Shionone

CAS# 10376-48-4

Shionone

2D Structure

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3D structure

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Shionone

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Chemical Properties of Shionone

Cas No. 10376-48-4 SDF Download SDF
PubChem ID 122861 Appearance Powder
Formula C30H50O M.Wt 426.72
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,4bS,6aS,8R,10aR,12aS)-1,4b,6a,8,10a,12a-hexamethyl-8-(4-methylpent-3-enyl)-1,3,4,4a,5,6,7,9,10,10b,11,12-dodecahydrochrysen-2-one
SMILES CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC(C4)(C)CCC=C(C)C)C)C)C)C
Standard InChIKey HXPXUNQUXCHJLL-PYOYDRRISA-N
Standard InChI InChI=1S/C30H50O/c1-21(2)10-9-14-26(4)16-19-30(8)25-13-15-28(6)22(3)23(31)11-12-24(28)29(25,7)18-17-27(30,5)20-26/h10,22,24-25H,9,11-20H2,1-8H3/t22-,24?,25?,26+,27-,28+,29-,30+/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 Shionone

The flower of Chrysanthemum morifolium

Biological Activity of Shionone

DescriptionShionone has anti-inflammatory effect, the mechanism is related to decrease the phosphorylation level of ERK1/2 protein and IκBα and the protein expression of i NOS. It can inhibit the activity of ubiquitin-specific protease 2 (USP2) and provide a lead compound for future development of new USP2 inhibitors.
TargetsERK | IkB | NOS | IKK
In vitro

Study on anti-inflammatory mechanism of shionone based on NF-κB pathway in vitro.[Reference: WebLink]

China Journal of Traditional Chinese Medicine & Pharmacy, 2016(4):1430-3.

To explore anti-inflammatory effect and mechanism of Shionone in vitro.
METHODS AND RESULTS:
Lipopolysaccharide(LPS)-activated macrophage cells(RAW264.7) were employed as an inflammatory model, which was intervened by the Shionone. After the experiment, Western blot was used to detect the protein expression of p-ERK1/2, IκBαand iNOS on the macrophage cells. Compared with the LPS group, the Shionone significantly decreased the protein expression of p-ERK1/2 and i NOS(P0.05) and significantly increased the protein expression of IκBα(P0.05).
CONCLUSIONS:
The antiinflammatory mechanism of Shionone was related to decrease the phosphorylation level of ERK1/2 protein and IκBα and the protein expression of i NOS.

In vivo

Expectorant, antitussive, anti-inflammatory activities and compositional analysis of Aster tataricu[Pubmed: 25701752]

J Ethnopharmacol. 2015 Apr 22;164:328-33.

The root of Aster tataricus L. f., recorded in all versions of Chinese Pharmacopoeia, is a traditional Chinese medicine with the function of dispelling phlegm and relieving cough for more than 2000 years. This study was designed to evaluate the expectorant, antitussive, and anti-inflammatory activities of the root of A. tataricus and to explore the chemical substances responsible for these activities.
METHODS AND RESULTS:
The 70% ethanol extract of the root of A. tataricus (RA-70) was divided into three fractions, Fr-0, Fr-50 and Fr-95. They were all orally administrated to the mice to investigate their potential expectorant activities by a tracheal phenol red secretion method. The most effective fraction, together with Shionone, was evaluated the expectorant, antitussive and anti-inflammatory activities by the mouse models of phenol red secretion, ammonia-induced cough, and xylene-induced ear swelling. Furthermore, the chemical components of the effective fraction were analyzed and identified by an HPLC-Q-TOF/MS method. Treatment with RA-70, Fr-0 and Fr-50 increased the amount of phenol red secretion by 65.3%, 56.5%, and 76.9%, respectively. Fr-50 was chosen for the further investigation and the results showed that Fr-50 at 40, 80 mg/kg significantly enhanced the phenol red secretion of tracheas, increased the latent period and decreased the frequency of cough and inhibited the ear edema in mice. Shionone at 80 mg/kg showed the trend of enhancing sputum secreting, but had no effect on ammonia-induced cough and xylene-induced ear edema. HPLC-Q-TOF/MS analysis indicated that Fr-50 was mainly composed of 12 caffeoylquinic acids (40.8%, in relative peak area), 7 astersaponins (12.0%) and 13 astins/asterinins (pentapeptides, 26.5%).
CONCLUSIONS:
The root of A. tataricus has significant expectorant, antitussive and anti-inflammatory effects. Caffeoylquinic acids, astersaponins, and aster peptides, rather than Shionone, may be the main constituents responsible for the expectorant and antitussive activities of A. tataricus and act in a synergistic way.

