3-alkyl pyridinium alkaloids: Topics by WorldWideScience.org

A new alkaloid isolated from Maytenus guianensis

The fluorescence properties of protopine and allocryptopine in aqueous and organic environments are described for the first time. The fluorescence of alkaloids and their pH-dependent interconversion to cationic forms (transannular interaction) were studied using steady-state and time-resolved fluorescence techniques. For the analysis of tricyclic base and cis/trans tetracyclic cations of the alkaloids, NMR and X-ray crystallography were used. - Highlights: ? We describe fundamental fluorescence characteristics of alkaloids protopine and allocryptopine. ? We analyzed the pH-dependent transitions and cis/trans isomerization. ? These two alkaloids can be better distinguished by their fluorescence decay characteristics. ? The fluorescence parameters are related to the NMR and crystallographic structural data.

2011-07-01

Cyclopeptide alkaloids. Synthesis of the ring system and its ion affinity

Portuguese (Jul 1981). Brazil Sousa, JR de Souza, E. de . Minas Gerais Univ.,

Reaction of ethyl azidoformate with acenaphthylene: isolation and structure of an acenaphthylene-pyridinium-2,6 betaine adduct

Several examples of the 14-membered, para-bridged ring system of the cyclopeptide alkaloids have been synthesized via an active ester cyclization. The yield of monomeric cyclopeptide varied from 1 to 33% and was affected by the amino acid substitution pattern and amide conformation of the linear peptide precursors. Both the synthetic models and a naturally occurring cyclopeptide alkaloid, ceanothine B, bind monovalent (Li"+) and divalent (Ca"2"+, Mg"2"+) cations. 4 figures, 1 table.

Fluoride ion catalyzed alkylation of purines, pyrimidines, nucleosides and nucleotides using alky halides.

Ethyl azidoformate reacts, on thermolysis with acenaphthylene, to give a 1:2 adduct involving sequential aziridine formation, ring-opening to a 1,3-dipolar pyridinium-2,6-betaine, and trapping of the dipole with acenaphthylene. The structure of the adduct was confirmed by X-ray crystallography.

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

Alkyl halides react rapidly with purines and pyrimidines in the presence of fluoride ion. Alkylation of thymidine leads to novel dimeric nucleoside derivatives bridged through N3. Alkylation of thymidine...Full Text Available

1979-04-01

Inhibition of the visual cycle by A2E through direct interaction with RPE65 and implications in Stargardt disease

SummaryThe numerous applications of hydrogelators have led to rapid expansion of this field. In the present work we report the facile synthesis of amphiphilic hydrogelators having a quaternary...Full Text Available

Site of lupanine and sparteine biosynthesis in intact plants and in vitro organ cultures

Stargardt disease (STGD) is the major form of inherited juvenile macular degeneration. Pyridinium bis-retinoid A2E is a major component of lipofuscin which accumulates in retinal pigment epithelium...Full Text Available

2010-10-12

Approach to the homoerythrina alkaloids using a tandem N-alkylation/azomethine ylide cycloaddition.

["1"4C]Cadaverine was applied to leaves of Lupinus polyphyllus, L. albus, L. angustifolius, L. perennis, L. mutabilis, L. pubescens, and L. hartwegii and it was preferentially incorporated into lupanine. In Lupinus arboreus sparteine was the main labelled alkaloid, in L. hispanicus it was lupanine. A pulse chase experiment with L. angustifolius and L. arboreus showed that the incorporation of cadaverine into lupanine and sparteine was transient with a maximum between 8 and 20 h. Only leaflets and chlorophyllous petioles showed active alkaloid biosynthesis, whereas no incorporation of cadaverine into lupanine was observed in roots. Using in vitro organ cultures of Lupinus polyphyllus, L. succulentus, L. subcarnosus, Cytisus scoparius and Laburnum anagyroides the inactivity of roots was confirmed. Therefore, the green aerial parts are the major site of alkaloid biosynthesis in lupins and in other legumes. (orig.).

