GLPBio

1,3-Dicaffeoylquinic acid

Catalog No.: GC35037Purity:>98.50%Synonyms: 1,5-DCQA, 1,3-Dicaffeoylquinic Acid
COASDSData Sheet
1,3-Dicaffeoylquinic acid inhibits the 3' end processing, terminal connection, and disintegration process of HIV-1 integrase, with IC50 values of 0.35, 0.56, and 0.84μg/ml respectively.

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1,3-Dicaffeoylquinic acid
Cas No.: 19870-46-3
10mM (in 1mL DMSO)In Stock
$102.00
1
1mgIn Stock
$370.00
1
5mgIn Stock
$84.00
1
10mgIn Stock
$132.00
1
25mgIn Stock
$270.00
1
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Description

1,3-Dicaffeoylquinic acid inhibits the 3' end processing, terminal connection, and disintegration process of HIV-1 integrase, with IC50 values of 0.35, 0.56, and 0.84μg/ml respectively [1]. 1,3-Dicaffeoylquinic acid is a type of phenolic compound found in artichokes [2]. 1,3-Dicaffeoylquinic acid possesses antioxidant activity and is a free radical scavenger [3].

In vitro, 1,3-Dicaffeoylquinic acid (0.25-1μM; 30min) reduces the free radical levels released by human polymorphonuclear cells (PMNs) stimulated by the chemokine N-formyl-Met-Leu-Phe in a dose-dependent manner [4]. 1,3-Dicaffeoylquinic acid (0, 5, 10, 50, 100, and 500μM; 2h) pretreatment increases the cell viability of rat primary cortical neurons stimulated by amyloid β1-42 (Aβ42) in a concentration-dependent manner, activates Trk A and PI3K/Akt and Erkl/2 pathways, inhibits GSK3β and regulates Bcl-2/Bax expression [5].

In vivo, local administration of 1,3-Dicaffeoylquinic acid (5-500μg/mL; 5μL; 7 days) dose-dependently reduces corneal epithelial defects in dry eye disease (DED) model mice and increases tear production, while inhibiting inflammatory cytokines and T cell infiltration in the ocular surface and lacrimal glands [6]. In the forced swimming test and tail suspension test, treatment with 1,3-Dicaffeoylquinic acid (30mg/kg/day; 5 days; p.o.) significantly improves depressive-like behavior in ovariectomized (OVX) model mice [7].

References:
[1] Robinson, W.E., Jr., Cordeiro, M., Abdel-Malek, S., et al. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 50(4), 846-855 (1996).
[2] Jun N J, Jang K C, Kim S C, et al. Radical scavenging activity and content of cynarin (1, 3-dicaffeoylquinic acid) in Artichoke (Cynara scolymus L.)[J]. Journal of applied biological chemistry, 2007, 50(4): 244-248.
[3] Danino O, Gottlieb H E, Grossman S, et al. Antioxidant activity of 1, 3-dicaffeoylquinic acid isolated from Inula viscosa[J]. Food research international, 2009, 42(9): 1273-1280.
[4] Heilmann, J., Merfort, I., and Weiss, M.Radical scavenger activity of different 3',4'-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescencePlanta Med.61(5)435-438(1995).
[5] Xiao HB, Cao X, Wang L, 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;124(17):2628-2635.
[6] Yoon CH, Jang HJ, Ryu JS, et al. 1,5-Dicaffeoylquinic acid from Pseudognaphalium affine ameliorates dry eye disease via suppression of inflammation and protection of the ocular surface. Ocul Surf. 2023;29:469-479.
[7] Lim D W, Kim M, Yoon M, et al. 1, 3-Dicaffeoylquinic acid as an active compound of Arctium lappa root extract ameliorates depressive-like behavior by regulating hippocampal nitric oxide synthesis in ovariectomized mice[J]. Antioxidants, 2021, 10(8): 1281.

Protocol

Cell experiment [1]:

Cell lines

Neurons cells

Preparation Method

Neurons were grown in a 96-well plate (approximate 5x104 cells/ml). Cells were first treated with several concentrations of Aβ42 (0, 5, 10, 20, 40, and 80μM) for 6 hours to explore the appropriate toxic concentration. In another part of the experiment, to observe the protective effect of 1,3-Dicaffeoylquinic acid, the neurons were pretreated with several concentrations of 1,3-Dicaffeoylquinic acid (0, 5, 10, 50, 100, and 500μM) alone for 2 hours and then co-treated with 40μM Aβ42 for 6 hours and washed carefully several times with phosphate-buffered saline (PBS). The cell viability was determined using the CCK-8 method.

Reaction Conditions

0, 5, 10, 50, 100 and 500μM; 2h

Applications

1,3-Dicaffeoylquinic acid pretreatment increased the cell viability of rat primary cortical neurons stimulated by Aβ42 in a concentration-dependent manner.
Animal experiment [2]:

Animal models

C57BL/6N mice (Ovariectomy)

Preparation Method

After the 1-week acclimatization period, female C57BL/6N mice were anesthetized with 2% isoflurane. Both ovaries were ovariectomized (OVX) via small bilateral dorsal flank incisions and subsequent removal of ovaries at 6 weeks of age. OVX mice were divided into four groups (n = 8 mice per group) as follows: (1) Group 1, OVX animals receiving 0.9% saline (p.o.) and vehicle (i.p.); (2) Group 2, OVX animals receiving 1,3-Dicaffeoylquinic acid 30mg/day (p.o.) and vehicle (i.p.); (3) Group 3, OVX animals receiving 0.9% saline (p.o.) and 7-NI (selective nNOS inhibitor, i.p.); (4) Group 4, OVX animals receiving 1,3-Dicaffeoylquinic acid 30mg/day (p.o.) and 7-NI (i.p.). The OVX mice were administered i.p. injection of 7-NI (50mg/kg) once daily for 5 days, while those in the untreated 7-NI groups were injected with an equal volume of vehicle (0.9% saline with 1% DMSO and 1% Tween 80). On day 5, behavior analysis was initiated 1h after treatment was administered.

Dosage form

30mg/kg/day; 5 days; p.o.

Applications

In the forced swimming test and tail suspension test, 1,3-Dicaffeoylquinic acid treatment significantly improved the depressive-like behaviors in mice induced by OVX.

References:
[1] Xiao HB, Cao X, Wang L, et al. 1,5-dicaffeoylquinic acid protects primary neurons from amyloid ? 1-42-induced apoptosis via PI3K/Akt signaling pathway. Chin Med J (Engl). 2011;124(17):2628-2635.
[2] Lim D W, Kim M, Yoon M, et al. 1, 3-Dicaffeoylquinic acid as an active compound of Arctium lappa root extract ameliorates depressive-like behavior by regulating hippocampal nitric oxide synthesis in ovariectomized mice[J]. Antioxidants, 2021, 10(8): 1281.

Product Documents

Purity:>98.50%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
19870-46-3
Synonyms
1,5-DCQA, 1,3-Dicaffeoylquinic Acid
SMILES
O=C([C@@]1(OC(/C=C/C2=CC=C(O)C(O)=C2)=O)C[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@H](O)[C@H](O)C1)O
Molecular Formula
C25H24O12
Molecular Weight
516.45
Solubility
DMSO: 100 mg/mL (193.63 mM)
Storage
Store at -20°C, protect from light
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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