EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt (8CI)

Supplier Sponsors

CAS Number: 535-83-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-620-5
Beilstein Number:3905114
XlogP3-AA:1.20 (est)
Molecular Weight:137.13819000
Formula:C7 H7 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Physical Properties:
Appearance:colorless prisms (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): -3.910 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Trigonelline 98%
BOC Sciences
For experimental / research use only.
Trigonelline >98%
Odor: characteristic
Use: Trigonelline (1-methylpyridinium-3-carboxylate), an alkaloid present in coffee and fenugreek seed, has been reported to exhibit phytoestrogenic activity. phytoestrogenic
For experimental / research use only.
For experimental / research use only.
Trigonelline (HPLC) ≥95%
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 5000 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 210, Pg. 27, 1974.

Dermal Toxicity:
subcutaneous-rat LD50 5000 mg/kg
Proceedings of the Society for Experimental Biology and Medicine. Vol. 62, Pg. 19, 1946.

Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for trigonelline usage levels up to:
 not for fragrance use.
Recommendation for trigonelline flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5570
National Institute of Allergy and Infectious Diseases:Data
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5570
Pubchem (sid):135023822
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C01004
HMDB (The Human Metabolome Database):HMDB00875
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
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 barley seed
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 bean banner bean
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 bean black bean fruit
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 bean field bean
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 cacao bean
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 pea black-eyed pea
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 betain nicotinate
 betaine nicotinate
3-carboxy-1-methylpyridinium hydroxide inner salt
3-carboxy-1-methylpyridinium hydroxide, inner salt
 nicotinic acid N-methylbetaine
 pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt (8CI)


PubMed:The role of choline and glycine betaine in the formation of N,N-dimethylpiperidinium (mepiquat) under Maillard reaction conditions.
PubMed:Conversion of nicotinic acid to trigonelline is catalyzed by N-methyltransferase belonged to motif B' methyltransferase family in Coffea arabica.
PubMed:Trigonelline accumulation in leaves of Panicum virgatum seedlings.
PubMed:Antiarrhythmic effect of lithium in rats after myocardial infarction by activation of Nrf2/HO-1 signaling.
PubMed:Coffee inhibits adipocyte differentiation via inactivation of PPARγ
PubMed:Cardiometabolic effects of two coffee blends differing in content for major constituents in overweight adults: a randomized controlled trial.
PubMed:Accumulation and function of trigonelline in non-leguminous plants.
PubMed:Trigonelline and diosgenin attenuate ER stress, oxidative stress-mediated damage in pancreas and enhance adipose tissue PPARγ activity in type 2 diabetic rats.
PubMed:Bioactive micronutrients in coffee: recent analytical approaches for characterization and quantification.
PubMed:The co-occurrence of two pyridine alkaloids, mimosine and trigonelline, in Leucaena leucocephala.
PubMed:Unfavorable effect of trigonelline, an alkaloid present in coffee and fenugreek, on bone mechanical properties in estrogen-deficient rats.
PubMed:Catalase overexpression prevents nuclear factor erythroid 2-related factor 2 stimulation of renal angiotensinogen gene expression, hypertension, and kidney injury in diabetic mice.
PubMed:Effect of agronomical practices on carpology, fruit and oil composition, and oil sensory properties, in olive (Olea europaea L.).
PubMed:Metabolomics in nutritional epidemiology: identifying metabolites associated with diet and quantifying their potential to uncover diet-disease relations in populations.
PubMed:Nuclear magnetic resonance metabolomics of iron deficiency in soybean leaves.
PubMed:New biomarkers of coffee consumption identified by the non-targeted metabolomic profiling of cohort study subjects.
PubMed:Coffee: biochemistry and potential impact on health.
PubMed:Strategy of metabolic phenotype modulation in Portunus trituberculatus exposed to low salinity.
PubMed:Antithrombotic effects of pyridinium compounds formed from trigonelline upon coffee roasting.
PubMed:The hypoglycemic effect of pumpkin seeds, Trigonelline (TRG), Nicotinic acid (NA), and D-Chiro-inositol (DCI) in controlling glycemic levels in diabetes mellitus.
PubMed:Coffea arabica instant coffee--chemical view and immunomodulating properties.
PubMed:Comparative metabolite profiling of foxglove aphids (Aulacorthum solani Kaltenbach) on leaves of resistant and susceptible soybean strains.
PubMed:A dark brown roast coffee blend is less effective at stimulating gastric acid secretion in healthy volunteers compared to a medium roast market blend.
