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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H24O9
Molecular Weight 372.3671
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ELEUTHEROSIDE B

SMILES

COC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

InChI

InChIKey=QJVXKWHHAMZTBY-GCPOEHJPSA-N
InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H24O9
Molecular Weight 372.3671
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Syringin is a compound, extracted from Eleutherococcus senticosus. It is a component of herbs, which are used in traditional Chinese medicine. Several studies have demonstrated the multiple pharmacological properties of syringin, including anti-inflammatory, anti-tumor, and immunomodulatory effect. It was tested in several preclinical studies against type 2 diabetes, cardiac hypertrophy, edema, and arthritis. Syringin was shown to inhibit ICAM-1 expression and is considered as a possible treatment for acute gout.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P05362
Gene ID: 3383.0
Gene Symbol: ICAM1
Target Organism: Homo sapiens (Human)
Conditions

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
[Therapeutic effect of syringin on adjuvant arthritis in rats and its mechanisms].
2010 Aug
Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy.
2017 Jan
Syringin attenuates insulin resistance via adiponectin-mediated suppression of low-grade chronic inflammation and ER stress in high-fat diet-fed mice.
2017 Jun 17
Patents

Sample Use Guides

In a preclinical study, diabetic mice were given an every-other-day intraperitoneal injection of syringin (5 mg/kg. In another study, mice with cardiac hypertrophy were gavaged with syringin at doses of 50 mg/kg body weight (L-syringin) or 100 mg/kg body weight (syringin) for 7 weeks.
Route of Administration: Other
Murine RAW264.7 macrophages (10(6) cells/ml) were stimulated by LPS (1 ug/ml) in presence of syringin at concentrations of 62.5, 125, 250, 500, 1000 uM for 6 (TNF-alpha production assay) or 24 h (NO production assay). To study the effect of syringin on CD4+­T lymphocyte proliferation, splenocytes (5*10(6) cells/mL) were incubated with various concentrations of the drug (62.5, 125, 250, 500, 1000 uM) in the presence of Con A (1ug/ml) for 48 h. In order to test the effect of syringin on CTLL-2 proliferation stimulated by 25 IU/ml of IL-2, the cells (5*10(5) cells/mL) were incubated with the same range of concentrations of syringin in the presence of 25 IU/mL of IL-2 for 48 h.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:44:37 GMT 2023
Edited
by admin
on Fri Dec 15 19:44:37 GMT 2023
Record UNII
I6F5B11C96
Record Status Validated (UNII)
Record Version
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Name Type Language
ELEUTHEROSIDE B
USP-RS  
Common Name English
SYRINGIN
MI  
Common Name English
SINAPYL ALCOHOL 4-O-GLUCOSIDE
Common Name English
LILACIN
Common Name English
ILEXANTHIN A
Common Name English
ELEUTHEROSIDE B [USP-RS]
Common Name English
4-((1E)-3-HYDROXY-1-PROPEN-1-YL)-2,6-DIMETHOXYPHENYL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
SYRINGIN [MI]
Common Name English
LIGUSTRIN
Common Name English
NSC-287441
Code English
ELEUTHEROSIDE B (CONSTITUENT OF ELEUTHERO) [DSC]
Common Name English
MAGNOLENIN
Common Name English
SYRINGOSIDE
Common Name English
METHOXYCONIFERINE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 67006
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1234668
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
NSC
287441
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
FDA UNII
I6F5B11C96
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
MERCK INDEX
m10416
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY Merck Index
PUBCHEM
5316860
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
MESH
C028305
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
CAS
118-34-3
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
CHEBI
9380
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
WIKIPEDIA
SYRINGIN
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID2042438
Created by admin on Fri Dec 15 19:44:37 GMT 2023 , Edited by admin on Fri Dec 15 19:44:37 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT