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Estelle Ayme-Dietrich, Roland Lawson, Francine Côté, Claudia de Tapia, Sylvia Da Silva, Claudine Ebel, Béatrice Hechler, Christian Gachet, Jérome Guyonnet, Hélène Rouillard, Jordane Stoltz, Emily Quentin, Sophie Banas, François Daubeuf, Nelly Frossard, Bernard Gasser, Jean-Philippe Mazzucotelli, Olivier Hermine, Luc Maroteaux, Laurent Monassier
BACKGROUND: Valvular heart disease is highly prevalent in industrialized countries. Chronic use of anorexigens, amphetamine or ergot derivatives targeting the serotonin system has been associated with valvular heart disease. PURPOSE AND EXPERIMENTAL APPROACH: Here, we investigated the contribution of serotonin receptors in a mouse model of valve degeneration induced by nordexfenfluramine, the main metabolite of the anorexigens dexfenfluramine and benfluorex. KEY RESULTS: Chronically activated 5-HT2B receptors by nordexfenfluramine in mice mimicked early steps of mitral valve remodelling attested by increased valve thickness, and cell density in a thick extracellular matrix...
August 14, 2017: British Journal of Pharmacology
Tatsiana Shymanovich, Nikki D Charlton, Ashleigh M Musso, Jonathan Scheerer, Nadja B Cech, Stanley H Faeth, Carolyn A Young
The endophyte presence and diversity in natural populations of Poa alsodes were evaluated along a latitudinal transect from the southern distribution range in North Carolina to New York. Two distinct Epichloë hybrid taxa were identified from 23 populations. Each taxon could easily be distinguished by polymerase chain reaction (PCR) genotyping with primers designed to mating type genes and alkaloid biosynthesis genes that encode key pathway steps for ergot alkaloids, indole-diterpenes, lolines, and peramine...
June 26, 2017: Mycologia
Jia-Tian Lu, Zi-Fa Shi, Xiao-Ping Cao
An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.
July 17, 2017: Journal of Organic Chemistry
Dale S Adler
Only 75% of severe tricuspid regurgitation is classified as functional, or related primarily to pulmonary hypertension, right ventricular dysfunction, or a combination of both. Non-functional tricuspid regurgitation occurs when there is damage to the tricuspid leaflets, chordae, papillary muscles, or annulus, independent of right ventricular dysfunction or pulmonary hypertension. The entities that cause non-functional tricuspid regurgitation include rheumatic and myxomatous disease, acquired and genetic connective tissue disorders, endocarditis, sarcoid, pacing, RV biopsy, blunt trauma, radiation, carcinoid, ergot alkaloids, dopamine agonists, fenfluramine, cardiac tumors, atrial fibrillation, and congenital malformations...
May 2017: Annals of Cardiothoracic Surgery
Alakesh Bisai, Subhajit Bhunia, Saikat Chaudhuri
We report a catalytic enantioselective construction of vicinal stereocenters that takes advantage of thiourea-catalyzed intramolecular nitronate addition onto ,-unsaturated ester to afford exceptional levels of enantioselectivity (up to 97% ee) with moderate diastereoselectivity (up to 4:1). Using this method, a cross-conjugated ester was synthesized in few steps, from where a 6-endo-trig cyclisation led to the formation of all required functionalities for total syntheses of ergot alkaloids. The strategy not only offers first total syntheses of ergot alkaloids, festuclavine (1c), and pyroclavine (1e), and but also an efficient and general approach to other congeners such as, lysergol (1b), and isolysergol (1d)...
July 7, 2017: Chemistry: a European Journal
Julia I Bauer, Madeleine Gross, Benedikt Cramer, Sandra Wegner, Heike Hausmann, Gerd Hamscher, Ewald Usleber
A newly developed enzyme immunoassay (EIA) for the detection of the tremorgenic indole-diterpene alkaloid paxilline (PAX) and closely related analogs was used to analyze ergot sclerotia collected from rye and barley fields. The mean EIA standard curve detection limit was 0.47 ± 0.14 ng/mL; relative cross-reactivity of toxin standard solutions was found for 11-hydroxy-paspaline (terpendole E, 1.1%) but not for lolitrem B or ergot alkaloids. Sclerotia from all fields were positive in the PAX-EIA at concentration levels of 620 ± 200 and 160 ± 37 μg/kg in ergot of rye and 130 ± 47 μg/kg in ergot of barley...