PubMed:[Quality standard of uygur medicine Medicago sativa seeds].
PubMed:Quantification of caffeine, trigonelline and nicotinic acid in espresso coffee: the influence of espresso machines and coffee cultivars.
PubMed:N-methylpyridinium, a degradation product of trigonelline upon coffee roasting, stimulates respiratory activity and promotes glucose utilization in HepG2 cells.
PubMed:Serum and urine metabolomic fingerprinting in diagnostics of inflammatory bowel diseases.
PubMed:Preliminary studies on trigonelline as potential anti-Alzheimer disease agent: determination by hydrophilic interaction liquid chromatography and modeling of interactions with beta-amyloid.
PubMed:Trigonelline attenuates the adipocyte differentiation and lipid accumulation in 3T3-L1 cells.
PubMed:Acinetobacter qingfengensis sp. nov., isolated from canker bark of Populus x euramericana.
PubMed:Characterization of secondary metabolites from the raphides of calcium oxalate contained in three araceae family plants using laser microdissection and ultra-high performance liquid chromatography-quadrupole/time of flight-mass spectrometry.
PubMed:N,N-dimethylpiperidinium (mepiquat) Part 2. Formation in roasted coffee and barley during thermal processing.
PubMed:N,N-dimethylpiperidinium (mepiquat): Part 1. Formation in model systems and relevance to roasted food products.
PubMed:Quantitative studies on roast kinetics for bioactives in coffee.
PubMed:Application of ¹H NMR for the characterisation and authentication of ''Tonda Gentile Trilobata" hazelnuts from Piedmont (Italy).
PubMed:Trigonelline isolated from fenugreek seed protects against isoproterenol-induced myocardial injury through down-regulation of Hsp27 and αB-crystallin.
PubMed:Gender-specific metabolomic profiling of obesity in leptin-deficient ob/ob mice by 1H NMR spectroscopy.
PubMed:Assessment of peeling of Astragalus roots using 1H NMR- and UPLC-MS-based metabolite profiling.
PubMed:Bioappearance and pharmacokinetics of bioactives upon coffee consumption.
PubMed:A new β-carboline alkaloid from the seeds of Griffonia simplicifolia.
PubMed:Development of a hydrophilic interaction chromatography-UPLC assay to determine trigonelline in rat plasma and its application in a pharmacokinetic study.
PubMed:Synchronized regulation of different zwitterionic metabolites in the osmoadaption of phytoplankton.
PubMed:Experimental diabetes treated with trigonelline: effect on key enzymes related to diabetes and hypertension, β-cell and liver function.
PubMed:Inhibition of key digestive enzymes related to diabetes and hyperlipidemia and protection of liver-kidney functions by trigonelline in diabetic rats.
PubMed:Efficacy and safety of standardized extract of Trigonella foenum-graecum L seeds as an adjuvant to L-Dopa in the management of patients with Parkinson's disease.
PubMed:Unusual amino acids and monofluoroacetate from Dichapetalum michelsonii (Umutambasha), a toxic plant from Rwanda.
PubMed:Neurobehavioral assessment of hydroalcoholic extract of Trigonella foenum-graecum seeds in rodent models of Parkinson's disease.
PubMed:Urinary phenotyping indicates weight loss-independent metabolic effects of Roux-en-Y gastric bypass in mice.
PubMed:Protection of trigonelline on experimental diabetic peripheral neuropathy.
PubMed:Trigonelline ameliorates oxidative stress in type 2 diabetic Goto-Kakizaki rats.
PubMed:Peach fruit: metabolic comparative analysis of two varieties with different resistances to insect attacks by NMR spectroscopy.
PubMed:Inhibition of the Nrf2 transcription factor by the alkaloid trigonelline renders pancreatic cancer cells more susceptible to apoptosis through decreased proteasomal gene expression and proteasome activity.
PubMed:Trigonelline ameliorates diabetic hypertensive nephropathy by suppression of oxidative stress in kidney and reduction in renal cell apoptosis and fibrosis in streptozotocin induced neonatal diabetic (nSTZ) rats.
PubMed:Short-term changes of the urine metabolome after bariatric surgery.
PubMed:(13)C NMR-based metabolomics for the classification of green coffee beans according to variety and origin.
PubMed:Comparison of the formation of nicotinic acid conjugates in leaves of different plant species.
PubMed:Rapid mixed mode solid phase extraction method for the determination of acrylamide in roasted coffee by HPLC-MS/MS.
