• The relationship between ergot and ergotism was established only in 1717, and the alkaloid ergotamine, one of the main active ingredients of ergot, was isolated in 1918. (wikipedia.org)
  • The latter include terpenoid structural elements, synthesized by living organisms from dimethylallyl pyrophosphate (DMAPP) and/or isopentenyl pyrophosphate (IPP): Non-isoprenoid: Simple derivatives of indole Simple derivatives of β-carboline Pyrroloindole alkaloids Indole-3-carbinol Indole-3-acetic acid Tryptamines Carbazoles Isoprenoid: hemiterpenoids: ergot alkaloids monoterpenoids. (wikipedia.org)
  • Ergot alkaloids are a class of hemiterpenoid indole alkaloids related to lysergic acid, which, in turn, is formed in a multistage reactions involving tryptophan and DMAPP. (wikipedia.org)
  • Many ergot alkaloids are amides of lysergic acid. (wikipedia.org)
  • Ergoline alkaloids were first isolated from ergot , a fungus that infects grain and causes the disease ergotism . (wikidoc.org)
  • With the determination of the basic chemical structure of the ergot alkaloids in the early 1930s, an era of intensive exploration of synthetic derivatives began. (wikidoc.org)
  • Roduct belonging to a class of diverse molecules broadly known as ergot alkaloids. (atminhibitor.com)
  • accessible in PMC 2022 June 21.Jamieson et al.Pagevasoconstrictive and convulsive symptoms of the disease, mania and psychosis happen to be observed, underlining the psychoactivity of ergot alkaloids.171 Ergot alkaloids, derived from L-tryptophan 11, are characterized by a special tetracyclic ergoline skeleton exactly where the indole comprises the A and B rings. (atminhibitor.com)
  • was the purification and characterization of 4dimethylallyl- L-tryptophan synthetase (DMATS) that catalyzes the first committed step in ergot alkaloid biosynthesis: C-prenylation of L-tryptophan 11 with dimethylallylpyrophosphate in the indole C4 position to form 4-dimethylallyl-L-tryptophan 55 (Fig. 19, also see Fig. 4D).176 Recently, several laboratories have focused on characterizing prenyltransferases, of which DMATS may be the original member of a new superfamily of prenyltransferase enzymes. (atminhibitor.com)
  • The ergot sclerotium contains high concentrations (up to 2% of dry mass) of ergotamine , a complex molecule consisting of a tripeptide-derived cyclol-lactam ring connected via amide linkage to a lysergic acid (ergoline) moiety, and other alkaloids of the ergoline group that are biosynthesized by the fungus. (wikidoc.org)
  • [1] Ergot alkaloids have a wide range of biological activities including effects on circulation and neurotransmission . (wikidoc.org)
  • Ergotism is the name for sometimes severe pathological syndromes affecting humans or animals that have ingested ergot alkaloid-containing plant material, such as ergot-contaminated grains. (wikidoc.org)
  • Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. (wikipedia.org)
  • Results & conclusion: Carboxamide, lactone and ß-carboline moieties were identified as interesting chemical groups for the design of new antifungal compounds. (bvsalud.org)
  • All of the compounds are zwitterionic and contain a dihydroindolizinium ring and a spiroketal moiety. (gnu.ac.kr)
  • These chemical compounds are derived from alkaloids and are conjugated with sugars. (foodsafetywatch.org)
  • The aglycone part is the alkaloid, which is responsible for the toxic effects of these compounds. (foodsafetywatch.org)
  • It is nutrient dense plant-based food containing flexibility of bioactive compounds such as alkaloids, polypeptide, vitamins and minerals. (wjpr.net)
  • The bioassay-guided separation of the extract provided ten active compounds, including three new N-methyladenine-containing diterpenoids, agelasines W-Y ( 1 - 3 ), a new bromopyrrole alkaloid, N(1)-methylisoageliferin ( 4 ), and six known ageliferin derivatives ( 5 - 10 ). (cancer.gov)
  • The spirooxindole structure is commonly found in a variety of complex alkaloids and many compounds that possess a spirooxindole moiety exhibit significant biological activity. (pdgfrsignals.com)
