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Daniel G Panaccione - One of the best experts on this subject based on the ideXlab platform.
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Genetic Reprogramming of the Ergot Alkaloid Pathway of Metarhizium brunneum.
Applied and environmental microbiology, 2020Co-Authors: Kyle A. Davis, Jessi K. Sampson, Daniel G PanaccioneAbstract:ABSTRACT Ergot Alkaloids are important specialized fungal metabolites that are used to make potent pharmaceuticals for neurological diseases and disorders. Lysergic acid (LA) and dihydrolysergic acid (DHLA) are desirable lead compounds for pharmaceutical semisynthesis but are typically transient intermediates in the Ergot Alkaloid and dihydroErgot Alkaloid pathways. Previous work with Neosartorya fumigata demonstrated strategies to produce these compounds as pathway end products, but their percent yield (percentage of molecules in product state as opposed to precursor state) was low. Moreover, Ergot Alkaloids in N. fumigata are typically retained in the fungus as opposed to being secreted. We used clustered regularly interspaced short palindromic repeat (CRISPR)–CRISPR-associated protein 9 (Cas9) and heterologous expression approaches to engineer these compounds in Metarhizium brunneum, representing an alternate expression host from a different lineage of fungi. The relative percent yields of LA (86.9%) and DHLA (72.8%) were much higher than those calculated here for previously engineered strains of N. fumigata (2.6% and 2.0%, respectively). Secretion of these Alkaloids also was measured, with averages of 98.4% of LA and 87.5% of DHLA being secreted into the growth medium; both values were significantly higher than those measured for the N. fumigata derivatives (both of which were less than 5.6% secreted). We used a similar approach to engineer a novel dihydroErgot Alkaloid in M. brunneum and, through high-performance liquid chromatography-mass spectrometry (LC-MS) analyses, provisionally identified it as the dihydrogenated form of lysergic acid α-hydroxyethylamide (dihydro-LAH). The engineering of these strains provides a strategy for producing novel and pharmaceutically important chemicals in a fungus more suitable for their production. IMPORTANCE Ergot Alkaloids derived from LA or DHLA are the bases for numerous pharmaceuticals with applications in the treatment of dementia, migraines, hyperprolactinemia, and other conditions. However, extraction of Ergot Alkaloids from natural sources is inefficient, and their chemical synthesis is expensive. The ability to control and redirect Ergot Alkaloid synthesis in fungi may allow more efficient production of these important chemicals and facilitate research on novel derivatives. Our results show that Metarhizium brunneum can be engineered to efficiently produce and secrete LA and DHLA and, also, to produce a novel derivative of DHLA not previously found in nature. The engineering of dihydroErgot Alkaloids, including a novel species, is important because very few natural sources of these compounds are known. Our approach establishes a platform with which to use M. brunneum to study the production of other Ergot Alkaloids, specifically those classified as lysergic acid amides and dihydroErgot Alkaloids.
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Ergot Alkaloid Synthesis Capacity of Penicillium camemberti.
