Rhodionin

CAS# 85571-15-9

Rhodionin

Catalog No. BCN1248----Order now to get a substantial discount!

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Quality Control of Rhodionin

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Chemical structure

Rhodionin

3D structure

Chemical Properties of Rhodionin

Cas No. 85571-15-9 SDF Download SDF
PubChem ID 21626477 Appearance Yellow powder
Formula C21H20O11 M.Wt 448.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3,5,8-trihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
SMILES CC1C(C(C(C(O1)OC2=C(C3=C(C(=C2)O)C(=O)C(=C(O3)C4=CC=C(C=C4)O)O)O)O)O)O
Standard InChIKey CIAXXTSXVCLEJK-JOEVVYSCSA-N
Standard InChI InChI=1S/C21H20O11/c1-7-13(24)16(27)18(29)21(30-7)31-11-6-10(23)12-15(26)17(28)19(32-20(12)14(11)25)8-2-4-9(22)5-3-8/h2-7,13,16,18,21-25,27-29H,1H3/t7-,13-,16+,18+,21-/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 Rhodionin

The herbs of Rhodiola rosea

Biological Activity of Rhodionin

DescriptionRhodionin and rhodionin can inhibit cytochrome P450 2D6 non-competitively with high specificity which could have implications for interactions with co-administered drugs; they can significantly suppress the elevation of the postprandial blood triglyceride level, suggests that they may be to the treatment of lifestyle-related diseases such as hyperlipidemia and exogeneous obesity and to health foods. Rhodionin has antioxidant activity, it exhibits potent 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging activities, with IC50 values of 19.49 ± 0.21 uM.
TargetsCYP450 2D6
In vitro

The antioxidant and anti-inflammatory effects of phenolic compounds isolated from the root of Rhodiola sachalinensis A. BOR.[Pubmed: 23018923]

Molecules. 2012 Sep 27;17(10):11484-94.

Isolation of compounds from the root of Rhodiola sachalinensis (RRS) yielded tyrosol (1), salidroside (2), multiflorin B (3), kaempferol-3,4'-di-O-β-D-glucopyranoside (4), afzelin (5), kaempferol (6), Rhodionin (7), and rhodiosin (8).
METHODS AND RESULTS:
Quantification of these compounds was performed by high-performance liquid chromatography (HPLC). To investigate the antioxidant and anti-inflammatory effects of the compounds, DPPH radical scavenging, NBT superoxide scavenging and nitric oxide production inhibitory activities were examined in LPS-stimulated Raw 264.7 cells. We suggest that the major active components of RRS are herbacetin glycosides, exhibiting antioxidant activity, and kaempferol, exhibiting anti-inflammatory activity.In this study, 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activity and nitrotetrazolium blue chloride (NBT) superoxide scavenging activity were measured to assess the antioxidant activity of the components from RRS. DPPH has the ability to easily accept hydrogen atoms because it contains an unstable element, the hydrazyl nitrogen, therefore, antioxidant activity can be measured because DPPH loses its violet color when it receives hydrogens from antioxidants [18]. Additionally, NBT has the ability to easily receive superoxide because it contains unstable anions. Therefore, antioxidant activity may be measured when NBT loses its yellow color upon reaction with abundant superoxide [19]. Among the compounds from RRS, 7(Rhodionin) and 8 exhibited the most potent DPPH free radical scavenging activities, with IC50 values of 19.49 ± 0.21 and 27.77 ± 0.61 μM, respectively, compared to the positive control, L-ascorbic acid (IC50 = 32.89 ± 0.70 μM). The other compounds did not exhibit activities in this assay up to 100 μM (Table 2).

In vivo

Constituents of Rhodiola rosea showing inhibitory effect on lipase activity in mouse plasma and alimentary canal.[Pubmed: 18982538 ]

Planta Med. 2008 Nov;74(14):1716-9.