August 2017: Analytical and Bioanalytical Chemistry
Kanon Jatuworapruk, Thanate Kattipathanapong, Nuntana Kasitanon, Worawit Louthrenoo
No abstract text is available yet for this article.
August 2017: Journal of Clinical Rheumatology: Practical Reports on Rheumatic & Musculoskeletal Diseases
Richard B Lipton, Sagar Munjal, Dawn C Buse, Alix Bennett, Kristina M Fanning, Rami Burstein, Michael L Reed
OBJECTIVE: In a population sample of persons with migraine treating with a single category of acute migraine medication, to identify rates and factors associated with acute treatment outcomes, including 2-hour pain freedom (2hPF), 24-hour pain response (24hPR), and 24-hour sustained pain response (24hSPR). Key predictors include acute treatment type (triptans and other medication categories), the influence of allodynia on response to medication, and the interaction between medication category and presence of allodynia in response to treatment among people with migraine...
June 11, 2017: Headache
Haichao Liu, Xiwu Zhang, Dong Shan, Mallesham Pitchakuntla, Yongfan Ma, Yanxing Jia
A new approach for the divergent total synthesis of eight ergot alkaloids is reported. The approach allows the first total syntheses of pyroclavine, pibocin A, 9-deacetoxyfumigaclavine C, and fumigaclavine G and also enables the efficient synthesis of festuclavine, costaclavine, epi-costaclavine, and dihydrosetoclavine. The main feature of the synthesis is the use of an unprecedented Pd-catalyzed intramolecular Larock indole annulation/Tsuji-Trost allylation cascade to assemble the tetracyclic core in one step...
June 8, 2017: Organic Letters
Ph Vermeulen, M B Ebene, B Orlando, J A Fernández Pierna, V Baeten
The objective of this study is to assess NIR hyperspectral imaging for the detection of ergot bodies at the particle level in cereal flour. For this study, ground ergot body samples and wheat flour samples as well as mixtures of both from 100 mg/kg to 500,000 mg/kg were analysed. Partial least squares discriminant analysis (PLS-DA) models were developed and applied to spectral images in order to detect the ergot body particles. Ergot was detected in 100% of samples spiked at more than 10,000 mg/kg and no false positives were obtained with non-contaminated samples...
June 5, 2017: Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment
Claudia Oellig
Ergot alkaloids are generally determined by high-performance liquid chromatography (HPLC) coupled to fluorescence detection (FLD) or mass selective detection, analyzing the individual compounds. However, fast and easy screening methods for the determination of the total ergot alkaloid content are more suitable, since for monitoring only the sum of the alkaloids is relevant. The herein presented screening uses lysergic acid amide (LSA) as chemical marker, formed from ergopeptine alkaloids, and ergometrine for the determination of the total ergot alkaloids in rye with high-performance thin-layer chromatography-fluorescence detection (HPTLC-FLD)...
May 24, 2017: Journal of Chromatography. A
Stephanie L Arnold, Daniel G Panaccione
Ergot alkaloids are specialized fungal metabolites that are important as the bases of several pharmaceuticals. Many ergot alkaloids are derivatives of lysergic acid (LA) and have vasoconstrictive activity, whereas several dihydrolysergic acid (DHLA) derivatives are vasorelaxant. The pathway to LA is established, with the P450 monooxygenase CloA playing a key role in oxidizing its substrate agroclavine to LA. We analyzed the activities of products of cloA alleles from different fungi relative to DHLA biosynthesis by expressing them in a mutant of the fungus Neosartorya fumigata that accumulates festuclavine, the precursor to DHLA...
July 15, 2017: Applied and Environmental Microbiology
Sabine Kind, Selma Schurack, Janine Hinsch, Paul Tudzynski
To investigate its susceptibility to ergot infection we inoculated Brachypodium distachyon with Claviceps purpurea and compared the infection symptoms to those on rye (Secale cereale). We showed that after inoculation of Brachypodium with Claviceps the same disease symptoms occurred in comparable temporal and spatial patterns as on rye. The infection rate of Claviceps on this host is reduced compared to rye, but the disease can be surveyed by fungal gDNA quantification. Mutants of Claviceps which are virulence-attenuated on rye were also affected on Brachypodium...