Applied and Environmental Microbiology, 2018Co-Authors: Samantha J. Fabian, Matthew D. Maust, Daniel G PanaccioneAbstract:ABSTRACT Ergot Alkaloids are specialized fungal metabolites with potent biological activities. They are encoded by well-characterized gene clusters in the genomes of producing fungi. Penicillium camemberti plays a major role in the ripening of Brie and Camembert cheeses. The P. camemberti genome contains a cluster of five genes shown in other fungi to be required for synthesis of the important Ergot Alkaloid intermediate chanoclavine-I aldehyde and two additional genes (easH and easQ) that may control modification of chanoclavine-I aldehyde into other Ergot Alkaloids. We analyzed samples of Brie and Camembert cheeses, as well as cultures of P. camemberti, and did not detect chanoclavine-I aldehyde or its derivatives. To create a functioning facsimile of the P. camembertieas cluster, we expressed P. camemberti easH and easQ in a chanoclavine-I aldehyde-accumulating easA knockout mutant of Neosartorya fumigata. The easH-easQ-engineered N. fumigata strain accumulated a pair of compounds of m/z 269.1288 in positive-mode liquid chromatography-mass spectrometry (LC-MS). The analytes fragmented in a manner typical of the stereoisomeric Ergot Alkaloids rugulovasine A and B, and the related rugulovasine producer Penicillium biforme accumulated the same isomeric pair of analytes. The P. camemberti eas genes were transcribed in culture, but comparison of the P. camemberti eas cluster with the functional cluster from P. biforme indicated 11 polymorphisms. Whereas other P. camembertieas genes functioned when expressed in N. fumigata, P. camembertieasC did not restore Ergot Alkaloids when expressed in an easC mutant. The data indicate that P. camemberti formerly had the capacity to produce the Ergot Alkaloids rugulovasine A and B. IMPORTANCE The presence of Ergot Alkaloid synthesis genes in the genome of Penicillium camemberti is significant, because the fungus is widely consumed in Brie and Camembert cheeses. Our results show that, although the fungus has several functional genes from the Ergot Alkaloid pathway, it produces only an early pathway intermediate in culture and does not produce Ergot Alkaloids in cheese. Penicillium biforme, a close relative of P. camemberti, contains a similar but fully functional set of Ergot Alkaloid synthesis genes and produces Ergot Alkaloids chanoclavine-I, chanoclavine-I aldehyde, and rugulovasine A and B. Our reconstruction of the P. camemberti pathway in the model fungus Neosartorya fumigata indicated that P. camemberti formerly had the capacity to produce these same Ergot Alkaloids. Neither P. camemberti nor P. biforme produced Ergot Alkaloids in cheese, indicating that nutritionally driven gene regulation prevents these fungi from producing Ergot Alkaloids in a dairy environment.
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Ergot Alkaloid biosynthesis in the maize zea mays Ergot fungus claviceps gigantea
Journal of Agricultural and Food Chemistry, 2017Co-Authors: Paige E Bragg, Matthew D. Maust, Daniel G PanaccioneAbstract:Biosynthesis of the dihydrogenated forms of Ergot Alkaloids is of interest because many of the Ergot Alkaloids used as pharmaceuticals may be derived from dihydrolysergic acid (DHLA) or its precursor dihydrolysergol. The maize (Zea mays) Ergot pathogen Claviceps gigantea has been reported to produce dihydrolysergol, a hydroxylated derivative of the common Ergot Alkaloid festuclavine. We hypothesized expression of C. gigantea cloA in a festuclavine-accumulating mutant of the fungus Neosartorya fumigata would yield dihydrolysergol because the P450 monooxygenase CloA from other fungi performs similar oxidation reactions. We engineered such a strain, and high performance liquid chromatography and liquid chromatography–mass spectrometry analyses demonstrated the modified strain produced DHLA, the fully oxidized product of dihydrolysergol. Accumulation of high concentrations of DHLA in field-collected C. gigantea sclerotia and discovery of a mutation in the gene lpsA, downstream from DHLA formation, supported o...
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Ergot Alkaloids contribute to virulence in an insect model of invasive aspergillosis
Scientific reports, 2017Co-Authors: Daniel G Panaccione, Stephanie L. ArnoldAbstract:Neosartorya fumigata (Aspergillus fumigatus) is the most common cause of invasive aspergillosis, a frequently fatal lung disease primarily affecting immunocompromised individuals. This opportunistic fungal pathogen produces several classes of specialised metabolites including products of a branch of the Ergot Alkaloid pathway called fumigaclavines. The biosynthesis of the N. fumigata Ergot Alkaloids and their relation to those produced by alternate pathway branches in fungi from the plant-inhabiting Clavicipitaceae have been well-characterised, but the potential role of these Alkaloids in animal pathogenesis has not been studied extensively. We investigated the contribution of Ergot Alkaloids to virulence of N. fumigata by measuring mortality in the model insect Galleria mellonella. Larvae were injected with conidia (asexual spores) of two different wild-type strains of N. fumigata and three different Ergot Alkaloid mutants derived by previous gene knockouts and differing in Ergot Alkaloid profiles. Elimination of all Ergot Alkaloids significantly reduced virulence of N. fumigata in G. mellonella (P
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Ergot Alkaloids of the Family Clavicipitaceae.
