SENEGENIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H45ClO6
Molecular Weight	537.128
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1(CCC3=C2[C@@H](CCl)C[C@@]4([H])[C@@]3(C)CC[C@@]5([H])[C@@](C)([C@@H](O)[C@@H](O)C[C@]45C)C(O)=O)C(O)=O

InChI

InChIKey=CWHJIJJSDGEHNS-MYLFLSLOSA-N

InChI=1S/C30H45ClO6/c1-26(2)10-11-30(25(36)37)9-6-17-22(18(30)13-26)16(15-31)12-21-27(17,3)8-7-20-28(21,4)14-19(32)23(33)29(20,5)24(34)35/h16,18-21,23,32-33H,6-15H2,1-5H3,(H,34,35)(H,36,37)/t16-,18+,19+,20-,21+,23+,27+,28+,29+,30-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23029109 | https://www.ncbi.nlm.nih.gov/pubmed/19208093 | https://www.ncbi.nlm.nih.gov/pubmed/28711507 | http://www.jbc.org/content/119/1/155.short

Senegenin (Tenuigenin) is a natural product from Polygala tenuifolia used in Chinese medicine to improve memory and intelligence. Senegenin attenuated hepatic ischemia-reperfusion induced cognitive dysfunction via increasing NR2B expression in rat hippocampus. Senegenin displayed antiapoptotic and antioxidative activity in hippocampal neurons due to scavenging of intracellular reactive oxygen species, regulating Bcl-2 family and suppressing caspase-3 activity. In vitro studies have indicated that senegenin treatment suppresses secretion of amyloid β protein and attenuate its cytotoxicity. Anti-inflammatory effect of senegenin is expressed via inhibition of NF-κB activation and was investigated in preclinical models of pneumonia, osteoarthritis, acute liver injury and other diseases.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic, NMDA 2B 5 Target ID: Q13224 Gene ID: 2904.0 Gene Symbol: GRIN2B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23029109	Activator 1430
Beta-secretase 1 21 Target ID: P56817\|\|\|Q9UJT5 Gene ID: 23621.0 Gene Symbol: BACE1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19208093	Inhibitor 8297
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26846886	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19208093	Primary	Basic research	Unknown Approved Use Unknown
Postoperative cognitive dysfunction 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23029109	Primary	Preclinical	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26846886	Primary	Basic research	Unknown Approved Use Unknown
Pneumonia 90 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28711507	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tenuifolin, an extract derived from tenuigenin, inhibits amyloid-beta secretion in vitro.	2009 Aug	19208093
Senegenin attenuates hepatic ischemia-reperfusion induced cognitive dysfunction by increasing hippocampal NR2B expression in rats.	2012	23029109
Tenuigenin Prevents IL-1β-induced Inflammation in Human Osteoarthritis Chondrocytes by Suppressing PI3K/AKT/NF-κB Signaling Pathway.	2016 Apr	26846886
Protective effects of tenuigenin on Staphylococcus aureus-induced pneumonia in mice.	2017 Sep	28711507

Patents

Sample Use Guides

In Vivo Use Guide

In a study of ischemia-reperfusion induced cognitive dysfunction in rats, senegenin was administered orally at doses 15, 30 and 60 mg/kg once per day.

Route of Administration: Oral

In Vitro Use Guide

To measure effect of senegenin on amyloid-beta secretion, COS-7 cells transfected with APP695 cDNA or the Swedish mutation (COS 695 Swe) were cultured in humidified air with tenuifolin (0.5-2.0 ug/mL). Cell media were collected after tenuifolin treatment and then diluted within the linear range of each assay. Sandwiched enzyme-linked immunosorbent assays were used to detect Ab1-40 and Ab1-42 levels following the manufacturer’s instructions. Ab was visualized using a horseradish peroxidase-conjugated anti-rabbit immunoglobulin antibody.

Name

Type

Language

SENEGENIN

Common Name

English

SENEGENIN [MI]

Common Name

English

TENUIGENIN

Common Name

English

12-(CHLOROMETHYL)-2.BETA.,3.BETA.-DIHYDROXY-27-NOROLEAN-13-ENE-23,28-DIOIC ACID

Systematic Name

English

27-NOROLEAN-13-ENE-23,28-DIOIC ACID, 12-(CHLOROMETHYL)-2,3-DIHYDROXY-, (2.BETA.,3.BETA.,4.ALPHA.,12.ALPHA.)-

Systematic Name

English

Code System Code Type Description

FDA UNII

06S1QH951L