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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(OC)C5=C(OCO5)C=C4C[C@H](C)[C@H](C)C3

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

Description

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

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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.