1987-01-01

Science.gov (United States)

Synthetic efforts toward the homoerythrina alkaloids 1-3 are described. Two separate model systems guided the pivotal [3 + 2] azomethine ylide cycloaddition cascade to form the A-C rings of these alkaloids. The cycloaddition precursors 63 and 68, prepared in nine and ten steps, respectively, from alkyne 47, each contain an enolizable ketone, a tethered electrophile, and an electron-poor dipolarophile. Heating 63 and 68 with the stannyl amine 17 generated demethoxyschelhammeridine 65 and demethoxyschelhammericine 70, the products of intramolecular azomethine ylide cycloadditions. Subsequent attempts to install the C-3 methoxy group of 1-3 are also described. PMID:17465572

2007-04-28

Genetic Evidence for Inhibition of Bacterial Division Protein FtsZ by Berberine

Enantioselective organocatalytic ?-sulfenylation of substituted diketopiperazines

BackgroundBerberine is a plant alkaloid that is widely used as an anti-infective in traditional medicine. Escherichia coli exposed to berberine form filaments, suggesting...Full Text Available

Auxins Induce Tryptophan Decarboxylase Activity in Radicles of Catharanthus Seedlings ¹

The asymmetric organocatalytic α-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents....Full Text Available

2009-12-11

Determination of Cinchona alkaloids and Vitamin B_6 by high-performance liquid chromatography with fluorescence detection

Germinating seedlings of Catharanthus roseus produce monoterpenoid indole alkaloids as a result of a transient increase of tryptophan decarboxylase (TDC) activity. The influence of...Full Text Available

1992-10-01

Separation and Measurement of Plant Alkaloid Enantiomers by RP-HPLC Analysis of their Fmoc-Alanine Analogs

A simple and specific method has been developed for the simultaneous determination of the four major Cinchona alkaloids and their dihydroderivatives and pyridoxine hydrochloride (Vitamin B_6) by high-performance liquid chromatography (HPLC) with fluorescence detection (#lambda#_e_m=420 nm with #lambda#_e_x=330 nm). The chromatographic separation was performed on a Phenomenex Prodigy ODS column (5 #mu#m, 250 mmx3.2 mm i.d.), recommended for basic compounds, under isocratic reversed-phase conditions. The method allowed a good peak shape and an effective resolution of the tested compounds. The extraction of alkaloids from the Cinchona succirubra bark was carried out in mild and fast conditions (ambient temperature, 20 min) by ultrasonication. The procedure showed to be advantageous respect to a reference method, which involved Soxhlet extraction. The results were compared statistically by means of the Student's t-test and the variance ratio ...

2004-06-04

Science.gov (United States)

Plants often synthesize secondary metabolites that are enantiomers. Enantiomers can cause very different physiological responses. Ammodendrine (1) and anabasine (2) are teratogens that can cause congenital malformations in livestock and enantiomeric forms of each have been found in Lupinus spp. an...

Investigation of Symphytum cordatum alkaloids by liquid-liquid partitioning, thin-layer chromatography and liquid chromatography-ion-trap mass spectrometry

Induced mutation in Lupinus mutabilis sweet in Peru

From the alkalised crude extract of Symphytum cordatum (L.) W.K. roots, pyrrolizidine alkaloids (PAs) were extracted as free tertiary bases and polar N-oxides in a merely one-step liquid-liquid partitioning (LLP) in separation funnel and subsequently pre-fractionated by preparative multiple-development (MD) thin-layer chromatography (TLC) on silica gel plates. In this way three alkaloid fractions of different polarities and retention on silica gel plates were obtained as: the most polar N-oxides of the highest retention, the tertiary bases of medium retention, and diesterified N-oxides of the lowest retention. The former fraction was reduced into free bases by sodium hydrosulfite and purified by LLP on Extrelut-NT3 cartridge. It was further analysed together with the two other fractions by high-performance liquid chromatography (HPLC)-ion-trap mass spectrometry with atmospheric pressure chemical ionization (APCI) interface on XTerra C{sub 18} ...

