SCHISANDRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H32O7
Molecular Weight	432.5067
Optical Activity	UNSPECIFIED
Additional Stereochemistry	Yes
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0
Stereo Comments	AXIAL, R

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C(OC)=C1OC)C3=C(OC)C(OC)=C(OC)C=C3C[C@](C)(O)[C@@H](C)C2

InChI

InChIKey=YEFOAORQXAOVJQ-RZFZLAGVSA-N

InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.sciencedirect.com/science/article/pii/S0040403901916843 | https://www.ncbi.nlm.nih.gov/pubmed/25573619 | https://www.ncbi.nlm.nih.gov/pubmed/20727999 | https://www.ncbi.nlm.nih.gov/pubmed/19585470

Schisandrin is a bioactive compound found in Schisandra chinensis. Schisandrin exhibits antioxidant properties and ameliorates ovariectomy-induced memory impairment in rats, and Aβ1-42-induced memory impairment in mice. Schisandrin has an anti-asthmatic effect on OVA-induced airway inflammation in a murine asthma model. The compound inhibits proliferation of breast cancer cell lines at concentrations of 20-100 uM.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet-activating factor receptor 3 Target ID: P25105 Gene ID: 5724.0 Gene Symbol: PTAFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10220282	Antagonist 2778		250.0 µM [IC50]
reactive oxygen species biosynthetic process 37 Target ID: GO:1903409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20727999	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22829961	Primary	Preclinical	Unknown Approved Use Unknown
Allergic asthma 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20727999	Primary	Preclinical	Unknown Approved Use Unknown
Drug-induced liver injury 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1668771	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19585470	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Bioactivity of neolignans from fructus Schizandrae.	1991	1668771
Structure-activity relationships of lignans from Schisandra chinensis as platelet activating factor antagonists.	1999 Mar	10220282
Growth inhibition and cell cycle arrest in the G0/G1 by schizandrin, a dibenzocyclooctadiene lignan isolated from Schisandra chinensis, on T47D human breast cancer cells.	2010 Feb	19585470
Anti-asthmatic effect of schizandrin on OVA-induced airway inflammation in a murine asthma model.	2010 Nov	20727999
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	25753323
Schizandrin ameliorates ovariectomy-induced memory impairment, potentiates neurotransmission and exhibits antioxidant properties.	2015 May	25573619

Patents

Sample Use Guides

In Vivo Use Guide

In a study of cognitive dysfunction in ovariectomized rats schizandrin was administered orally at 10 and 30 mg/kg

Route of Administration: Oral

In Vitro Use Guide

Effect of schisandrin on proliferation of breast cancer cell lines was determined with the sulforhodamine B protein staining method. T47D and MDA-MB-213 cells were treated with 0.8 - 100 uM of schisandrin for 3 days.

Name

Type

Language

SCHISANDRIN

Official Name

English

7ALPHA-HYDROXYSCHIZANDRONOL

Common Name

English

SCHISANDRINE

Common Name

English

SCHISANDRIN [INCI]

Common Name

English

WUWEIZICHUN A

Common Name

English

SCHIZANDRINE

Common Name

English

SCHISANDRIN (SCHISANDROL A) (CONSTITUENT OF NORTHERN SCHISANDRA) [DSC]

Common Name

English

DIBENZO(A,C)CYCLOOCTEN-6-OL, 5,6,7,8-TETRAHYDRO-1,2,3,10,11,12-HEXAMETHOXY-6,7-DIMETHYL-, (6S,7S,12AR)-

Systematic Name

English

SCHISANDRIN [USP-RS]

Common Name

English

WUWEIZI ALCOHOL A

Common Name

English

(+)-SCHIZANDRIN

Common Name

English

SCHIZANDROL

Common Name

English

SCHIZANDRIN

Common Name

English

Code System Code Type Description

FDA UNII

G01BQC0879