Biologically Active Mesomeric Betaines and Alkaloids, Derived from 3-Hydroxypyridine, Pyridine N-Oxide, Nicotinic Acid and Picolinic Acid: Three Types of Conjugation and Their Consequences

ChemInform ◽  
2005 ◽  
Vol 36 (1) ◽  
Author(s):  
Andreas Schmidt
Keyword(s):  
Nicotinic Acid ◽  
Picolinic Acid ◽  
Biologically Active

Similarity Between the Action of Pteridines and Tryptophan Metabolites on Lipid Metabolism

Pteridines ◽  
1999 ◽  
Vol 10 (3) ◽  
pp. 133-140 ◽  
Author(s):  
Vera Rudzite ◽  
Edite Jurika ◽  
Bernhard Widner ◽  
Dietmar Fuchs
Keyword(s):  
Fatty Acids ◽  
Nicotinic Acid ◽  
Anthranilic Acid ◽  
Kynurenic Acid ◽  
Picolinic Acid ◽  
Test System ◽  
Xanthurenic Acid ◽  
Phospholipid Biosynthesis ◽  
Wet Weight

Abstract Incorporation of fatty acids into phospholipids has been investigated using samples of rat liver tissue homogenate, Krebs-Ringer-phosphate buffer (pH=7.4) containing 0.3% albumin, fatty acid mixture and glycerol. The addition of anthranilic acid (2.2 and 4 nmol/g wet weight), kynurenic acid (4 and 40 nmol/ g wet weight), xanthurenic acid (4 and 40 nmol/g wet weight), picolinic acid (0.2 and 2 nmol/g wet weight) induced an increase of saturated and a decrease of polyunsaturated fatty acids incorporation into phospholipids as well as an eleyation of choksterol concentration in samples used for phospholipid biosynthesis in vitro. These changes were similar to those observed after addition of kynurenine and neopterin to the same test system, An inverse relationship has been observed after addition of nicotinic acid to samples used for phospholipid biosynthesis in vitro. Nicrotinic acid induced .1 decrease of saturated and an increase of unsaturated fatty acids incorporation into phospholipids as well as decrease of cholesterol concentration in samples, These changes were similar to those observed after addition of 3-hydroxykynurenine, 3-hydroxyanthranilic acid, quinolinic, acid, 5,6],8-tetrahydrobiopterin and its precursors to the same test system used rex phospholipid biosynthesis in vitro. In parallel anthranilic acid, kynurenic acid, xanthurenic acid and picolinic acid decrease while nicotinic acid increases membrane fluidity in the studied concentrations.

Terahertz spectroscopy and solid-state density functional theory calculations of structural isomers: Nicotinic acid, isonicotinic acid and 2-picolinic acid

2017 ◽  
Vol 31 (13) ◽  
pp. 1750149 ◽  
Author(s):  
Ling Ding ◽  
Wen-Hui Fan ◽  
Xu Chen ◽  
Ze-You Chen ◽  
Chao Song
Keyword(s):  
Density Functional Theory ◽  
Nicotinic Acid ◽  
Density Functional ◽  
Isonicotinic Acid ◽  
Picolinic Acid ◽  
Molecular Crystals ◽  
Density Functional Theory Calculations ◽  
State Density ◽  
Functional Theory ◽  
Absorption Features

We report, for the first time to our knowledge, the terahertz (THz) spectra of isonicotinic acid and 2-picolinic acid. The distinct THz spectral differences among these two isomers and nicotinic acid have also been observed, indicating that the THz vibrational modes are highly sensitive to the structural differences even in similar molecular crystals. Besides, solid-state density functional theory calculations reveal better qualitative agreement with the measured absorption features, which are related to the molecular vibrations of nicotinic acid and isonicotinic acid. As for 2-picolinic acid, the calculation based on the primitive cell reproduces the absorption features at 1.46, 1.82 and 2.46 THz originating from intermolecular vibrations. These results suggest that THz spectra can identify the complex intermolecular interactions even in similar molecular crystals, which shows potential applications in identifying isomers in food and pharmaceutical production.

scholarly journals Effects of Kynurenine Pathway Metabolites on Intracellular NAD+ Synthesis and Cell Death in Human Primary Astrocytes and Neurons

2009 ◽  
Vol 2 ◽  
pp. IJTR.S2318 ◽  
Author(s):  
Nady Braidy ◽  
Ross Grant ◽  
Bruce J Brew ◽  
Seray Adams ◽  
Tharusha Jayasena ◽  
...  
Keyword(s):  
Cell Death ◽  
Picolinic Acid ◽  
Pyridine Nucleotide ◽  
Kynurenine Pathway ◽  
Biologically Active ◽  
Active Metabolites ◽  
Nad Synthesis ◽  
Hydroxyanthranilic Acid ◽  
Dose Dependent Decrease ◽  
Dose Dependent

