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Rubiadin 1-methyl ether

CAS# 7460-43-7

Rubiadin 1-methyl ether

Catalog No. BCN4298----Order now to get a substantial discount!

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Quality Control of Rubiadin 1-methyl ether

Number of papers citing our products

Chemical structure

Rubiadin 1-methyl ether

3D structure

Chemical Properties of Rubiadin 1-methyl ether

Cas No. 7460-43-7 SDF Download SDF
PubChem ID 96191 Appearance Yellow powder
Formula C16H12O4 M.Wt 268.3
Type of Compound Anthraquinones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-hydroxy-1-methoxy-2-methylanthracene-9,10-dione
SMILES CC1=C(C=C2C(=C1OC)C(=O)C3=CC=CC=C3C2=O)O
Standard InChIKey NTBUBTCXACOEEC-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H12O4/c1-8-12(17)7-11-13(16(8)20-2)15(19)10-6-4-3-5-9(10)14(11)18/h3-7,17H,1-2H3
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 Rubiadin 1-methyl ether

The herbs of Paederia scandens (Lour.) Merr

Biological Activity of Rubiadin 1-methyl ether

DescriptionRubiadin-1-methyl ether probed as Type I photosensitizers. Rubiadin 1-methyl ether decreases the number of parasites (schizonts) in a dose-dependent manner, and 100% of inhibition was obtained with 30 to 40 micrograms. Rubiadin-1-methyl ether shows strong enhancing activity for adipocyte differentiation, it could be beneficial in the treatment of diabetes. Rubiadin-1-methyl ether has therapeutic potential against osteoporosis, it can promote osteoblast proliferation and inhibit osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone, antiosteoporotic activity of M. officinalis .
TargetsAntifection
In vitro

Anthraquinones from Morinda officinalis roots enhance adipocyte differentiation in 3T3-L1 cells.[Pubmed: 22008000]

Nat Prod Res. 2012;26(18):1750-4.

To search for anti-diabetic and insulin-sensitising natural products, the effect on adipocyte differentiation was investigated by assessing fat accumulation in 3T3-L1 preadipocytes using Oil Red O staining.
METHODS AND RESULTS:
Fractionation and separation of n-hexane and CHCl₃ fractions of Morinda officinalis (Rubiaceae) using several chromatographic methods led to the isolation of three anthraquinones, 1,2-dimethoxyanthraquinone (1), alizarin-2-methyl ether (2) and rubiadin-1-methyl ether (3). Among them, alizarin-2-methyl ether (2) showed the strongest enhancing activity, followed by Rubiadin 1-methyl ether (3) and 1,2-dimethoxyanthraquinone (1). At a concentration of 100 µM, alizarin-2-methyl ether (2) enhanced adipocyte differentiation by up to 131% (compared to insulin-treated cells).
CONCLUSIONS:
Thus, these compounds could be beneficial in the treatment of diabetes.

Effects of three compounds extracted from Morinda lucida on Plasmodium falciparum.[Pubmed: 1484892]

Planta Med. 1992 Dec;58(6):533-4.

The effects of three compounds, digitolutein (1), Rubiadin 1-methyl ether (2) and damnacanthal (3) extracted from the stem bark and the roots of Morinda lucida Benth. on the growth of Plasmodium falciparum in vitro were investigated.
METHODS AND RESULTS:
The number of parasites (schizonts) decreased significantly in a dose-dependent manner, and 100% of inhibition was obtained with 30 to 40 micrograms of each compound tested. The IC50 values were calculated.

Natural anthraquinones probed as Type I and Type II photosensitizers: singlet oxygen and superoxide anion production.[Pubmed: 15629252 ]

J Photochem Photobiol B. 2005 Jan 14;78(1):77-83.

The photosensitizing properties of six anthraquinones (AQs): soranjidiol (1), soranjidiol-1-methyl ether (2), rubiadin (3), rubiadin-1-methyl ether (4), damnacanthal (5) and damnacanthol (6), isolated from leaves and stems of Heterophyllaea pustulata Hook. f. (Rubiaceae) were studied.
METHODS AND RESULTS:
By means of photobiological and photophysical methods in vitro, the type of photosensitization that these metabolites are capable of producing was determined. Whereas the photosensitized generation of superoxide anion radical (O(2)(-)) (Type I) was evaluated in leukocyte suspensions, singlet molecular oxygen ((1)O(2)) production (Type II) was examined in organic solution. In addition, the quantum yield of (1)O(2) (Phi) in chloroform was measured for those AQs that generate it.
CONCLUSIONS:
It was established that 4 behaves exclusively as a Type I photosensitizer. By contrast, the others AQs act by both types of mechanisms, among which 5 showed the largest Phi of (1)O(2).

Protocol of Rubiadin 1-methyl ether

Cell Research

Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts.[Pubmed: 19169204]

Molecules. 2009 Jan 23;14(1):573-83.

Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis.
METHODS AND RESULTS:
Compounds 4-8 are isolated for the first time from M. officinalis. Among them, compounds 2 and 3 promoted osteoblast proliferation, while compounds 4, 5 increased osteoblast ALP activity. All of the isolated compounds inhibited osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone resorption of compounds 1 and 5 were stronger than that of other compounds.
CONCLUSIONS:
Taken together, antiosteoporotic activity of M. officinalis and its anthraquinones suggest therapeutic potential against osteoporosis.

Rubiadin 1-methyl ether Dilution Calculator

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Rubiadin 1-methyl ether Molarity Calculator

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Preparing Stock Solutions of Rubiadin 1-methyl ether

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7272 mL 18.6359 mL 37.2717 mL 74.5434 mL 93.1793 mL
5 mM 0.7454 mL 3.7272 mL 7.4543 mL 14.9087 mL 18.6359 mL
10 mM 0.3727 mL 1.8636 mL 3.7272 mL 7.4543 mL 9.3179 mL
50 mM 0.0745 mL 0.3727 mL 0.7454 mL 1.4909 mL 1.8636 mL
100 mM 0.0373 mL 0.1864 mL 0.3727 mL 0.7454 mL 0.9318 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 Rubiadin 1-methyl ether

Effects of three compounds extracted from Morinda lucida on Plasmodium falciparum.[Pubmed:1484892]

Planta Med. 1992 Dec;58(6):533-4.

The effects of three compounds, digitolutein (1), Rubiadin 1-methyl ether (2) and damnacanthal (3) extracted from the stem bark and the roots of Morinda lucida Benth. on the growth of Plasmodium falciparum in vitro were investigated. The number of parasites (schizonts) decreased significantly in a dose-dependent manner, and 100% of inhibition was obtained with 30 to 40 micrograms of each compound tested. The IC50 values were calculated.

Anthraquinones from Morinda officinalis roots enhance adipocyte differentiation in 3T3-L1 cells.[Pubmed:22008000]

Nat Prod Res. 2012;26(18):1750-4.

To search for anti-diabetic and insulin-sensitising natural products, the effect on adipocyte differentiation was investigated by assessing fat accumulation in 3T3-L1 preadipocytes using Oil Red O staining. Fractionation and separation of n-hexane and CHCl(3) fractions of Morinda officinalis (Rubiaceae) using several chromatographic methods led to the isolation of three anthraquinones, 1,2-dimethoxyanthraquinone (1), alizarin-2-methyl ether (2) and rubiadin-1-methyl ether (3). Among them, alizarin-2-methyl ether (2) showed the strongest enhancing activity, followed by rubiadin-1-methyl ether (3) and 1,2-dimethoxyanthraquinone (1). At a concentration of 100 microM, alizarin-2-methyl ether (2) enhanced adipocyte differentiation by up to 131% (compared to insulin-treated cells). Thus, these compounds could be beneficial in the treatment of diabetes.

Natural anthraquinones probed as Type I and Type II photosensitizers: singlet oxygen and superoxide anion production.[Pubmed:15629252]

J Photochem Photobiol B. 2005 Jan 14;78(1):77-83.

The photosensitizing properties of six anthraquinones (AQs): soranjidiol (1), soranjidiol-1-methyl ether (2), rubiadin (3), rubiadin-1-methyl ether (4), damnacanthal (5) and damnacanthol (6), isolated from leaves and stems of Heterophyllaea pustulata Hook. f. (Rubiaceae) were studied. By means of photobiological and photophysical methods in vitro, the type of photosensitization that these metabolites are capable of producing was determined. Whereas the photosensitized generation of superoxide anion radical (O(2)(-)) (Type I) was evaluated in leukocyte suspensions, singlet molecular oxygen ((1)O(2)) production (Type II) was examined in organic solution. In addition, the quantum yield of (1)O(2) (Phi) in chloroform was measured for those AQs that generate it. It was established that 4 behaves exclusively as a Type I photosensitizer. By contrast, the others AQs act by both types of mechanisms, among which 5 showed the largest Phi of (1)O(2).

Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts.[Pubmed:19169204]

Molecules. 2009 Jan 23;14(1):573-83.

Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds 4-8 are isolated for the first time from M. officinalis. Among them, compounds 2 and 3 promoted osteoblast proliferation, while compounds 4, 5 increased osteoblast ALP activity. All of the isolated compounds inhibited osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone resorption of compounds 1 and 5 were stronger than that of other compounds. Taken together, antiosteoporotic activity of M. officinalis and its anthraquinones suggest therapeutic potential against osteoporosis.

Description

Rubiadin-1-methyl ether is a natural anthraquinone isolated from Morinda officinalis How, and inhibits osteoclastic bone resorption via inhibition on the phosphorylation of NF-κB p65 and the degradation of IκBα as well as decrease in the nuclear translocation of p65.

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