PubMed:Determination of trigonelline, nicotinic acid, and caffeine in Yunnan Arabica coffee by microwave-assisted extraction and HPLC with two columns in series.
PubMed:Trigonelline and other betaines in species of Laminariales.
PubMed:Metabolic fate of 14C-labelled nicotinamide and adenine in germinating propagules of the mangrove Bruguiera gymnorrhiza.
PubMed:Potential metabolomic biomarkers for evaluation of adriamycin efficacy using a urinary (1) H-NMR spectroscopy.
PubMed:Trigonelline: a plant alkaloid with therapeutic potential for diabetes and central nervous system disease.
PubMed:A review of chemistry and biological activities of the genus Aerva--a desert plant.
PubMed:Effects of genotype and environment on the contents of betaine, choline, and trigonelline in cereal grains.
PubMed:Ameliorative effects of standardized extract from Trigonella foenum-graecum L. seeds on painful peripheral neuropathy in rats.
PubMed:Pyridine metabolism in tea plants: salvage, conjugate formation and catabolism.
PubMed:[Determination of trigonelline in coffee powder and instant coffee by ultrasonic extraction and high performance liquid chromatography].
PubMed:Pyridine metabolism and trigonelline synthesis in leaves of the mangrove legume trees Derris indica (Millettia pinnata) and Caesalpinia crista.
PubMed:NMR based geographical characterization of roasted coffee.
PubMed:Metabolic discrimination of mango juice from various cultivars by band-selective NMR spectroscopy.
PubMed:Determination of nonprotein amino acids and betaines in vegetable oils by flow injection triple-quadrupole tandem mass spectrometry: a screening method for the detection of adulterations of olive oils.
PubMed:Experimental diabetes treated with trigonelline: effect on β cell and pancreatic oxidative parameters.
PubMed:Surface plasmon resonance based biosensors for exploring the influence of alkaloids on aggregation of amyloid-β peptide.
PubMed:Multi-parametric approach to identify coffee components that regulate mechanisms of gastric acid secretion.
PubMed:Identification of nutritional descriptors of roasting intensity in beverages of Arabica and Robusta coffee beans.
PubMed:Food components with anticaries activity.
PubMed:Identification of coffee components that stimulate dopamine release from pheochromocytoma cells (PC-12).
PubMed:Variation of polyphenols and betaines in aerial parts of young, field-grown Amaranthus genotypes.
PubMed:Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark.
PubMed:Comparative genomics and functional analysis of the NiaP family uncover nicotinate transporters from bacteria, plants, and mammals.
PubMed:Betaines in fruits of Citrus genus plants.
PubMed:[Simultanenous determination of contents of four nitrogenous compounds in Pinellia peda-tisecta by HPLC].
PubMed:Methyl jasmonate deficiency alters cellular metabolome, including the aminome of tomato (Solanum lycopersicum L.) fruit.
PubMed:Identification of H₂O₂ as a major antimicrobial component in coffee.
PubMed:A validated RP-HPLC method for quantitation of trigonelline from herbal formulations containing Trigonella foenum-graecum (L.) seeds.
PubMed:Effect of coffee extracts on plasma fibrinolysis and platelet aggregation.
PubMed:Urinary N-methylpyridinium and trigonelline as candidate dietary biomarkers of coffee consumption.
PubMed:Metabolic influence of Botrytis cinerea infection in champagne base wine.
PubMed:Organic and conventional Coffea arabica L.: a comparative study of the chemical composition and physiological, biochemical and toxicological effects in Wistar rats.
PubMed:Determination of betaines in vegetable oils by capillary electrophoresis tandem mass spectrometry--application to the detection of olive oil adulteration with seed oils.
PubMed:OAT2 catalyses efflux of glutamate and uptake of orotic acid.
PubMed:Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids.
PubMed:Evaluation of selected ubiquitous contaminants in the aquatic environment and their transformation products. A pilot study of their removal from a sewage treatment plant.
PubMed:Acute effects of decaffeinated coffee and the major coffee components chlorogenic acid and trigonelline on incretin hormones.
PubMed:Nicotinamide metabolism in ferns: formation of nicotinic acid glucoside.
PubMed:Chemometric models for the quantitative descriptive sensory analysis of Arabica coffee beverages using near infrared spectroscopy.
PubMed:Anti-hyperglycemic compound (GII) from fenugreek (Trigonella foenum-graecum Linn.) seeds, its purification and effect in diabetes mellitus.