Phytopathology, 2017Co-Authors: Simona Florea, Daniel G Panaccione, Christopher L SchardlAbstract:Ergot Alkaloids are highly diverse in structure, exhibit diverse effects on animals, and are produced by diverse fungi in the phylum Ascomycota, including pathogens and mutualistic symbionts of plants. These mycotoxins are best known from the fungal family Clavicipitaceae and are named for the Ergot fungi that, through millennia, have contaminated grains and caused mass poisonings, with effects ranging from dry gangrene to convulsions and death. However, they are also useful sources of pharmaceuticals for a variety of medical purposes. More than a half-century of research has brought us extensive knowledge of Ergot-Alkaloid biosynthetic pathways from common early steps to several taxon-specific branches. Furthermore, a recent flurry of genome sequencing has revealed the genomic processes underlying Ergot-Alkaloid diversification. In this review, we discuss the evolution of Ergot-Alkaloid biosynthesis genes and gene clusters, including roles of gene recruitment, duplication and neofunctionalization, as well as gene loss, in diversifying structures of clavines, lysergic acid amides, and complex ergopeptines. Also reviewed are prospects for manipulating Ergot-Alkaloid profiles to enhance suitability of endophytes for forage grasses.
Alexandr Jegorov - One of the best experts on this subject based on the ideXlab platform.
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norleucine a natural occurrence in a novel Ergot Alkaloid γ ergokryptinine
Amino Acids, 2005Co-Authors: Ladislav Cvak, Bohumil Kratochvil, Petr Sedmera, Alexandr Jegorov, Ivana Cisařova, J Cejka, Svetlana PakhomovaAbstract:A novel natural peptide Ergot Alkaloid γ-ergokryptinine containing norleucine has been isolated from Ergot sclerotia of the field-growing parasitic fungus Claviceps purpurea CCM 8059. Its structure was deduced from the NMR and mass spectral data. The final structural proof was provided by the crystal structure determination, which is the first X-ray structure of a natural Nle-containing secondary metabolite. The conformations of three ergopeptinines: γ-ergokryptinine, ergoladinine, and α-ergokryptinine were compared.
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crystal forms of semisynthetic Ergot Alkaloid terguride
Collection of Czechoslovak Chemical Communications, 2002Co-Authors: Michal Husak, Ladislav Cvak, Bohumil Kratochvil, Alexandr Jegorov, Ivana Cisařova, Stanislav BohmAbstract:Two new structures of semisynthetic Ergot Alkaloid terguride created by unusual number of symmetry-independent molecules were determined by X-ray diffraction methods at 150 K. Form A (monoclinic, P2 1 2 1 2 1 , Z = 12) contains three symmetry-independent terguride molecules and two molecules of water in the asymmetric part of the unit cell. The form C A (monoclinic, P2 1 , Z = 8) is an anhydrate remarkable by the presence of four symmetry-independent molecules in the crystal structure. Conformations of twelve symmetry-independent molecules that were found in four already described terguride structures are compared with torsion angles obtained by ab initio quantum-mechanical calculations for the simplified model of N -cyclohexyl- N' -diethylurea.
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8α hydroxy α ergokryptine an Ergot Alkaloid
Phytochemistry, 1997Co-Authors: Ladislav Cvak, Svetlana Pakhomova, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr Jegorov, Josef MinařAbstract:A new natural ergopeptine Alkaloid hydroxylated at C-8 of the lysergic acid moiety has been isolated from sclerotia of the field-growing parasitic fungus Claviceps purpurea. Its structure was established by spectroscopic and X-ray diffraction analyses.
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ergoladinine an Ergot Alkaloid
Phytochemistry, 1996Co-Authors: Ladislav Cvak, Josef Minař, Svetlana Pakhomova, Jan Ondracek, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr JegorovAbstract:A new natural peptide Ergot Alkaloid, ergoladinine, containing methionine, has been isolated from sclerotia of the field-growing parasitic fungus, Claviceps purpurea. Its structure was deduced from the X-ray analysis, NMR and mass spectral data.
