Schisanhenol

CAS# 69363-14-0

Schisanhenol

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Quality Control of Schisanhenol

Number of papers citing our products

Chemical structure

Schisanhenol

3D structure

Chemical Properties of Schisanhenol

Cas No. 69363-14-0 SDF Download SDF
PubChem ID 73057 Appearance White powder
Formula C23H30O6 M.Wt 402.48
Type of Compound Lignans Storage Desiccate at -20°C
Synonyms Schizanhenol; Gomisin-K3
Solubility Soluble in chloroform and DMSO
SMILES CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1C)OC)OC)OC)O)OC)OC
Standard InChIKey FYSHYFPJBONYCQ-QWHCGFSZSA-N
Standard InChI InChI=1S/C23H30O6/c1-12-8-14-10-16(25-3)21(27-5)20(24)18(14)19-15(9-13(12)2)11-17(26-4)22(28-6)23(19)29-7/h10-13,24H,8-9H2,1-7H3/t12-,13+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Schisanhenol

The fruits of Schisandrachinensis (Turcz.) Baill

Biological Activity of Schisanhenol

DescriptionSchisanhenol has antioxidative effect on human LDL oxidation, may be through scavenging free radicals; it also has anti-apoptosis effect on BACSs, may be related to its inhibition of ROS generation. Schisanhenol can protect against adriamycin induced heart mitochondrial toxicity.
TargetsROS | LDL | ATPase
In vitro

Schisanhenol derivatives and their biological evaluation against tobacco mosaic virus (TMV).[Pubmed: 25598185]

Fitoterapia. 2015 Mar;101:117-24.

Schisanhenol (Sol) was isolated from Schisandra rubriflora, and a series of derivatives (1-16, 15a-16a, and 15b-16b) were designed and prepared by chemical modification. The curative and protective effects of these dibenzocyclooctadiene lignan analogues against tobacco mosaic virus (TMV) were evaluated.
METHODS AND RESULTS:
Most analogues exhibited stronger protective effects than the positive control ningnanmycin. DibromoSchisanhenol (6) at 0.25mM exhibited the strongest protective activity (83.5±1.8% at 0.25mM), and 14-(3, 5-dibenzyloxy)-benzoyloxySchisanhenol (16) showed a significant curative effect (78.0±3.8% at 0.15mM) that was much stronger than that of the commercial virucide ningnanmycin.
CONCLUSIONS:
This study is the first to demonstrate that natural dibenzocyclooctadiene lignans and analogues are active against plant viruses.

Protective effect of schisanhenol against oxygen radical induced mitochondrial toxicity on rat heart and liver.[Pubmed: 1586468]

Biomed Environ Sci. 1992 Mar;5(1):57-64.

Schisanhenol (SAL) had been shown to have potent antioxidant activities. The protective effects of SAL against oxygen radical induced mitochondrial injuries of rat heart and liver were investigated in the present study.
METHODS AND RESULTS:
The ferrous-cysteine induced mitochondrial lipid peroxidation was significantly inhibited by SAL, while the loss of ATPase activity induced by the lipid peroxidation was prevented. The rigidification of mitochondrial membrane, as well as swelling, lysis and disintegration of the mitochondria induced by ferrous-cysteine were all significantly inhibited by SAL.
CONCLUSIONS:
These results further confirm that SAL possesses antioxidant activity.

In vivo

Protective effects of schisanhenol, salvianolic acid A and SY-L on oxidative stress induced injuries of cerebral cells and their mechanisms.[Pubmed: 12501701]

Sheng Li Ke Xue Jin Zhan. 1998 Jan;29(1):35-8.

Oxidative stress may play an important role in neuronal degenerative diseases such as Parkinson's disease, Alzheimer's disease, and amyotrophic lateral sclerosis. These disorders make the elderly not being able to live normally and move freely. So it is necessary to find effective antioxidants to prevent or cure the aged persons from diseases related to neuronal degeneration.
METHODS AND RESULTS:
Schisanhenol (Sal) and salvianolic acid A (Sal A) are known antioxidants which were isolated from Chinese herbs respectively. SY-L is a totally synthetic new compound.
CONCLUSIONS:
The results showed that Sal, Sal A and SY-L significantly protect cerebral cells from the injuries induced by oxidative stress.

