Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H28O6 |
| Molecular Weight | 400.4648 |
| Optical Activity | ( - ) |
| Additional Stereochemistry | Yes |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
| Stereo Comments | AXIAL, S |
SHOW SMILES / InChI
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
| 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 |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins. | 2003 Aug 15 |
|
| Schisandrin B-induced increase in cellular glutathione level and protection against oxidant injury are mediated by the enhancement of glutathione synthesis and regeneration in AML12 and H9c2 cells. | 2006 |
|
| Schisandrin B enhances doxorubicin-induced apoptosis of cancer cells but not normal cells. | 2006 Feb 28 |
|
| 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 |
|
| Inhibitory effect of schisandrin B on gastric cancer cells in vitro. | 2007 Dec 28 |
|
| Schisandrin B prevents doxorubicin-induced cardiotoxicity via enhancing glutathione redox cycling. | 2007 Nov 15 |
|
| Schisandrin B stimulates a cytoprotective response in rat liver exposed to mercuric chloride. | 2009 Nov |
|
| Schisandrin B elicits a glutathione antioxidant response and protects against apoptosis via the redox-sensitive ERK/Nrf2 pathway in AML12 hepatocytes. | 2011 Apr |
|
| Different role of Schisandrin B on mercury-induced renal damage in vivo and in vitro. | 2011 Aug 15 |
|
| Prevention and treatment of doxorubicin-induced cardiotoxicity by dexrazoxane and schisandrin B in rabbits. | 2011 Dec |
|
| The protective effects of tea polyphenols and schisandrin B on nephrotoxicity of mercury. | 2011 Dec |
|
| (-)Schisandrin B ameliorates paraquat-induced oxidative stress by suppressing glutathione depletion and enhancing glutathione recovery in differentiated PC12 cells. | 2011 Jan-Feb |
|
| The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals. | 2012 Jan |
|
| 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 |
|
| The Nrf2-ARE pathway is associated with Schisandrin b attenuating benzo(a)pyrene-Induced HTR cells damages in vitro. | 2016 Nov |
Sample Use Guides
Mice: 100, 30, or 10 mg/kg body weight every day for a total of 7 doses.
Route of Administration:
Intragastric
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
Edited
Sat Dec 16 10:29:16 UTC 2023
by
admin
on
Sat Dec 16 10:29:16 UTC 2023
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| Record UNII |
DKO6O75Z5V
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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158103
Created by
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69176-52-9
Created by
admin on Sat Dec 16 10:29:16 UTC 2023 , Edited by admin on Sat Dec 16 10:29:16 UTC 2023
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DKO6O75Z5V
Created by
admin on Sat Dec 16 10:29:16 UTC 2023 , Edited by admin on Sat Dec 16 10:29:16 UTC 2023
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