Rubiadin

CAS# 117-02-2

Rubiadin

Catalog No. BCN6047----Order now to get a substantial discount!

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Quality Control of Rubiadin

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Chemical structure

Rubiadin

3D structure

Chemical Properties of Rubiadin

Cas No. 117-02-2 SDF Download SDF
PubChem ID 124062 Appearance Yellow powder
Formula C15H10O4 M.Wt 254.2
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms 1,3-Dihydroxy 2-methylanthraquinone
Solubility Soluble in acetonitrile, DMSO, ethanol and ethyl acetate
Chemical Name 1,3-dihydroxy-2-methylanthracene-9,10-dione
SMILES CC1=C(C=C2C(=C1O)C(=O)C3=CC=CC=C3C2=O)O
Standard InChIKey IRZTUXPRIUZXMP-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H10O4/c1-7-11(16)6-10-12(13(7)17)15(19)9-5-3-2-4-8(9)14(10)18/h2-6,16-17H,1H3
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

The roots of Rubia cordifolia

Biological Activity of Rubiadin

DescriptionRubiadin has hepatoprotective, antioxidant, and antitumor promoting effects. Rubiadin can decrease bone loss through the inhibition of osteoclast formation,differentiation and bone resorption.
TargetsCaspase | PARP
In vitro

Photochemotherapy using natural anthraquinones: Rubiadin and Soranjidiol sensitize human cancer cell to die by apoptosis.[Pubmed: 24561303]

Photodiagnosis Photodyn Ther. 2014 Jun;11(2):182-92.

Over the past decade the science has studied synthetic photosensitizers used in photodynamic therapy (PDT) or photochemotherapy as anticancer candidates. In this context, compounds extracted from vegetable species present interesting potential in the cancer field.
METHODS AND RESULTS:
In our laboratory, we studied Heterophyllaea pustulata a phototoxic shrub that habit the northwest of Argentina. From this vegetal, by in vitro germination, we obtained Rubiadin and Soranjidiol, two anthraquinones that exhibited significant photocytotoxicity on human cancer cells. In addition, the fraction obtained from callus cultures allowed us to get a satisfactory content of these compounds compared to those found from the original plant. Under PDT regimen, we found that cell destruction resulted in a dose-dependent manner and occasioned apoptosis on photosensitized cells. Biochemical analysis revealed the involvement of caspase-3, PARP cleavage and DNA fragmentation in Rubiadin induced apoptosis. Moreover, Soranjidiol-PDT led to μ-calpain-induced apoptosis involving caspases-3-independent DNA fragmentation. We also showed that both anthraquinones are cytoplasmatically distributed and out of nucleus. In addition, we demonstrated a synergic cytotoxic effect when we combined them.
CONCLUSIONS:
Our data demonstrated that Rubiadin and Soranjidiol could be further considered as natural photocytotoxic compounds against cancer cells and callus cultures are a plausible source of these anthraquinonic compounds.

Free radical scanvenging and antioxidant effects of some anthraquinone derivatives.[Pubmed: 22313303]

Med Chem. 2011 Nov;7(6):639-44.


METHODS AND RESULTS:
In this study, the screening of five anthraquinones (purpurin, xanthopurpurin, Rubiadin, kermisic acid and flavokermisic acid), for their free radical scavenging and antioxidant effects was carried out, using three complementary methods. DPPH (2,2'-diphenyl-1-picrylhydrazyl) revealed that purpurin has a scavenging effect with IC50 = 3.491 ± 0.014 µg/ml. Results of β-carotene/linoleic acid assay showed that kermisic and flavokermisic acids have significant inhibition of lipid peroxidation with I % = 76.1 ± 1.5% and 68.6 ± 2.5%, respectively. In addition, the ferrous ion chelating test showed that only purpurin, with small concentrations, interferes in a dose dependant manner with the formation of Fe2+-ferrozine complex.
CONCLUSIONS:
These results are promising for further studies of the biological and pathological effects of these natural products.

Antitumor promoting and actioxidant activities of anthraquinones isolated from the cell suspension culture of Morinda elliptica[Reference: WebLink]

Asia-Pacific Journal of Molecular Biology and Biotechnology, 2003, 11(1):3-7.

Six anthraquinones (nordamnacanthal, alizarin-1-methyl ether, Rubiadin, soranjidiol, lucidin-ω-methyl ether and morindone) isolated from the cell suspension culture of Morinda elliptica were assayed for antitumor promoting and antioxidant activities.
METHODS AND RESULTS:
All compounds exhibited strong antitumor promoting activity at the concentration of 2.0 μg/ml when assayed using the inhibition test of Epstein Barr Virus (EBV) activation on Raji cells. At the concentration of 0.4 μg/ml, only nordamnacanthal exhibited strong antitumor promoting activity with the inhibition rate and the cell viability of 75.0% and 75.8%, respectively, which was stronger than the reference compounds genistein and quercetin. In antioxidant assay using ferric thiocyanate (FTC) method, nordamnacanthal and morindone showed stronger antioxidant activity than α-tocopherol. However when the compounds were assayed for scavenging activity of the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals, only morindone was considered to be active as free radical scavenger with fifty percent inhibition concentration (IC50) of 40.6 μg/ml.