PubMed:Antiradical activity, phenolics profile, and hydroxymethylfurfural in espresso coffee: influence of technological factors.
PubMed:Metabolic signatures of lung cancer in biofluids: NMR-based metabonomics of urine.
PubMed:Methylxanthines and human health: epidemiological and experimental evidence.
PubMed:Metabolomic characterization of Italian sweet pepper (Capsicum annum L.) by means of HRMAS-NMR spectroscopy and multivariate analysis.
PubMed:[Determination of trigonelline in Trigonella foenum-graecum L. by hydrophilic interaction chromatography].
PubMed:1H NMR-based metabonomic investigation of tributyl phosphate exposure in rats.
PubMed:Coffee constituents as modulators of Nrf2 nuclear translocation and ARE (EpRE)-dependent gene expression.
PubMed:Antioxidant effectiveness of coffee extracts and selected constituents in cell-free systems and human colon cell lines.
PubMed:Determination of trigonelline in seeds and vegetable oils by capillary electrophoresis as a novel marker for the detection of adulterations in olive oils.
PubMed:Betaine yields from marine algal species utilized in the preparation of seaweed extracts used in agriculture.
PubMed:Anti-diabetic effect of trigonelline and nicotinic acid, on KK-A(y) mice.
PubMed:(1)H nuclear magnetic resonance metabolomics analysis identifies novel urinary biomarkers for lung function.
PubMed:Gut microbiome-derived metabolites characterize a peculiar obese urinary metabotype.
PubMed:Quantitative determination of caffeine, formic acid, trigonelline and 5-(hydroxymethyl)furfural in soluble coffees by 1H NMR spectrometry.
PubMed:Development of a hydrophilic liquid interaction chromatography-high-performance liquid chromatography-tandem mass spectrometry based stable isotope dilution analysis and pharmacokinetic studies on bioactive pyridines in human plasma and urine after coffee consumption.
PubMed:Pyridine salvage and nicotinic acid conjugate synthesis in leaves of mangrove species.
PubMed:Profiles of the biosynthesis and metabolism of pyridine nucleotides in potatoes (Solanum tuberosum L.).
PubMed:Association constants of pyridine and piperidine alkaloids to amyloid beta peptide determined by electrochemical impedance spectroscopy.
PubMed:Trigonelline is a novel phytoestrogen in coffee beans.
PubMed:Acetylcholinesterase enzyme inhibitory potential of standardized extract of Trigonella foenum graecum L and its constituents.
PubMed:Eusynstyelamides A, B, and C, nNOS inhibitors, from the ascidian Eusynstyela latericius.
PubMed:Anti-diabetic effects of pumpkin and its components, trigonelline and nicotinic acid, on Goto-Kakizaki rats.
PubMed:Anti-cariogenic effects of polyphenols from plant stimulant beverages (cocoa, coffee, tea).
PubMed:Betaines in four additional phyla of green plants.
PubMed:High-dosage pyridoxine-induced auditory neuropathy and protection with coffee in mice.
PubMed:Acute effects of decaffeinated coffee and the major coffee components chlorogenic acid and trigonelline on glucose tolerance.
PubMed:Protective effects of coffee-derived compounds on lipopolysaccharide/D-galactosamine induced acute liver injury in rats.
PubMed:Metabolomic studies on geographical grapes and their wines using 1H NMR analysis coupled with multivariate statistics.
PubMed:Simultaneous measurement of proline and related compounds in oak leaves by high-performance ligand-exchange chromatography and electrospray ionization mass spectrometry for environmental stress studies.
PubMed:Changes in pyridine metabolism profile during growth of trigonelline-forming Lotus japonicus cell cultures.
PubMed:Quantitative investigation of trigonelline, nicotinic acid, and nicotinamide in foods, urine, and plasma by means of LC-MS/MS and stable isotope dilution analysis.
PubMed:Electrochemiluminescent behaviors of alkaloids and tris(2,2'-bipyridine) ruthenium in organically modified silicate film.
PubMed:Discrimination between arabica and robusta green coffee varieties according to their chemical composition.
PubMed:Coffee improves auditory neuropathy in diabetic mice.
PubMed:Application of cryoprobe 1H nuclear magnetic resonance spectroscopy and multivariate analysis for the verification of corsican honey.
PubMed:Low molecular weight melanoidins in coffee brew.
PubMed:Metabonomics evaluation of urine from rats given acute and chronic doses of acetaminophen using NMR and UPLC/MS.