  • Since the terpenoid indole alkaloids (TIAS) biosynthesis pathway is adjustable, modification of underlying substrate and enzymes concentration by biotic and abiotic elicitors are important approaches for overproduction of these metabolites. (jmp.ir)
  • The fungal species produces an alkaloid terpenoid, flavunoidine, through a hybrid biosynthetic pathway combining both terpene cyclase and nonribosomal peptide synthetase enzymes. (anl.gov)
  • Indole alkaloids are distinguished depending on their biosynthesis. (wikipedia.org)
  • 9. Hedhili S, Courdavault V, Giglioli-Guivarc'h N, Gantet P. Regulation of the terpene moiety biosynthesis of Catharanthus roseus terpene indole alkaloids. (jmp.ir)
  • Here we demonstrate that, in the biosynthesis of the bis-methyloxazolic alkaloid muscoride A, the YcaO enzyme MusD carries out both ATP-dependent cyclodehydration and peptide bond cleavage, which is a mechanism unprecedented for such a reaction. (illinois.edu)
  • Phylogenetic analysis of FlvF and related fungal homologues reveals conservation of residues that interact with the tetracyclic sesquiterpene in this model, but less conservation of residues interacting with the pendant amino moiety. (anl.gov)
  • By applying knowledge of these fragmentation pathways to the aconitines in the ethanolicextract of aconite roots, all the known aconitines were detected and also 23 unknown aconitine-typealkaloids, in which the lipo-alkaloids containing residues of 15C, 17C and 19C saturated orunsaturated fatty acids were characterized. (healthdrugpdf.com)
  • Ergoline is a chemical compound whose structural skeleton is contained in a diverse range of alkaloids and a few psychedelic drugs ( ololiuhqui , LSD ). (wikidoc.org)
  • With the isolation of ergotamine in 1918 by A. Stoll came the first therapeutic use of isolated ergoline alkaloids. (wikidoc.org)
  • This review also describes the chemical structure of 232 NPs presenting anti-CRC activity with the being majority of quinones, lactones, alkaloids, peptides, and glycosides. (frontiersin.org)
  • It also contains steroidal saponins called charantin, act a like peptides and certain alkaloids that successfully control sugar level in blood. (wjpr.net)
  • YcaO enzymes catalyze ATP-dependent post-translation modifications on peptides, including the installation of (ox/thi)azoline, thioamide and/or amidine moieties. (illinois.edu)
  • Strictosidine Catharanthine Yohimbine Vinca Strychnine Ellipticine There are also purely structural classifications based on the presence of carbazole, β-carboline or other units in the carbon skeleton of the alkaloid molecule. (wikipedia.org)
  • An indole moiety of the terguride molecule is almost perfect planar, ring C has an E 6 envelope conformation and ring D adopts a 1 C 4 chair shape. (cas.cz)
  • The asymmetric syntheses of all eight tetraponerine alkaloids (T1-T8) were achieved using the diastereoselective conjugate additions of lithium amide reagents in the key stereodefining steps. (researcher-app.com)
  • Conjugate addition of either lithium ( R )- N -allyl- N -(α-methylbenzyl)amide or lithium ( R )- N -(but-3-en-1-yl)- N -(α-methylbenzyl)amide to tert -butyl sorbate was followed by ring-closing metathesis of the resultant N -alkenyl β-amino esters, reduction to the corresponding aldehydes, and reaction with tert -butyl (triphenylphosphoranylidene)acetate. (researcher-app.com)
  • Subsequent conjugate addition of the requisite antipode of lithium N -benzyl- N -(α-methylbenzyl)amide to the resultant α,β-unsaturated esters gave a range of diamines for elaboration to T1-T8 via a sequence involving reduction of the ester moiety to give the corresponding aldehyde, olefination, tandem hydrogenation/hydrogenolysis, and cyclization upon reaction with 4-bromobutanal to give the tricyclic skeleton. (researcher-app.com)
  • Aconitine-type crude extract of aconite are characterized, based on these alkaloids isolated from aconite have been shown to have potential toxicity and wide bioactivity. (healthdrugpdf.com)
