ChemicalBook CAS DataBase List 61281-38-7

61281-38-7

Name	Schisandrin A
CAS	61281-38-7
Molecular Formula	C22H28O6
MDL Number	MFCD00221760
Molecular Weight	388.45
MOL File	61281-38-7.mol

Chemical Properties

Melting point	116-117 °C
Boiling point	544.2±50.0 °C(Predicted)
density	1.080±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	powder
color	White to Off-White
Major Application	metabolomics vitamins, nutraceuticals, and natural products
InChI	1S/C24H32O6/c1-13-9-15-11-17(25-3)21(27-5)23(29-7)19(15)20-16(10-14(13)2)12-18(26-4)22(28-6)24(20)30-8/h11-14H,9-10H2,1-8H3/t13-,14+
InChIKey	JEJFTTRHGBKKEI-OKILXGFUSA-N
SMILES	C[C@@H](C1)[C@H](C)CC2=C(C3=C1C=C(OC)C(OC)=C3OC)C(OC)=C(OC)C(OC)=C2
LogP	5.870 (est)

Safety Data

Safety Statements	24/25 less more
WGK Germany	3
RTECS	HP1595000
HS Code	29093090
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

White powder

Description

Schisandrin A is a lignan that has been found in Schisandra and has diverse biological activities. It binds to adiponectin receptor 2 (IC₅₀ = 3.2 μM). Schisandrin A (10, 20, and 50 μM) reduces LPS-induced production of nitric oxide (NO), IL-6, and TNF-α and apoptosis in primary mouse microglial cells. It reverses P-glycoprotein-mediated doxorubicin resistance in MCF-7/dox cells when used at a concentration of 20 μM. Schisandrin A (4, 12, and 36 mg/kg) reverses short-term and spatial memory deficits, as well as decreases in cerebral superoxide dismutase (SOD) and glutathione peroxidase (GPX) activities induced by amyloid β (1-42) (Aβ42; ) in a mouse model of Alzheimer’s disease.

Uses

Schizandrin A is an extract from Schisandra chinesis. a dibenzocyclooctadiene lignan with antiinflammatory activity.

in vivo

Schisandrin A (SchA) significantly inhibits CYP3A activity in rat hepatic microsomes and V_max value of each group in a concentration-dependent manner. The double-reciprocal plots and the secondary plot show that Schisandrin A inhibits CYP3A activity, with an apparent K_i value of 30.67 mg/kg. In each Schisandrin A-treated group, Schisandrin A also significantly decreases 1-hydroxymidazolam plasma concentrations compared with the negative group (to levels similar to the positive group)^[2].

IC 50

CYP3A: 6.6 μM (IC₅₀); Autophagy

References

[1] YIYI SUN. Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay.[J]. PLoS ONE, 2013: e63354. DOI: 10.1371/journal.pone.0063354
[2] FANG-JIAO SONG. Schizandrin A Inhibits Microglia-Mediated Neuroninflammation through Inhibiting TRAF6-NF-κB and Jak2-Stat3 Signaling Pathways[J]. PLoS ONE, 2016, 11 1. DOI: 10.1371/journal.pone.0149991
[3] ZONG-LIN ZHANG Su R W Qing Cheng Jiang. Schisandrin A reverses doxorubicin-resistant human breast cancer cell line by the inhibition of P65 and Stat3 phosphorylation.[J]. Breast Cancer, 2018, 25 2: 233-242. DOI: 10.1007/s12282-017-0821-9
[4] DI HU. Deoxyschizandrin isolated from the fruits of Schisandra chinensis ameliorates Aβ????-induced memory impairment in mice.[J]. Planta medica, 2012, 78 12: 1332-1336. DOI: 10.1055/s-0032-1315019

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