As a methanol extract of the rhizome of Rhodiola rosea inhibits the activity of lipase in isolated mouse plasma in vitro and in the mouse gastrointestinal tube in vivo, the active components in this plant were investigated.
METHODS AND RESULTS:
After fractionation and separation processes, Rhodionin and rhodiosin were isolated as active ingredients. Their IC50 values were 0.093 mM and 0.133 mM in vitro, respectively. Both compounds significantly suppressed the elevation of the postprandial blood triglyceride level, e.g., by 45.6 % (150 mg/kg, 60 min after oral administration) and 57.6 % (200 mg/kg, 180 min after oral administration), respectively.
CONCLUSIONS:
Consequently, we anticipate the application of this plant and its constituents to the treatment of lifestyle-related diseases such as hyperlipidemia and exogeneous obesity and to health foods.

Protocol of Rhodionin

Kinase Assay

Two potent cytochrome P450 2D6 inhibitors found in Rhodiola rosea.[Pubmed: 24400445]

Pharmazie. 2013 Dec;68(12):974-6.

Throughout the world, in particular in Russia, Northern Europe and China, Rhodiola species are used as herb supplements. Previously, we found that the extract of Rhodiola rosea, one of the most widely used Rhodiola species, had an inhibitory effect on the catalytic activity of cytochrome P450 2D6. Here, its inhibitory components were identified.
METHODS AND RESULTS:
A human liver microsomal in vitro system was used with dextromethorphan as substrate. The production rate of destrorphan, a metabolite of dextromethorphan, was used to measure enzyme activity. The concentration of destrorphan in the samples was measured using LC-MS/MS. Inhibitory activity of eight main components from Rhodiola rosea was evaluated. Rhodiosin and Rhodionin showed inhibitory activity with IC50 values of 0.761 microM and 0.420 microM, respectively. The other components showed no obvious inhibition (with a residual enzyme activity of more than 90%). Both rhodiosin and Rhodionin were determined to be non-competitive inhibitors with Ki values of 0.769 microM and 0.535 microM.
CONCLUSIONS:
Two of the main Rhodiola rosea compounds, rhodiosin and Rhodionin, can inhibit cytochrome P450 2D6 non-competitively with high specificity which could have implications for interactions with co-administered drugs.

Structure Identification
Chem Pharm Bull (Tokyo). 2008 Jun;56(6):807-14.

Identification and comparative determination of rhodionin in traditional tibetan medicinal plants of fourteen Rhodiola species by high-performance liquid chromatography-photodiode array detection and electrospray ionization-mass spectrometry.[Pubmed: 18520085]


METHODS AND RESULTS:
Using the HPLC/PDA/ESI/MS method, a comparative analysis of Rhodionin (RH) was undertaken in order to conduct a qualitative and quantitative study in 38 batches of fourteen species of Rhodiola for quality control purposes. Alongside of this RH analysis, a simultaneous determination of salidroside (SA), tyrosol (TY), and gallic acid (GA) was carried out. Rhodiola plants are a popularly used ethnodrug from the Qinghai-Tibetan plateau of China. The identity of RH was unambiguously determined based on the quasimolecular ions in negative ESI-MS mode. This method was validated in respect to sensitivity, linearity, precision, repeatability and recovery using optimized chromatographic conditions. The linear calibration curve was acquired with R(2)>0.999, and the limit of detection (S/N=3) was estimated to be 43.75 microg/g. The relative standard deviations (RSDs) of the intra- and inter-day precisions were 0.75% and 0.50%, respectively. The repeatability was evaluated by a replicated analysis of samples with the RSD value found within 0.67%. The recovery rates varied within the range of 98.79-100.08% with RSD less than 1.10%. In the present study, the content of RH was quantified within 0.4192-4.7260 mg/g for 16 batches of R. crenulata. It was also found in eight other species plants.
CONCLUSIONS:
The results demonstrated that RH is a useful characteristic standard compound for quality evaluation and chemical differentiation among species of Rhodiola. The study also indicated that the analytical procedure is precise, reproducible and a potential tool for both quality assessment and species identification.

