Schisandrol A

Names

[ Name ]:
Schisandrol A

[Synonym ]:
Schizandrin
Schisandrol A
Dibenzo[a,c]cycloocten-6-ol, 5,6,7,8-tetrahydro-1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-
schizandra
1,2,3,10,11,12-Hexamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-6-ol
Schisandrol

Biological Activity

[Description]:

Schisandrin has various therapeutic effects on a range of medical conditions such as anti-asthmatic, anti-cancer, and anti-inflammatory effects.IC50 value:Target:in vitro: Sch inhibited the pro-fibrotic activity of TGF-β1 in AML12 cells; thus, it suppressed the accumulation of ECM proteins. Also, Sch inhibited the EMT as assessed by reduced expression of vimentin and fibronectin, and increased E-cadherin and ZO-1 in TGF-β1 induced AML12 cells. Sch reduced TGF-β1-mediated phosphorylation of Smad2/3 and Smad3/4 DNA binding activity. On the other hand, Sch reduced TGF-β1-induced ERK1/2 and PI3K/Akt phosphorylation in the non-Smad pathway [1]. the anti-inflammatory properties of schisandrin result from the inhibition of nitric oxide (NO) production, prostaglandin E(2) (PGE(2)) release, cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression, which in turn results from the inhibition of nuclear factor-kappaB (NF-kappaB), c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase (MAPK) activities in a RAW 264.7 macrophage cell line [2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

Natural Products >> Phenylpropanoids

[References]

[1]. Park JH, et al. Schizandrin inhibits fibrosis and epithelial-mesenchymal transition in transforming growth factor-β1-stimulated AML12 cells. Int Immunopharmacol. 2015 Apr;25(2):276-84.

[2]. Guo LY, et al. Anti-inflammatory effects of schisandrin isolated from the fruit of Schisandra chinensis Baill. Eur J Pharmacol. 2008 Sep 4;591(1-3):293-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
576.7±50.0 °C at 760 mmHg

[ Melting Point ]:
128-129ºC

[ Molecular Formula ]:
C₂₄H₃₂O₇

[ Molecular Weight ]:
432.507

[ Flash Point ]:
302.6±30.1 °C

[ Exact Mass ]:
432.214813

[ PSA ]:
75.61000

[ LogP ]:
4.18

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.535

[ Storage condition ]:
room temp

[ Water Solubility ]:
DMSO: ≥13mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HP1626000

CHEMICAL NAME :: Dibenzo(a,c)cycloocten-6-ol, 5,6,7,8-tetrahydro-6,7-dimethyl-1,2 3,10,11,12-hexamethoxy-, stereoisomer

CAS REGISTRY NUMBER :: 7432-28-2

LAST UPDATED :: 199106

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C24-H32-O7

MOLECULAR WEIGHT :: 432.56

WISWESSER LINE NOTATION :: L B686&T&J CO1 DO1 EO1 IQ I1 J1 NO1 OO1 PO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1448 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - smooth muscle relaxant (mechanism undefined, spasmolytic) Lungs, Thorax, or Respiration - other changes Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 518 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - smooth muscle relaxant (mechanism undefined, spasmolytic) Lungs, Thorax, or Respiration - other changes Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1861 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 101,1030,1981

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
22-50/53

[ Safety Phrases ]:
60-61

[ RIDADR ]:
UN 3077 9 / PGIII

[ Hazard Class ]:
9.0

[ HS Code ]:
2932999099

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Effects of acupuncture at ST36 on pharmacokinetics of Schisandra lignans in rats.

Acupunct. Med. 33 , 223-9, (2015)

To investigate the influence of acupuncture at ST36 on the pharmacokinetics of Schisandra lignans including schisandrin, deoxyschisandrin and schisandrin B after intragastric administration of Schisan...

Comparative pharmacokinetics and tissue distribution profiles of lignan components in normal and hepatic fibrosis rats after oral administration of Fuzheng Huayu recipe.

J. Ethnopharmacol. 166 , 305-12, (2015)

Fuzheng Huayu recipe (FZHY) is formulated on the basis of Chinese medicine theory in treating liver fibrosis.To illuminate the influence of the pathological state of liver fibrosis on the pharmacokine...

The Lignan-containing Extract of Schisandra chinensis Berries Inhibits the Growth of Chlamydia pneumonia.

Nat. Prod. Commun. 10 , 1001-4, (2015)

The purpose of this study was to investigate the effect and selectivity of an extract of Schisandra chinensis berries against Chlamydia pneumoniae and C. trachomatis. Among the ethnopharmacological us...

Related Compounds

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