PubMed:Metabolic fate of nicotinamide in higher plants.
PubMed:In vitro anticholinesterase activity of various alkaloids.
PubMed:Biosynthesis of trigonelline from nicotinate mononucleotide in mungbean seedlings.
PubMed:Novel, cell-penetrating molecular transporters with flexible backbones and permanently charged side-chains.
PubMed:Validated high-performance thin-layer chromatography method for determination of trigonelline in herbal extract and pharmaceutical dosage form.
PubMed:Natural products isolated from species of Halgerda bergh, 1880 (Mollusca: Nudibranchia) and their ecological and evolutionary implications.
PubMed:Simple, sensitive, selective and validated spectrophotometric methods for the estimation of a biomarker trigonelline from polyherbal gels.
PubMed:Hydrophilic interaction chromatography coupled to nuclear magnetic resonance spectroscopy and mass spectroscopy--a new approach for the separation and identification of extremely polar analytes in bodyfluids.
PubMed:Antibacterial activity of coffee extracts and selected coffee chemical compounds against enterobacteria.
PubMed:Interrelations between glycine betaine catabolism and methionine biosynthesis in Sinorhizobium meliloti strain 102F34.
PubMed:[Coffee consumption and the decreased risk of diabetes mellitus type 2].
PubMed:A pyridinium derivative from Red Sea soft corals inhibited voltage-activated potassium conductances and increased excitability of rat cultured sensory neurones.
PubMed:[HPLC-MSn analysis of trigonelline and its metabolites in rat urine].
PubMed:Comparison of bean biochemical composition and beverage quality of Arabica hybrids involving Sudanese-Ethiopian origins with traditional varieties at various elevations in Central America.
PubMed:Formaldehyde and some fully n-methylated substances in boar seminal fluids. Short communication.
PubMed:Coffee consumption and development of type 2 diabetes.
PubMed:Validation of (1)H NMR spectroscopy as an analytical tool for methylamine metabolites in urine.
PubMed:[Transcriptional regulation of noeAB from Sinorhizobium meliloti 042BM].
PubMed:Search for natural products related to regeneration of the neuronal network.
PubMed:Interactions between volatile and nonvolatile coffee components. 1. Screening of nonvolatile components.
PubMed:Changes in trigonelline (N-methylnicotinic acid) content and nicotinic acid metabolism during germination of mungbean (Phaseolus aureus) seeds.
PubMed:Antioxidant properties of roasted coffee residues.
PubMed:Anti-invasive activity of niacin and trigonelline against cancer cells.
PubMed:Quantitative analysis of camptothecin derivatives in Nothapodytes foetida using 1H-NMR method.
PubMed:[IE-HPLC analysis of trigonelline in Fructus Quisqualis].
PubMed:NMR and HPLC-UV profiling of potatoes with genetic modifications to metabolic pathways.
PubMed:A nuclear-magnetic-resonance-based assay for betaine-homocysteine methyltransferase activity.
PubMed:Determination of biologically active substances in roasted coffees using a diode-array HPLC system.
PubMed:Trigonelline is not responsible for the acute increase in plasma homocysteine following ingestion of instant coffee.
PubMed:Betaine analogues alter homocysteine metabolism in rats.
PubMed:Effects of coffee components on the response of GABA(A) receptors expressed in Xenopus oocytes.
PubMed:[Determination of trigonelline by HPLC and study on its pharmacokinetics].
PubMed:Cassava cyanogens and free amino acids in raw and cooked leaves.
PubMed:Assessment of antimicrobial activity of hydrophilic betaines in osmotically stressed bacteria.
PubMed:[Determination of trigonelline in Trigonella foenum-graecum by HPLC].
PubMed:Identification and mapping of a major gene (Ft1) involved in fructification time in the interspecific cross Coffea pseudozanguebariae x C. liberica var. Dewevrei: impact on caffeine content and seed weight.
PubMed:Impact of the Coffea canephora gene introgression on beverage quality of C. arabica.
PubMed:Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification.
PubMed:Changes in the concentration of trigonelline in a semi-arid leguminous plant (Prosopis laevigata) induced by an arbuscular mycorrhizal fungus during the presymbiotic phase.
PubMed:Quantitative Trait Loci Associated with Foliar Trigonelline Accumulation in Glycine Max L.
PubMed:Gbu glycine betaine porter and carnitine uptake in osmotically stressed Listeria monocytogenes cells.
