7432-28-2

Usage

Uses

Used in Oxidative Stress-Related Cell Signaling Studies:
Schizandrin is utilized as a research compound for oxidative stress-related cell signaling studies. It demonstrates protective effects against glutamate-induced cytotoxicity, inhibits the production of nitric oxide (NO) and reactive oxygen species (ROS), and preserves the mitochondrial membrane potential in isolated rat cortical cells. This makes Schizandrin a promising candidate for understanding and potentially treating conditions associated with oxidative stress.
Used in Cancer Research:
Schizandrin is used as an experimental compound in cancer research, particularly for its ability to induce cell cycle arrest at the G0/G1 phase and inhibit the growth of T47D and MDA-MB-231 breast cancer cells at concentrations of 100 μM. This suggests that Schizandrin may have potential applications in the development of novel cancer treatments.
Used in Neuroprotection:
Schizandrin is employed as a neuroprotective agent, as it has been shown to reduce apoptosis induced by cisplatin in HK-2 human kidney cells. Additionally, it reverses scopolamine-induced impairment of spatial memory and the passive avoidance response in rats, indicating its potential use in the treatment of neurodegenerative diseases and conditions related to cognitive decline.
Used in Allergy Research:
Schizandrin is used as a research compound in allergy studies, as it has been shown to reduce serum levels of IgE, IgG1, IL-4, and IFN-γ in an ovalbumin-sensitized mouse model of allergy. This suggests that Schizandrin may have potential applications in the development of treatments for allergic reactions and related conditions.

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 
• 156769-17-4 schisandrin A 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 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 
• 143552-05-0 C₂₄H₃₀O₉ 
• 110397-81-4 (3aR,S-Biar)-3a,4-dihydro-6,7,8,9,10,11-hexamethoxydibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one 
• 143552-04-9 ((E)-(R)-7-Hydroxymethyl-1,2,3,10,11,12-hexamethoxy-5,6-dihydro-dibenzo[a,c]cycloocten-6-yl)-methanol 
• 103047-73-0 (R)-4-(3,4,5-Trimethoxy-benzyl)-3-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-dihydro-furan-2-one 
• 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 
• 114394-15-9 (S)-1,2,3,10,11,12-Hexamethoxy-6-methyl-7-methylene-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctene 
• 130611-54-0 C₂₄H₃₀O₇ 
• 130611-52-8 3-(6'-Bromomethyl-4,5,6,2',3',4'-hexamethoxy-biphenyl-2-yl)-2-methyl-propionaldehyde 
• 917-54-4 methyllithium 

Downstream Products

• 61281-38-7 (+)-deoxyschizandrin 
• 7432-28-2 (+)-Isoschizandrin 
• 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 
• 61281-38-7 (8R,8'R)-deoxyschizandrin 

Relevant academic research and scientific papers

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.

Regio- and stereoselective 12-O-demethylation of schizandrin into gomisin T, an important intermediate to gomisin A, by Mortierella sp. (TM-I1104)

A strain TM-I1104 identified as Mortierella sp. was discovered from soil as the most efficient fungus, which converted schizandrin into gomisin T in 91% regioselectivity by microbial 12-O-demethylation. Under optimum conditions, the yield of gomisin T reached around 80%. The faculty of 12-O-demethylation was specific on (+)-schizandrin (natural form) and the optical purity of gomisin T converted from (±)-schizandrin was 96% ee.

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.

Synthesis of optically pure gomisi lignans: The total synthesis of (+)-schizandrin, (+)-gomisin A, and (+)-isoschizandrin in naturally occurring forms

The total syntheses of (+)-schizandrin (1), (+)-gomisin A (2), and (+)-isoschizandrin (3) having natural configurations were accomplished. Optically pure butyrolactones ((-)-9, (-)-31) were transformed to α-benzylidenebutyrolactones ((+)-10, (+)-32, (+)-35). By a highly efficient iron(III) perchlorate-mediated oxidative coupling reaction of 10, 32, and 35, the key intermediates with biphenyl skeletons ((-)-11, (-)-33) were constructed with high stereoselectivity. Several methods for the stereoselective introduction of the C6-hydroxyl group were examined. For the synthesis of schizandrin and gomisin A, the Mukaiyama hydration reaction of (-)-11 and(-)-33 provided the desired products with satisfactory selectivity. For the synthesis of isoschizandrin, the stereoselective epoxidation of allylic alcohol (+)-48 was successfully utilized taking advantage of its conformational features.

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.

Synthesis of (±)-dibenzocyclooctadiene lignans, (±)-schizandrin, (±)- gomisin A and their stereoisomers, utilizing the samarium-Grignard reaction

Several (±)-dibenzocyclooctadiene lignans, (±)-schizandrin (1a) (±)- gomisin A (1b), and their stereoisomers 2a and 2b, were synthesized by the samarium-Grignard reaction of the phenylpropyl bromides 4 and the phenylacetone derivative 5 to give the erythro and threo-butanols 6 and 7 followed by oxidative aryl-aryl coupling reaction of each butanol.

The stereoselective first total synthesis of isoschizandrin having the natural configuration

The total synthesis of isoschizandrin 1 having the natural configuration was accomplished confirming the structure of 1 in unambiguous manner. Starting from optically pure 9, allylic alcohol 11 was obtained in good yield, and was then converted into epoxide 12 stereoselectively. Finally, reductive C-O bond fission afforded the natural enantiomer of isoschizandrin 1.

Synthesis of optically pure gomisin A and schizandrin: The first total synthesis of gomisin A and schizandrin having naturally occurring configurations

The total synthesis of gomisin A and schizandrin having natural configurations were accomplished for the first time. The key feature of these syntheses is a highly efficient intramolecular oxidative coupling of the intermediates 9 and 21, which can be obtained as both enantiomers in optically pure forms. The manipulation of the lactone moieties of 7 and 22 afforded natural enantiomers of schizandrin and gomisin A.

TWO LIGNANS FROM SCHISANDRA SPHENANTHERA

Two new dibenzocyclooctadiene lignans, benzoylgomisin U and tigloylgomisin O were isolated from the fruits of Schisandra sphenanthera together with known lignans, gomisin U and epigomisin O.Their structures were determined by chemical and spectral studies.The structure of isoschizandrin was also revised by advanced chemical and spectral studies.