Protocol of Rubiadin

Kinase Assay

Effects of Rubiadin from Morinda officinalis on Osteoclastic Bone Resorption[Reference: WebLink]

Pharmaceutical Journal of Chinese Peoples Liberation Army, 2009, 25(6):505-9.

To investigate the cellular mechanism of Rubiadin inhibitory effects on bone resorption.
METHODS AND RESULTS:
Multinucleated osteoclasts were induced by 1,25-dihydroxyvitamine D 3 and dexamethasone from bone marrow cells and cocultured with primary osteoblastic cells.The activity of TRAP was measured by p-nitrophenyl sodium phosphate assay.The bone resorption pit area on the bone slices formed by osteoclast was measured by computer image processing.The cathepsin K was measured by fluorescence microplate reader. At the concentration of 0.1,1 and 10μmol · L-1,Rubiadin dose-dependently suppressed the formation of TRAP-positive multinucleated cells,the TRAP activity and the osteoclastic bone resorption.
CONCLUSIONS:
Rubiadin can decrease bone loss through the inhibition of osteoclast formation,differentiation and bone resorption.

Rubiadin Dilution Calculator

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Rubiadin Molarity Calculator

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Preparing Stock Solutions of Rubiadin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.9339 mL 19.6696 mL 39.3391 mL 78.6782 mL 98.3478 mL
5 mM 0.7868 mL 3.9339 mL 7.8678 mL 15.7356 mL 19.6696 mL
10 mM 0.3934 mL 1.967 mL 3.9339 mL 7.8678 mL 9.8348 mL
50 mM 0.0787 mL 0.3934 mL 0.7868 mL 1.5736 mL 1.967 mL
100 mM 0.0393 mL 0.1967 mL 0.3934 mL 0.7868 mL 0.9835 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

Rubiadin, a new antioxidant from Rubia cordifolia.[Pubmed:9425750]

Indian J Biochem Biophys. 1997 Jun;34(3):302-6.

Rubiadin, a dihydroxy anthraquinone, isolated from alcoholic extract of Rubia cordifolia, possesses potent antioxidant property. It prevents lipid peroxidation induced by FeSO4 and t-butylhydroperoxide (t-BHP) in a dose dependent manner. The per cent inhibition was more in the case of Fe2+ induced lipid peroxidation. The antioxidant property of the preparation has been found to be better than that of EDTA, Tris, mannitol, Vitamin E and p-benzoquinone.

Free radical scanvenging and antioxidant effects of some anthraquinone derivatives.[Pubmed:22313303]

Med Chem. 2011 Nov;7(6):639-44.

In this study, the screening of five anthraquinones (purpurin, xanthopurpurin, Rubiadin, kermisic acid and flavokermisic acid), for their free radical scavenging and antioxidant effects was carried out, using three complementary methods. DPPH (2,2'-diphenyl-1-picrylhydrazyl) revealed that purpurin has a scavenging effect with IC50 = 3.491 +/- 0.014 microg/ml. Results of beta-carotene/linoleic acid assay showed that kermisic and flavokermisic acids have significant inhibition of lipid peroxidation with I % = 76.1 +/- 1.5% and 68.6 +/- 2.5%, respectively. In addition, the ferrous ion chelating test showed that only purpurin, with small concentrations, interferes in a dose dependant manner with the formation of Fe2+-ferrozine complex. These results are promising for further studies of the biological and pathological effects of these natural products.

Photochemotherapy using natural anthraquinones: Rubiadin and Soranjidiol sensitize human cancer cell to die by apoptosis.[Pubmed:24561303]

Photodiagnosis Photodyn Ther. 2014 Jun;11(2):182-92.

Over the past decade the science has studied synthetic photosensitizers used in photodynamic therapy (PDT) or photochemotherapy as anticancer candidates. In this context, compounds extracted from vegetable species present interesting potential in the cancer field. In our laboratory, we studied Heterophyllaea pustulata a phototoxic shrub that habit the northwest of Argentina. From this vegetal, by in vitro germination, we obtained Rubiadin and Soranjidiol, two anthraquinones that exhibited significant photocytotoxicity on human cancer cells. In addition, the fraction obtained from callus cultures allowed us to get a satisfactory content of these compounds compared to those found from the original plant. Under PDT regimen, we found that cell destruction resulted in a dose-dependent manner and occasioned apoptosis on photosensitized cells. Biochemical analysis revealed the involvement of caspase-3, PARP cleavage and DNA fragmentation in Rubiadin induced apoptosis. Moreover, Soranjidiol-PDT led to mu-calpain-induced apoptosis involving caspases-3-independent DNA fragmentation. We also showed that both anthraquinones are cytoplasmatically distributed and out of nucleus. In addition, we demonstrated a synergic cytotoxic effect when we combined them. Our data demonstrated that Rubiadin and Soranjidiol could be further considered as natural photocytotoxic compounds against cancer cells and callus cultures are a plausible source of these anthraquinonic compounds.

Description

Rubiadin is a dihydroxy anthraquinone isolated from Rubia cordifolia. Rubiadin has a potent antixidant activity.

Keywords:

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