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ergogaline a new Ergot Alkaloid produced by claviceps purpurea isolation identification crystal structure and molecular conformation
Journal of The Chemical Society-perkin Transactions 1, 1994Co-Authors: Ladislav Cvak, Svetlana Pakhomova, Jan Ondracek, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr Jegorov, Michal Husak, Joachim GranzinAbstract:A new peptide Ergot Alkaloid containing L-homoisoleucine has been isolated from Ergot sclerotia of the field-growing parasitic fungus Claviceps purpurea. The molecular and crystal structures have been studied by X-ray analysis [ergogaline monohydrate, monoclinic space group P21 with two molecules per unit cell of the dimensions a= 9.972(1), b= 10.902(1) and c= 14.761 (1)A, β= 94.05(1)°] and compared with the structures in solution as determined by 2D NMR spectroscopy.
N S Hill - One of the best experts on this subject based on the ideXlab platform.
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Ergot Alkaloid concentrations in high and low moisture tall fescue silage
Crop Science, 2014Co-Authors: C A Roberts, Robert L Kallenbach, David Davis, George E Rottinghaus, M L Looper, N S HillAbstract:Ergot Alkaloids are mycotoxins found in foods and forage crops, including common tall fescue [Lolium arundinaceum (Schreb.) Darbysh. = Schedonorus arundinaceus (Schreb.) Dumort.], which hosts a fungal endophyte. The objective of this study was to determine changes in ergovaline and total Ergot Alkaloid concentrations in tall fescue silage produced at high moisture (650 to 680 g H₂O kg⁻¹) and low moisture (340 to 400 g H₂O kg⁻¹). The study was conducted on endophyte-infected pastures of tall fescue in northern and southern Missouri. Tall fescue was clipped after seedhead emergence but before anthesis, wilted to high or low moisture, baled, and wrapped. After >100 d of ensiling, bales were cored and samples analyzed for ergovaline and total Ergot Alkaloid concentrations. Ergovaline concentration decreased (P < 0.05) during ensiling at both locations and moisture levels, and the decrease ranged from 24 to 58%. In contrast, total Ergot Alkaloid concentrations increased during ensiling in high moisture silage in northern (P < 0.10) and southern (P < 0.05) Missouri but did not change in low moisture silage. The opposing responses of ergovaline and total Ergot Alkaloids offer partial explanations for differences reported in studies involving tall fescue silage. These responses also caution against recommendations to ensile tall fescue to reduce toxins because one analyte indicates detoxification is possible, while the other analyte does not.
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seasonal fluctuation of ergovaline and total Ergot Alkaloid concentrations in tall fescue regrowth
Crop Science, 2011Co-Authors: Wendi Rogers, N S Hill, C A Roberts, John Andrae, Robert L Kallenbach, David Davis, George E Rottinghaus, Don E SpiersAbstract:Common cultivars of tall fescue [Schedonorus arundinaceus (Schreb.) Dumort = Lolium arundinaceum (Schreb.) Darbysh.] host a fungal endophyte that produces Ergot Alkaloids. These Alkaloids are linked to fescue toxicosis, a serious livestock disorder in the United States. This study was conducted to determine how Ergot Alkaloid concentrations fluctuate throughout the growing season in tall fescue regrowth. In 2005, plots were established in pastures of endophyte-infected tall fescue growing in Missouri, Georgia, and South Carolina. Each month of the growing season, plots were clipped and forage allowed to regrow; regrowth was sampled from April through October 2006 and analyzed for ergovaline and total Ergot Alkaloid concentrations. At all three sites, ergovaline concentration was lowest during the spring, increasing slightly through the summer months and then sharply in the early autumn. This pattern of ergovaline fluctuation did not mimic data published from experiments in which tall fescue was grazed or was allowed to grow without defoliation. Total Ergot Alkaloid concentration followed a bimodal curve, with highest concentration in the spring and fall and lowest concentration in the summer. We conclude that common cultivars of endophyte-infected tall fescue should be regarded as highly toxic in the autumn and less toxic in the summer, even if pastures are clipped. We also conclude that the toxicity potential of tall fescue regrowth in the spring depends on which Ergot Alkaloids prove most responsible for fescue toxicosis.