2006-05-04

Design, synthesis and evaluation of redox radiopharmaceuticals: a potential new approach for the development of brain imaging agents

Mutagenesis of Lupinus mutabilis was started at the UNA LM (Peru) to obtain mutants with low alkaloid content and early germination. Varieties SCG 25 and Lib 020 were irradiated with gamma radiation. The optimum dose for the SCG 25 variety was 15 Krad and for Lib 020 15 to 20 Krad. The relation between the plant height and radiation dose fits the quadratic polynomial model.

1984-04-01

Characterisation of polynuclear aromatic sulfur-heterocycles in a coal extract by GC/MS

The goals of this paper are to describe the fabrication and complete evaluation of a dihydropyridine <- -> pyridinium salt type redox system for the delivery of radioiodinated agents to the brain. Tissue distribution studies of "1"2"5I-labeled 4-iodoaniline and the redox agents were performed in rats. ["1"2"5I]Iodoaniline initially showed moderate brain uptake with subsequent release of the radioactivity from the brain. ["1"2"5I]Iodoaniline, however, when coupled to a dihydropyridine carrier showed significantly higher uptake and retention in the brain. (author).

LiPF{sub 6}. Synthesis and stability in EC/DMC and PC/DMC mixtures; LiPF{sub 6}. Synthese et stabilite dans les melanges EC/DMC et PC/DMC

Polynuclear aromatic sulphur heterocycles (PASHs) were isolated from a coal extract by two-step separation method using silica gel column chromatography and ligand exchanges thin layer chromatography (PdCl{sub 2}/SiO{sub 2}). The subfraction was examined by capillary column gas chromatography with flame ionization detector and flame photometric detector and gas chromatography - mass spectrometry. Identification was accomplished by comparison of chromatographic retention indices and mass spectra of compounds with those reported in the literature. It was found that the principal structures of the sulphur-containing fraction of Guiding coal extract have 3-4 aromatic rings. Dibenzothiophene, C{sub 1} - C{sub 3} alkylated dibenzothiophenes, benzonaphthothiophene and its alkylated derivatives were the main compounds. Only a few other polynuclear sulfur heterocycles were detected. No benzothiophene and its derivatives were presented. 8 refs., 2 figs., ...

1994-06-01

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Inhibition of corrosion resistant alloys in hot hydrochloric acid solutions

Lithium hexa-fluoro-phosphate LiPF{sub 6} is recommended for the replacement of the toxic LiAsF{sub 6} and the explosive perchlorates (like LiClO{sub 4}) in rechargeable lithium electrochemical generators. The aim of this work is to develop a new method of synthesis of this salt and to check its stability with respect to carbonated solvents: ethylene carbonate (EC), propylene carbonate (PC) and dimethyl-carbonate (DMC) in already optimized EC/DMC and PC/DMC binary mixtures. Two methods using HPF{sub 6} are proposed: the first one uses the direct neutralization of this commercial acid by LiOH in aqueous, alcoholic or acetonitrile environment, while in the second one LiPF{sub 6} is obtained from pyridinium hexa-fluoro-phosphate synthesized from HPF{sub 6} using a new and simple protocol. (J.S.) 24 refs.

1996-12-31

Design, synthesis and evaluation of redox radiopharmaceuticals: a potential new approach for the development of brain imaging agents

Weight loss measurements were performed in 20% and 28% hydrochloric acid at 90/sup 0/C on carbon steel, 22Cr5Ni duplex stainless steel, and two superaustenitic steels - 27Cr31Ni3Mo and 19Cr25Ni4Mo -, in presence of organic substances used singly or mixed. The organic substances examined were quaternary ammonium salts (1-4-pyridyl)-pyridinium chloride hydrochloride, dodecylpyridiniumchloride, benzyldimethylstearylammonium chloride, and dodecyltrimethylammonium bromide), alkynols (1-octyn-3-ol, propargyl alcohol) and trans-cinnamaldehyde. The synergistic effect of potassium iodide on the inhibitive efficiency of the organic substances was studied. The variations of corrosion rate during the test time (normally six hours) were recorded by means of polarization resistance measurements. Polarization curves were also recorded. The results showed that the corrosion rates of the four steels examined can be reduced to less than 1 mg/cm/sup -2/ . h/sup -1/ using ternary ...