Protocol of Schisanhenol

Kinase Assay

Antioxidative effect of schisanhenol on human low density lipoprotein and its quantum chemical calculation.[Pubmed: 15301737]

Acta Pharmacol Sin. 2004 Aug;25(8):1038-44.

To investigate the effect of Schisanhenol (Sal) on copper ion-induced oxidative modulation of human low density lipoprotein (LDL).
METHODS AND RESULTS:
The antioxidative activity of eight schisandrins (DCL) on microsome lipid peroxidation induced by Vit C/NADPH system was first observed, and then, the effect of Sal on Cu2+-induced human LDL oxidation was studied. The generation of malondialdehyde (MDA), lipofuscin, reactive oxygen species (ROS), consumption of a-tocopherol as well as electrophoretic mobility of LDL were determined as criteria of LDL oxidation. Finally, the quantum chemical method was used to calculate the theoretical parameters of eight DCL for elucidating the difference of their antioxidant ability. Sal was shown to be the most active one among eight schizandrins in inhibiting microsome lipid oxidation induced by Vit C/NADPH. Sal 100, 50, and 10 micromol/L inhibited production of MDA, lipofuscin and ROS as well as the consumption of a-tocopherol in Cu2+-induced oxidation of human LDL in a dose-dependent manner. Sal also reduced electrophoretic mobility of the oxidized human LDL. Further study of quantum chemistry found that Sal was the strongest one among eight DCL to scavenge O2, R, RO and ROO radicals.
CONCLUSIONS:
Sal has antioxidative effect on human LDL oxidation. The mechanism of Sal against LDL oxidation may be through scavenging free radicals.

Cell Research

Schisanhenol attenuated ox-LDL-induced apoptosis and reactive oxygen species generation in bovine aorta endothelial cells in vitro.[Pubmed: 18696334]

J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):799-806.

The aim of this paper was to investigate the protective effect of Schisanhenol (Sal) isolated from Schisandra rubriflora Rhed, on human ox-LDL-induced bovine aorta endothelial cells (BAECs) apoptosis and intracellular reactive oxygen species (ROS) production in vitro.
METHODS AND RESULTS:
The BAECs were cultured with ox-LDL (200 microg/ml) in the presence and absence of Sal (10 and 50 micromol L(- 1)) for 24 h. The cytotoxicity of ox-LDL was evaluated by LDH leakage, cell viability and morphological change. Cell apoptosis was estimated by DNA ladder, chromatin condensation, and flow cytometry assay. The intracellular ROS production was detected by using DCF, a ROS probe, with laser confocal microscopy and flow cytometry. Sal was shown to reduce LDH leakage and increase cell viability. Sal also attenuated ox-LDL-induced BAECs apoptosis as indicated in typical internucleosomal DNA degradation (DNA ladder), condensed chromatin, and the sub-G1 peak appearance in flow cytometry assay. Furthermore, Sal was shown to inhibit ROS generation in BAECs with stimulation of ox-LDL.
CONCLUSIONS:
The results indicated that the anti-apoptosis effect of Sal on BACSs might be related to its inhibition of ROS generation.

