based media being the best options. Conversely, D. toxica was not able to produce spores on agar media, but only on lupin beans. Moreover, a thorough analysis of PHO-A production revealed an increase over time, reaching values up to 1082.17 ppm after 21 days on artificially rehydrated samples. On the other side, the analysis of alkaloids revealed impressive results, as this species produced great quantities of the quinolizidine alkaloids (QA) that are normally present in lupin seeds such as lupanine, sparteine, multiflorine, and hydroxylupanine. On balance, considering these results, different metabolic pathways were demonstrated in D. toxica, which are not adequately described in the existing literature. These data are of paramount importance to deepen the knowledge about a fungal species that is important to ensure the safety of lupin and lupin-based products. Full article
(This article belongs to the Special Issue Toxins: 15th Anniversary)
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21 pages, 3258 KiB  
Article
Combined Gamma Conglutin and Lupanine Treatment Exhibits In Vivo an Enhanced Antidiabetic Effect by Modulating the Liver Gene Expression Profile
by Paloma Lucía Guerra-Ávila, Tereso J. Guzmán, José Alfredo Domínguez-Rosales, Pedro Macedonio García-López, Alejandra Beatriz Cervantes-Garduño, Michael Wink and Carmen Magdalena Gurrola-Díaz
Pharmaceuticals 2023, 16(1), 117; https://doi.org/10.3390/ph16010117 - 13 Jan 2023
Cited by 7 | Viewed by 3547
Abstract
Previous studies have individually shown the antidiabetic potential of gamma conglutin (Cγ) and lupanine from lupins. Until now, the influence of combining both compounds and the effective dose of the combination have not been assessed. Moreover, the resulting gene expression profile from this [...] Read more.
Previous studies have individually shown the antidiabetic potential of gamma conglutin (Cγ) and lupanine from lupins. Until now, the influence of combining both compounds and the effective dose of the combination have not been assessed. Moreover, the resulting gene expression profile from this novel combination remains to be explored. Therefore, we aimed to evaluate different dose combinations of Cγ and lupanine by the oral glucose tolerance test (OGTT) to identify the higher antidiabetic effect on a T2D rat model. Later, we administered the selected dose combination during a week. Lastly, we evaluated biochemical parameters and liver gene expression profile using DNA microarrays and bioinformatic analysis. We found that the combination of 28 mg/kg BW Cγ + 20 mg/kg BW lupanine significantly reduced glycemia and lipid levels. Moreover, this treatment positively influenced the expression of Pdk4, G6pc, Foxo1, Foxo3, Ppargc1a, Serpine1, Myc, Slc37a4, Irs2, and Igfbp1 genes. The biological processes associated with these genes are oxidative stress, apoptosis regulation, and glucose and fatty-acid homeostasis. For the first time, we report the beneficial in vivo effect of the combination of two functional lupin compounds. Nevertheless, further studies are needed to investigate the pharmacokinetics and pharmacodynamics of the Cγ + lupanine combined treatment. Full article
(This article belongs to the Special Issue Natural Products in Diabetes Mellitus)
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15 pages, 4875 KiB  
Article
Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins
by Astrid Ramírez-Betancourt, Arianna Michelle Hernández-Sánchez, Guadalupe Salcedo-Morales, Elsa Ventura-Zapata, Norma Robledo, Michael Wink and Kalina Bermúdez-Torres
Diversity 2021, 13(8), 375; https://doi.org/10.3390/d13080375 - 14 Aug 2021
Cited by 9 | Viewed by 4446
Abstract
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 [...] Read more.
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. Full article
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23 pages, 1233 KiB  
Article
Bioactive Variability and In Vitro and In Vivo Antioxidant Activity of Unprocessed and Processed Flour of Nine Cultivars of Australian lupin Species: A Comprehensive Substantiation
by Kishor Mazumder, Afia Nabila, Asma Aktar and Asgar Farahnaky
Antioxidants 2020, 9(4), 282; https://doi.org/10.3390/antiox9040282 - 27 Mar 2020
Cited by 81 | Viewed by 6385
Abstract
The aim of this present investigation was to analyze bioactive compounds, as well as demonstrate the antioxidant activities of nine cultivars of Australian lupin species accompanied by observing the effect of domestic heat processing on their antioxidant activities adopting in vivo and in [...] Read more.
