MEXICAN WILD LUPINES AS A SOURCE OF QUINOLIZIDINE ALKALOIDS OF ECONOMIC POTENTIAL

Quinolizidine alkaloids such as lupanine,13-hydroxylupanine, multiflorine, angustifoline and sparteine, which are present inthe species of the genus Lupinus, have beenreported to have biopesticide and pharmacological activities. The aim of this studywas to quantify the content and variationof the individual alkaloids in seeds of L.mexicanus, L. exaltatus, L. montanus andL. stipulatus collected in different states ofMexico. Lupanine was the major (5.05 ±0.37 mg/g) alkaloid found in L. mexicanus,whereas sparteine was the main alkaloidpresent in L. montanus (3.97 ± 0.49 mg/g).Conversely, L. stipulatus contained onlysmall quantities of lupanine and sparteine(0.1 ± 0.002 and 0.04 ± 0.01 mg/g, respectively). Angustifoline was detected only in L.montanus, but in a very low amount (0.048± 0.03). The results of this study indicatethat L. mexicanus and L. montanus can beconsidered as important sources of lupanine and sparteine for their use as natural pesticide or pharmacological agents.Los alcaloides quinolizidinicos lupanina,13-hidroxilupanina, multiflorina, angustifolina y esparteina, presentes en el géneroLupinus poseen actividades bioplagiciday farmacológica. El objetivo del presenteestudio fue cuantificar el contenido y variación de los alcaloides mencionados ensemillas de L. mexicanus, L. exaltatus, L.montanus y L. stipulatus, colectados endiferentes estados de México. La lupaninafue el principal (5.05 ± 0.37mg /g) alcaloideencontrado en L. mexicanus, mientras que laesparteína fue el mayor alcaloide presente en L. montanus (3.97 ± 0.49 mg/g). Sinembargo, en L. stipulatus se encontraron pequeñas cantidades de lupanina y esparteína(0.1 ± 0.002 y 0.04 ± 0.01 mg/g, respectivamente). La angustifolina sólo se detectóen bajos niveles en L. montanus (0.048 ±0.03). Los resultados de este estudio indicanque L. mexicanus y L. montanus pueden serconsiderados como una fuente importantede lupanina y esparteína, los cuales puedenser utilizados como pesticidas o hipoglucé-micos naturales

Decomposition and nitrogen mineralisation of two wild lupins (Leguminosae) species with potential as green manures

The amount of biomass produced by various native species of genus Lupinus (L.) growing in Mexico ranges from 2.9- 8.2 Mg/ha of dry matter, which can add up to 200 kg/ha of N to soil as green manure. However, information is scarce on the decomposition and mineralisation this biomass in the soil. The above-ground decomposition and N mineralisation of Lupinus mexicanus Cerv. ex Lag. and Lupinus rotundiflorus M.E. Jones species from Mexico using fine-mesh litter bags was evaluated. Litter bags containing 5 g of above-ground air-dried biomass at the vegetative and flowering stages were buried at a depth of 20 cm. Were dug up every 3 weeks over the course of 4 months, dried and re-weighed to determine the lost mass and total N by the Kjeldahl method. The largest decrease in residue mass occurred during the first 3 weeks of incubation. However, the lost mass was higher in younger green manure (75 days old) than in older plants (85 days old) after 18 weeks of exposure in the field. It was found that 60-75% of the total N in the plant material was released in the first 6 weeks. In L. rotundiflorus green manure, it was found that 79.14% of the initial N in the vegetative stage and 77.6% of N in the flowering stage was released 18 weeks after litter bag installation, whereas L. mexicanus were 74.6% and 74.7%, respectively. It was found that both decomposition and N mineralisation occurred quickly in the green manures evaluated

Composition of alkaloids in seeds of Lupinus mexicanus (FABACEAE) and antifungal and allelopathic evaluation of the alkaloid extract [Composición de alcaloides en semillas de Lupinus mexicanus (FABACEAE) y evaluación antifúngica y alelopática del extracto alcaloideo]