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Ergot Alkaloid concentrations in tall fescue hay during production and storage
Crop Science, 2009Co-Authors: C A Roberts, N S Hill, Robert L Kallenbach, George E Rottinghaus, Tim J EvansAbstract:Common tall fescue [Lolium arundinaceum (Schreb.) Darbysh. = Schedonorus arundinaceus (Schreb.) Dumort.] is infected with a fungus that produces Ergot Alkaloids, a class of compounds associated with fescue toxicosis. The objective of this research was to monitor the change in concentrations of Ergot Alkaloids from time of clipping through storage of tall fescue hay. A 2-yr field study was conducted in Mt. Vernon, MO, in which tall fescue was baled at high moisture (204-219 g H 2 O kg ―1 dry matter [DM]) and low moisture (102-112 g H 2 O kg ―1 DM) then stored for 18 mo. Hay samples were collected over the 540-d period from clipping through storage and analyzed for ergovaline and total Ergot Alkaloid concentration. Data were analyzed using standard ANOVA procedures and break-point regression. In both years, ergovaline concentrations decreased sharply within the first month after harvest and gradually over the remaining 17 mo. In three of the four cases, most of the ergovaline disappearance occurred within 3 d after clipping. The final ergovaline concentration remained above 250 μg kg ―1 DM, which is still considered toxic to livestock. In the first year, Ergot Alkaloid concentration followed a pattern similar to ergovaline concentration. In the second year, however, the decrease in total Ergot Alkaloid was gradual throughout the entire 18 mo. A general recommendation to producers would be to delay feeding toxic tall fescue hay until at least 1 mo after clipping.
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determination of Ergot Alkaloid content in tall fescue by near infrared spectroscopy
Crop Science, 2005Co-Authors: C A Roberts, N S Hill, Robert L Kallenbach, H R Benedict, George E RottinghausAbstract:Ergot Alkaloids are a class of toxic compounds, some of which are produced by a fungal endophyte in tall fescue (Festuca arundinacea Schreb.). The objective of this research was to measure total Ergot Alkaloid content in tall fescue by near-infrared (NIR) spectroscopy with a calibration developed from immunochemical reference data. Eighty-four tall fescue samples were collected from experiments at the University of Missouri. Samples were from plants that varied in maturity, endophyte status, genotype, growing environment, and storage and preservation treatment. Samples were scanned by NIR radiation and analyzed chemically for Ergot Alkaloid content using a commercial immunoassay. An empirical prediction equation was developed by regressing NIR reflectance data against absorbance data from the immunoassay. The initial calibrations achieved a 1 - variance ratio (VR) of 0.86 with a mean and standard error of cross validation (SECV) of 0.606 ± 0.12; however, this was possible only when stockpiled tall fescue samples were omitted from the population. Stockpiled samples were checked for chemical accuracy and spectral similarity to the population, and another set of calibrations was developed. The final calibration, which omitted only those stockpiled samples that were infected with a toxic endophyte, had a 1 - VR of 0.89, with a mean and SECV of 0.682 ± 0.11. We concluded that total Ergot Alkaloid content in tall fescue can be quantified by NIR spectroscopy with a calibration developed from immunochemcial data, though it may not be possible to include samples of stockpiled tall fescue if they are infected with a toxic endophyte. Such a calibration can be robust and precise, reliably predicting an entire class of compounds in a diverse population of tall fescue samples.