The aim of this present investigation was to analyze bioactive compounds, as well as demonstrate the antioxidant activities of nine cultivars of Australian lupin species accompanied by observing the effect of domestic heat processing on their antioxidant activities adopting in vivo and in vitro approaches. Gas chromatography mass spectroscopy (GC-MS) analysis was performed for profiling bioactive compounds present in lupin cultivars. Multiple assay techniques involving quantification of polyphenolics, flavonoids and flavonol, electron transfer (ET) based assay, hydrogen atom transfer (HAT)-based assay and in vivo assays were performed. The major compounds found were hexadecanoic acid methyl ester, 9,12-octadecadienoic acid methyl ester, methyl stearate, lupanine,13-docosenamide and 11-octadecenoic acid (Z)- methyl ester. Mandelup was found to show excellent antioxidant activity. Moreover, Jurien, Gunyidi and Barlock had strong antioxidant activity. Both positive and negative impacts of heat processing were observed on antioxidant activity. Heating and usage of excess water during processing were the key determinants of loss of antioxidants. Negligible loss of antioxidant activity was observed in most of the assays whereas inhibition of both lipid peroxidation (33.53%) and hemolysis of erythrocytes (37.75%) were increased after processing. In addition, in vitro and in vivo antioxidant assays are found to show statistically significant (* p < 0.05 and ** p < 0.01) results, which are supported by the presence of a number of antioxidant compounds in GC-MS analysis. Full article
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13 pages, 2286 KiB  
Article
Coagulant Effects and Mechanism of Schefflera heptaphylla (L.) Frodin
by Xuqiang Liu, Jing Dong, Qiongxin Liang, Hui-min David Wang, Zhenhua Liu, Ruian Xu and Wenyi Kang
Molecules 2019, 24(24), 4547; https://doi.org/10.3390/molecules24244547 - 12 Dec 2019
Cited by 9 | Viewed by 4246
Abstract
Schefflera heptaphylla (L.) Frodin, are commonly used in anti-inflammatory, analgesic, traumatic bleeding and hemostasisas. In this paper, the coagulation effect of the ethanol extract (Set), ethyl acetate phase (Sea) and n-butanol phase (Sbu) was evaluated by prothrombin time (PT), activated partial thromboplastin [...] Read more.
Schefflera heptaphylla (L.) Frodin, are commonly used in anti-inflammatory, analgesic, traumatic bleeding and hemostasisas. In this paper, the coagulation effect of the ethanol extract (Set), ethyl acetate phase (Sea) and n-butanol phase (Sbu) was evaluated by prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen content (FIB) assays in vitro. Then, Three main lupanine triterpenes (compounds AC) were isolated and identified from Sea and Sbu by a bioassay-guided method and their structure were identified as 3α-Hydroxy-lup-20(29)-ene-23, 28-dioic acid, betulinic acid 3-O-sulfate and 3α-Hydroxy-lup-20(29)-ene-23, 28-dioic acid 28-O-(α-l-rhamnopyranosyl(1→4)-O-β-d-glucopyranosyl(1→6))-β-d-glucopyranoside) by spectroscopic data analysis. Among of them, compound B was confirmed to have significant coagulant effect in vitro. Furthermore, the pro-coagulation mechanism of S. heptaphylla extracts and compound B were investigated by measuring whole blood viscosity (WBV), plasma viscosity (PV), erythrocyte sedimentetion rate (ESR), pack cell volume (PCV), APTT, PT, TT, and FIB in vivo. Meanwhile, the levels of thromboxane B2 (TXB2), 6-keto prostaglandin F (6-keto-PGF), endothelial nitric oxide synthase (eNOS) and (endothelin-1) ET-1 were detected. The bleeding time (BT) was tested by tail bleeding method, which proved the traumatic bleeding and hemostasis activities of S. heptaphylla. The pharmacology experiments showed that the Set, Sea, Sbu and compound B has significant pro-coagulation effect. In addition, compound B might be the main constituent of pro-coagulation in S. heptaphylla These results could support the fact that S. heptaphylla could be used traditionally to cure traumatic bleeding, and the pro-coagulation effects were associated with the regulation of vascular endothelium active substance and hemorheology parameters. Full article
(This article belongs to the Special Issue Cytotoxic Activity of Plant Extracts)
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17 pages, 1255 KiB  
Article
Chromatographic Fingerprinting of the Old World Lupins Seed Alkaloids: A Supplemental Tool in Species Discrimination
by Wojciech Święcicki, Katarzyna Czepiel, Paulina Wilczura, Paweł Barzyk, Zygmunt Kaczmarek and Magdalena Kroc
Plants 2019, 8(12), 548; https://doi.org/10.3390/plants8120548 - 27 Nov 2019
Cited by 18 | Viewed by 3601
Abstract
The total contents and qualitative compositions of alkaloids in seeds of 10 Old World lupin species (73 accessions) were surveyed using gas chromatography. The obtained results, combined with those for three lupin crops, Lupinus angustifolius, Lupinus albus, and Lupinus luteus, [...] Read more.
