Rhoifolin

CAS# 17306-46-6

Rhoifolin

Catalog No. BCN1112----Order now to get a substantial discount!

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Quality Control of Rhoifolin

Number of papers citing our products

Chemical structure

Rhoifolin

3D structure

Chemical Properties of Rhoifolin

Cas No. 17306-46-6 SDF Download SDF
PubChem ID 5282150 Appearance Yellow powder
Formula C27H30O14 M.Wt 578.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Apigenin 7-O-β-D-neohesperidoside; Rhoifoloside; 4',5,7-Trihydroxyflavone 7-neohesperidoside
Solubility Soluble in methan
Chemical Name 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
Standard InChIKey RPMNUQRUHXIGHK-PYXJVEIZSA-N
Standard InChI InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/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 Rhoifolin

1 Uraria sp.

Biological Activity of Rhoifolin

DescriptionRhoifolin possesses a variety of significant biological activities including antioxidant, anti-inflammatory, antimicrobial, hepatoprotective and anticancer effects, it may be beneficial for diabetic complications through its enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-β and GLUT4 translocation. Rhoifolin has a radioprotective effect against radiation-induced decrease of blood platelets and cardiac biochemical lesions in whole body irradiated mice.
TargetsGLUT | TNF-α | PGE | SOD
In vitro

Insulin-Mimetic Action of Rhoifolin and Cosmosiin Isolated from Citrus grandis (L.) Osbeck Leaves: Enhanced Adiponectin Secretion and Insulin Receptor Phosphorylation in 3T3-L1 Cells.[Pubmed: 20008903]

Evid Based Complement Alternat Med. 2011;2011:624375.

Citrus grandis (L.) Osbeck (red wendun) leaves have been used in traditional Chinese medicine to treat several illnesses including diabetes. However, there is no scientific evidence supporting these actions and its active compounds.
METHODS AND RESULTS:
Two flavone glycosides, Rhoifolin and cosmosiin were isolated for the first time from red wendun leaves and, identified these leaves are rich source for Rhoifolin (1.1%, w/w). In differentiated 3T3-L1 adipocytes, Rhoifolin and cosmosiin showed dose-dependent response in concentration range of o.oo1-5 μM and 1-20 μM, respectively, in biological studies beneficial to diabetes. Particularly, Rhoifolin and cosmosiin at 0.5 and 20 μM, respectively showed nearly similar response to that 10 nM of insulin, on adiponectin secretion level. Furthermore, 5 μM of Rhoifolin and 20 μM of cosmosiin showed equal potential with 10 nM of insulin to increase the phosphorylation of insulin receptor-β, in addition to their positive effect on GLUT4 translocation.
CONCLUSIONS:
These findings indicate that Rhoifolin and cosmosiin from red wendun leaves may be beneficial for diabetic complications through their enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-β and GLUT4 translocation.

[Chemical constituents from Callicarpa nudiflora and their cytotoxic activities].[Pubmed: 25509294]

Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(16):3094-101.

The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin, silica gel and Sephadex LH-20 column chromatographies.
METHODS AND RESULTS:
The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities, leading to the isolation of twelve compounds, which were identified as luteoloside(1), lutedin-4'-O-β-D-glucoside(2), 6-hydroxyluteolin-7-O-β-glucoside(3), lutedin-7-O-neohesperidoside(4), Rhoifolin (5), luteolin-7, 4'-di-O-glucoside (6), forsythoside B (7), acteoside (8), alyssonoside (9), catalpol(10), nudifloside(11), and leonuride(12). Compounds 3-6, 10 and 12 were isolated from this genus for the first time, and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6, in various concentrations, showed monolithic proliferation inhibitory activities against Hela, A549 and MCF-7 cell lines. Compounds 3, 5 and iridoid glycoside 11 possessed higher cytotoxicacivities.
CONCLUSIONS:
In short, flavonoids are the main components of cytotoxic extract from C. nudiflora, while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition, the minor iridoid glycoside expressed weak cytotoxic activity.

Study on the protective effect of rhoifolin against hepatic injury induced by triptolide[Reference: WebLink]

Pharmacology & Clinics of Chinese Materia Medica, 2012(6):18-20.