J Sep Sci. 2014 Sep;37(17):2314-21.

Application and recovery of ionic liquids in the preparative separation of four flavonoids from Rhodiola rosea by on-line three-dimensional liquid chromatography.[Pubmed: 24916654]


METHODS AND RESULTS:
A novel on-line three-dimensional liquid chromatography method was developed to separate four main flavonoids from Rhodiola rosea. Ethyl acetate/0.5 mol/L ionic liquid 1-butyl-3-methylimidazolium chloride aqueous solution was selected as the solvent system. In the first-dimension separation, the target flavonoids were entrapped and subsequently desorbed into the second-dimension high-speed countercurrent chromatographic column for separation. In the third-dimension chromatography, the residual ionic liquid in the four separated flavonoids was removed and the used ionic liquid was recovered. As a result, 35.1 mg of compound 1, 20.4 mg of compound 2, 8.5 mg of compound 3, and 10.6 mg of compound 4 were obtained from 1.53 g R. rosea extract. They were identified as rhodiosin, Rhodionin, herbacetin, and kaempferol, respectively. The recovery of ionic liquid reached 99.1% of the initial amount.
CONCLUSIONS:
The results showed that this method is a powerful technology for the separation of R. rosea flavonoids and that the ionic-liquid-based solvent system has advantages over traditional solvent systems in renewable and environmentally friendly properties.

Rhodionin Dilution Calculator

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Rhodionin Molarity Calculator

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Preparing Stock Solutions of Rhodionin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2303 mL 11.1513 mL 22.3025 mL 44.605 mL 55.7563 mL
5 mM 0.4461 mL 2.2303 mL 4.4605 mL 8.921 mL 11.1513 mL
10 mM 0.223 mL 1.1151 mL 2.2303 mL 4.4605 mL 5.5756 mL
50 mM 0.0446 mL 0.223 mL 0.4461 mL 0.8921 mL 1.1151 mL
100 mM 0.0223 mL 0.1115 mL 0.223 mL 0.4461 mL 0.5576 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 Rhodionin

Two potent cytochrome P450 2D6 inhibitors found in Rhodiola rosea.[Pubmed:24400445]

Pharmazie. 2013 Dec;68(12):974-6.

OBJECTIVES: Throughout the world, in particular in Russia, Northern Europe and China, Rhodiola species are used as herb supplements. Previously, we found that the extract of Rhodiola rosea, one of the most widely used Rhodiola species, had an inhibitory effect on the catalytic activity of cytochrome P450 2D6. Here, its inhibitory components were identified. METHODS: A human liver microsomal in vitro system was used with dextromethorphan as substrate. The production rate of destrorphan, a metabolite of dextromethorphan, was used to measure enzyme activity. The concentration of destrorphan in the samples was measured using LC-MS/MS. Inhibitory activity of eight main components from Rhodiola rosea was evaluated. RESULTS: Rhodiosin and Rhodionin showed inhibitory activity with IC50 values of 0.761 microM and 0.420 microM, respectively. The other components showed no obvious inhibition (with a residual enzyme activity of more than 90%). Both rhodiosin and Rhodionin were determined to be non-competitive inhibitors with Ki values of 0.769 microM and 0.535 microM. CONCLUSION: Two of the main Rhodiola rosea compounds, rhodiosin and Rhodionin, can inhibit cytochrome P450 2D6 non-competitively with high specificity which could have implications for interactions with co-administered drugs.

The antioxidant and anti-inflammatory effects of phenolic compounds isolated from the root of Rhodiola sachalinensis A. BOR.[Pubmed:23018923]

Molecules. 2012 Sep 27;17(10):11484-94.