Plants synthesize secondary metabolites that can be isolated and used in agriculture as an alternative for the control of pests and diseases. Capillary gas chromatography mass spectrometry (CG-MS) was used to analyze the composition of alkaloids in seeds of Lupinus mexicanus. In addition, an in vitro study was made of the antifungal and allelopathic activity of the crude extract of alkaloids. The antifungal action of the extract was evaluated based on the inhibition of the mycelial growth of the phytopathogenic fungi Sclerotium rolfsii, Rhizoctonia solani and Fusarium oxysporum, while the allelopathic activity was evaluated on the germination of seeds of Amaranthus hybridus and Echinochloa crus-galli. The analysis of alkaloids from the extract revealed the presence of lupanine, 3β-hydroxylupanine, multiflorine aphylline, epiaphylline and α-isolupanine as majority compounds. The extract, at the concentration of 3 mg mL-1, significantly inhibited the mycelial growth of R. solani by 87.7%, whereas the mycelial growth of S. rolfsii was only inhibited 72.5% with the highest concentration. Only the germination of seeds of A. hybridus showed significant differences from the effect of the extract, and inhibition of germination was 80% with the highest concentration (1 mg mL-1). Lupanine was the most abundant alkaloid (76.2%) in the extract of seeds of L. mexicanus. The extract showed inhibitory activity of the mycelial growth of R. solani and S. rolfsii, and a phytotoxic or inhibitory effect on the germination of seeds of A. hybridus

Profiling isoflavone conjugates in different organs of Lupinus exaltatus Zucc

The profiles of isoflavone conjugates in extracts obtained from different parts of Lupinus exaltatus Zucc. grown in Mexico were compared using HPLC-UV and HPLC-ESI/MSn. Collision-induced dissociation-MSn experiments were performed using an ion trap analyser during HPLC-ESI/MS analyses. Nineteen isoflavone conjugates were identified in samples obtained from air-dried roots, leaves, stems and inflorescences of lupin plants. It was possible to determine the structures of the studied compounds on the basis of the MS recorded. The compounds identified were di- and mono-glucosides of genistein and 2′-hydroxygenistein with a different pattern of C- and O-glycosylation. Some glucosides were acylated with malonic acid. It was not possible to establish the glycosylation sites on the basis of MS alone; however, it was possible to differentiate isoflavone C- and O-glucosides. The highest levels of isoflavones and their conjugates were detected in roots and the lowest in stems. Free aglycones were identified in roots and inflorescences but they were not found in stems and leaves. Copyright © 2006 John Wiley & Sons, Ltd

LC-MSMS profiling of flavonoid conjugates in wild mexican lupine, lupinus reflexus

Profiles of flavonoid conjugates present in the root and leaf tissues of the Mexican wild lupine, Lupinus reflexus, were established using two LC-MSMS systems in the positive and negative ion modes. The ion trap mass spectrometer and quadrupole time-of flight instrument provided sequential MSn spectra and MSMS spectra with accurate m/z values of [M + H]+ and [M - H] - ions, respectively. Sixty-two flavone and isoflavone glycoconjugates were found and tentatively identified. Numerous isomeric or isobaric compounds with the same molecular mass could be differentiated. Isomeric di- and mono glucosides of biochanin A, genistein, 2′- hydroxygenistein, luteone, and 2,3-didehydrokievitone were distinguished on the basis of relative abundances of product ions. The studied flavonoid glycoconjugates were acylated with dicarboxylic aliphatic acids and their methyl esters at either the aglycone or glycosidic moiety. © 2010 The American Chemical Society and American Society of Pharmacognosy

Alkaloid composition and concentration in Lupinus exaltatus zucc. during its growth and development [Composición y concentración de alcaloides en Lupinus exaltatus zucc. durante su crecimiento y desarrollo]

