Isogomisin O

CAS# 83916-76-1

Isogomisin O

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Quality Control of Isogomisin O

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Chemical structure

Isogomisin O

3D structure

Chemical Properties of Isogomisin O

Cas No. 83916-76-1 SDF Download SDF
PubChem ID 634476 Appearance Powder
Formula C23H28O7 M.Wt 416.5
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-ol
SMILES CC1CC2=CC(=C(C(=C2C3=C(C4=C(C=C3C(C1C)O)OCO4)OC)OC)OC)OC
Standard InChIKey YVMJUSKDPJGDHW-UHFFFAOYSA-N
Standard InChI InChI=1S/C23H28O7/c1-11-7-13-8-15(25-3)20(26-4)22(27-5)17(13)18-14(19(24)12(11)2)9-16-21(23(18)28-6)30-10-29-16/h8-9,11-12,19,24H,7,10H2,1-6H3
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 Isogomisin O

The seeds of Schisandra chinensis (Turcz.) Baill.

Biological Activity of Isogomisin O

DescriptionStandard reference
In vitro

Composition and biological activity of different extracts from Schisandra sphenanthera and Schisandra chinensis.[Pubmed: 17611932]

Planta Med. 2007 Aug;73(10):1116-26.

Plants of the Schisandraceae family contain a variety of pharmacologically active lignans like schizandrin, deoxyschizandrin, deangeloylgomisin B, gomisin A, gomisin O, gamma-schizandrin and Isogomisin O.
METHODS AND RESULTS:
Here we have compared the composition of different polar and non-polar extracts of Schisandra sphenanthera and Schisandra chinensis. We also have screened the extracts for antiproliferative and anti-inflammatory effects in different cell-based and cell-free assays. Extracts produced with the non-polar solvents CO(2), hexane and CO(2)/5% ethanol had a similar composition. In contrast, polar extraction with ethanol provided a considerably higher yield, but a lower content of volatiles and lignans in comparison to the non-polar extracts. The proliferation of the epidermal cell lines HaCaT and A431 was dose-dependently inhibited by both the Schisandra sphenanthera and Schisandra chinensis extracts, the non-polar extracts being superior to the polar ones. The non-polar Schisandra sphenanthera extract was the most active with a half-maximal inhibitory concentration of 20 microg/mL. In a cell-free enzyme inhibition assay with recombinant cyclooxygenase-2 (COX-2) the non-polar Schisandra sphenanthera extract dose-dependently inhibited COX-2 catalysed prostaglandin (PG) production (IC(50) = 0.2 microg/mL). It also reduced the ultraviolet-B (UVB)-induced PGE (2) production (IC(50) = 4 microg/mL) and COX-2 expression in HaCaT keratinocytes.
CONCLUSIONS:
We conclude that non-polar SChisandra extracts obtained by CO(2) extraction might be useful in the prevention and treatment of hyperproliferative and inflammatory skin diseases.

Protocol of Isogomisin O

Structure Identification
Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1281-3.

Lignans from Schisandra propinqua var. propinqua.[Pubmed: 17666862]


METHODS AND RESULTS:
Two new dibenzocyclooctadiene lignans angeloyl-(+)-gomisin K(3) (1) and methylIsogomisin O (2), together with six known ones, Isogomisin O, angeloylIsogomisin O, gomisin O, angeloygomisin O, benzoylgomisin O, epigomisin O, and four 1,4-bis(phenyl)-2,3-dimethylbutane type lignans, pregomisin, meso-dihydroguaiaretic acid, isoanwulignan, and sphenanlignan were isolated from the aerial parts of Schisandra propinqua var. propinqua.
CONCLUSIONS:
The structures of 1 and 2 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques.

Isogomisin O Dilution Calculator

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Isogomisin O Molarity Calculator

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Preparing Stock Solutions of Isogomisin O

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.401 mL 12.0048 mL 24.0096 mL 48.0192 mL 60.024 mL
5 mM 0.4802 mL 2.401 mL 4.8019 mL 9.6038 mL 12.0048 mL
10 mM 0.2401 mL 1.2005 mL 2.401 mL 4.8019 mL 6.0024 mL
50 mM 0.048 mL 0.2401 mL 0.4802 mL 0.9604 mL 1.2005 mL
100 mM 0.024 mL 0.12 mL 0.2401 mL 0.4802 mL 0.6002 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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References on Isogomisin O

Lignans from Schisandra propinqua var. propinqua.[Pubmed:17666862]

Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1281-3.

Two new dibenzocyclooctadiene lignans angeloyl-(+)-gomisin K(3) (1) and methylIsogomisin O (2), together with six known ones, Isogomisin O, angeloylIsogomisin O, gomisin O, angeloygomisin O, benzoylgomisin O, epigomisin O, and four 1,4-bis(phenyl)-2,3-dimethylbutane type lignans, pregomisin, meso-dihydroguaiaretic acid, isoanwulignan, and sphenanlignan were isolated from the aerial parts of Schisandra propinqua var. propinqua. The structures of 1 and 2 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques.

Composition and biological activity of different extracts from Schisandra sphenanthera and Schisandra chinensis.[Pubmed:17611932]

Planta Med. 2007 Aug;73(10):1116-26.

Plants of the Schisandraceae family contain a variety of pharmacologically active lignans like schizandrin, deoxyschizandrin, deangeloylgomisin B, gomisin A, gomisin O, gamma-schizandrin and Isogomisin O. Here we have compared the composition of different polar and non-polar extracts of Schisandra sphenanthera and Schisandra chinensis. We also have screened the extracts for antiproliferative and anti-inflammatory effects in different cell-based and cell-free assays. Extracts produced with the non-polar solvents CO(2), hexane and CO(2)/5% ethanol had a similar composition. In contrast, polar extraction with ethanol provided a considerably higher yield, but a lower content of volatiles and lignans in comparison to the non-polar extracts. The proliferation of the epidermal cell lines HaCaT and A431 was dose-dependently inhibited by both the Schisandra sphenanthera and Schisandra chinensis extracts, the non-polar extracts being superior to the polar ones. The non-polar Schisandra sphenanthera extract was the most active with a half-maximal inhibitory concentration of 20 microg/mL. In a cell-free enzyme inhibition assay with recombinant cyclooxygenase-2 (COX-2) the non-polar Schisandra sphenanthera extract dose-dependently inhibited COX-2 catalysed prostaglandin (PG) production (IC(50) = 0.2 microg/mL). It also reduced the ultraviolet-B (UVB)-induced PGE (2) production (IC(50) = 4 microg/mL) and COX-2 expression in HaCaT keratinocytes. We conclude that non-polar SChisandra extracts obtained by CO(2) extraction might be useful in the prevention and treatment of hyperproliferative and inflammatory skin diseases.

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