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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O7
Molecular Weight 416.4642
Optical Activity UNSPECIFIED
Additional Stereochemistry Yes
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0
Stereo Comments AXIAL, R

SHOW SMILES / InChI
Structure of BESIGOMSIN

SMILES

COC1=C(OC)C(OC)=C2C(C[C@](C)(O)[C@@H](C)CC3=C2C(OC)=C4OCOC4=C3)=C1

InChI

InChIKey=ZWRRJEICIPUPHZ-MYODQAERSA-N
InChI=1S/C23H28O7/c1-12-7-13-8-16-20(30-11-29-16)22(28-6)17(13)18-14(10-23(12,2)24)9-15(25-3)19(26-4)21(18)27-5/h8-9,12,24H,7,10-11H2,1-6H3/t12-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H28O7
Molecular Weight 416.4642
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/17241377

Gomisin A (BESIGOMSIN/GA) one of the major dibenzocyclooctadiene lignans isolated from Schisandra chinensis Baill, has proved to possess a variety of pharmacological effects. It has been found to promote hepatocyte growth factor, limit lipid peroxidation, and inhibit apoptosis in acute hepatic injury animal models. Besigomsine also acts as an anti-inflammatory by preventing the release of arachidonic acid in macrophages in vitro. Laboratory evidence suggests that Besigomsine may have anticarcinogenic effects. Chronic administration of Gomisin A had an antihypertensive effect in AngII-induced hypertensive mice. Gomisin A may exert neuroprotective effects by attenuating the microglia-mediated neuroinflammatory response via inhibiting the TLR4-mediated NF-κB and MAPKs signaling pathways. Also it induces marked protective effects against hepatic and renal injury induced by CCl(4) exposure through differential regulation of the MAPK signal transduction pathway.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of gomisin A on the promotor action and serum bile acid concentration in hepatocarcinogenesis induced by 3'-methyl-4-dimethylamino-azobenzene.
1995 Oct
Hepato-protective effects of six schisandra lignans on acetaminophen-induced liver injury are partially associated with the inhibition of CYP-mediated bioactivation.
2015 Apr 25
Schisandrol B protects against acetaminophen-induced hepatotoxicity by inhibition of CYP-mediated bioactivation and regulation of liver regeneration.
2015 Jan
Patents

Sample Use Guides

rats: 100 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Schisandrol B (BESIGOMSIN) was investigated for their inhibitory activity on NFAT transcription. IC 50 is 16.37 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:40:41 UTC 2023
Edited
by admin
on Sat Dec 16 17:40:41 UTC 2023
Record UNII
L5U70J87J8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BESIGOMSIN
INN   JAN  
INN  
Official Name English
besigomsin [INN]
Common Name English
SCHISANTHERINOL B
Common Name English
WUWEIZICHUN B
Common Name English
(+)-GOMISIN A
Common Name English
TJN-101
Code English
GOMISIN A
Common Name English
(+)-(6S,7S, BIAR-R)-5,6,7,8-TETRAHYDRO-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYLBENZO(3,4)CYCLOOCTA(1,2-F)(1,3)BENZODIOXOL-6-OL
Common Name English
SCHISANDROL B (GOMISIN A) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC]
Common Name English
SCHIZANDROL B
Common Name English
TJN 101
Code English
BENZO(3,4)CYCLOOCTA(1,2-F)(1,3)BENZODIOXOL-6-OL, 5,6,7,8-TETRAHYDRO-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYL-, (6S,7S,13AR)-
Systematic Name English
WUWEIZI ALCOHOL B
Common Name English
BESIGOMSIN [JAN]
Common Name English
SCHISANDROL B
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2080
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL403578
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
CAS
58546-54-6
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
FDA UNII
L5U70J87J8
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
SMS_ID
100000086072
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
WIKIPEDIA
Gomisin A
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
NCI_THESAURUS
C74244
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
INN
7001
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
PUBCHEM
3001662
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID7048950
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
EVMPD
SUB05787MIG
Created by admin on Sat Dec 16 17:40:41 UTC 2023 , Edited by admin on Sat Dec 16 17:40:41 UTC 2023
PRIMARY
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