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reinfection of tall fescue cultivars with non Ergot Alkaloid producing endophytes
Agronomy Journal, 2002Co-Authors: Joe Bouton, N S Hill, Garrick C M Latch, C S Hoveland, M A Mccann, Richard H Watson, Jane A Parish, Larry L Hawkins, F N ThompsonAbstract:For tall fescue (Festuca arundinacea Schreb.) in the southeastern USA, persistence and yield are directly related to infection with a fungal endophyte [Neotyphodium coenophialum (Morgan-Jones & Gams.) Glenn, Bacon, & Hanlin comb, nov.]. However, most endophyte-infected (E+) tall fescue cultivars produce toxic Ergot Alkaloids resulting in poor weight gain and reproduction in grazing livestock. The objective of this paper was to assess the strategy of reinfecting 'Jesup' and 'Georgia 5' tall fescue with non-Ergot Alkaloid-producing endophyte strains. Different cultivar-strain combinations were tested against the E+ and endophyte-free (E-) versions of the same cultivars for stand survival and dry matter yield; in separate experiments, they were assessed for toxicity in lambs (Ovis aries). Most cultivar-strain combinations produced no Ergot Alkaloids but varied in ability to transmit through seed. The best combination, Jesup (AR542), possessed yield and stand survival better (P < 0.05) than the E- checks and equivalent (P < 0.05) to the E+ checks. Lambs gained an average of 124 g/d on both cultivars containing AR542, which was equivalent to gains on E- forage but approximately 57% greater than gains on E+ forage. Animals consuming forage from E- or non-Ergot-producing strains did not exhibit depressed serum prolactin or elevated body temperatures of animals on E+ forage. The strategy of reinfecting tall fescue cultivars with naturally occurring, non-Ergot-producing endophytes appears promising for removing toxicity symptoms and retaining agronomic performance, but intense screening is needed to identify the best cultivar-strain combinations.
Bohumil Kratochvil - One of the best experts on this subject based on the ideXlab platform.
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norleucine a natural occurrence in a novel Ergot Alkaloid γ ergokryptinine
Amino Acids, 2005Co-Authors: Ladislav Cvak, Bohumil Kratochvil, Petr Sedmera, Alexandr Jegorov, Ivana Cisařova, J Cejka, Svetlana PakhomovaAbstract:A novel natural peptide Ergot Alkaloid γ-ergokryptinine containing norleucine has been isolated from Ergot sclerotia of the field-growing parasitic fungus Claviceps purpurea CCM 8059. Its structure was deduced from the NMR and mass spectral data. The final structural proof was provided by the crystal structure determination, which is the first X-ray structure of a natural Nle-containing secondary metabolite. The conformations of three ergopeptinines: γ-ergokryptinine, ergoladinine, and α-ergokryptinine were compared.
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crystal forms of semisynthetic Ergot Alkaloid terguride
Collection of Czechoslovak Chemical Communications, 2002Co-Authors: Michal Husak, Ladislav Cvak, Bohumil Kratochvil, Alexandr Jegorov, Ivana Cisařova, Stanislav BohmAbstract:Two new structures of semisynthetic Ergot Alkaloid terguride created by unusual number of symmetry-independent molecules were determined by X-ray diffraction methods at 150 K. Form A (monoclinic, P2 1 2 1 2 1 , Z = 12) contains three symmetry-independent terguride molecules and two molecules of water in the asymmetric part of the unit cell. The form C A (monoclinic, P2 1 , Z = 8) is an anhydrate remarkable by the presence of four symmetry-independent molecules in the crystal structure. Conformations of twelve symmetry-independent molecules that were found in four already described terguride structures are compared with torsion angles obtained by ab initio quantum-mechanical calculations for the simplified model of N -cyclohexyl- N' -diethylurea.
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8α hydroxy α ergokryptine an Ergot Alkaloid
Phytochemistry, 1997Co-Authors: Ladislav Cvak, Svetlana Pakhomova, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr Jegorov, Josef MinařAbstract:A new natural ergopeptine Alkaloid hydroxylated at C-8 of the lysergic acid moiety has been isolated from sclerotia of the field-growing parasitic fungus Claviceps purpurea. Its structure was established by spectroscopic and X-ray diffraction analyses.
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ergoladinine an Ergot Alkaloid
Phytochemistry, 1996Co-Authors: Ladislav Cvak, Josef Minař, Svetlana Pakhomova, Jan Ondracek, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr JegorovAbstract:A new natural peptide Ergot Alkaloid, ergoladinine, containing methionine, has been isolated from sclerotia of the field-growing parasitic fungus, Claviceps purpurea. Its structure was deduced from the X-ray analysis, NMR and mass spectral data.
