| Identification | Back Directory | [Name]
WUWEIZISU C | [CAS]
61301-33-5 | [Synonyms]
WUWEIZISU C
,8-dimethyl-
SCHIZANDRIN C
WUWEIZISU C USP/EP/BP
(S)-(-)-Schisandrin C
Schisandrin C >=98% (HPLC)
Schisandrin C (Schizandrin-C
Schisandrin C
(S)-(-)-Schisandrin C
cycloocta(1,2-f:3,4-f’)bis(1,3)benzodioxole6,7,8,9-tetrahydro-1,13-dimethoxy-7
(6R,7S,13aS)-5,6,7,8-Tetrahydro-13,14-dimethoxy-6,7-dimethylcycloocta[1,2-f:3,4-f']bis[1,3]benzodioxole
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)- | [Molecular Formula]
C22H24O6 | [MDL Number]
MFCD00272170 | [MOL File]
61301-33-5.mol | [Molecular Weight]
384.42 |
| Chemical Properties | Back Directory | [Melting point ]
122-123℃ | [Boiling point ]
549.2±50.0 °C(Predicted) | [density ]
1.232 | [storage temp. ]
2-8°C | [solubility ]
DMSO : 8.33 mg/mL (21.67 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble) | [form ]
powder | [color ]
White | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [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 | [InChIKey]
HTBWBWWADZJXID-UHFFFAOYSA-N | [SMILES]
COC1=C2C(OCO2)=CC3=C1C(C(OC)=C(OCO4)C4=C5)=C5CC(C)C(C)C3 | [LogP]
5.623 (est) |
| Hazard Information | Back Directory | [Description]
Schisandrin C is a lignan originally isolated from Schizandrae that has diverse biological activities.1,2,3,4,5 It decreases viability of U937 cells in a concentration-dependent manner and induces cell cycle arrest at the G1 phase when used at a concentration of 100 μM.2 Schisandrin C (5-20 μM) decreases hydrogen peroxide-induced cell death and production of reactive oxygen species (ROS) in C2C12 skeletal muscle cells.3 It also decreases levels of matrix metalloproteinase-2 (MMP-2), MMP-9, COX-2, VCAM-1, IL-1β, and TNF-α in hydrogen peroxide-stimulated C2C12 cells. Schisandrin C decreases lipoteichoic acid-induced production of nitric oxide (NO), prostaglandin E2 (PGE2; Item No. 14010), TNF-α, IL-1β, and IL-6 in mouse primary microglia.4 In vivo, schisandrin C (200 mg/kg) decreases serum alanine amino transferase (ALT) and aspartate amino transferase (AST) activity, increases hepatic mitochondrial and total glutathione (GSH) levels, and reduces liver injury in a mouse model of acetaminophen-induced liver injury partially via inhibition of the cytochrome P450 (CYP) isoforms CYP2E1, CYP1A2, and CYP3A11.5 | [Chemical Properties]
Colorless crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Schisandra chinensis. | [Uses]
Schisandrin C potently inhibits proprotein convertase subtillsin-kexin type 9 (PCSK9) mRNA expression. Also, it displays strong protective effects in SH-SY5Y cells against serum and glucose deprivation (SGD) injury. | [in vivo]
Schisandrin C (lateral ventricle injection (i.c.v.); 15-150 μg/kg; 5 days) reduces Aβ1-42-induced memory deficits in the Y-maze test. Neurons in the hippocampus of SCH-C (15 μg/kg)-treated group returned to normal level, and and SCH-C group (150 μg/kg) has slight neuroprotective effects Aβ1-42-induced group. SCH-C (15 μg/kg) recoveres the activities of SOD and GSHPx and the ratios of GSH, decreases the levels of ChEtotal in the brain of the Aβ1–42-induced amnesic mice simultaneously[3]. | Animal Model: | Aβ1-42-induced Alzheimer’s disease mice[3] | | Dosage: | 15-150 μg/kg | | Administration: | Lateral ventricle injection (i.c.v.); 15-150 μg/kg; 5 days | | Result: | Exhibited potent neuroprotective effects linking to anti-ChEtotal activities and anti-oxidative mechanisms in Aβ1-42-induced amnestic mice. |
| [References]
[1] LI X Y. Bioactivity of neolignans from fructus Schizandrae.[J]. Memorias do Instituto Oswaldo Cruz, 1991, 86 Suppl 2: 31-37. DOI: 10.1590/s0074-02761991000600010
[2] CHEOL PARK. Induction of G1 arrest and apoptosis by schisandrin C isolated from Schizandra chinensis Baill in human leukemia U937 cells.[J]. International journal of molecular medicine, 2009, 24 4: 495-502. DOI: 10.3892/ijmm_00000258
[3] JEONG-SEOK KIM Ho K Y. Schisandrin C enhances mitochondrial biogenesis and autophagy in C2C12 skeletal muscle cells: potential involvement of anti-oxidative mechanisms.[J]. Naunyn-Schmiedeberg’s archives of pharmacology, 2018, 391 2: 197-206. DOI: 10.1007/s00210-017-1449-1
[4] SUN YOUNG PARK . Schizandrin C exerts anti-neuroinflammatory effects by upregulating phase II detoxifying/antioxidant enzymes in microglia[J]. International immunopharmacology, 2013, 17 2: Pages 415-426. DOI: 10.1016/j.intimp.2013.06.032
[5] YIMING JIANG . Hepato-protective effects of six schisandra lignans on acetaminophen-induced liver injury are partially associated with the inhibition of CYP-mediated bioactivation[J]. Chemico-Biological Interactions, 2015, 231: Pages 83-89. DOI: 10.1016/j.cbi.2015.02.022 |
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