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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
Structure of TRIGONELLINE

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

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Elevated glycine betaine excretion in diabetes mellitus patients is associated with proximal tubular dysfunction and hyperglycemia.
1999 Feb
Substrate recognition and activation mechanism of D-amino acid oxidase: a study using substrate analogs.
2000 Aug
Free amino acids present in commercially available seedlings sold for human consumption. A potential hazard for consumers.
2000 Mar
Trigonelline is not responsible for the acute increase in plasma homocysteine following ingestion of instant coffee.
2004 Sep
Search for natural products related to regeneration of the neuronal network.
2005
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles.
2011 Aug
Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark.
2011 Oct 28
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
The estrogenic effect of trigonelline and 3,3-diindolymethane on cell growth in non-malignant colonocytes.
2016 Jan
Patents

Patents

Sample Use Guides

500 mg trigonelline
Route of Administration: Oral
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.
Name Type Language
TRIGONELLINE
HSDB   MI  
Common Name English
CAFFEARINE
Common Name English
COFFEARINE
Common Name English
GYNESINE
Common Name English
TRIGONELLINE [MI]
Common Name English
TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED) [DSC]
Common Name English
NICOTINIC ACID N-METHYLBETAINE
Common Name English
3-CARBOXY-1-METHYLPYRIDINIUM INNER SALT
Common Name English
TRIGONELLINE [HSDB]
Common Name English
TRIGONELLINE [USP-RS]
Common Name English
Code System Code Type Description
CHEBI
18123
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-620-5
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
MESH
C009560
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
WIKIPEDIA
TRIGONELLINE
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
RS_ITEM_NUM
1686411
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
CAS
535-83-1
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
MERCK INDEX
m11133
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID2026230
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
HSDB
7684
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
PUBCHEM
5570
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY
FDA UNII
3NQ9N60I00
Created by admin on Fri Dec 15 18:01:28 GMT 2023 , Edited by admin on Fri Dec 15 18:01:28 GMT 2023
PRIMARY