Study on the protective effect of Rhoifolin against hepatic injury induced by triptolide.
METHODS AND RESULTS:
The protective effects of Rhoifolin at the concentration of 75,150,300μg/ml,on the in vitro damage of human L02 liver cells injured by triptolide at the concentration of 40μg/ml were evaluated with cell survival rates,which were determined by MTT assay.Sixty mice were randomly divided into six groups as follows: The drug groups mice were treated with Rhoifolin for six day at the dose of 140,70,35mg/kg,respectively.The normal control group and the model control group took equivalent amount of distilled water by the same route.And mice in the positive control group were treated with 70mg/kg diammonium glycyrrhizinate.After the last administration,all groups except the normal control were administered with triptolide at dose of 0.625mg/kg by gavage to induce acute hepatic injury.Thereafter,the contents of ALT,AST in serum,the activities of SOD,MDA,GSH-Px and GST in the liver were measured and the hepatic histological changes were observed by optical microscope. The cell survival rates of human L02 liver cells injured by triptolide and then treated with Rhoifolin at the concentration of 75,150,300μg/ml were significantly increased.The contents of ALT,AST in serum were significantly decreased,the content of MDA in the liver was also significantly lowered,and the activities of SOD,MDA,GSH-Px and GST in liver were significantly improved after preventive treatment with Rhoifolin at the dose of 140,70,35mg/kg.Rhoifolin can ameliorated the hepatic pathological changes.
CONCLUSIONS:
The protective effect of Rhoifolin against hepatic injury induced by triptolide was significant in vitro and in vivo.

In vivo

Anti-inflammatory effect of Apigenin-7-neohesperidoside (Rhoifolin) in carrageenin-induced rat edema model[Reference: WebLink]

J. Appl. Pharmaceut. Sci., 2012, 2(8):74-9.

Flavonoids are normal constituents of the human diet and are known for a variety of biological activities. They have been reported to bring benefits in lowering inflammation and oxidative stress.
METHODS AND RESULTS:
The present investigation was performed first, to evaluate the anti-inflammatory activity of Rhoifolin and second, to search for the possible contributing mechanisms for this hypothesized effect. Rhoifolin caused a time and reverse dose dependent reduction of carrageenin-induced rat paw oedema. Following 4 hr of treatment, Rhoifolin at doses 2.5, 25 & 250 mg/kg caused a significant inhibition of rat paw edema volume by 14, 25 & 45 % respectively in comparison to the control group (74%). In addition to significantly abrogating prostaglandin E2 level, increasing doses of Rhoifolin significantly diminished the TNF-a release in the inflammatory exudates. In the same animal model, Rhoifolin increased the total antioxidant capacity in a reverse dose order, with the highest capacity obtained with the lowest dose tested.
CONCLUSIONS:
This study demonstrates for the first time the effectiveness.

Protocol of Rhoifolin

Cell Research

Rhoifolin; A Potent Antiproliferative Effect on Cancer Cell Lines[Reference: WebLink]

Brit. J. Pharmaceut. Res., 2013, 3(1):46-53.


METHODS AND RESULTS:
Rhoifolin, Apigenin 7-O-β neohesperidoside was isolated in a copious amount from the leaves of Chorisia crispiflora (Bombaceae). Its identity was unambiguously confirmed via different spectroscopic methods (UV, 1 HNMR, 13 CNMR and HMBC) and Viability assay test was used to evaluate its cytotoxic activity. It exhibited potent anticancer activities, nearly similar to that of vinblastine, when evaluated against human epidermoid larynex (Hep 2) and human cervical (HeLa) carcinoma cell lines. Promising activities were also obtained against hepatocellular (Hep G2), colon (HCT-116) and fetal human lung fibroblast (MRC-5) carcinoma cell lines. A unique effect of Rhoifolin was in having no cytotoxic activity against healthy normal cells (Vero cells) which indicates a high selectivity of the compound selected.
CONCLUSIONS:
The findings of this study showed that Rhoifolin could be used as an ideal anticancer agent. It discriminates between cancerous and non cancerous cell as it kills only the former one. So the side effects which may appear during chemotherapy could be overcome.

Animal Research

Protective Effect of Rhoifolin on Gamma Irradiation Induced Cardiac Dysfunctions in Albino Mice.[Reference: WebLink]

Journal of Nuclear Science and Applications, 2014,47(1):198-204.

