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Home > Products >  Methylophiopogonanone A

Methylophiopogonanone A CAS NO.74805-92-8

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  • Methylophiopogonanone A
  • 74805-92-8
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Quick Details

  • ProName: Methylophiopogonanone A
  • CasNo: 74805-92-8
  • Molecular Formula: C19H18O6
  • Appearance: detailed see specifications
  • Application: analysis,activity test,Botanical Refer...
  • DeliveryTime: 1-3?working?days?after?confirming?the?...
  • PackAge: According to the clients requirement.
  • Port: China main port
  • ProductionCapacity: 1 Metric Ton/Day
  • Purity: ≥98%
  • Storage: Store at 2~8°C
  • Transportation: by air or by ocean shipping
  • LimitNum: 10 Milligram
  • Plant of Origin: Chinese herbal medicine
  • Testing Method: NMR/MS/HPLC
  • Product Ecification: 1mg-1kg
  • Heavy Metal: <10ppm
  • Voluntary Standards: company standard
  • Storage: Store in dry, dark and ventilated plac...
  • PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers. 
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.
 
Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library
 

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Methylophiopogonanone A

Cas No. 74805-92-8    
PubChem ID 53466984 Appearance Light yellow powder
Formula C19H18O6 M.Wt 342.34
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in chloroform and methanol; insoluble in water
Chemical Name (3R)-3-(1,3-benzodioxol-5-ylmethyl)-5,7-dihydroxy-6,8-dimethyl-2,3-dihydrochromen-4-one
SMILES CC1=C(C2=C(C(=C1O)C)OCC(C2=O)CC3=CC4=C(C=C3)OCO4)O
Standard InChIKey BXTNNJIQILYHJB-GFCCVEGCSA-N
Standard InChI InChI=1S/C19H18O6/c1-9-16(20)10(2)19-15(17(9)21)18(22)12(7-23-19)5-11-3-4-13-14(6-11)25-8-24-13/h3-4,6,12,20-21H,5,7-8H2,1-2H3/t12-/m1/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 Methylophiopogonanone A

The roots of Ophiopogon japonicus

Biological Activity of Methylophiopogonanone A

Description Methylophiopogonanone A has anti-inflammatory and anti-oxidative properties, it also has therapeutic potential against cerebral I/R injury through its ability to attenuate BBB disruption by regulating the expression of MMP-9 and tight junction proteins.
Targets MMP(e.g.TIMP)
In vivo

Methylophiopogonanone A Protects against Cerebral Ischemia/Reperfusion Injury and Attenuates Blood-Brain Barrier Disruption In Vitro.[Pubmed: 25897666]

PLoS One. 2015 Apr 21;10(4):e0124558.

Methylophiopogonanone A (MO-A), an active homoisoflavonoid of the Chinese herb Ophiopogon japonicus which has been shown to have protective effects on cerebral ischemia/reperfusion (I/R) injury, has been demonstrated to have anti-inflammatory and anti-oxidative properties. However, little is known about its role in cerebral I/R injury.
METHODS AND RESULTS:
Therefore, in this study, by using a middle cerebral artery occlusion (MCAO) and reperfusion rat model, the effect of MO-A on cerebral I/R injury was examined. The results showed that MO-A treatment reduced infarct volume and brain edema, improved neurological deficit scores, reversed animal body weight decreases, and increased animal survival time in the stroke groups. Western blotting showed that MO-A suppressed MMP-9, but restored the expression of claudin-3 and claudin-5. Furthermore, transmission electron microscopy were monitored to determine the blood-brain barrier (BBB) alterations in vitro. The results showed that MO-A markedly attenuated BBB damage in vitro. Additionally, MO-A inhibited ROS production in ECs and MMP-9 release in differentiated THP-1 cells in vitro, and suppressed ICAM-1 and VCAM-1 expression in ECs and leukocyte/EC adhesion.
CONCLUSIONS:
In conclusion, our data indicate that MO-A has therapeutic potential against cerebral I/R injury through its ability to attenuate BBB disruption by regulating the expression of MMP-9 and tight junction proteins.