PubMed:In vitro effect of fenugreek extracts on intestinal sodium-dependent glucose uptake and hepatic glycogen phosphorylase A.
PubMed:Development of an analytical method for the determination of betaines in higher plants by capillary electrophoresis at low pH.
PubMed:Radical scavenging activities of niacin-related compounds.
PubMed:Antiadhesive effect of green and roasted coffee on Streptococcus mutans' adhesive properties on saliva-coated hydroxyapatite beads.
PubMed:Alkylpyridiniums. 2. Isolation and quantification in roasted and ground coffees.
PubMed:Alkylpyridiniums. 1. Formation in model systems via thermal degradation of trigonelline.
PubMed:Characterization of glycine betaine porter I from Listeria monocytogenes and its roles in salt and chill tolerance.
PubMed:Multivariate methods for characterization and classification of espresso coffees from different botanical varieties and types of roast by foam, taste, and mouthfeel.
PubMed:Betaine distribution in the Malvaceae.
PubMed:Amino acids in seeds and seedlings of the genus Lens.
PubMed:Nonprotein amino acids in edible lentil and garden pea seedlings.
PubMed:Betaine distribution in the Bromeliaceae.
PubMed:Discriminate analysis of roasted coffee varieties for trigonelline, nicotinic acid, and caffeine content.
PubMed:Inactivation of DNA replication origins by the cell cycle regulator, trigonelline, in root meristems of Lactuca sativa.
PubMed:Substrate recognition and activation mechanism of D-amino acid oxidase: a study using substrate analogs.
PubMed:Free amino acids present in commercially available seedlings sold for human consumption. A potential hazard for consumers.
PubMed:Absorption of trigonelline from the small intestine of the specific pathogen-free (SPF) and germ-free (GF) rats in vivo.
PubMed:Investigation of some methylated compounds and peroxidase activity during plant ontogenesis in snap bean.
PubMed:Changes in formaldehyde contents of germinating acorns of Quercus cerris L. under low temperature stress conditions.
PubMed:Drought stress, peroxidase activity and formaldehyde metabolism in bean plants.
PubMed:Trigonelline-induced neurite outgrowth in human neuroblastoma SK-N-SH cells.
PubMed:Benzylisoquinoline alkaloids from gnetum parvifolium
PubMed:Inhibitors of bacterial growth in urine: what is the role of betaines?
PubMed:Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia.
PubMed:The protein phosphatase inhibitor cantharidin induces head and foot formation in buds of Cassiopea andromeda (Rhizostomae, Scyphozoa).
PubMed:Taxonomic study of bacteria isolated from natural mineral waters: proposal of Pseudomonas jessenii sp. nov. and Pseudomonas mandelii sp. nov.
PubMed:Rhizobium tropici teu genes involved in specific uptake of Phaseolus vulgaris bean-exudate compounds.
PubMed:Osmoprotective properties and accumulation of betaine analogues by Staphylococcus aureus.
PubMed:Ultraviolet-B-radiation-induced changes in nicotinamide and glutathione metabolism and gene expression in plants.
PubMed:Trigonelline, a naturally occurring constituent of green coffee beans behind the mutagenic activity of roasted coffee?
PubMed:DNA relatedness among Pseudomonas strains isolated from natural mineral waters and proposal of Pseudomonas veronii sp. nov.
PubMed:UV-B- and oxidative stress-induced increase in nicotinamide and trigonelline and inhibition of defensive metabolism induction by poly(ADP-ribose)polymerase inhibitor in plant tissue.
PubMed:Accumulation of natural and synthetic betaines by a mammalian renal cell line.
PubMed:Urinary excretion of N1-methyl-2-pyridone-5-carboxylic acid and the fate of remaining of trigonelline.
PubMed:Finding of a homarine-synthesizing enzyme in turban shell and some properties of the enzyme.
PubMed:Constituents and cytotoxic principles of Nothapodytes foetida.
PubMed:Effect of natural amino alcohols on the yield of essential amino acids and the amino acid pattern in stressed barley.
PubMed:Nicotinamide, a missing link in the early stress response in eukaryotic cells: a hypothesis with special reference to oxidative stress in plants.
PubMed:Trigonelline in coffee. II. Content of green, roasted and instant coffee.
PubMed:[Trigonelline in coffee. I. Comparison of thin layer chromatography with high-performance liquid chromatography. Simultaneous determination of caffeine].
