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Myrciaphenone A

CAS# 26089-54-3

Myrciaphenone A

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Chemical structure

Myrciaphenone A

3D structure

Chemical Properties of Myrciaphenone A

Cas No. 26089-54-3 SDF Download SDF
PubChem ID 179470 Appearance Powder
Formula C14H18O9 M.Wt 330.3
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
SMILES CC(=O)C1=C(C=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)O)O
Standard InChIKey GFKQVLKFPJGJEP-RGCYKPLRSA-N
Standard InChI InChI=1S/C14H18O9/c1-5(16)10-7(18)2-6(17)3-8(10)22-14-13(21)12(20)11(19)9(4-15)23-14/h2-3,9,11-15,17-21H,4H2,1H3/t9-,11-,12+,13-,14-/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 Myrciaphenone A

The leaves of Limoniastrum feei (Girard) Batt.

Biological Activity of Myrciaphenone A

DescriptionMyrciaphenone A is a natural product from Limoniastrum feei (Girard) Batt.
In vitro

Activity-guided isolation of antioxidant principles from Limoniastrum feei (Girard) Batt.[Pubmed: 19227826]

Z Naturforsch C. 2008 Nov-Dec;63(11-12):801-7.


METHODS AND RESULTS:
Bioguided fractionation of a leaves extract from Limoniastrum feei (Girard) Batt. (Plumbaginaceae) led to the isolation of seven polyphenolic constituents: gallic acid (1), Myrciaphenone A (2), myricetin-3-O-beta-galactopyranoside (3-1), epigallocatechin gallate (3-2), myricetin 3-O-alpha-rhamnopyranoside (4), quercetin (5) and myricetin (6).
CONCLUSIONS:
Gallic acid was the most antioxidant compound in DPPH [(0.94 +/- 0.68) microg/mL] and FRAP [(0.83 +/- 0.15) microM Fe2+/mL] tests, whereas myricetin was a more specific superoxide radical scavenger since it was the most active product in the superoxide nitroblue tetrazolium hypoxanthine/xanthine oxidase test [(1.86 +/- 0.12) microg/mL].

Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): structures of myrciacitrins I and II and myrciaphenones A and B[Pubmed: 9468642]

Chem Pharm Bull (Tokyo). 1998 Jan;46(1):113-9.


METHODS AND RESULTS:
The methanolic extract and ethyl acetate-soluble portion from a Brazilian natural medicine, the leaves of Myrcia multiflora DC., which has been used as a specific medicine against diabetes, were found to show inhibitory activities on aldose reductase and alpha-glucosidase and on the increase of serum glucose level in sucrose-loaded rats and in alloxan-induced diabetic mice. From the ethyl acetate-soluble portion, new flavanone glucosides, myrciacitrins I and II, and new acetophenone glucosides, Myrciaphenone A and myrciaphenone B, were isolated together with several known compounds such as five flavonol glycosides, myricitrin, mearnsitrin, quercitrin, desmanthin-1, and guaijaverin.
CONCLUSIONS:
The structures of new compounds were determined on the basis of physicochemical and chemical evidence. The principal components of this natural medicine including new glucosides, myrciacitrin I and myrciaphenone B, were found to show potent inhibitory activities on aldose reductase and alpha-glucosidase.

Myrciaphenone A Dilution Calculator

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Preparing Stock Solutions of Myrciaphenone A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0276 mL 15.1378 mL 30.2755 mL 60.551 mL 75.6888 mL
5 mM 0.6055 mL 3.0276 mL 6.0551 mL 12.1102 mL 15.1378 mL
10 mM 0.3028 mL 1.5138 mL 3.0276 mL 6.0551 mL 7.5689 mL
50 mM 0.0606 mL 0.3028 mL 0.6055 mL 1.211 mL 1.5138 mL
100 mM 0.0303 mL 0.1514 mL 0.3028 mL 0.6055 mL 0.7569 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 Myrciaphenone A

Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2''-O-sulfate from the leaves of Syzygium samarangense and their biological activities.[Pubmed:25273060]

Chem Pharm Bull (Tokyo). 2014;62(10):1013-8.

Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6'-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6'-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2''-O-sulfate (3), together with 14 known compounds, lupeol (4), demethoxymatteucinol (5), cryptostrobin (6), betulinic acid (7), beta-sitosterol glucoside (8), 2R-prunasin (9), Myrciaphenone A (10), 1-feruloyl-beta-D-glucopyranoside (11), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (12), guaijaverin (13), myricetin 4'-methyl ether 3-O-alpha-L-rhamnopyranoside (14), myricetrin (15), gallic acid (16) and actinidioionoside (17). The structures of the new compounds were determined through a combination of spectroscopic, HPLC and chemical analyses.

Activity-guided isolation of antioxidant principles from Limoniastrum feei (Girard) Batt.[Pubmed:19227826]

Z Naturforsch C. 2008 Nov-Dec;63(11-12):801-7.

Bioguided fractionation of a leaves extract from Limoniastrum feei (Girard) Batt. (Plumbaginaceae) led to the isolation of seven polyphenolic constituents: gallic acid (1), Myrciaphenone A (2), myricetin-3-O-beta-galactopyranoside (3-1), epigallocatechin gallate (3-2), myricetin 3-O-alpha-rhamnopyranoside (4), quercetin (5) and myricetin (6). Gallic acid was the most antioxidant compound in DPPH [(0.94 +/- 0.68) microg/mL] and FRAP [(0.83 +/- 0.15) microM Fe2+/mL] tests, whereas myricetin was a more specific superoxide radical scavenger since it was the most active product in the superoxide nitroblue tetrazolium hypoxanthine/xanthine oxidase test [(1.86 +/- 0.12) microg/mL].

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