ECHINOCYSTIC ACID Chemical Properties

Melting point:

299-300°C

Boiling point:

585.0±50.0 °C(Predicted)

Density 

1.14

storage temp. 

2-8°C

solubility 

DMF:30.0(Max Conc. mg/mL);63.46(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:2):0.33(Max Conc. mg/mL);0.7(Max Conc. mM)

form 

powder

pka

4.43±0.70(Predicted)

color 

White

InChIKey

YKOPWPOFWMYZJZ-XVTBUTEGNA-N

SMILES

[C@@]12(CCC(C)(C)C[C@@]1([H])C1=CC[C@]3([H])[C@@]4(C)CC[C@H](O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)C[C@H]2O)C(=O)O |&1:0,7,12,14,18,23,27,29,32,r|

LogP

7.580 (est)

ECHINOCYSTIC ACID Usage And Synthesis

Description

Echinocystic acid is a triterpene that has been found in G. sinensis and has diverse biological activities. It induces nuclear translocation of the glucocorticoid receptor (GR) and reduces TNF-α-induced NF-κB signaling in HEK293 cells overexpressing GFP-GR. Echinocystic acid (12.5, 25, and 50 μM) suppresses RANKL-induced NF-κB activation, ERK phosphorylation, and osteoclastogenesis in mouse bone marrow macrophages (BMMs). It induces neurite outgrowth in Neuro2A cells in a concentration-dependent manner, an effect that can be blocked by the JNK inhibitor SP 600125 . In vivo, echinocystic acid (10 mg/kg per day) decreases escape latency in the Morris water maze and increases the length of neurite processes in the hippocampus of aged mice. Topical administration of echinocystic acid reduces expression of COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β and ear edema induced by phorbol 12-myristate 13-acetate (TPA; ) in a mouse model of dermatitis. Echinocystic acid also recovers reductions in femoral bone mineral density and trabecular thickness and number in a rat model of ovariectomy-induced osteoporosis.

Chemical Properties

White powder, soluble in methanol, ethanol, DMSO and other organic solvents, from the soap horn, legumes from the acacia Albizzia julibrissin Durazz. inflorescences, pig's tooth soap.

Uses

Echinocystic Acid is a potential entry inhibitor for the HCV infection.

Definition

ChEBI: Echinocystic acid is a triterpenoid.

in vivo

References

[1] DEMETRA GEORGATZA . The triterpene echinocystic acid and its 3-O-glucoside derivative are revealed as potent and selective glucocorticoid receptor agonists[J]. International Journal of Biochemistry & Cell Biology, 2016, 79: Pages 277-287. DOI: 10.1016/j.biocel.2016.08.028
[2] JIAN-HUI YANG . Echinocystic acid inhibits RANKL-induced osteoclastogenesis by regulating NF-κB and ERK signaling pathways[J]. Biochemical and biophysical research communications, 2016, 477 4: Pages 673-677. DOI: 10.1016/j.bbrc.2016.06.118
[3] HYE JIN PARK. Echinocystic Acid Facilitates Neurite Outgrowth in Neuroblastoma Neuro2a Cells and Enhances Spatial Memory in Aged Mice.[J]. Biological & pharmaceutical bulletin, 2017, 40 10: 1724-1729. DOI: 10.1248/bpb.b17-00324
[4] EUN-HA JOH  Dong H K  Jin Ju Jeong. Inhibitory effect of echinocystic acid on 12-O-tetradecanoylphorbol-13-acetate-induced dermatitis in mice[J]. Archives of Pharmacal Research, 2013, 37 2: 225-231. DOI: 10.1007/s12272-013-0092-8
[5] YA-TING DENG. Osteoprotective Effect of Echinocystic Acid, a Triterpone Component from Eclipta prostrata, in Ovariectomy-Induced Osteoporotic Rats.[J]. PLoS ONE, 2015: e0136572. DOI: 10.1371/journal.pone.0136572

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