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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H46O18
Molecular Weight 742.7182
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELEUTHEROSIDE E

SMILES

COC1=CC(=CC(OC)=C1O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]3OC[C@@H]4[C@@H]3CO[C@H]4C5=CC(OC)=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(OC)=C5

InChI

InChIKey=FFDULTAFAQRACT-JSGUJALWSA-N
InChI=1S/C34H46O18/c1-43-17-5-13(6-18(44-2)31(17)51-33-27(41)25(39)23(37)21(9-35)49-33)29-15-11-48-30(16(15)12-47-29)14-7-19(45-3)32(20(8-14)46-4)52-34-28(42)26(40)24(38)22(10-36)50-34/h5-8,15-16,21-30,33-42H,9-12H2,1-4H3/t15-,16+,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,33+,34+/m1/s1

HIDE SMILES / InChI

Molecular Formula C34H46O18
Molecular Weight 742.7182
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Eleutheroside E is one of the active constituents of the Eleutherococcus senticosus (Rupr. & Maxim.) is also called Harms (ES), Acanthopanax senticosus, Siberian ginseng, or Gasiogapi in Korea. It is a diastereoisomer of Eleutheroside D. Eleutheroside E (EE) significantly decreased the inflammatory cell infiltration, pannus formation, cartilage damage, and bone erosion of collagen-induced arthritis mice, highlighting Eleutheroside E as a potential therapeutic agent for rheumatoid arthritis. Treatment of rat mesangial cells with Eleutheroside E markedly attenuated high glucose induced cells proliferation and in a dose-dependent manner. Intervention with EE also significantly blocked high glucose induced intracellular ROS production by decreasing NADPH oxidase activity. Intervention with EE also significantly blocked high glucose induced intracellular ROS production by decreasing NADPH oxidase activity. EE mediates the hyperglycemic effects of Eleutherococcus senticosus by regulating insulin signaling and glucose utilization. The beneficial effects of EE may provide an effective and powerful strategy to alleviate diabetes. Eleutheroside E exhibited weak inhibition against CYP2C9, CYP2E1 activity, and no effect on CYP2D6 and CYP3A4. The inhibition can result in the increase of the plasma concentration and toxicity of concomitant drugs, especially for those with narrow therapeutic windows such as warfarin, phenobarbital and phenytoin.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
188.4 µM [IC50]
261.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice: 10 or 50 mg/kg body weight for 10 days, 1 h before each behavioral test
Route of Administration: Other
In Vitro Use Guide
To evaluate the effect of Eleutheroside E (EE) on impaired glucose uptake in an insulin-resistant state, we induced insulin resistance using TNF-𝛼 treatment in 3T3-L1 adipocytes and measured the effect of EE on TNF-𝛼-mediated suppression of glucose uptake. Treatment of 10 𝜇M EE for 24 h increased basal glucose uptake as well as improved TNF-𝛼-mediated suppression of glucose uptake. These data suggest that EE increases glucose uptake and could have a beneficial role in insulin-resistant diabetes.
Substance Class Chemical
Record UNII
8JP2P44H3Z
Record Status Validated (UNII)
Record Version