Due to its nutritional characteristics, Lupinus exaltatus is considered as an alternative source of animal feed in temperate regions. However, the presence of quinolizidine alkaloids in different plant organs limits its consumption. The composition and concentration of alkaloids in leaves, stems, flowers, and inmature fruits of L. exaltatus was determined in five different phenological stages with the final purpose of suggesting alternatives for its management and use as forage. Plants were sowed in pots and at each phenological stage six plants were harvested and separated in roots, stems, leaves, flowers, and inmature pods that were air dried to constant weight. Each organ was analyzed for alkaloid composition and content by capillary gas chromatography- mass spectrometry (GC-MS). In each phenological stage and in all organs the alkaloid profile was characterized by the presence of six major alkaloids: epiaphylline aphylline, α-isolupanine, lupanine, dehydro-oxosparteine and 3-β-hydroxylupanine. Although the alkaloid profile was constant, the total concentration in the different organs showed a significant variation (0.31-2.1%) in the different phenological stages. In general, after the five growth stages the stems showed the lowest average total alkaloid concentration (0.63%) whereas inmature pods had the highest total alkaloids (1.95%). Lupanine was the major alkaloid in stems and fruits. Although alkaloids with the highest toxicity (sparteine, anagyrine and ammodendrine) were not detected, the results indicate that the major risk for intoxication could occur during pod growth and seed ripening, due to high total alkaloid content and larger abundance of lupanine in immature fruits

Alkaloid composition and concentration in Lupinus exaltatus zucc. during its growth and development [Composición y concentración de alcaloides en Lupinus exaltatus zucc. durante su crecimiento y desarrollo]

Due to its nutritional characteristics, Lupinus exaltatus is considered as an alternative source of animal feed in temperate regions. However, the presence of quinolizidine alkaloids in different plant organs limits its consumption. The composition and concentration of alkaloids in leaves, stems, flowers, and inmature fruits of L. exaltatus was determined in five different phenological stages with the final purpose of suggesting alternatives for its management and use as forage. Plants were sowed in pots and at each phenological stage six plants were harvested and separated in roots, stems, leaves, flowers, and inmature pods that were air dried to constant weight. Each organ was analyzed for alkaloid composition and content by capillary gas chromatography- mass spectrometry (GC-MS). In each phenological stage and in all organs the alkaloid profile was characterized by the presence of six major alkaloids: epiaphylline aphylline, ?-isolupanine, lupanine, dehydro-oxosparteine and 3-?-hydroxylupanine. Although the alkaloid profile was constant, the total concentration in the different organs showed a significant variation (0.31-2.1%) in the different phenological stages. In general, after the five growth stages the stems showed the lowest average total alkaloid concentration (0.63%) whereas inmature pods had the highest total alkaloids (1.95%). Lupanine was the major alkaloid in stems and fruits. Although alkaloids with the highest toxicity (sparteine, anagyrine and ammodendrine) were not detected, the results indicate that the major risk for intoxication could occur during pod growth and seed ripening, due to high total alkaloid content and larger abundance of lupanine in immature fruits

Evaluation of sewage sludge as an organic fertilizer in volcanic soils of agricultural and forestal use in jalisco, Mexico [Evaluación de lodos residuales como abono orgúnico en suelos volcúnicos de uso agrícola yforestal en Jalisco, México]

Sewage sludge applications to agricultural and forest soils represent an important alternative for reuse of materials with a high nutrient content. The effects of different application rates of sewage sludge as organic fertilizer on corn production and Pinus douglasiana development were studied. The experiments were established in a volcanic soil of the central region of Jalisco, Mexico. The application 10 and 20t ha-1 of dry sewage sludge and of sludge compost mixed with garden residues on corn yield was evaluated. The materials were homogeneously applied on the ground, using a randomized complete block design with five replications. Both the corn and fodder yield (dry matter base) increased as a result of the addition of sludge and compost in 18 and 22%, respectively. The effects of different application rates of dry sewage sludge (0, 30, 60 and 100g/ tree) on the initial development of Pinus douglasiana were also evaluated. Application of sludge at the highest rate significantly improved the establishment of Pinus douglasiana (83%) after 14 months, whereas the control only reached 67%. At the highest rates of application, both height and diameter of tree steams were increased by ?18%. Application of sewage sludges as an organic fertilizer improved the corn production and the initial development of Pinus douglasiana on volcanic soils