April 27, 2017: Molecular Plant Pathology
Ryan S Mote, Nicholas S Hill, Karan Uppal, ViLinh T Tran, Dean P Jones, Nikolay M Filipov
Fescue toxicosis (FT) results from consumption of tall fescue (Lolium arundinaceum) infected with an endophyte (Epichloë coenophiala) that produces ergot alkaloids (EA), which are considered key etiological agents of FT. Decreased weight gains, hormonal imbalance, circulating cholesterol disruption, and decreased volatile fatty acid absorption suggest toxic (E+) fescue-induced metabolic perturbations. Employing untargeted high-resolution metabolomics (HRM) to analyze E+ grazing-induced plasma and urine metabolome changes, fescue-naïve Angus steers were placed on E+ or non-toxic (Max-Q) fescue pastures and plasma and urine were sampled before, 1, 2, 14, and 28 days after pasture assignment...
April 18, 2017: Food and Chemical Toxicology
Alphienes S Xavier, Mageshwaran Lakshmanan, Vikneswaran Gunaseelan
Migraine is a recurrent, disabling, complex and highly prevalent neurological disorder. The mystery behind the cause of migraine is continuously evolving, according to the scientific understanding of the disease. This growing understanding helps to identify novel therapeutic targets for the management of migraine to treat the ailing migraineurs. The role of serotonin (5HT) in migraine is recognized to be the cornerstone for the currently available therapeutic options namely ergot alkaloids and triptans. The role of mediators such as Calcitonin Gene-Related Peptide (CGRP), nitric oxide and excitatory neurotransmitter glutamate, has been realized and ignited the development of drugs targeting these factors...
2017: Current Clinical Pharmacology
C R Burnett, W C Bridges, S L Pratt
There are many positive agronomic traits that make tall fescue a desirable forage, however, reduced fertility rates are reported for beef cattle grazing pasture containing the ergot alkaloid-producing endophyte, Epichloë coenophiala. The objective of this study was to assess the influence of consuming tall fescue containing ergot alkaloids on sperm physiology, as measured by survival of sperm following cryopreservation. Yearling Angus bulls (n=25), having passed a breeding soundness exam (BSE), were assigned to one of two treatments accounting for body weight (BW) and body condition score (BCS)...
March 28, 2017: Animal Reproduction Science
B E Harlow, J P Goodman, B C Lynn, M D Flythe, H Ji, G E Aiken
The objectives of this study were to evaluate degradation of ergovaline in a tall fescue [ (Schreb.) Darbysh.] seed extract by rumen microbiota ex vivo and to identify specific bacteria capable of ergovaline degradation in vitro. Rumen cell suspensions were prepared by harvesting rumen fluid from fistulated wether goats ( = 3), straining, and differential centrifugation. Suspensions were dispensed into anaerobic tubes with added Trypticase with or without extract (∼10 μg kg ergovaline). Suspensions were incubated for 48 h at 39°C...
February 2017: Journal of Animal Science
Luigi Servillo, Nunzia DʼOnofrio, Maria Luisa Balestrieri
Ergothioneine (ESH), the betaine of 2-mercapto-L-histidine, is a water-soluble naturally occurring amino acid with antioxidant properties. ESH accumulates in several human and animal tissues up to millimolar concentration through its high affinity transporter, namely the organic cation transporter 1 (OCTN1). ESH, first isolated from the ergot fungus (Claviceps purpurea), is synthesized only by Actinomycetales and non-yeast-like fungi. Plants absorb ESH via symbiotic associations between their roots and soil fungi, whereas mammals acquire it solely from dietary sources...
April 2017: Journal of Cardiovascular Pharmacology
Birgitt Oeser, Sabine Kind, Selma Schurack, Thomas Schmutzer, Paul Tudzynski, Janine Hinsch
BACKGROUND: The economically important Ergot fungus Claviceps purpurea is an interesting biotrophic model system because of its strict organ specificity (grass ovaries) and the lack of any detectable plant defense reactions. Though several virulence factors were identified, the exact infection mechanisms are unknown, e.g. how the fungus masks its attack and if the host detects the infection at all. RESULTS: We present a first dual transcriptome analysis using an RNA-Seq approach...
April 4, 2017: BMC Genomics
Bastian Milde, Martin Pawliczek, Peter G Jones, Daniel B Werz
The enantioselective synthesis of (+)-lysergol was completed in 12 steps and an overall yield of 13% starting from a known literature precursor. The key step relies on a domino reaction containing a formal anti-carbopalladation, which is terminated by a β-silyl-directed Heck reaction. During this transformation, the two six-membered rings of the ergot scaffold are formed in a completely stereospecific manner.
April 7, 2017: Organic Letters
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