Protocol of Methylophiopogonanone A

Structure Identification

Chinese Traditional & Herbal Drugs, 2015, 46(20):3091-5.

Comparison on homoisoflavones extracted from Ophiopogon japonicus in Sichuan and Zhejiang and their anti-oxidative activity.[Reference: WebLink]

To compare the contents of three homoisoflavones and their anti-oxidative activity of Ophiopogon japonicus in Sichuan(OJS) and Zhejiang(OJZ).
METHODS AND RESULTS:
The determination was performed on ACQUITYTM UPLC BEH C18 column(100 mm × 2.1 mm, 1.7 μm), the Ultra Performance Liquid Chromatography-Photo-Diode Array(UPLC-PDA) technology was applied, and the mobile phase consisted of acetonitrile and 0.2% formic acid aqueous solution(55 : 45) with gradient elution program, flow rate was 0.20 m L/min with 2 μL of sample quantity at 296 nm, and the anti-DPPH radical efficiency of water extract from Ophiopogonis Radix were evaluated by UV-photometer. The average values of methylophiopogonone A, Methylophiopogonanone A, and methylophiopogonanone B were(3.06 ± 0.54),(40.10 ± 5.63), and(29.51 ± 5.06) μg/g in OJS, respectively; while those in OJZ were(9.22 ± 3.52),(106.63 ± 27.56), and(256.97 ± 61.79) μg/g, separately. The IC50 value was 16.59 mg/m L in OJS, while that in OJZ was 14.48 mg/m L. The IC50 value of positive control VC was 7.06 μg/m L.
CONCLUSIONS:
Compared with OJS, the contents of homoisoflavones in OJZ are higher, and the anti-radical efficiency of water extract from OJZ is stronger. It provides the basis for the quality evaluation and geo-authentic research of Ophiopogonis Radix.

Preparing Stock Solutions of Methylophiopogonanone A

  1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9211 mL 14.6054 mL 29.2107 mL 58.4215 mL 73.0268 mL
5 mM 0.5842 mL 2.9211 mL 5.8421 mL 11.6843 mL 14.6054 mL
10 mM 0.2921 mL 1.4605 mL 2.9211 mL 5.8421 mL 7.3027 mL
50 mM 0.0584 mL 0.2921 mL 0.5842 mL 1.1684 mL 1.4605 mL
100 mM 0.0292 mL 0.1461 mL 0.2921 mL 0.5842 mL 0.7303 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.

 

References on Methylophiopogonanone A

Methylophiopogonanone A Protects against Cerebral Ischemia/Reperfusion Injury and Attenuates Blood-Brain Barrier Disruption In Vitro.[Pubmed:25897666]

PLoS One. 2015 Apr 21;10(4):e0124558.

Methylophiopogonanone A (MO-A), an active homoisoflavonoid of the Chinese herb Ophiopogon japonicus which has been shown to have protective effects on cerebral ischemia/reperfusion (I/R) injury, has been demonstrated to have anti-inflammatory and anti-oxidative properties. However, little is known about its role in cerebral I/R injury. Therefore, in this study, by using a middle cerebral artery occlusion (MCAO) and reperfusion rat model, the effect of MO-A on cerebral I/R injury was examined. The results showed that MO-A treatment reduced infarct volume and brain edema, improved neurological deficit scores, reversed animal body weight decreases, and increased animal survival time in the stroke groups. Western blotting showed that MO-A suppressed MMP-9, but restored the expression of claudin-3 and claudin-5. Furthermore, transmission electron microscopy were monitored to determine the blood-brain barrier (BBB) alterations in vitro. The results showed that MO-A markedly attenuated BBB damage in vitro. Additionally, MO-A inhibited ROS production in ECs and MMP-9 release in differentiated THP-1 cells in vitro, and suppressed ICAM-1 and VCAM-1 expression in ECs and leukocyte/EC adhesion. In conclusion, our data indicate that MO-A has therapeutic potential against cerebral I/R injury through its ability to attenuate BBB disruption by regulating the expression of MMP-9 and tight junction proteins.

Description

Methylophiopogonanone A, a major homoisoflavonoid in Ophiopogon japonicas, has both anti-oxidative and anti-inflammatory properties.

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