Evaluation of sewage sludge as an organic fertilizer in volcanic soils of agricultural and forestal use in jalisco, Mexico [Evaluación de lodos residuales como abono orgánico en suelos volcánicos de uso agrícola yforestal en Jalisco, México]

Sewage sludge applications to agricultural and forest soils represent an important alternative for reuse of materials with a high nutrient content. The effects of different application rates of sewage sludge as organic fertilizer on corn production and Pinus douglasiana development were studied. The experiments were established in a volcanic soil of the central region of Jalisco, Mexico. The application 10 and 20t·ha-1 of dry sewage sludge and of sludge compost mixed with garden residues on corn yield was evaluated. The materials were homogeneously applied on the ground, using a randomized complete block design with five replications. Both the corn and fodder yield (dry matter base) increased as a result of the addition of sludge and compost in 18 and 22%, respectively. The effects of different application rates of dry sewage sludge (0, 30, 60 and 100g/ tree) on the initial development of Pinus douglasiana were also evaluated. Application of sludge at the highest rate significantly improved the establishment of Pinus douglasiana (83%) after 14 months, whereas the control only reached 67%. At the highest rates of application, both height and diameter of tree steams were increased by ∼18%. Application of sewage sludges as an organic fertilizer improved the corn production and the initial development of Pinus douglasiana on volcanic soils

Structural analysis and profiling of phenolic secondary metabolites of Mexican lupine species using LC-MS techniques

Flavonoid glycoconjugates from roots and leaves of eight North America lupine species (Lupinus elegans, Lupinus exaltatus, Lupinus hintonii, Lupinus mexicanus, Lupinus montanus, Lupinus rotundiflorus, Lupinus stipulatus, Lupinus sp.), three Mediterranean species (Lupinus albus, Lupinus angustifolius, Lupinus luteus) and one species from South America domesticated in Europe (Lupinus mutabilis) were analyzed using two LC/MS systems: low-resolution ion trap instrument and high-resolution quadrupole-time-of-flight spectrometer. As a result of the LC/MS profiling using the CID/MSn experiments structures of 175 flavonoid glycoconjugates found in 12 lupine species were identified at three confidence levels according to the Metabolomic Standard Initiative, mainly at level 2 and 3, some of them were classified to the level 1. Among the flavonoid derivatives recognized in the plant extracts were isomeric or isobaric compounds, differing in the degree of hydroxylation of the aglycones and the presence of glycosidic, acyl or alkyl groups in the molecules. The elemental composition of the glycoconjugate molecules was established from the exact m/z values of the protonated/deprotonated molecules ([M+H] +/[M-H]-) measured with the accuracy better than 5 ppm. Information concerning structures of the aglycones, the type of sugar moieties (hexose, deoxyhexose or pentose) and, in some cases, their placement on the aglycones as well as the acyl substituents of the flavonoid glycoconjugates was achieved in experiments, in which collisioninduced dissociation was applied. Flavonoid aglycones present in the studied O-glycoconjugates were unambiguously identified after the comparison of the pseudo-MS3 spectra with the spectra registered for the standards. Isomers of flavonoid glycoconjugates, in which one or two sugar moieties were attached to 40- or 7-hydroxyl groups or directly to the C-6 or C-8 of the aglycones, could be distinguished on the basis of the MS2 spectra. However, the collision energy applied in the CID experiments had to be optimized for each group of the compounds and there were no universal settings that allowed the acquisition of structural information for all the compounds present in the sample. Information obtained from the flavonoid conjugate profiling was used for the chemotaxonomic comparison of the studied lupine species. A clear-cut discrimination of the Mediterranean and North American lupines was obtained as a result of this analysis. � 2013 Elsevier Ltd. All rights reserved