PubMed:Trigonelline and Stachydrine Released from Alfalfa Seeds Activate NodD2 Protein in Rhizobium meliloti.
PubMed:Cholinomimetic compound distinct from caffeine contained in coffee. II: Muscarinic actions.
PubMed:Betaine use by rhizosphere bacteria: genes essential for trigonelline, stachydrine, and carnitine catabolism in Rhizobium meliloti are located on pSym in the symbiotic region.
PubMed:Characterization of an osmoregulated periplasmic glycine betaine-binding protein in Azospirillum brasilense sp7.
PubMed:Betaines of alfalfa : characterization by fast atom bombardment and desorption chemical ionization mass spectrometry.
PubMed:Genetic analysis of a region of the Rhizobium meliloti pSym plasmid specifying catabolism of trigonelline, a secondary metabolite present in legumes.
PubMed:Improved delivery of acyclovir to the skin using a dihydrotrigonelline in equilibrium with trigonelline redox carrier.
PubMed:Identification of an osmotically induced periplasmic glycine betaine-binding protein from Rhizobium meliloti.
PubMed:Synthesis and availability of niacin in roasted coffee.
PubMed:The excretion of N1-methyl-2-pyridone-5-carboxylic acid and related compounds in human subjects after oral administration of nicotinic acid, trigonelline and N1-methyl-2-pyridone-5-carboxylic acid.
PubMed:Rhizobium meliloti Genes Encoding Catabolism of Trigonelline Are Induced under Symbiotic Conditions.
PubMed:Proton release from flavoprotein D-amino acid oxidase on complexation with the zwitterionic ligand, trigonelline.
PubMed:Role of inhibitors in the induction of differentiation in callus cultures of Brassica, Datura and Nicotiana.
PubMed:Uptake of glycine betaine and its analogues by bacteroids of Rhizobium meliloti.
PubMed:Nuclear incorporation of [adenine 14C]NAD is altered by compounds which affect poly(ADP-ribose) formation.
PubMed:Comparison of secondary product accumulation in photoautotrophic, photomixotrophic and heterotrophic Nicotiana tabacum cell suspension cultures.
PubMed:Development of two isogenic sweet corn hybrids differing for glycinebetaine content.
PubMed:Improved anticonvulsant activity of phenytoin by a redox brain delivery system I: Synthesis and some properties of the dihydropyridine derivatives.
PubMed:Brain-specific chemical delivery systems for beta-lactam antibiotics. In vitro and in vivo studies of some dihydropyridine and dihydroisoquinoline derivatives of benzylpenicillin in rats.
PubMed:A dihydropyridine carrier system for sustained delivery of 2',3'-dideoxynucleosides to the brain.
PubMed:Application of high performance liquid chromatography to the analysis of some non-volatile coffee components.
PubMed:Diagnostic positive and negative ion fast atom bombardment mass spectrometry of low-molecular-weight ammonium compounds of marine origin.
PubMed:Mutagenic activity of some coffee flavor ingredients.
PubMed:Further Chromone Alkaloids from Schumanniophyton magnificum.
PubMed:Improved delivery through biological membranes XXV. Enhanced and sustained delivery of trifluorothymidine to the brain using a dihydropyridine in equilibrium pyridinium salt type redox delivery system.
PubMed:Homarine (N-methylpicolinic acid) and trigonelline (N-methylnicotinic acid) appear to be involved in pattern control in a marine hydroid.
PubMed:Expression of the nodulation gene nodA in Rhizobium meliloti and localization of the gene product in the cytosol.
PubMed:Improved delivery through biological membranes XX: Nicotinamide----dihydronicotinamide based ester-linked redox carrier systems.
PubMed:Isolation and identification of N1-methylnicotinic acid (trigonelline) from rat urine.
PubMed:Epidemiological and bacteriological investigation of Serratia marcescens epidemic in a nursery and in a neonatal intensive care unit.
PubMed:The chemical components of coffee.
PubMed:[Donors and receptors of biologically labile methyl groups: characterization with a nicotinamide-trigonelline system].
PubMed:Findings of trigonelline demethylating enzyme activity in various organisms and some properties of the enzyme from hog liver.
PubMed:Determination of purine alkaloids and trigonelline in instant coffee and other beverages using high performance liquid chromatography.
PubMed:Improved delivery through biological membranes. 11. A redox chemical drug-delivery system and its use for brain-specific delivery of phenylethylamine.
PubMed:The metabolic origin of trigonelline in the rat.