Schisanhenol Dilution Calculator

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Preparing Stock Solutions of Schisanhenol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4846 mL 12.423 mL 24.846 mL 49.6919 mL 62.1149 mL
5 mM 0.4969 mL 2.4846 mL 4.9692 mL 9.9384 mL 12.423 mL
10 mM 0.2485 mL 1.2423 mL 2.4846 mL 4.9692 mL 6.2115 mL
50 mM 0.0497 mL 0.2485 mL 0.4969 mL 0.9938 mL 1.2423 mL
100 mM 0.0248 mL 0.1242 mL 0.2485 mL 0.4969 mL 0.6211 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Schisanhenol

Schisanhenol is a natural compound solated from Schisandra rubriflora; UGT2B7 UDP-glucuronosyltransferases inhibitor. IC50 value: Target: in vitro: Schisanhenol exhibited strong inhibition toward UGT2B7, with the residual activity to be 7.9% of control activity [1]. The BAECs were cultured with ox-LDL (200 microg/ml) in the presence and absence of Sal (10 and 50 micromol L(- 1)) for 24 h. The cytotoxicity of ox-LDL was evaluated by LDH leakage, cell viability and morphological change. Cell apoptosis was estimated by DNA ladder, chromatin condensation, and flow cytometry assay. The intracellular ROS production was detected by using DCF, a ROS probe, with laser confocal microscopy and flow cytometry. Sal was shown to reduce LDH leakage and increase cell viability. Sal also attenuated ox-LDL-induced BAECs apoptosis as indicated in typical internucleosomal DNA degradation (DNA ladder), condensed chromatin, and the sub-G1 peak appearance in flow cytometry assay [2]. in vivo: Sal significantly impeded production of MDA and loss of ATPase activity induced by reoxygenation following anoxia. Oral administration of Sal induced increase of cytosol glutathione-peroxidase of brain in mice under the condition of reoxygenation following anoxia [4].

References:
[1]. Song JH, et al. Inhibition of UDP-Glucuronosyltransferases (UGTs) Activity by constituents of Schisandra chinensis. Phytother Res. 2015 Jun 18. [2]. Yu LH, et al. Schisanhenol attenuated ox-LDL-induced apoptosis and reactive oxygen species generation in bovine aorta endothelial cells in vitro. J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):799-806. [3]. Wang QY, et al. Schisanhenol derivatives and their biological evaluation against tobacco mosaic virus (TMV). Fitoterapia. 2015 Mar;101:117-24. [4]. Xue JY, et al. Antioxidant activity of two dibenzocyclooctene lignans on the aged and ischemic brain in rats. Free Radic Biol Med. 1992;12(2):127-35.

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References on Schisanhenol

[Protective effects of schisanhenol, salvianolic acid A and SY-L on oxidative stress induced injuries of cerebral cells and their mechanisms].[Pubmed:12501701]

Sheng Li Ke Xue Jin Zhan. 1998 Jan;29(1):35-8.

Oxidative stress may play an important role in neuronal degenerative diseases such as Parkinson's disease, Alzheimer's disease, and amyotrophic lateral sclerosis. These disorders make the elderly not being able to live normally and move freely. So it is necessary to find effective antioxidants to prevent or cure the aged persons from diseases related to neuronal degeneration. Schisanhenol (Sal) and salvianolic acid A (Sal A) are known antioxidants which were isolated from Chinese herbs respectively. SY-L is a totally synthetic new compound. The results showed that Sal, Sal A and SY-L significantly protect cerebral cells from the injuries induced by oxidative stress.

Antioxidative effect of schisanhenol on human low density lipoprotein and its quantum chemical calculation.[Pubmed:15301737]

Acta Pharmacol Sin. 2004 Aug;25(8):1038-44.

AIM: To investigate the effect of Schisanhenol (Sal) on copper ion-induced oxidative modulation of human low density lipoprotein (LDL). METHODS: The antioxidative activity of eight schisandrins (DCL) on microsome lipid peroxidation induced by Vit C/NADPH system was first observed, and then, the effect of Sal on Cu2+-induced human LDL oxidation was studied. The generation of malondialdehyde (MDA), lipofuscin, reactive oxygen species (ROS), consumption of a-tocopherol as well as electrophoretic mobility of LDL were determined as criteria of LDL oxidation. Finally, the quantum chemical method was used to calculate the theoretical parameters of eight DCL for elucidating the difference of their antioxidant ability. RESULTS: Sal was shown to be the most active one among eight schizandrins in inhibiting microsome lipid oxidation induced by Vit C/NADPH. Sal 100, 50, and 10 micromol/L inhibited production of MDA, lipofuscin and ROS as well as the consumption of a-tocopherol in Cu2+-induced oxidation of human LDL in a dose-dependent manner. Sal also reduced electrophoretic mobility of the oxidized human LDL. Further study of quantum chemistry found that Sal was the strongest one among eight DCL to scavenge O2, R, RO and ROO radicals. CONCLUSION: Sal has antioxidative effect on human LDL oxidation. The mechanism of Sal against LDL oxidation may be through scavenging free radicals.