The kynurenine pathway (KP) is a major route of L-tryptophan catabolism resulting in the production of the essential pyridine nucleotide nicotinamide adenine dinucleotide, (NAD+). Up-regulation of the KP during inflammation leads to the release of a number of biologically active metabolites into the brain. We hypothesised that while some of the extracellular KP metabolites may be beneficial for intracellular NAD+ synthesis and cell survival at physiological concentrations, they may contribute to neuronal and astroglial dysfunction and cell death at pathophysiological concentrations. In this study, we found that treatment of human primary neurons and astrocytes with 3-hydroxyanthranilic acid (3-HAA), 3-hydroxykynurenine (3-HK), quinolinic acid (QUIN), and picolinic acid (PIC) at concentrations below 100 nM significantly increased intracellular NAD+ levels compared to non-treated cells. However, a dose dependent decrease in intracellular NAD+ levels and increased extracellular LDH activity was observed in human astrocytes and neurons treated with 3-HAA, 3-HK, QUIN and PIC at concentrations >100 nM and kynurenine (KYN), at concentrations above 1 μM. Intracellular NAD+ levels were unchanged in the presence of the neuroprotectant, kynurenic acid (KYNA), and a dose dependent increase in intracellular NAD+ levels was observed for TRP up to 1 mM. While anthranilic acid (AA) increased intracellular NAD+ levels at concentration below 10 μM in astrocytes. NAD+ depletion and cell death was observed in AA treated neurons at concentrations above 500 nM. Therefore, the differing responses of astrocytes and neurons to an increase in KP metabolites should be considered when assessing KP toxicity during neuroinflammation.

scholarly journals Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners

2021 ◽  
Author(s):  
Nicolas A. Frank ◽  
Márió Széles ◽  
Sergi H. Akone ◽  
Sari Rasheed ◽  
Stephan Hüttel ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Nicotinic Acid ◽  
Biosynthetic Pathway ◽  
Product Family ◽  
Biologically Active ◽  
Acid Moiety ◽  
Genome Data ◽  
Pure Compounds ◽  
Directed Biosynthesis ◽  
Improve Access

Myxobacteria represent a viable source of chemically diverse and biologically active secondary metabolites. The myxochelins are a well-studied family of catecholate-type siderophores produced by various myxobacterial strains. Here, we report the discovery, isolation and structure elucidation of three new myxochelins N1–N3 from the terrestrial myxobacterium Corallococcus sp. MCy9049, featuring an unusual nicotinic acid moiety. Precursor-directed biosynthesis (PDB) experiments and total synthesis were performed in order to confirm structures, improve access to pure compounds for bioactivity testing and to devise a biosynthesis proposal. The combined evaluation of metabolome and genome data covering myxobacteria supports the notion that the new myxochelin congeners reported here are in fact frequent side products of the known myxochelin A biosynthetic pathway in myxobacteria.

Inhibition of glucose-6-phosphate phosphohydrolase by 3-mercaptopicolinate and two analogs is metabolically directive

1993 ◽  
Vol 71 (3-4) ◽  
pp. 113-121 ◽  
Author(s):  
Ann M. Bode ◽  
James D. Foster ◽  
Robert C. Nordlie
Keyword(s):  
Nicotinic Acid ◽  
Quinolinic Acid ◽  
Phosphoenolpyruvate Carboxykinase ◽  
Reduced Glutathione ◽  
Picolinic Acid ◽  
Liver Microsomes ◽  
Glucose Production ◽  
Metabolic Effects ◽  
Hepatic Glucose ◽  
Fasted Rats

3-Mercaptopicolinae (3-MP) blocks gluconeogenesis from lactate, pyruvate, alanine, and other substrates through its inhibition of phosphoenolpyruvate carboxykinase. Nevertheless, we observed increased glycogenesis, net glucose uptake, and glucose-6-P levels in livers perfused with glucose in the presence of 3-MP. In perfusions with 20 mM dihydroxyacetone, increased glycogenesis and decreased glucose production were observed with 3-MP. These metabolic effects suggested additional site(s) of action of 3-MP. Further studies showed that 3-MP inhibits glucose-6-P phosphohydrolase activity of intact liver microsomes. Several compounds with structural similarities to 3-MP (2-mercaptonicotinic acid, picolinic acid, cysteine, reduced glutathione, nicotinic acid, quinolinic acid, tryptophan, and pyridine) were tested for their effect on glucose-6-P phosphohydrolase activity. Two of these compounds, 2-mercaptonicotinic acid and picolinic acid, were found to inhibit. In perfusions including 7.5 mM fructose, the addition of 3-MP, 2-mercaptonicotinic acid, or picolinic acid increased glycogenesis, decreased glucose production, and increased hepatic glucose-6-P concentrations. These observations indicate that the inhibition of glucose-6-P phosphohydrolase may play a role in enhanced glycogenesis from glucose, dihydroxyacetone, and fructose in isolated livers from 48-h fasted rats perfused with 3-MP or certain sulfhydryl-containing and sulfhydryl-devoid analogs.Key words: glucogenesis, 3-mercaptopicolinate, glucose-6-P phosphohydrolase.

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