Trigonelline chloride

Names

[ Name ]:
Trigonelline chloride

[Synonym ]:
Pyridinium, 3-carboxy-1-methyl-, chloride (1:1)
3-Carboxy-1-methylpyridinium chloride
Trigonelline hydroch
TRIGONELLINE HCL
trigonellinium chloride
1-Methyl-3-pyridiniumcarboxylathydrochlorid
TRIGONELLIN HYDROCHLORIDE
1-Methylpyridinium-3-carboxylate hydrochloride (1:1)
EINECS 228-119-5
N-METHYLNICOTINIC ACID BETAINE HYDROCHLORIDE
1-Méthyl-3-pyridiniumcarboxylate chlorhydrate
1-methylnicotinic acid chloride
Pyridinium, 3-carboxy-1-methyl-, chloride
N-methylpyridinium-3-carboxylate hydrochloride
1-Methyl-3-pyridiniumcarboxylate hydrochloride
MFCD00077250
Trigonelline chloride

Biological Activity

[Description]:

Trigonelline chloride, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Metabolic Disease

[In Vitro]

It is found that Trigonelline chloride (TG) significantly rescues the morphology of the H9c2 cells. Treatment of cells with Trigonelline chloride attenuates H2O2 induced cell deaths and improves the antioxidant activity. In addition, Trigonelline chloride regulates the apoptotic gene caspase-3, caspase-9 and anti-apoptotic gene Bcl-2, Bcl-XL during H2O2 induced oxidative stress in H9c2 cells. For evident, flow cytometer results also confirm that Trigonelline chloride significantly reduces the H2O2 induced necrosis and apoptosis in H9c2 cells. However, further increment of Trigonelline chloride concentration against H2O2 can induce the necrosis and apoptosis along with H2O2[1].

[In Vivo]

Trigonelline chloride decreases bone mineralization and tends to worsen bone mechanical properties in streptozotocin-induced diabetic rats. In nicotinamide/streptozotocin-treated rats, Trigonelline chloride significantly increases bone mineral density (BMD) and tends to improve cancellous bone strength. Trigonelline chloride differentially affects the skeletal system of rats with streptozotocin-induced metabolic disorders, intensifying the osteoporotic changes in streptozotocin-treated rats and favorably affecting bones in the non-hyperglycemic (nicotinamide/streptozotocin-treated) rats[2].

[Cell Assay]

The H9c2 cells are seeded in the 96 well at a density of 1×105 cells/well. The cells are treated with different concentrations of Trigonelline chloride (TG) (25 to 150 μM) and hydrogen peroxide (25 to 125 μM). It is incubated at 37°C in 5% CO2 incubator for 24 h and 6 h respectively and then the culture is treated with the water soluble tetrazolium (WST) reagent incubated for 2 h to 4 h. The living cells absorb the WST then it is converted into an orange colour product. Then, the intensity of colour is measured at 450 nm using spectra count ELISA reader. For cardio protective activity, the cells are seeded and separated into six groups: control, H2O2 alone, the rest of groups are initially exposed to different concentration (25 to 125 μM) of Trigonelline chloride for 48 hours. Then, 100 μM of H2O2 is added and incubated for 4 hours, after, read the absorbance at 450 nm for cell viability assay[1].

[Animal admin]

Three-month-old female Wistar rats are used in this study. The animals are divided into five groups (n=10): Control rats, Streptozotocin-treated control rats, Streptozotocin-treated rats receiving Trigonelline chloride (50 mg/kg p.o. daily), Nicotinamide/streptozotocin-treated control rats, and Nicotinamide/streptozotocin-treated rats receiving Trigonelline chloride (50 mg/kg p.o. daily). Administration of Trigonelline chloride starts two weeks after streptozotocin and lasts four weeks. Trigonelline chloride is administered once daily by a stomach tube. All control rats receive tap water (the vehicle) at the same volume of 2 mL/kg p.o. The four-week period of Trigonelline chloride administration is long enough to demonstrate skeletal effects of Trigonelline chloride and other compounds of plant origin in rats. The rats are fasted overnight after the last Trigonelline chloride or vehicle administration. The next day, the blood glucose level is measured and the rats are anesthetized with ketamine and xylazine, and then sacrificed by cardiac exsanguination[2].

[References]

[1]. Ilavenil S, et al. Trigonelline protects the cardiocyte from hydrogen peroxide induced apoptosis in H9c2 cells. Asian Pac J Trop Med. 2015 Apr;8(4):263-8.

[2]. Joanna Folwarczna, et al. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System. Nutrients. 2016 Mar; 8(3): 133.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
~260 °C (dec.)

[ Molecular Formula ]:
C₇H₈ClNO₂

[ Molecular Weight ]:
173.597

[ Exact Mass ]:
173.024353

[ PSA ]:
44.01000

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Preliminary studies on trigonelline as potential anti-Alzheimer disease agent: determination by hydrophilic interaction liquid chromatography and modeling of interactions with beta-amyloid.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 968 , 101-4, (2014)

For trigonelline, a quaternary-base pyridine alkaloid of presumed Alzheimer's disease-preventing activity, a method of determination has been proposed, based on the hydrophilic interaction chromatogra...

Conversion of nicotinic acid to trigonelline is catalyzed by N-methyltransferase belonged to motif B' methyltransferase family in Coffea arabica.

Biochem. Biophys. Res. Commun. 452(4) , 1060-6, (2014)

Trigonelline (N-methylnicotinate), a member of the pyridine alkaloids, accumulates in coffee beans along with caffeine. The biosynthetic pathway of trigonelline is not fully elucidated. While it is qu...

Pyridine metabolism in tea plants: salvage, conjugate formation and catabolism.

J. Plant Res. 125(6) , 781-91, (2012)

Pyridine compounds, including nicotinic acid and nicotinamide, are key metabolites of both the salvage pathway for NAD and the biosynthesis of related secondary compounds. We examined the in situ meta...