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Methylgomisin O

CAS# 1276654-07-9

Methylgomisin O

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Quality Control of Methylgomisin O

Number of papers citing our products

Chemical structure

Methylgomisin O

3D structure

Chemical Properties of Methylgomisin O

Cas No. 1276654-07-9 SDF Download SDF
PubChem ID 46192500 Appearance Powder
Formula C24H30O7 M.Wt 430.5
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8R,9S,10S)-3,4,5,8,19-pentamethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene
SMILES CC1CC2=CC3=C(C(=C2C4=C(C(=C(C=C4C(C1C)OC)OC)OC)OC)OC)OCO3
Standard InChIKey FCFAWFPHAOTXPJ-KQHSUYLTSA-N
Standard InChI InChI=1S/C24H30O7/c1-12-8-14-9-17-22(31-11-30-17)23(28-6)18(14)19-15(20(26-4)13(12)2)10-16(25-3)21(27-5)24(19)29-7/h9-10,12-13,20H,8,11H2,1-7H3/t12-,13-,20+/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 Methylgomisin O

The fruits of Schisandra viridis

Biological Activity of Methylgomisin O

DescriptionMethylgomisin O has anti- inflammatory activity, it -induced attenuation of inflammatory cytokine production upon exposure to LPS was at least partially mediated by the suppression of NF-κB and MAPK pathway. Methylgomisin O exhibits strong cytotoxic effects on HL-60. It exhibits considerable inhibitory activity against tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6).
TargetsNF-κB | MAPK | TNF-α | IL Recepter
In vitro

Anti-inflammatory effect and mechanism of methylgomisin O.[Reference: WebLink]

Chinese journal of veterinary science, 2011, 31(9):1309-1308.

Methylgomisin O was a new dibenzocyclooctadiene lignan isolated from the fruits of Schisandra sphenanthera.
METHODS AND RESULTS:
In this paper,we investigated in vitro[LPS-induced murine RAW264.7 macrophages],the effect of Methylgomisin O on the generation of cytokines involved in the inflammatory process,such as TNF-α,IL-1β,IL-6 and IL-10.We further investigated the effect of Methylgomisin O on the LPS-induced activation of NF-κB and MAPK pathway.The result was that 0.5,2.5 and 12.5 mg/L of Methylgomisin O significantly decreased the production of TNF-α and IL-6,but didn't have significant effect on IL-1β and IL-10.Signal transduction studies showed that Methylgomisin O significantly inhibited p65-NF-κB and MAPK in a dose-dependence manner.
CONCLUSIONS:
Accordingly,we concluded that Methylgomisin O-induced attenuation of inflammatory cytokine production upon exposure to LPS was at least partially mediated by the suppression of NF-κB and MAPK pathway.

The Antiproliferative Effects of Compounds Isolated from Schisandra chinensis.[Reference: WebLink]

Korean journal of food science & technology, 2014, 46(6):665-670.

We isolated twelve lignans and three terpenoids were isolated from the n-hexane fraction of Schisandra chinensis extract.
METHODS AND RESULTS:
Using spectroscopic data and comparison with available literature, the following compounds were identified: (1) wuweizisu C, (2) gomisin N, (3) deoxyschisandrin, (4) gomisin A, (5) schisandrin, (6) chamigrenal, (7) schisanlactone D, (8) Methylgomisin O, (9) angeloylgomisin O, (10) (-)-gomisin L2, (11) schisandronic acid, (12) (-)-gomisin L1, (13) (+)-gomisin K3, (14) gomisin J, and (15) tigloylgomisin H. Notably, this was the first finding that compound (8) was isolated from this plant. Each compound was evaluated for its in vitro cytotoxic activities toward HL-60 (human leukemia), HeLa (human cervical carcinoma), and MCF-7 (breast cancer) cell lines.
CONCLUSIONS:
Compounds (7), (8), and (9) exhibited strong cytotoxic effects on HL-60 (IC50 7.37, 6.60, and 8.00 μM, respectively), whereas compound (6) exhibited weak cytotoxicity towards MCF-7 (IC50 30.50 μM). In addition, compound (8) showed the strongest activity towards HeLa cells (IC50 1.46 μM).

New Dibenzocyclooctadiene Lignans from Schisandra sphenanthera and Their Proinflammatory Cytokine Inhibitory Activities.[Reference: WebLink]

Zeitschrift Für Naturforschung B, 2010, 65(2):1-8.


METHODS AND RESULTS:
Investigation of the fruits of Schisandra sphenanthera led to the isolation of two new dibenzocyclooctadiene lignans, Methylgomisin O (1) and chloromethyl schisantherin B (2), together with twelve known lignans (3-14). Their structures were elucidated by using extensive spectroscopic techniques including 1D and 2D NMR spectra. Compound 2 was identified as a cyclooctadiene moiety substituted with a chloromethyl group, which is rarely found in natural products, especially in terrestrial higher plants.
CONCLUSIONS:
Among these isolates, compounds 1 and 7 exhibited considerable inhibitory activity against tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) production, and did not display any cellular toxicity against RAW264.7 cells.

Methylgomisin O Dilution Calculator

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Preparing Stock Solutions of Methylgomisin O

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3229 mL 11.6144 mL 23.2288 mL 46.4576 mL 58.072 mL
5 mM 0.4646 mL 2.3229 mL 4.6458 mL 9.2915 mL 11.6144 mL
10 mM 0.2323 mL 1.1614 mL 2.3229 mL 4.6458 mL 5.8072 mL
50 mM 0.0465 mL 0.2323 mL 0.4646 mL 0.9292 mL 1.1614 mL
100 mM 0.0232 mL 0.1161 mL 0.2323 mL 0.4646 mL 0.5807 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 Methylgomisin O

Isolation and anti-hepatitis B virus activity of dibenzocyclooctadiene lignans from the fruits of Schisandra chinensis.[Pubmed:25882501]

Phytochemistry. 2015 Aug;116:253-261.

Seven lignans with a dibenzocyclooctadiene skeleton, termed schinlignans A-G, and a 6,7-seco-homolignan, schischinone, together with seven known lignans, were isolated from the fruits of Schisandra chinensis (Turcz.) Baill. Their structures were elucidated by extensive spectroscopic methods, including HRESIMS, IR, UV, and 2D NMR (COSY, HMQC, COSY, and HMBC experiments). The stereochemistry at the chiral centers and the biphenyl moiety, were determined using ROESY, as well as via interpretation of their ECD spectra. Schinlignan G and Methylgomisin O exhibited potent anti-hepatitis B virus activity against HBV DNA replication with IC50 values of 5.13 and 5.49mugmL(-1), respectively.

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