1988-12-01

A fixed cations and low Tg polymer: the poly(4-vinyl-pyridine) quaternized by poly(ethylene oxide) links. Conductivity study; Un electrolyte polymere a cations fixes et bas Tg: les poly(4-vinylpyridine) quaternisees par des chainons de poly(oxyde d`ethylene). Etude de la conductivite

The fabrication and complete evaluation are described of a dihydropyridine in equilibrium pyridinium salt type redox system for the delivery of radioiodinated agents to the brain. The pivotal intermediate, N-succinimidyl (1-methylpyridinium iodide)-3-carboxylate was prepared by condensation of nicotinic acid and N-hydroxysuccinimide in the presence of dicyclohexylcarbodimide, followed by quaternization of III with methyl iodide. Tissue distribution studies of "1"2"5I-labeled 4-iodoaniline and the redox agents were performed in rats. ["1"2"5I]Iodoaniline initially showed moderate (0.58% dose/gm) brain uptake with subsequent release of the radioactivity from the brain. ["1"2"5I]Iodoaniline, when coupled to a dihydropyridine carrier showed higher uptake and retention in the brain. The ["1"2"5I]iodophenylethyl analogue showed uptake and retention in the brain to be very similar. Apparently the lipophilic agents cross the blood-brain barrier and are oxidized ...

Effects of irradiation in medicinal and eatable herbs

The spontaneous ionic polymerization of 4-vinyl-pyridine in presence of mono-tosylated or bromated short chains of poly(ethylene oxide)-(PEO) is used to prepare amorphous comb-like poly-cations with low Tg. The polymer electrolyte properties of these new structures have been studied without any addition of salts. The ionic conductivity of these fixed cation poly-electrolytes depends on the length of the grafted PEO and varies from 10{sup -7} to 10{sup -4} S/cm between 25 and 80 deg. C. It is only weakly dependent on the nature of the cation but it is controlled by the movements of the pyridinium cation which are facilitated by the plastifying effect of the POE chains which do not directly participate to the ionic transport. (J.S.) 17 refs.

1996-12-31

Acid/base and hydrogen bonding effects on the proton-coupled electron transfer of quinones and hydroquinones in acetonitrile: Mechanistic investigation by voltammetry, "1H NMR and computation

For ages, herbs have been used as medicine and food. Nowadays, the interest in phytotherapeutics is increasing as well as the consumer attention. Some biochemical compounds synthesized by plants as alkaloids, phenolics, flavonoids, essential oils, tannins and vitamins, influence the composition of these plant pharmacologicals, which may produce various reactions in the human body. The microbial contamination in these raw plant materials is common, and the radiation processing is one appropriate technique for the reduction of microorganism. In herbs used as food products, the changes in total #beta#-carotene and flavonoids upon the radiation treatment were tested. The powdered and dehydrated herbs were irradiated with "6"0Co gamma rays applying doses of 0, 10, 20 and 30 kGy. The botanical species investigated were rosemary (Rosmarinus officinalis Linne), watercress (Nasturtium officinale R. Br), artichoke (Cynara scolymus Linne) and sweet basil (Ocimum basilicum ...

2002-03-01

Antimalarial activity of selected Sudanese medicinal plants with emphasis to Maytenus senegalensis

This report seeks to address the role of hydrogen bonding with Bronsted acids and bases in proton-coupled electron transfer (PCET) as it pertains to concerted or stepwise pathways of quinone (Q) and hydroquinone (QH_2) electrochemistry. This study was performed using a series of techniques that included cyclic voltammetry (CV), digital simulations, computational chemistry and "1H NMR. Hydrogen bonding was inferred by a decrease in diffusion coefficient (D) values measured using a pulsed gradient echo- (PGE-) "1H NMR technique. Changes of 40.8% and 37.9% in D values were only noted after the addition of two equivalents of acetate to 1,4-hydroquinone (1,4-QH_2) and catechol (1,2-QH_2), respectively. In contrast, the D values for the addition of selected amines (pyridine, N,N-diisopropylethylamine and triethylamine) changed only 3.2% on average. Quantum mechanical calculations were conducted to determine the pK_a of all quinoid species to serve as a starting point for the determination of ...

2010-09-01