Protective effect of schisanhenol against oxygen radical induced mitochondrial toxicity on rat heart and liver.[Pubmed:1586468]

Biomed Environ Sci. 1992 Mar;5(1):57-64.

Schisanhenol (SAL) had been shown to have potent antioxidant activities. The protective effects of SAL against oxygen radical induced mitochondrial injuries of rat heart and liver were investigated in the present study. The ferrous-cysteine induced mitochondrial lipid peroxidation was significantly inhibited by SAL, while the loss of ATPase activity induced by the lipid peroxidation was prevented. The rigidification of mitochondrial membrane, as well as swelling, lysis and disintegration of the mitochondria induced by ferrous-cysteine were all significantly inhibited by SAL. These results further confirm that SAL possesses antioxidant activity.

Schisanhenol attenuated ox-LDL-induced apoptosis and reactive oxygen species generation in bovine aorta endothelial cells in vitro.[Pubmed:18696334]

J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):799-806.

The aim of this paper was to investigate the protective effect of Schisanhenol (Sal) isolated from Schisandra rubriflora Rhed, on human ox-LDL-induced bovine aorta endothelial cells (BAECs) apoptosis and intracellular reactive oxygen species (ROS) production in vitro. The BAECs were cultured with ox-LDL (200 microg/ml) in the presence and absence of Sal (10 and 50 micromol L(- 1)) for 24 h. The cytotoxicity of ox-LDL was evaluated by LDH leakage, cell viability and morphological change. Cell apoptosis was estimated by DNA ladder, chromatin condensation, and flow cytometry assay. The intracellular ROS production was detected by using DCF, a ROS probe, with laser confocal microscopy and flow cytometry. Sal was shown to reduce LDH leakage and increase cell viability. Sal also attenuated ox-LDL-induced BAECs apoptosis as indicated in typical internucleosomal DNA degradation (DNA ladder), condensed chromatin, and the sub-G1 peak appearance in flow cytometry assay. Furthermore, Sal was shown to inhibit ROS generation in BAECs with stimulation of ox-LDL. The results indicated that the anti-apoptosis effect of Sal on BACSs might be related to its inhibition of ROS generation.

Schisanhenol derivatives and their biological evaluation against tobacco mosaic virus (TMV).[Pubmed:25598185]

Fitoterapia. 2015 Mar;101:117-24.

Schisanhenol (Sol) was isolated from Schisandra rubriflora, and a series of derivatives (1-16, 15a-16a, and 15b-16b) were designed and prepared by chemical modification. The curative and protective effects of these dibenzocyclooctadiene lignan analogues against tobacco mosaic virus (TMV) were evaluated. Most analogues exhibited stronger protective effects than the positive control ningnanmycin. DibromoSchisanhenol (6) at 0.25mM exhibited the strongest protective activity (83.5+/-1.8% at 0.25mM), and 14-(3, 5-dibenzyloxy)-benzoyloxySchisanhenol (16) showed a significant curative effect (78.0+/-3.8% at 0.15mM) that was much stronger than that of the commercial virucide ningnanmycin. This study is the first to demonstrate that natural dibenzocyclooctadiene lignans and analogues are active against plant viruses.

Description

Schisanhenol is a natural compound solated from Schisandra rubriflora; UGT2B7 UDP-glucuronosyltransferases inhibitor.

Keywords:

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