  • Semisynthetic derivative of camptothecin, an alkaloid extract from the Camptotheca acuminate tree. (medscape.com)
  • Furthermore, we show that, in combination with asymmetric organocatalysis, the product alkaloid frameworks are obtained in excellent optical purity. (nature.com)
  • In connection with our studies on the syntheses of potentially bioactive 2-pyrrolidinones and 3-pyrrolin-2-ones [ 1 ], we describe in this paper the results of the performed study on the chemical reactivity of these structural moieties in reactions of addition, nucleophilic substitution, elimination, and reduction as well as the protection of the lactamic nitrogen. (hindawi.com)
  • These NMR experiments can help assign proton-deficient structural motifs like neopetrothiazide ( 1 ), which has 14 contiguous nonprotonated centers (C, N, and S). Neopetrothiazide ( 1 ), with an unprecedented thiazide-fused structural scaffold, is the first natural product containing a thiazide moiety. (cancer.gov)
  • related tetraamines bearing a 11-Acetyl-5,11-Dyhidro-6h-Pyrido[2,3-B] [1,4]-Benzodiazepin-6-One Moiety: structural requirements for optimum occupancy of muscarinic receptor subtypes as revealed by symmetrical and unsymmetrical polyamines, Journal of Medicinal Chemistry, 37, 3363-3372, 1994. (unibo.it)
  • The capillary voltage was tines (DDAs), in which the C8 position is occupied by an fixed at 5.0 V and capillary temperature was set 200°C. acetyl group, and lipo-alkaloids, in which the C8 position is Sample solutions were infused at 3 mL/min via a syringe occupied by a fatty acid acyl group.10 The other structural pump. (healthdrugpdf.com)
  • AC, HC and both ESI and MALDI-MS were applied to analyze complex MA were dissolved in chloroform to obtain a solution of mixtures of alkaloids from aconite.8,9 However, to our concentration of approx. (healthdrugpdf.com)
  • Bitterness is a particular issue for alkaloid-based medications, which contain basic nitrogen atoms in their structures. (chemistryworld.com)
  • It is a special kind of alkaloid originating from the herbal tree Cinchona 9 . (nature.com)
  • The same uncontrolled oligomerization was observed in the presence of bifunctional cinchona alkaloid catalysts with amine and thiourea moieties (Supplementary Figs. 11j,k and 12j,k).The increase in shale gas exploitation has motivated the studies towards new processes for converting light alkanes into higher valuable chemicals, including fuels. (baumaschinen-knell.de)
  • In many cases, these substances (particularly the alkaloids ) serve as plant defense mechanisms against predation by microorganisms, insects, and herbivores . (wikidoc.org)
  • 0.5 mg/mL. 8-Ole-14-benzoylmesa- knowledge, no reports have appeared in the literature on conine and other lipo-alkaloids were synthesized using the the application of ESI-MS to determine the fragmentation procedure reported by Pelletier et al.11 Aconitum alkaloids in mechanisms of aconitines and their relationship to molecular aconite were extracted with ethanol for 48 h at room structure. (healthdrugpdf.com)
  • They identified a functionalised terphen[3]arene compound to serve as a host and demonstrated that it can successfully bind to six different alkaloid medications, including atropinol (taken for poisonings) and colchicine (a common treatment for gout), through its internal cavity. (chemistryworld.com)
  • 8. Melchiorre C., Bolognesi M.L., Chiarini A., Minarini A., Spampinato S., Synthesis and biological activity of some methoctramine-related tetraamines bearing A 11-Acetyl-5,11-Dihydro-6h-Pyrido[2,3-B][1,4]-Benzodiazepin-6-One moiety as antimuscarinics: a second generation of highly selective M2 muscarinic receptor antagonists. (unibo.it)
  • Then some unknown minor lipo-alkaloids in the the most useful herbal medicines in China. (healthdrugpdf.com)
  • Camalexin is a simple indole alkaloid produced by the plant Arabidopsis thaliana, often used as a model for plant biology. (wikipedia.org)
  • One example of a plant-derived compound with potential utility in treating drug addiction is the indole alkaloid, ibogaine (2,3). (erowid.org)
