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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24O6
Molecular Weight 384.4224
Optical Activity UNSPECIFIED
Additional Stereochemistry Yes
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0
Stereo Comments AXIAL, S

SHOW SMILES / InChI
Structure of SCHISANDRIN C

SMILES

COC1=C2OCOC2=CC3=C1C4=C(C[C@@H](C)[C@@H](C)C3)C=C5OCOC5=C4OC

InChI

InChIKey=HTBWBWWADZJXID-TXEJJXNPSA-N
InChI=1S/C22H24O6/c1-11-5-13-7-15-19(27-9-25-15)21(23-3)17(13)18-14(6-12(11)2)8-16-20(22(18)24-4)28-10-26-16/h7-8,11-12H,5-6,9-10H2,1-4H3/t11-,12+

HIDE SMILES / InChI

Molecular Formula C22H24O6
Molecular Weight 384.4224
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Schisandrins (schizandrins) are a group of bioactive chemical compounds found in Schisandra chinensis, one member of which is Schisandrin C. Schizandrin C exerts anti-neuroinflammatory effects by upregulating phase II detoxifying/antioxidant enzymes via cAMP/PKA/CREB and Nrf-2 signaling. Also was shown, that among human hepatocellular carcinoma cells (Bel-7402), human breast cancer cells (Bcap37) and human nasopharyngeal carcinoma cells (KB-3-1), Bel-7402 cells were most sensitive with IC50 equal to 81.58 ± 1.06 μ M after treatment with schisandrin C. Although the mechanism of tumor inhibiting activity of schisandrin C is not clarified, there are some reports about dibenzocyclooctadiene lignans inducing cancer cell apoptosis. Further investigations are needed to determine in more detail the molecular mechanism, such as the dependent pathway of this apoptotic process, the signal transduction pathways involved and the possible changes in expression of other apoptosis-related genes. Recently was also speculated, that Schisandrin C offered protection against Aβ1-42 -induced dysfunction in learning and memory by inhibiting total cholinesterase and its antioxidant action.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Schisandrin C Ameliorates Learning and Memory Deficits by Aβ(1-42) -induced Oxidative Stress and Neurotoxicity in Mice.
2015 Sep
Patents

Patents

Sample Use Guides

mice: 1 mmol/kg at day, 3 days
Route of Administration: Other
In Vitro Use Guide
Among human hepatocelluar carcinoma cells (Bel-7402), human breast cancer cells (Bcap37) and human nasopharyngeal carcinoma cells (KB-3-1), Bel-7402 cells were most sensitive with IC50 equal to 81.58 ± 1.06 μ M after treatment with schisandrin C for 48 h. Cytotoxicity of schisandrin C on tumor cells depends on cellular accumulation of the drug. Cells were placed within 96-well culture plates (104 cells/well) respectively, and allowed to attach for 24 h before treatment. The cells were treated with schisandrin C ranging from 12.5 to 200 μ m or without (vehicle control, 0.5% DMSO) schisandrin C for cell lines. Schisandrin C cytotoxicity was measured after 48 h of culture using the MTT assay.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:51:21 UTC 2023
Edited
by admin
on Sat Dec 16 10:51:21 UTC 2023
Record UNII
C8754W6B3G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SCHISANDRIN C
Common Name English
CYCLOOCTA(1,2-F:3,4-F')BIS(1,3)BENZODIOXOLE, 5,6,7,8-TETRAHYDRO-13,14-DIMETHOXY-6,7-DIMETHYL-, (6R,7S,13AS)-
Systematic Name English
(-)-WUWEIZISU C
Common Name English
(S)-(-)-SCHISANDRIN C
Common Name English
SCHIZANDRIN C
Common Name English
WUWEIZISU C
Common Name English
Code System Code Type Description
FDA UNII
C8754W6B3G
Created by admin on Sat Dec 16 10:51:21 UTC 2023 , Edited by admin on Sat Dec 16 10:51:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID101317497
Created by admin on Sat Dec 16 10:51:21 UTC 2023 , Edited by admin on Sat Dec 16 10:51:21 UTC 2023
PRIMARY
PUBCHEM
443027
Created by admin on Sat Dec 16 10:51:21 UTC 2023 , Edited by admin on Sat Dec 16 10:51:21 UTC 2023
PRIMARY
CAS
61301-33-5
Created by admin on Sat Dec 16 10:51:21 UTC 2023 , Edited by admin on Sat Dec 16 10:51:21 UTC 2023
PRIMARY
SMS_ID
100000175519
Created by admin on Sat Dec 16 10:51:21 UTC 2023 , Edited by admin on Sat Dec 16 10:51:21 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT