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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
Structure of ECHINOCYSTIC ACID

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

HIDE SMILES / InChI
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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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

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
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.
Name Type Language
ECHINOCYSTIC ACID
Common Name English
OLEAN-12-EN-28-OIC ACID, 3,16-DIHYDROXY-, (3.BETA.,16.ALPHA.)-
Common Name English
OLEAN-12-EN-28-OIC ACID, 3.BETA.,16.ALPHA.-DIHYDROXY-
Common Name English
Code System Code Type Description
FDA UNII
L4DUW10YOF
Created by admin on Sat Dec 16 06:50:15 GMT 2023 , Edited by admin on Sat Dec 16 06:50:15 GMT 2023
PRIMARY
PUBCHEM
73309
Created by admin on Sat Dec 16 06:50:15 GMT 2023 , Edited by admin on Sat Dec 16 06:50:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-112-3
Created by admin on Sat Dec 16 06:50:15 GMT 2023 , Edited by admin on Sat Dec 16 06:50:15 GMT 2023
PRIMARY
CAS
510-30-5
Created by admin on Sat Dec 16 06:50:15 GMT 2023 , Edited by admin on Sat Dec 16 06:50:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID70965278
Created by admin on Sat Dec 16 06:50:15 GMT 2023 , Edited by admin on Sat Dec 16 06:50:15 GMT 2023
PRIMARY