The total contents and qualitative compositions of alkaloids in seeds of 10 Old World lupin species (73 accessions) were surveyed using gas chromatography. The obtained results, combined with those for three lupin crops, Lupinus angustifolius, Lupinus albus, and Lupinus luteus, provide the most complete and up-to-date overview of alkaloid profiles of 13 lupin species originating from the Mediterranean Basin. The qualitative alkaloid compositions served as useful supplementary tools of species discrimination. On the basis of the most abundant major alkaloids, lupanine, lupinine, and multiflorine, the Old World lupin species were divided into four groups. Those containing lupanine (L. angustifolius, L. albus, and Lupinus mariae-josephi), containing lupinine (Lupinus luteus, Lupinus hispanicus, and Lupinus × hispanicoluteus), containing lupinine and multiflorine (Lupinus atlanticus, Lupinus palaestinus, Lupinus anatolicus, Lupinus digitatus, Lupinus pilosus, and Lupinus cosentinii), and containing multiflorine (Lupinus micranthus). Within a given group, certain species can be, in most cases, further distinguished by the presence of other major alkaloids. The discrimination of species based on the total alkaloid content was found to be less reliable because of the significant intra-species variations, as well as the influences of environmental factors on the seed alkaloid content. Full article
(This article belongs to the Section Phytochemistry)
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12 pages, 972 KiB  
Article
Characterization and Antimicrobial Activity of Alkaloid Extracts from Seeds of Different Genotypes of Lupinus spp.
by Flora Valeria Romeo, Simona Fabroni, Gabriele Ballistreri, Serena Muccilli, Alfio Spina and Paolo Rapisarda
Sustainability 2018, 10(3), 788; https://doi.org/10.3390/su10030788 - 13 Mar 2018
Cited by 40 | Viewed by 6803
Abstract
Alkaloid profiles of 22 lupin genotypes belonging to three different cultivated species, Lupinus albus L., Lupinus luteus L., and Lupinus angustifolius L., collected from different Italian regions and grown in Sicily, were studied by gas chromatography mass spectrometry (GC-MS) to determine alkaloid composition. [...] Read more.
Alkaloid profiles of 22 lupin genotypes belonging to three different cultivated species, Lupinus albus L., Lupinus luteus L., and Lupinus angustifolius L., collected from different Italian regions and grown in Sicily, were studied by gas chromatography mass spectrometry (GC-MS) to determine alkaloid composition. More than 30 alkaloids were identified. The lowest alkaloid concentration was observed in the L. albus Luxor, Aster, and Rosetta cultivars, and in all the varieties of L. luteus and L. angustifolius. The highest content was observed in all the landraces of L. albus. Surprisingly, the white lupin Lublanc variety and the commercial seeds of cv Multitalia had a high alkaloid content. The tested species and the different genotypes exhibited different alkaloid profiles: lupanine, 13α-hydroxylupanine, and albine were the main alkaloids in the analyzed L. albus seeds; angustifoline and 13α-tigloyloxylupanine were well-represented in L. albus landraces; sparteine and lupinine were typical of L. luteus; and lupanine, 13α-hydroxylupanine, and angustifoline were the main alkaloids in L. angustifolius seeds. The samples with the highest amounts of total alkaloids proved to be interesting from a pharmaceutical viewpoint. The alkaloid extracts showed significant activity on Klebsiella pneumoniae and Pseudomonas aeruginosa clinical isolates. Full article
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16 pages, 1302 KiB  
Article
Lupanine Improves Glucose Homeostasis by Influencing KATP Channels and Insulin Gene Expression
by Mats Wiedemann, Carmen M. Gurrola-Díaz, Belinda Vargas-Guerrero, Michael Wink, Pedro M. García-López and Martina Düfer
Molecules 2015, 20(10), 19085-19100; https://doi.org/10.3390/molecules201019085 - 20 Oct 2015
Cited by 35 | Viewed by 7361
Abstract
The glucose-lowering effects of lupin seeds involve the combined action of several components. The present study investigates the influence of one of the main quinolizidine alkaloids, lupanine, on pancreatic beta cells and in an animal model of type-2 diabetes mellitus. In vitro studies [...] Read more.
The glucose-lowering effects of lupin seeds involve the combined action of several components. The present study investigates the influence of one of the main quinolizidine alkaloids, lupanine, on pancreatic beta cells and in an animal model of type-2 diabetes mellitus. In vitro studies were performed with insulin-secreting INS-1E cells or islets of C57BL/6 mice. In the in vivo experiments, hyperglycemia was induced in rats by injecting streptozotocin (65 mg/kg body weight). In the presence of 15 mmol/L glucose, insulin secretion was significantly elevated by 0.5 mmol/L lupanine, whereas the alkaloid did not stimulate insulin release with lower glucose concentrations. In islets treated with l-arginine, the potentiating effect of lupanine already occurred at 8 mmol/L glucose. Lupanine increased the expression of the Ins-1 gene. The potentiating effect on secretion was correlated to membrane depolarization and an increase in the frequency of Ca2+ action potentials. Determination of the current through ATP-dependent K+ channels (KATP channels) revealed that lupanine directly inhibited the channel. The effect was dose-dependent but, even with a high lupanine concentration of 1 mmol/L or after a prolonged exposure time (12 h), the KATP channel block was incomplete. Oral administration of lupanine did not induce hypoglycemia. By contrast, lupanine improved glycemic control in response to an oral glucose tolerance test in streptozotocin-diabetic rats. In summary, lupanine acts as a positive modulator of insulin release obviously without a risk for hypoglycemic episodes. Full article
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