Details
Stereochemistry | ACHIRAL |
Molecular Formula | C7H7NO2 |
Molecular Weight | 137.136 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[N+]1=CC(=CC=C1)C([O-])=O
InChI
InChIKey=WWNNZCOKKKDOPX-UHFFFAOYSA-N
InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28816550Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19324944 | https://www.ncbi.nlm.nih.gov/pubmed/28816550 | https://www.ncbi.nlm.nih.gov/pubmed/23108405
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28816550
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19324944 | https://www.ncbi.nlm.nih.gov/pubmed/28816550 | https://www.ncbi.nlm.nih.gov/pubmed/23108405
Trigonelline is a pyridine derivative known to contribute indirectly to the formation of desirable flavor products, including furans, pyrazine, alkyl-pyridines, and pyrroles, during coffee roasting. The amount of trigonelline in arabica is higher than that in robusta green coffee beans, and thus it can be used as a marker compound to distinguish the coffee bean species. During the roasting process of coffee beans, trigonelline changes into N-methylpyridinium and nicotinic acid as its major products, which makes it a useful index of the degree of roasting. The importance of trigonelline in coffee is connected to nutritional aspects. It has been revealed in recent studies that the administration of trigonelline allows diabetic rats to avoid diabetes-related organ damage and live longer, which can make it a potentially strong candidate for industrial application as a pharmacological agent for the treatment of hyperglycemia, hyperlipidemia, and liver/kidney dysfunctions. In addition, the urinary concentrations of trigonelline and its thermal product N-methylpyridinium of coffee drinkers are higher than those of noncoffee drinkers, which indicates that trigonelline and N-methylpyridinium may have potential as dietary biomarkers that could be used as analytical probes to control compliance in human intervention studies on coffee. Trigonelline has been isolated from many plants: fenugreek seeds (Trigonella foenum-graecum, hence the name), garden peas, hemp seed, oats, potatoes, Stachys species, dahlia, Strophanthus species, and Dichapetalum cymosum. In a randomized cross-over trial, the critical effect of Trigonelline on glucose tolerance has been studied during a 2-hour oral glucose tolerance test (OGTT) in 15 overweight men. Results showed that glucose and insulin concentrations significantly reduced 15minutes after Trigonelline consumption compared with placebo.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0038066 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23304193 |
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Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12444669 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia. | 1999 Feb |
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Substrate recognition and activation mechanism of D-amino acid oxidase: a study using substrate analogs. | 2000 Aug |
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Free amino acids present in commercially available seedlings sold for human consumption. A potential hazard for consumers. | 2000 Mar |
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Trigonelline is not responsible for the acute increase in plasma homocysteine following ingestion of instant coffee. | 2004 Sep |
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Search for natural products related to regeneration of the neuronal network. | 2005 |
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Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | 2010 May |
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Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles. | 2011 Aug |
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Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark. | 2011 Oct 28 |
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Pseudomonas aeruginosa pyocyanin activates NRF2-ARE-mediated transcriptional response via the ROS-EGFR-PI3K-AKT/MEK-ERK MAP kinase signaling in pulmonary epithelial cells. | 2013 |
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The estrogenic effect of trigonelline and 3,3-diindolymethane on cell growth in non-malignant colonocytes. | 2016 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19324944
500 mg trigonelline
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23108405
Panc1 and Colo357 cells were used for activity evaluation. Cells were cultured in RPMI 1640 containing 10% FCS, 1% L-glutamine and 1% sodium pyruvate (all from PAA-Laboratories). Cells were cultured at 37 C, 5% CO2 and 85% humidity. ARE-luciferase assays conducted with Panc1 and Colo357 cells subject to trig (Trigonelline) treatment at various concentrations (0.01–10 mkM) for 16 h revealed a dose-dependent inhibition of ARE-driven luciferase expression by trig.
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208-620-5
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C009560
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TRIGONELLINE
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SUBSTANCE RECORD