SCHISANDRIN B, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H28O6
Molecular Weight	400.4648
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RTZKSTLPRTWFEV-OLZOCXBDSA-N

InChI=1S/C23H28O6/c1-12-7-14-9-16(24-3)20(25-4)22(26-5)18(14)19-15(8-13(12)2)10-17-21(23(19)27-6)29-11-28-17/h9-10,12-13H,7-8,11H2,1-6H3/t12-,13+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H28O6
Molecular Weight	400.4648
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22848381 | https://www.ncbi.nlm.nih.gov/pubmed/1442110 | https://www.ncbi.nlm.nih.gov/pubmed/24260217 | https://www.ncbi.nlm.nih.gov/pubmed/24785966

Gomisin N is the most abundant dibenzocyclooctadiene lignan present in the traditional Chinese medicinal herb Schisandra chinensis (Turcz.) Baill. In vitro assays demonstrated that Gomisin N could inhibit TGF-β induced epithelial-mesenchymal transition of 4T1 cells and of primary human breast cancer cells. Gomisin N could maintain membrane stability of rat hepatocytes under oxidative stress. Gomisin N can reduce inflammation, inhibit apoptosis, and improve cardiac function after ischemic injury. It represents a potential novel therapeutic approach for treatment of ischemic heart disease. Gomisin N produced beneficial sedative and hypnotic bioactivity, which might be mediated by the modification of the serotonergic and GABAergic system.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
lipoprotein lipid oxidation 2 Target ID: GO:0034439 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1442110	Inhibitor 8297
TGF-beta signaling pathway 8 Target ID: map04350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22848381	Inhibitor 8297
Apoptosis 155 Target ID: WP1290 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24260217	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22848381	Primary	Preclinical	Unknown Approved Use Unknown
Liver disease 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1442110 https://www.ncbi.nlm.nih.gov/pubmed/8891674 https://www.ncbi.nlm.nih.gov/pubmed/11525242	Preventing	Preclinical	Unknown Approved Use Unknown
Myocardial infarction 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24260217	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins.	2003 Aug 15	12899939
Traditional Chinese medicines Wu Wei Zi (Schisandra chinensis Baill) and Gan Cao (Glycyrrhiza uralensis Fisch) activate pregnane X receptor and increase warfarin clearance in rats.	2006 Mar	16267138
Schisandrin B prevents doxorubicin-induced cardiotoxicity via enhancing glutathione redox cycling.	2007 Nov 15	18006777
Schisandrin B stimulates a cytoprotective response in rat liver exposed to mercuric chloride.	2009 Nov	19747521
Different role of Schisandrin B on mercury-induced renal damage in vivo and in vitro.	2011 Aug 15	21616119
Prevention and treatment of doxorubicin-induced cardiotoxicity by dexrazoxane and schisandrin B in rabbits.	2011 Dec	21994238
The protective effects of tea polyphenols and schisandrin B on nephrotoxicity of mercury.	2011 Dec	21369715
The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals.	2012 Jan	22003191
The Nrf2-ARE pathway is associated with Schisandrin b attenuating benzo(a)pyrene-Induced HTR cells damages in vitro.	2016 Nov	25946486

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 100, 30, or 10 mg/kg body weight every day for a total of 7 doses.

Route of Administration: Intragastric

In Vitro Use Guide

Malondialdehyde (MDA) formation markedly increased after the plasma of rat hepatocytes incubated with Fe2+/cysteine or Vitamin C/NADPH for 30min.Addition of Schisandrin B to the incubation mixture significantly inhibited MDA production. The inhibitory rates of MDA formation by Schisandrin B were 69 and 78, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:03:24 UTC 2023` Edited by `admin` on `Sat Dec 16 11:03:24 UTC 2023`
Record UNII	02XA4X3KZW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCHISANDRIN B, (±)-

Common Name

English

(±)-.GAMMA.-SCHIZANDRIN

Common Name

English

BENZO(3,4)CYCLOOCTA(1,2-F)(1,3)BENZODIOXOLE, 5,6,7,8-TETRAHYDRO-1,2,3,13-TETRAMETHOXY-6,7-DIMETHYL-, (6R,7S,13AR)-REL-

Systematic Name

English

.GAMMA.-SCHISANDRIN

Common Name

English

.GAMMA.-SCHIZANDRIN

Common Name

English

(±)-.GAMMA.-SCHISANDRIN

Common Name

English

SCHISANDRIN B (.GAMMA.-SCHISANDRIN) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC]

Common Name

English

WUWEIZISU B

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID60976772