  • Note the presence of an indole moiety in the structure of the iboga alkaloids and 5-HT. (erowid.org)
  • The structure of glycoalkaloids consists of a sugar moiety (glycone) and a non-sugar moiety (aglycone). (foodsafetywatch.org)
  • Isolation and structure elucidation of 24-epiclerosterol [24( R )-stigmasta-5, 25-dien-3β-ol], 24( R )-5α-stigmasta-7, 25-dien-3β-ol, 5α-stigmast-24-en-3β-ol and 25-methyl-5α-ergost-24 (28)-en-3β-ol from aerial parts was done 10 . (ijpsr.com)
  • The water-soluble compound forms a complex with alkaloids but subsequently releases them in the digestive tract, where they can go on to exert their pharmaceutical effect. (chemistryworld.com)
  • Tests showed that the complexes are pH responsive: the team recorded vastly different binding strengths at pH conditions representative of environments in the mouth (pH 6.8) and gastric acid (pH 1.2), meaning that the complex becomes unstable and releases the alkaloid once subjected to the acidic conditions of the stomach. (chemistryworld.com)
  • Indeed, the direct single-step synthesis of complex alkaloid frameworks remains an unresolved problem at the heart of organic chemistry in spite of the tremendous progress of the discipline. (nature.com)
  • Scientists in China have developed a macrocyclic compound that can mask the bitter taste of alkaloid drugs. (chemistryworld.com)
  • Previous studies tried trapping alkaloids inside cyclic oligosaccharides called cyclodextrins, but they either did not form effective complexes or did not promptly release their bound guest once inside the body. (chemistryworld.com)
  • Undergoes hydrolysis in liver and tissues to form the active moiety (fluorouracil), inhibiting thymidylate synthetase, which in turn blocks methylation of deoxyuridylic acid to thymidylic acid. (medscape.com)
  • Our combination of analysis methods allows suggestions for further lead development regarding specific chemical modification and substitutions for the naphtyl moiety in NIQs. (uni-wuerzburg.de)
  • Although their assignment to the alkaloid is not universally accepted, they are both found in plants and animals. (wikipedia.org)
  • 5. Alam MM, Naeem M, Khan MMA and Uddin M. Vincristine and vinblastine anticancer catharanthus alkaloids: pharmacological applications and strategies for yield improvement. (jmp.ir)
  • The title alkaloid crystallizes in the orthorhombic space group P2 1 2 1 2 1 with lattice parameters a = 10.438(1), b = 13.200(4), c = 15.495(5) Å, V = 2 134.8(9) Å 3 , Z = 4. (cas.cz)
  • Alkaloids remain a highly prized and elaborate subset of natural products and drug candidates 6 . (nature.com)
  • Two bispyrroloiminoquinone alkaloids, wakayin ( 1 ) and a new natural product 16-hydroxy-17-oxindole wakayin ( 2 ), were isolated from a Thai collection of the ascidian Clavelina sp. (cancer.gov)
  • Considering that acetylcholinesterase (AChE) inhibition is the most important mode of action expected of a potential drug used for the treatment of symptoms of Alzheimer's disease (AD), our previous pilot study of 4-aminoquinolines as potential human cholinesterase inhibitors was extended to twenty-two new structurally distinct 4-aminoquinolines bearing an adamantane moiety. (inra.fr)
  • Previously, it was proven that the carbohydrate moiety could affect the catalytic activity of the monoaza-15-crown-5 type macrocycles derived from sugars. (researchgate.net)
  • 7. Berlinck R.G.S., Braekman J.C., Daloze D., Bruno I., Riccio R., Ferri S., Spampinato S., Speroni E., Polycyclic guanidine alkaloids from the marine sponge Crambe Crambe and Ca++ channel blocker activity of Crambescidin 816. (unibo.it)
  • Here we describe the design and synthesis of conformationally restricted clathrodin analogues incorporating Cl-amidine the 4,5,6,7-tetrahydrobenzo[d]thiazol-2-amine moiety and evaluation of their modulatory activities on human voltage-gated sodium channel isoforms Na(V)1.3, Na(V)1.4 and Na(V)1.7, as well as their selectivity against cardiac isoform Nav1.5. (limkinase-signal.com)