7432-28-2

Basic information

• Product Name: Schisandrin
• Synonyms: SCHIZANDROL;SCHIZANDROL A;SCHIZANDRIN;SCHISANDRIN;SCHISANDROL A;WUWEIZI ALCOHOL A;dibenzo(a,c)cycloocten-6-ol,5,6,7,8-tetrahydro-6,7-dimethyl-1,23,10,11,12-hex;schizandra
• CAS NO: 7432-28-2
• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.51
• Product Categories: Miscellaneous Natural Products;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 7432-28-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 128.5°C
• Boiling Point: 466.17°C (rough estimate)
• Flash Point: 302.6 °C
• Appearance: white to beige/
• Density: 1.1480 (rough estimate)
• Vapor Pressure: 3.87E-14mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: room temp
• Solubility: DMSO: ≥13mg/mL
• PKA: 14.58±0.40(Predicted)
• CAS DataBase Reference: Schisandrin(CAS DataBase Reference)
• NIST Chemistry Reference: Schisandrin(7432-28-2)
• EPA Substance Registry System: Schisandrin(7432-28-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 7432-28-2(Hazardous Substances Data)

Usage

Description

Schizandrin is a dibenzocyclooctadiene lignan and a major component of S. chinensis and has diverse biological activities. It induces cell cycle arrest at the G0/G1 phase and inhibits growth of T47D and MDA-MB-231 breast cancer cells when used at a concentration of 100 μM. Schizandrin (10 and 100 μM) prevents glutamate-induced cytotoxicity, inhibits production of nitric oxide (NO) and reactive oxygen species (ROS), and preserves the mitochondrial membrane potential in isolated rat cortical cells. It reduces apoptosis induced by cisplatin in HK-2 human kidney cells. In vivo, schizandrin (1 and 10 mg/kg, p.o.) reverses scopolamine-induced impairment of spatial memory and the passive avoidance response in rats. It enhances oxotremorine-induced tremors in mice. Schizandrin (10 mg/kg) reduces serum levels of IgE, IgG1, IL-4, and IFN-γ in an ovalbumin-sensitized mouse model of allergy.

Uses

Schizandrin may be used in oxidative stress-related cell signaling studies.

Biochem/physiol Actions

Schizandrin is a natural product with several biological properties involved with antioxidant and anti-inflammatory activities. It reduces the formation of ROS, inhibits the mitochondrial pathway of the apoptotic process and oxidative stress. Schizandrin has been reported to have hepatoprotective, antitumor, antiviral, and antiamnesic effects, and has neuroprotective activity against glutamate induced neurotoxicity.

InChI:InChI=1/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1

Upstream product

• 72551-73-6 gomisin A 
• 77-78-1 dimethyl sulfate 
• 130611-54-0 C₂₄H₃₀O₇ 
• 143552-06-1 Methanesulfonic acid (6S,7R)-6-hydroxy-7-methanesulfonyloxymethyl-1,2,3,10,11,12-hexamethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-6-ylmethyl ester 
• 143552-06-1 Methanesulfonic acid (6S,7R)-7-hydroxy-7-methanesulfonyloxymethyl-1,2,3,10,11,12-hexamethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-6-ylmethyl ester 
• 143552-06-1 Methanesulfonic acid (6R,7S)-7-hydroxy-7-methanesulfonyloxymethyl-1,2,3,10,11,12-hexamethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cycloocten-6-ylmethyl ester 
• 63558-03-2 (6S,7R)-1,2,3,10,11,12-Hexamethoxy-6,7-dimethyl-6,7-dihydro-dibenzo[a,c]cyclooctene-5,8-dione 
• 143552-05-0 C₂₄H₃₀O₉ 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 103047-73-0 α-<3.4.5-Trimethoxy-benzyliden>-β-<3.4.5-trimethoxy-benzyl>-γ-butyrolacton 
• 65171-10-0 (+/-)-4-(3,4,5-trimethoxyphenyl)-4,5-dihydro-2(3H)-furanone 
• 110397-81-4 C₂₄H₂₆O₈ 
• 148812-44-6 ((E)-(S)-7-Hydroxymethyl-1,2,3,10,11,12-hexamethoxy-7,8-dihydro-dibenzo[a,c]cycloocten-6-yl)-methanol 

Downstream Products

• 7432-28-2 isoschizandrin 
• 119139-66-1 (7S,8S,R-biar)-6,7,8,9-tetrahydro-1,2,3,13,14-pentamethoxy-7,8-dimethyl-7,12-dibenzocyclooctenediol 
• 7432-28-2 (+)-Isoschizandrin 
• 61281-38-7 (+)-deoxyschizandrin 
• 61281-38-7 (8R,8'R)-deoxyschizandrin 

Relevant articles and documents

Extracts with liver-X-receptor modulators, compounds and their use in weight control and treatment of disorders of lipid metabolism

The invention relates to the use, or methods (especially with regard to animals, especially human, that are in need of such treatment) comprising the use, of an extract and/or one or more natural compounds from plants or parts of plants, respectively, from a genus selected from the group consisting of Schisandra, Illicium, Kadsura, Steganotaenia and Magnolia, alone or as supplement, as active ingredient in the regulation of body weight and/or fat loss and/or for the management of obesity, either in humans or in animals, to the use of said extract and/or natural compound(s) or mixtures in the manufacture of a pharmaceutical or nutraceutical formulation for the regulation of body weight and/or fat loss and/or for the management of obesity either in humans or in animals. The above extract and/or compound(s) can further be used to reduce one or more adverse metabolic parameters in a subject, such as the blood cholesterol level, especially the "bad" low density lipid (LDL) cholesterol. The invention relates also to said extract and/or compound(s) for use in the treatment or in the preparation of a medicament for the treatment of obesity and/or elevated blood cholesterol, as well as their preparation. It also relates to pharmaceutical or nutraceutical formulations comprising said extract and/or natural compound(s) which are useful in the regulation of body weight and/or fat loss and/or for the management of obesity.

Total Synthesis of (+)-Isoschizandrin Utilizing a Samarium(II) Iodide-Promoted 8-Endo Ketyl-Olefin Cyclization

The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine.

Non-enzymic and enzymic oxygenations of a dibenzocyclooctadiene lignan, (±)-deoxyschizandrin: Implications for biosynthesis of the corresponding lignans

Non-enzymic and enzymic oxygenation reactions of (±)-dibenzocyclooctadiene lignan, (±)-deoxyschizandrin (1) using a simple model system for mono-oxygenases Fe(MeCN)62+-Ac2O-H2O2 and rat liver S9 mix were investigated in connection with mammalian and plant metabolisms of the corresponding lignans. The non-enzymic reaction of 1 gave the two phenol acetates 4a and 5a and a quinone 6, and the enzymic reaction of 1 afforded several compounds for which three compounds characterized as 7, 8 and 9 were isolated. The latter results has implications for biosynthesis of these lignans.