1,3-Dicaffeoylquinic acid

Names

[ CAS No. ]:
19870-46-3

[ Name ]:
1,3-Dicaffeoylquinic acid

[Synonym ]:
(1S,3R,4R,5R)-1,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-4,5-dihydroxycyclohexanecarboxylic acid
1,5-Dicaffeoylquinic acid
1,3-Dicaffeoylquinic acid
Cynarine
1,5-di-O-Caffeoylquinic acid
1,3-O-Dicaffeoylquinic acid
(1S,3R,4R,5R)-1,3-Bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexanecarboxylic acid
Cyclohexanecarboxylic acid, 1,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-, (1S,3R,4R,5R)-
1,3-di-O-Caffeoylquinic acid

Biological Activity

[Description]:

1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative that exhibits antioxidant activity and radical scavenging activity.

[Related Catalog]:

Signaling Pathways >> PI3K/Akt/mTOR >> Akt

Signaling Pathways >> PI3K/Akt/mTOR >> PI3K

Natural Products >> Acids and Aldehydes

Research Areas >> Neurological Disease

[Target]

Akt

PI3K

[In Vitro]

1,3-Dicaffeoylquinic acid shows increased neuronal cell viability against Aβ(42) toxicity in a concentration-dependent manner in neurons. 1,3-Dicaffeoylquinic acid activates both phosphoinositide 3-kinase (PI3K)/Akt and extracellular regulated protein kinase 1/2 (Erk1/2) with stimulating their upstream tyrosine kinase A (Trk A). 1,3-Dicaffeoylquinic acid's anti-apoptotic potential is related to the enhanced inactivating phosphorylation of glycogen synthase kinase 3β (GSK3β) and the modulation of expression of apoptosis-related protein Bcl-2/Bax[2]. 1,3-Dicaffeoylquinic acid (10 μM, 20 μM, 50 μM, and 100 μM) significantly increases cell viablity before OGD/reperfusion, and prevents the depletion of GSH under OGD/reperfusion insult. 1,3-Dicaffeoylquinic acid induces nuclear translocation of Nrf2 in OGD/reperfusion treated astrocytes, and induces increased GCL activity, and the effect is lost in Nrf2 siRNA-transfected cells[3].

[In Vivo]

1,3-Dicaffeoylquinic acid (32.0 mg/kg, p.o.) and 1-O-ABL are absorbed very quickly in Wistar rats. The maximum plasma concentrations for 1,3-Dicaffeoylquinic acid and 1-O-ABL are 44.5 ± 7.1 and 19.1 ± 6.9 ng/mL, respectively[1].

[Kinase Assay]

The whole cellular lysate is prepared using a RIPA Lysis Buffer added to a reaction buffer containing 0.1 M Tris (pH 8.2), 0.15 M KCl, 10 mM ATP, 10 mM l-glutamate, 20 mM MgCl2, and 2 mM EDTA at 37°C for 3 min, and then 5 mM cysteine is added at 37°C for 15 min. The production of glutamylcysteine is immediately quantified for HPLC analysis by O-phthalaldehyde derivatization. GCL activity is presented in units of femtomoles of -GC produced per milligram of protein per minute[3].

[Cell Assay]

The viability of astrocytes is measured by the MTT reduction method. Briefly, the cells are rinsed with phosphate-buffered saline, pH 7.2, and incubated with 5 mg/mL MTT reagent for 3 h at 37°C. The medium is removed, and the cells are lysed with 1 mL of dimethyl sulfoxide. The absorbance is measured at 540 nm by a microplate reader[3].

[Animal admin]

Six male Wistar rats (200-250 g) are fasted for 12 h with free access to water prior to oral administration of I. britannica extract with an herb dose of 8.0 g/kg (equivalent to 32.0 mg/kg 1,3-Dicaffeoylquinic acid, and 4.01 mg/kg, 1-O-ABL). Blood samples (appr 0.25 mL) are collected from suborbital vein into heparinized tubes at 0, 0.08, 0.16, 0.33, 0.67, 1, 1.5, 2, 4, 6, 9 and 12 h after dosing, and then immediately centrifuged at 3500 rpm for 10 min. Harvested plasma samples are stored at -60°C until analysis. The plasma concentrations of 1,3-Dicaffeoylquinic acid and 1-O-ABL are calculated from the calibration curves obtained daily[1].

[References]

[1]. Wang Z, et al. An LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and 1-O-acetylbritannilactone in rat plasma and its application to a pharmacokinetic study.

[2]. Xiao HB, et al. 1,5-dicaffeoylquinic acid protects primary neurons from amyloid β 1-42-induced apoptosis via PI3K/Akt signaling pathway. Chin Med J (Engl). 2011 Sep;124(17):2628-35.

[3]. Cao X, et al. 1, 5-Dicaffeoylquinic acid-mediated glutathione synthesis through activation of Nrf2 protects against OGD/reperfusion-induced oxidative stress in astrocytes. Brain Res. 2010 Aug 6;1347:142-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
819.9±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₂₄O₁₂

[ Molecular Weight ]:
516.451

[ Flash Point ]:
278.1±27.8 °C

[ Exact Mass ]:
516.126770

[ PSA ]:
211.28000

[ LogP ]:
1.64

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.719

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
soluble5mg/mL, clear, colorless to light yellow

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport