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Cassiaside B2

CAS# 218155-40-9

Cassiaside B2

Catalog No. BCN8830----Order now to get a substantial discount!

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Quality Control of Cassiaside B2

Number of papers citing our products

Chemical structure

Cassiaside B2

3D structure

Chemical Properties of Cassiaside B2

Cas No. 218155-40-9 SDF Download SDF
PubChem ID 10557731 Appearance Powder
Formula C39H52O25 M.Wt 920.8
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-8-methoxy-2-methylbenzo[g]chromen-4-one
SMILES CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)OC)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)O)O)O)O)O
Standard InChIKey HFJDWELARBQGBQ-PFLZFKCOSA-N
Standard InChI InChI=1S/C39H52O25/c1-11-3-14(42)22-15(58-11)5-12-4-13(55-2)6-16(21(12)27(22)47)59-38-32(52)29(49)24(44)19(62-38)10-57-37-34(54)35(26(46)18(8-41)61-37)64-39-33(53)30(50)25(45)20(63-39)9-56-36-31(51)28(48)23(43)17(7-40)60-36/h3-6,17-20,23-26,28-41,43-54H,7-10H2,1-2H3/t17-,18-,19-,20-,23-,24-,25-,26-,28+,29+,30+,31-,32-,33-,34-,35+,36-,37-,38-,39+/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 Cassiaside B2

The seeds of Cassia obtusifolia L.

Biological Activity of Cassiaside B2

In vitro

Rubrofusarin as a Dual Protein Tyrosine Phosphate 1B and Human Monoamine Oxidase-A Inhibitor: An in Vitro and in Silico Study.[Pubmed: 31460269]

ACS Omega. 2019 Jul 3;4(7):11621-11630.

A number of nature-derived biologically active compounds comprise glycosides. In some cases, the glycosidic residue is needed for bioactivity; however, in other cases, glycosylation just improves some pharmacokinetic/dynamic parameters. The patterns of protein tyrosine phosphatase 1B (PTP1B) and human monoamine oxidase A (hMAO-A) inhibition by rubrofusarin 6-O-β-d-glucopyranoside (1), rubrofusarin 6-O-β-d-gentiobioside (2), rubrofusarin triglucoside (3), and Cassiaside B2 (4) were compared with the aglycone, rubrofusarin, isolated from Cassia obtusifolia seeds.
METHODS AND RESULTS:
Rubrofusarin showed potent inhibition against the PTP1B enzyme (IC50; 16.95 ± 0.49 μM), and its glycosides reduced activity (IC50; 87.36 ± 1.08 μM for 1 and >100 μM for 2-4) than did the reference drug, ursolic acid (IC50; 2.29 ± 0.04 μM). Similarly, in hMAO-A inhibition, rubrofusarin displayed the most potent activity with an IC50 value of 5.90 ± 0.99 μM, which was twice better than the reference drug, deprenyl HCl (IC50; 10.23 ± 0.82 μM). An enzyme kinetic and molecular docking study revealed rubrofusarin to be a mixed-competitive inhibitor of both these enzymes. In a western blot analysis, rubrofusarin increased glucose uptake significantly and decreased the PTP1B expression in a dose-dependent manner in insulin-resistant HepG2 cells, increased the expression of phosphorylated protein kinase B (p-Akt) and phosphorylated insulin receptor substrate-1 (p-IRS1) (Tyr 895), and decreased the expression of glucose-6-phosphatase (G6Pase) and phosphoenol pyruvate carboxykinase (PEPCK), key enzymes of gluconeogenesis.
CONCLUSIONS:
Our overall results show that glycosylation retards activity; however, it reduces toxicity. Thus, Cassia seed as functional food and rubrofusarin as a base can be used for the development of therapeutic agents against comorbid diabetes and depression.

Protocol of Cassiaside B2

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2017 Sep;42(17):3385-3390.

Study on naphthopyrone reference extract and application on assay of Semen Cassiae.[Pubmed: 29192451 ]

A quality control method of Semen Cassiae was established by using naphthopyrone reference extract(NRE). Meanwhile, the feasibility about NRE replacing single component reference in quality control of traditional Chinese medicine was explored.
METHODS AND RESULTS:
After NRE of Semen Cassiae being prepared by chromatographic separation technology, we determined the three main components, Cassiaside B2, rubrofusarin-6-O-β-D-gentiobioside and cassiaside C. In the meantime, an HPLC analytical method, based on the NRE as standard substance, was developed to determinate the contents of three main components in Semen Cassiae. T-test was used for comparison of the determination results of the two methods(single chemical component and NRE as reference substances, respectively), and the T-test result demonstrated that there was no significant difference between the two methods.
CONCLUSIONS:
The results developed scientific basis for the application of NRE of Semen Cassia in the quality control, which could be applied for the quality control of traditional Chinese medicine using reference extract substituting single chemical reference, and provide a new research model for the quality control of Chinese medicine.

Cassiaside B2 Dilution Calculator

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Cassiaside B2 Molarity Calculator

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Preparing Stock Solutions of Cassiaside B2

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.086 mL 5.4301 mL 10.8601 mL 21.7202 mL 27.1503 mL
5 mM 0.2172 mL 1.086 mL 2.172 mL 4.344 mL 5.4301 mL
10 mM 0.1086 mL 0.543 mL 1.086 mL 2.172 mL 2.715 mL
50 mM 0.0217 mL 0.1086 mL 0.2172 mL 0.4344 mL 0.543 mL
100 mM 0.0109 mL 0.0543 mL 0.1086 mL 0.2172 mL 0.2715 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 Cassiaside B2

Mechanisms of Action of Cassiae Semen for Weight Management: A Computational Molecular Docking Study of Serotonin Receptor 5-HT2C.[Pubmed:32079105]

Int J Mol Sci. 2020 Feb 16;21(4). pii: ijms21041326.

Overweight and obesity is a growing global health concern. Current management of obesity includes lifestyle intervention, bariatric surgery and medication. The serotonin receptor, 5-HT2C, is known to mediate satiety, appetite and consumption behaviour. Lorcaserin, an appetite control drug, has demonstrated efficacy in appetite control by targeting 5-HT2C but causes undesirable side effects. This study aimed to explore the potential usage of Cassiae semen (CS), a well-known traditional Chinese medicine used to treat obesity. A computational molecular docking study was performed to determine the binding mechanism of CS compounds to the 5-HT2C receptors in both active, agonist-bound and inactive, antagonist-bound conformations. By comparing binding poses and predicted relative binding affinities towards the active or inactive forms of the receptor, we hypothesise that two of the CS compounds studied may be potent agonists which may mimic the appetite suppression effects of lorcaserin: obtusifoliol and Cassiaside B2. Furthermore, two ligands, beta-sitosterol and juglanin, were predicted to bind favourably to 5-HT2C outside of the known agonist binding pocket in the active receptor, suggesting that such ligands may serve as positive allosteric modulators of 5-HT2C receptor function. Overall, this study proposed several CS compounds which may be responsible for exerting anti-obesity effects via appetite suppression by 5-HT2C receptor activation.

Rubrofusarin as a Dual Protein Tyrosine Phosphate 1B and Human Monoamine Oxidase-A Inhibitor: An in Vitro and in Silico Study.[Pubmed:31460269]

ACS Omega. 2019 Jul 3;4(7):11621-11630.

A number of nature-derived biologically active compounds comprise glycosides. In some cases, the glycosidic residue is needed for bioactivity; however, in other cases, glycosylation just improves some pharmacokinetic/dynamic parameters. The patterns of protein tyrosine phosphatase 1B (PTP1B) and human monoamine oxidase A (hMAO-A) inhibition by rubrofusarin 6-O-beta-d-glucopyranoside (1), rubrofusarin 6-O-beta-d-gentiobioside (2), rubrofusarin triglucoside (3), and Cassiaside B2 (4) were compared with the aglycone, rubrofusarin, isolated from Cassia obtusifolia seeds. Rubrofusarin showed potent inhibition against the PTP1B enzyme (IC50; 16.95 +/- 0.49 muM), and its glycosides reduced activity (IC50; 87.36 +/- 1.08 muM for 1 and >100 muM for 2-4) than did the reference drug, ursolic acid (IC50; 2.29 +/- 0.04 muM). Similarly, in hMAO-A inhibition, rubrofusarin displayed the most potent activity with an IC50 value of 5.90 +/- 0.99 muM, which was twice better than the reference drug, deprenyl HCl (IC50; 10.23 +/- 0.82 muM). An enzyme kinetic and molecular docking study revealed rubrofusarin to be a mixed-competitive inhibitor of both these enzymes. In a western blot analysis, rubrofusarin increased glucose uptake significantly and decreased the PTP1B expression in a dose-dependent manner in insulin-resistant HepG2 cells, increased the expression of phosphorylated protein kinase B (p-Akt) and phosphorylated insulin receptor substrate-1 (p-IRS1) (Tyr 895), and decreased the expression of glucose-6-phosphatase (G6Pase) and phosphoenol pyruvate carboxykinase (PEPCK), key enzymes of gluconeogenesis. Our overall results show that glycosylation retards activity; however, it reduces toxicity. Thus, Cassia seed as functional food and rubrofusarin as a base can be used for the development of therapeutic agents against comorbid diabetes and depression.

[Study on naphthopyrone reference extract and application on assay of Semen Cassiae].[Pubmed:29192451]

Zhongguo Zhong Yao Za Zhi. 2017 Sep;42(17):3385-3390.

A quality control method of Semen Cassiae was established by using naphthopyrone reference extract(NRE). Meanwhile, the feasibility about NRE replacing single component reference in quality control of traditional Chinese medicine was explored. After NRE of Semen Cassiae being prepared by chromatographic separation technology, we determined the three main components, Cassiaside B2, rubrofusarin-6-O-beta-D-gentiobioside and cassiaside C. In the meantime, an HPLC analytical method, based on the NRE as standard substance, was developed to determinate the contents of three main components in Semen Cassiae. T-test was used for comparison of the determination results of the two methods(single chemical component and NRE as reference substances, respectively), and the T-test result demonstrated that there was no significant difference between the two methods. The results developed scientific basis for the application of NRE of Semen Cassia in the quality control, which could be applied for the quality control of traditional Chinese medicine using reference extract substituting single chemical reference, and provide a new research model for the quality control of Chinese medicine.

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