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ergogaline a new Ergot Alkaloid produced by claviceps purpurea isolation identification crystal structure and molecular conformation
Journal of The Chemical Society-perkin Transactions 1, 1994Co-Authors: Ladislav Cvak, Svetlana Pakhomova, Jan Ondracek, Bohumil Kratochvil, Petr Sedmera, Vladimir Havlicek, Alexandr Jegorov, Michal Husak, Joachim GranzinAbstract:A new peptide Ergot Alkaloid containing L-homoisoleucine has been isolated from Ergot sclerotia of the field-growing parasitic fungus Claviceps purpurea. The molecular and crystal structures have been studied by X-ray analysis [ergogaline monohydrate, monoclinic space group P21 with two molecules per unit cell of the dimensions a= 9.972(1), b= 10.902(1) and c= 14.761 (1)A, β= 94.05(1)°] and compared with the structures in solution as determined by 2D NMR spectroscopy.
J G Menzies - One of the best experts on this subject based on the ideXlab platform.
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The effects of selected factors on measured Ergot Alkaloid content in Claviceps purpurea-infected hexaploid and durum wheat
World Mycotoxin Journal, 2016Co-Authors: Sheryl A. Tittlemier, Dainna Drul, Mike Roscoe, J G MenziesAbstract:Four wheat genotypes, including the Ergot-susceptible durum ‘AC Avonlea’ and hard red spring wheat ‘AC Cadillac’, as well as the resistant durum wheat line 9260B-173A and the hard red spring wheat line ‘Kenya Farmer’ wereinoculated with different Claviceps purpurea isolates. Honeydew and sclerotia were collected and analysed for 10 Ergot Alkaloids. Total concentrations of the 10 Ergot Alkaloids ranged from 16 µg/kg in honeydew to 1,798 mg/kg insclerotia. Ergonovine and ergosine were the predominant Alkaloids in honeydew obtained from plants inoculated with various isolates, whereas ergocristine and ergocryptine were the main Alkaloids observed in sclerotia. Bothhost plant and C. purpurea isolate were significant factors affecting total Ergot Alkaloid concentrations in sclerotia. Irrespective of host plant line, all mean total Ergot Alkaloid concentrations were higher in sclerotia produced from the EI-2 isolate (695-1,010 mg/kg), as compared to EI-4 (255-594 mg/kg). The mass of total Ergot Alkaloids was al...
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The effects of selected factors on measured Ergot Alkaloid content in Claviceps purpurea-infected hexaploid and durum wheat
World Mycotoxin Journal, 2016Co-Authors: Sheryl A. Tittlemier, Dainna Drul, Mike Roscoe, J G MenziesAbstract:Four wheat genotypes, including the Ergot-susceptible durum ‘AC Avonlea’ and hard red spring wheat ‘AC Cadillac’, as well as the resistant durum wheat line 9260B-173A and the hard red spring wheat line ‘Kenya Farmer’ wereinoculated with different Claviceps purpurea isolates. Honeydew and sclerotia were collected and analysed for 10 Ergot Alkaloids. Total concentrations of the 10 Ergot Alkaloids ranged from 16 µg/kg in honeydew to 1,798 mg/kg insclerotia. Ergonovine and ergosine were the predominant Alkaloids in honeydew obtained from plants inoculated with various isolates, whereas ergocristine and ergocryptine were the main Alkaloids observed in sclerotia. Bothhost plant and C. purpurea isolate were significant factors affecting total Ergot Alkaloid concentrations in sclerotia. Irrespective of host plant line, all mean total Ergot Alkaloid concentrations were higher in sclerotia produced from the EI-2 isolate (695-1,010 mg/kg), as compared to EI-4 (255-594 mg/kg). The mass of total Ergot Alkaloids was alsopositively correlated with the mass of individual sclerotia produced from these two C. purpurea isolates, with the slope of the regression higher for the EI-2 isolate. The total Ergot Alkaloid concentrations in sclerotia from various plants inoculated with the same C. purpurea isolate differed; however, the resistance of host plant line did notappear to be consistent with Ergot Alkaloid content in sclerotia. Concentrations of total Ergot Alkaloids were highestand lowest in sclerotia from the two lines that are both classified as ‘resistant’, suggesting that the mechanism ofresistance for these lines is not restriction on the production of Ergot Alkaloids in sclerotia.