Isolation of compounds from the root of Rhodiola sachalinensis (RRS) yielded tyrosol (1), salidroside (2), multiflorin B (3), kaempferol-3,4'-di-O-beta-D-glucopyranoside (4), afzelin (5), kaempferol (6), Rhodionin (7), and rhodiosin (8). Quantification of these compounds was performed by high-performance liquid chromatography (HPLC). To investigate the antioxidant and anti-inflammatory effects of the compounds, DPPH radical scavenging, NBT superoxide scavenging and nitric oxide production inhibitory activities were examined in LPS-stimulated Raw 264.7 cells. We suggest that the major active components of RRS are herbacetin glycosides, exhibiting antioxidant activity, and kaempferol, exhibiting anti-inflammatory activity.

Constituents of Rhodiola rosea showing inhibitory effect on lipase activity in mouse plasma and alimentary canal.[Pubmed:18982538]

Planta Med. 2008 Nov;74(14):1716-9.

As a methanol extract of the rhizome of Rhodiola rosea inhibits the activity of lipase in isolated mouse plasma in vitro and in the mouse gastrointestinal tube in vivo, the active components in this plant were investigated. After fractionation and separation processes, Rhodionin and rhodiosin were isolated as active ingredients. Their IC50 values were 0.093 mM and 0.133 mM in vitro, respectively. Both compounds significantly suppressed the elevation of the postprandial blood triglyceride level, e.g., by 45.6 % (150 mg/kg, 60 min after oral administration) and 57.6 % (200 mg/kg, 180 min after oral administration), respectively. Consequently, we anticipate the application of this plant and its constituents to the treatment of lifestyle-related diseases such as hyperlipidemia and exogeneous obesity and to health foods.

Identification and comparative determination of rhodionin in traditional tibetan medicinal plants of fourteen Rhodiola species by high-performance liquid chromatography-photodiode array detection and electrospray ionization-mass spectrometry.[Pubmed:18520085]

Chem Pharm Bull (Tokyo). 2008 Jun;56(6):807-14.

Using the HPLC/PDA/ESI/MS method, a comparative analysis of Rhodionin (RH) was undertaken in order to conduct a qualitative and quantitative study in 38 batches of fourteen species of Rhodiola for quality control purposes. Alongside of this RH analysis, a simultaneous determination of salidroside (SA), tyrosol (TY), and gallic acid (GA) was carried out. Rhodiola plants are a popularly used ethnodrug from the Qinghai-Tibetan plateau of China. The identity of RH was unambiguously determined based on the quasimolecular ions in negative ESI-MS mode. This method was validated in respect to sensitivity, linearity, precision, repeatability and recovery using optimized chromatographic conditions. The linear calibration curve was acquired with R(2)>0.999, and the limit of detection (S/N=3) was estimated to be 43.75 microg/g. The relative standard deviations (RSDs) of the intra- and inter-day precisions were 0.75% and 0.50%, respectively. The repeatability was evaluated by a replicated analysis of samples with the RSD value found within 0.67%. The recovery rates varied within the range of 98.79-100.08% with RSD less than 1.10%. In the present study, the content of RH was quantified within 0.4192-4.7260 mg/g for 16 batches of R. crenulata. It was also found in eight other species plants. The results demonstrated that RH is a useful characteristic standard compound for quality evaluation and chemical differentiation among species of Rhodiola. The study also indicated that the analytical procedure is precise, reproducible and a potential tool for both quality assessment and species identification.

Description

Rhodionin, isolated from the root of Rhodiola crenulata, is a specific non-competitive cytochrome P450 2D6 inhibitor with an IC50 of 0.761 μM and a Ki of 0.769 μM. Rhodionin exhibits potent, dose-dependent inhibitory effects on acetylcholinesterase (AChE) with IC50 ranged from 57.50 to 2.43 μg/mL. Rhodionin exhibits potent DPPH free radical scavenging activities, with an IC50 of 19.49 μM.

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