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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H38O17
Molecular Weight 682.6232
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TENUIFOLISIDE A

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2[C@H](O)[C@@H](CO)O[C@@]2(CO)O[C@H]3O[C@H](COC(=O)C4=CC=C(O)C=C4)[C@@H](O)[C@H](O)[C@H]3O)=CC(OC)=C1OC

InChI

InChIKey=BBUQNXDJRVCZTI-FNUXIAMKSA-N
InChI=1S/C31H38O17/c1-41-18-10-15(11-19(42-2)27(18)43-3)4-9-22(35)46-28-24(37)20(12-32)47-31(28,14-33)48-30-26(39)25(38)23(36)21(45-30)13-44-29(40)16-5-7-17(34)8-6-16/h4-11,20-21,23-26,28,30,32-34,36-39H,12-14H2,1-3H3/b9-4+/t20-,21-,23-,24-,25+,26-,28+,30-,31+/m1/s1

HIDE SMILES / InChI

Molecular Formula C31H38O17
Molecular Weight 682.6232
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24076326

Tenuifoliside a (TFSA) is a bioactive oligosaccharide ester component of Polygala tenuifolia Wild, a traditional Chinese medicine that was used to manage mental disorders effectively. It was found, that TFSA exhibited cytoprotective effects on neuronal cells. Further preclinical and clinical trials evaluating their safety, bio efficacy, and bioavailability are suggested to prove the valuable role of natural drugs in the management of depressive disorders. The strong anti-inflammatory effects of tenuifoliside A were mediated by the inhibition of the NF-κB and MAPK pathways, thus tenuifoliside A can be developed as therapeutic for inflammatory diseases.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The inhibition of JNK MAPK and NF-κB signaling by tenuifoliside A isolated from Polygala tenuifolia in lipopolysaccharide-induced macrophages is associated with its anti-inflammatory effect.
2013 Dec 5
Effect of Tenuifoliside A isolated from Polygala tenuifolia on the ERK and PI3K pathways in C6 glioma cells.
2014 Sep 15
Plant-derived natural medicines for the management of depression: an overview of mechanisms of action.
2015
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: C6 cells was exposed to Tenuifoliside A (TFSA) (or combined with ERK, PI3K and TrkB inhibitors) to examine the effects of TFSA on the cell viability and the expression and phosphorylation of key proteins in the ERK and PI3K signaling pathway. TFSA increased levels of phospho-ERK and phospho-Akt, enhanced release of BDNF, which were blocked by ERK and PI3K inhibitors, respectively (U0126 and LY294002). Moreover, the TFSA caused the enhanced phosphorylation of cyclic AMP response element binding protein (CREB) at Ser133 site, the effect was revoked by U0126, LY294002 and K252a.
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:41:03 GMT 2023
Edited
by admin
on Sat Dec 16 01:41:03 GMT 2023
Record UNII
S36S8L9Y70
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENUIFOLISIDE A
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-(1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPENYL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE), (E)-
Systematic Name English
.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE)
Systematic Name English
.ALPHA.-D-GLUCOPYRANOSIDE, 3-O-((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPENYL)-.BETA.-D-FRUCTOFURANOSYL, 6-(4-HYDROXYBENZOATE)
Systematic Name English
Code System Code Type Description
CAS
139726-35-5
Created by admin on Sat Dec 16 01:41:03 GMT 2023 , Edited by admin on Sat Dec 16 01:41:03 GMT 2023
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FDA UNII
S36S8L9Y70
Created by admin on Sat Dec 16 01:41:03 GMT 2023 , Edited by admin on Sat Dec 16 01:41:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID201104704
Created by admin on Sat Dec 16 01:41:03 GMT 2023 , Edited by admin on Sat Dec 16 01:41:03 GMT 2023
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PUBCHEM
46933844
Created by admin on Sat Dec 16 01:41:03 GMT 2023 , Edited by admin on Sat Dec 16 01:41:03 GMT 2023
PRIMARY