Rhoifolin (apigenin 7 neohesperidoside) is a flavone glycoside, a natural product belonging to the flavonoid.
METHODS AND RESULTS:
This study aimed to estimate the optimum dose level of Rhoifolin against the lethality of 10Gy irradiation dose in mice. Also, to evaluate the modulator effect of Rhoifolin against 10 Gy irradiation induced certain haematological and cardiac biochemical abnormalities. Six groups of mice (n =15) were used. The 1 st group subjected to a single dose (10 Gy) irradiation and used as control. The other five groups administered different doses of Rhoifolin (12, 24, 30, 36, and 40 mg/kg) po for 7 consecutive days pre irradiation (10 gray). The optimum dose of Rhoifolin against radiation induced mortality and body weight loss was evaluated and found to be 36 mg/kg body weight. Conclusion:
CONCLUSIONS:
The present study suggests a radioprotective effect of Rhoifolin against radiation-induced decrease of blood platelets and cardiac biochemical lesions in whole body irradiated mice.

Rhoifolin Dilution Calculator

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Rhoifolin Molarity Calculator

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Preparing Stock Solutions of Rhoifolin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7286 mL 8.643 mL 17.2861 mL 34.5722 mL 43.2152 mL
5 mM 0.3457 mL 1.7286 mL 3.4572 mL 6.9144 mL 8.643 mL
10 mM 0.1729 mL 0.8643 mL 1.7286 mL 3.4572 mL 4.3215 mL
50 mM 0.0346 mL 0.1729 mL 0.3457 mL 0.6914 mL 0.8643 mL
100 mM 0.0173 mL 0.0864 mL 0.1729 mL 0.3457 mL 0.4322 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 Rhoifolin

[Chemical constituents from Callicarpa nudiflora and their cytotoxic activities].[Pubmed:25509294]

Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(16):3094-101.

The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin, silica gel and Sephadex LH-20 column chromatographies. The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities, leading to the isolation of twelve compounds, which were identified as luteoloside(1), lutedin-4'-O-beta-D-glucoside(2), 6-hydroxyluteolin-7-O-beta-glucoside(3), lutedin-7-O-neohesperidoside(4), Rhoifolin (5), luteolin-7, 4'-di-O-glucoside (6), forsythoside B (7), acteoside (8), alyssonoside (9), catalpol(10), nudifloside(11), and leonuride(12). Compounds 3-6, 10 and 12 were isolated from this genus for the first time, and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6, in various concentrations, showed monolithic proliferation inhibitory activities against Hela, A549 and MCF-7 cell lines. Compounds 3, 5 and iridoid glycoside 11 possessed higher cytotoxicacivities. In short, flavonoids are the main components of cytotoxic extract from C. nudiflora, while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition, the minor iridoid glycoside expressed weak cytotoxic activity.

Insulin-Mimetic Action of Rhoifolin and Cosmosiin Isolated from Citrus grandis (L.) Osbeck Leaves: Enhanced Adiponectin Secretion and Insulin Receptor Phosphorylation in 3T3-L1 Cells.[Pubmed:20008903]

Evid Based Complement Alternat Med. 2011;2011:624375.

Citrus grandis (L.) Osbeck (red wendun) leaves have been used in traditional Chinese medicine to treat several illnesses including diabetes. However, there is no scientific evidence supporting these actions and its active compounds. Two flavone glycosides, Rhoifolin and cosmosiin were isolated for the first time from red wendun leaves and, identified these leaves are rich source for Rhoifolin (1.1%, w/w). In differentiated 3T3-L1 adipocytes, Rhoifolin and cosmosiin showed dose-dependent response in concentration range of o.oo1-5 muM and 1-20 muM, respectively, in biological studies beneficial to diabetes. Particularly, Rhoifolin and cosmosiin at 0.5 and 20 muM, respectively showed nearly similar response to that 10 nM of insulin, on adiponectin secretion level. Furthermore, 5 muM of Rhoifolin and 20 muM of cosmosiin showed equal potential with 10 nM of insulin to increase the phosphorylation of insulin receptor-beta, in addition to their positive effect on GLUT4 translocation. These findings indicate that Rhoifolin and cosmosiin from red wendun leaves may be beneficial for diabetic complications through their enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-beta and GLUT4 translocation.

Description

Rhoifolin is a flavone glycoside isolated from Citrus grandis (L.) Osbeck leaves. Rhoifolin is beneficial for diabetic complications through enhanced adiponectin secretion, tyrosine phosphorylation of insulin receptor-β and glucose transporter 4 (GLUT 4) translocation. Rhoifolin ameliorates titanium particle-stimulated osteolysis and attenuates osteoclastogenesis via RANKL-induced NF-κB and MAPK pathways.

Keywords:

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