Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H48O4 |
Molecular Weight | 472.6997 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1([C@H](O)C[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O
InChI
InChIKey=YKOPWPOFWMYZJZ-PRIAQAIDSA-N
InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21+,22-,23+,27-,28+,29+,30+/m0/s1
Echinocystic acid (EA) is a pentacyclic triterpene isolated from the fruits of Gleditsia sinensis Lam, has potent antioxidant, anti-inflammatory and anti-tumor properties. Echinocystic acid (EA) inhibit the formation of osteoclast. EA inhibit RANKL-induced NF-κB activation and ERK phosphorylation in BMMs. Echinocystic acid inhibits IL-1β-induced COX-2 and iNOS expression in human osteoarthritis chondrocytes. Echinocystic acid also inhibited TPA-induced myeloperoxidase activity, as well as COX-2, iNOS, TNF-α and IL-1β expressions. Echinocystic acid inhibited NF-κB in TPA-treated mouse ears, as well as in lipopolysaccharide-stimulated peritoneal macrophages. Its potency is comparable with that of dexamethasone. These findings indicate that echinocystic acid may ameliorate inflammatory diseases, such as dermatitis. EA inhibited ACAT and DGAT, with IC50 values of 103 and 139 uM, respectively, and exhibited no significant effect on HMG-CoA reductase activity. The present findings suggest that EA may exert hypolipidemic effect by inhibiting the activity of ACAT and DGAT.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28966244
Curator's Comment: In in vivo experiments, EA treatment increased neurite outgrowth in aged mouse hippocampus. Moreover, EA treatment enhanced spatial learning and memory in aged mice.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 |
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Target ID: CHEMBL2782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24669228 |
103.0 µM [IC50] | ||
Target ID: CHEMBL6009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24669228 |
139.0 µM [IC50] | ||
Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24650713 |
1.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Anti-AIDS agents, 21. Triterpenoid saponins as anti-HIV principles from fruits of Gleditsia japonica and Gymnocladus chinensis, and a structure-activity correlation. | 1995 Sep |
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Beta-D-xylopyranosyl-(1-->3)-beta-D-glucuronopyranosyl echinocystic acid isolated from the roots of Codonopsis lanceolata induces caspase-dependent apoptosis in human acute promyelocytic leukemia HL-60 cells. | 2005 May |
|
Protective effects of echinocystic acid isolated from Gleditsia sinensis Lam. against acute myocardial ischemia. | 2010 Jan |
|
Synthesis and anti-HCV entry activity studies of β-cyclodextrin-pentacyclic triterpene conjugates. | 2014 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28966244
The effect of EA (10 mg/kg/d for 3 d, p.o.)
on spatial learning and memory of aged mice was evaluated
using the Morris water maze task.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28966244
To investigate the influences
of Echinocystic acid (EA) on neurite outgrowth, Neuro2a cells were
treated with EA in a concentration-dependent manner (0, 5,
10, 15 and 20 uM) for 6 h. EA promoted neurite outgrowth
in a concentration-dependent manner.
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L4DUW10YOF
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73309
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208-112-3
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510-30-5
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DTXSID70965278
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SUBSTANCE RECORD