Schizandrin C

Names

[ Name ]:
Schizandrin C

[Synonym ]:
(6R,7S)-13,14-dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole (non-preferred name)
1,3-Benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole, 5,6,7,8-tetrahydro-13,14-dimethoxy-6,7-dimethyl-, (6R,7S)-
13,14-Dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole
1,3-Benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole, 5,6,7,8-tetrahydro-13,14-dimethoxy-6,7-dimethyl-
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)-
Schisandrin C
(6R,7S)-13,14-Dimethoxy-6,7-dimethyl-5,6,7,8-tetrahydro[1,3]benzodioxolo[5',6':3,4]cycloocta[1,2-f][1,3]benzodioxole

Biological Activity

[Description]:

Schisandrin C is a phytochemical lignan isolated from Schizandra chinensis Baill; shows anticancer-effects in human leukemia U937 cells.IC50 value:Target: in vitro: Schisandrin C inhibited cell growth in a dose-dependent manner, which was associated with the induction of G1 arrest of the cell cycle and apoptosis. Schisandrin C induced G1 arrest was correlated with down-regulation of cyclin D1, cyclin E, cyclin-dependent kinase (Cdk) 4 and E2Fs expression, inhibition of phosphorylation of retinoblastoma protein (pRB), and up-regulation of the Cdk inhibitor p21(WAF1/CIP1). In addition, schisandrin C-induced apoptosis was associated with down-regulation of expression of the anti-apoptotic proteins Bcl-2 and Bcl-xL, proteolytic activation of caspase-3 and -9, and a concomitant degradation of poly(ADP-ribose) polymerase (PARP). Furthermore, schisandrin C-induced apoptosis was significantly inhibited by a caspase-3 specific inhibitor z-DEVD-fmk [1]. Schisandrin C was found to reduce nitric oxide (NO) production from LPS-stimulated Raw 264.7 cells. Pre-treatment of Raw 264.7 cells with gomisin J, gomisin N, or schisandrin C reduced the expression of mRNA and the secretion of pro-inflammatory cytokines [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Phenylpropanoids

[References]

[1]. Park C, et al. Induction of G1 arrest and apoptosis by schisandrin C isolated from Schizandra chinensis Baill in human leukemia U937 cells. Int J Mol Med. 2009 Oct;24(4):495-502.

[2]. Oh SY, et al. Anti-inflammatory effects of gomisin N, gomisin J, and schisandrin C isolated from the fruit of Schisandra chinensis. Biosci Biotechnol Biochem. 2010;74(2):285-91.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
549.2±50.0 °C at 760 mmHg

[ Melting Point ]:
122-123ºC

[ Molecular Formula ]:
C₂₂H₂₄O₆

[ Molecular Weight ]:
384.422

[ Flash Point ]:
226.7±30.0 °C

[ Exact Mass ]:
384.157288

[ PSA ]:
55.38000

[ LogP ]:
7.05

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.573

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GX9500000

CAS REGISTRY NUMBER :: 61301-33-5

LAST UPDATED :: 199309

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H24-O6

MOLECULAR WEIGHT :: 384.46

WISWESSER LINE NOTATION :: T F5 D6 C865 GO IO TO VO HH UH&&T&&J BO1 EO1 N1 O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

REFERENCE :: CMJODS Chinese Medical Journal (Beijing, English Edition). (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1975- Adopted vol. no. 92 in 1979. Volume(issue)/page/year: 93,41,1980

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
Xi

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
GX9500000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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