PubMed:Measurement of niacin metabolites in urine by high pressure liquid chromatography. A simple, sensitive assay of niacin nutritional status.
PubMed:Production of higher levels of trigonelline by cell cultures of Trigonella foenum-graecum than by the differentiated plant.
PubMed:New synthesis of the 4- and 6-pyridones of 1-methylnicotinamide and 1-methylnicotinic acid (trigonelline).
PubMed:Chemical characterization of a hormone that promotes cell arrest in g2 in complex tissues.
PubMed:Biotyping of Serratia marcescens and its use in epidemiological studies.
PubMed:[Coffee and health].
PubMed:Isolation of homarine (N-methyl picolinic acid) and trigonelline (N-methyl nicotinic acid) from the hydroid Tubularia larynx.
PubMed:[Metabolism of nicotinic acid in plant cell suspension cultures, IV: Occurrence and metabolism of nicotinic acid N-alpha-arabinoside (author's transl)].
PubMed:[Metabolism of nicotinic acid in plant cell suspension cultures, III: Formation and metabolism of trigonelline (author's transl)].
PubMed:Trigonelline as a major urinary metabolite of niacytin in the rat.
PubMed:The metabolism of niacytin in the rat. Trigonelline as a major metabolite of niacytin in the urine.
PubMed:Hypoglycaemic effect of trigonelline.
PubMed:[Kinin-like effect of trigonelline in the yellowing test].
PubMed:Metabolism of trigonelline.
PubMed:[Tryptophan loading and vitamin B6 deficiency. I. Excretion of xanthurenic acid, kynurenine, trigonelline amide, and 5-hydroxyindoleacetic acid in various diseases].
PubMed:Biosynthesis of trigonelline.
PubMed:[N-Containing components with low molecular weight in the red field snail, Arion empiricorum. II. Hydroxylysine, alpha, gamma-diaminobutyric acid, herzynine, homarine, trigonelline, glycocoll betaine, putrescine, imidazolyl-acetic acid, -propionic acid, -lactic acid, -acrylic acid and choline].
PubMed:[Incidence of herzynine, ergothioneine, homarine, trigonelline, glycocoll betaine, choline, trimethylamine, adenine and almost all amino acids of proteins in Limulus polyphemus L].
PubMed:[Liver protective effect of trigonelline on fatty liver from carbon tetrachloride; experimental research].
PubMed:[Occurrence of trimethylamine oxide, homarine, trigonelline, and a base C4H9O2N in the crab, Crangon vulgaris].
PubMed:[Trigonelline in hormonal metabolism; fractionated determination of 17-ketosteroids in pregnant liver disease patients before and after administration of trigonelline].
PubMed:[Influence of ethionine administration on urinary excretion of trigonelline].
PubMed:Speculation on DPN as a biochemical precursor of caffeine and trigonelline in coffee.
PubMed:[Interrelationship of vitamins: effect of cocarboxylase on urinary elimination of nicotinic acid and trigonelline].
PubMed:[The occurrence of homarine, trigonelline and an new anemonine base in the Anthozoan Anemonia sulcata].
PubMed:[Studies on the metabolites of tryptophan. II. Urinary elimination of nicotinic acid and trigonelline in the child after loading with tryptophan and vitamin B6].
PubMed:[Level of nicotinic acid, trigonelline and trogonellinamide in duodenal juice in normal men].
PubMed:Studies on the biosynthesis of nicotinic acid. Part III. Effect of germination on the nicotinic-acid, nicotinuric-acid, N1-methyl-nicotinamide and trigonelline values of pulses and cereals.
PubMed:[Studies on urinary elimination of nicotinic acid, nicotinuric acid, and trigonelline in nicotinic acid and its amides tolerance tests].
PubMed:[Determination of urinary nicotinic acid and trigonelline in nicotinic acid tolerance test].
PubMed:[Not Available].
PubMed:The synthesis of 1-methyl-3-carboxylamide-6-pyridone from trigonelline.
PubMed:Conversion of trigonelline to nicotinic acid.
PubMed:On the excretion of nicotinic acid following a test dose of trigonelline.
PubMed:The urinary excretion of trigonelline- and nicotinic acid-like substances in human subjects after the ingestion of trigonelline and after smoking.
in hydra among other organisms. Alkaloid from fenugreek (Trigonella foenum-graecum) (Leguminosae), and very many other spp.; also present in coffee beans and many animals Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. It is found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth.; Trigonelline is an alkaloid with chemical formula C7H7NO2. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine.
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