Protocol of Shionone

Kinase Assay

Inhibitory effect of shionone on activity of ubiquitin-specific protease 2[Reference: WebLink]

Journal of Shanghai Jiaotong University, 2014, 34(11):1563-7.

To identify new ubiquitin-specific protease 2 (USP2) inhibitors from natural compounds.
METHODS AND RESULTS:
The Ub-CHOP-Reporter Kit was used to screen USP2 inhibitors. NB4 cells were treated by Shionone (SH) of 100 μmol/L for different periods of time. Variations of the expression of USP2 targeted protein Cyclin D1 were detected by the Western blotting. The distribution of cell cycle was detected by the flow cytometry and molecular docking was used to analyze the binding of SH and USP2. The results of screening in vitro showed that SH inhibited the activity of USP2 with the 50% inhibition concentration (IC50) of 69 μmol/L. The results of Western blotting indicated that SH led to the decrease of Cyclin D1 expression. The results of flow cytometry showed that typical apoptotic peak (Sub-G1 peak) appeared and cells in S and G2/M phases decreased after being treated by SH for 48 h. The results of molecular docking indicated that the oxygen atom and skeleton core of SH and K503, W439, R363, and D440 of USP2 were essential for the binding of SH and USP2.
CONCLUSIONS:
SH can inhibit the activity of USP2 and provide a lead compound for future development of new USP2 inhibitors.

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2003 Aug;28(8):738-40.

[Determination of shionone in Radix Asteris by HPLC].[Pubmed: 15015355]

To determine the content of Shionone in Radix Aster from several different locations and markets.
METHODS AND RESULTS:
The HPLC analysis was used to determine Shionone directly, using Polaris C18 column and acetonitrile as the mobile phase with a flow rate of 1.0 mL.min-1, and the UV detection wavelength was 200 nm.
CONCLUSIONS:
The content of Shionone was from 0.06% to 0.18%, depending on different locations and markets.

Shionone Dilution Calculator

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Shionone Molarity Calculator

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Preparing Stock Solutions of Shionone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3435 mL 11.7173 mL 23.4346 mL 46.8691 mL 58.5864 mL
5 mM 0.4687 mL 2.3435 mL 4.6869 mL 9.3738 mL 11.7173 mL
10 mM 0.2343 mL 1.1717 mL 2.3435 mL 4.6869 mL 5.8586 mL
50 mM 0.0469 mL 0.2343 mL 0.4687 mL 0.9374 mL 1.1717 mL
100 mM 0.0234 mL 0.1172 mL 0.2343 mL 0.4687 mL 0.5859 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 Shionone

[Determination of shionone in Radix Asteris by HPLC].[Pubmed:15015355]

Zhongguo Zhong Yao Za Zhi. 2003 Aug;28(8):738-40.

OBJECTIVE: To determine the content of Shionone in Radix Aster from several different locations and markets. METHOD: The HPLC analysis was used to determine Shionone directly, using Polaris C18 column and acetonitrile as the mobile phase with a flow rate of 1.0 mL.min-1, and the UV detection wavelength was 200 nm. RESULT AND CONCLUSION: The content of Shionone was from 0.06% to 0.18%, depending on different locations and markets.

Expectorant, antitussive, anti-inflammatory activities and compositional analysis of Aster tataricus.[Pubmed:25701752]

J Ethnopharmacol. 2015 Apr 22;164:328-33.

ETHNOPHARMACOLOGICAL RELEVANCE: The root of Aster tataricus L. f., recorded in all versions of Chinese Pharmacopoeia, is a traditional Chinese medicine with the function of dispelling phlegm and relieving cough for more than 2000 years. This study was designed to evaluate the expectorant, antitussive, and anti-inflammatory activities of the root of A. tataricus and to explore the chemical substances responsible for these activities. MATERIALS AND METHODS: The 70% ethanol extract of the root of A. tataricus (RA-70) was divided into three fractions, Fr-0, Fr-50 and Fr-95. They were all orally administrated to the mice to investigate their potential expectorant activities by a tracheal phenol red secretion method. The most effective fraction, together with Shionone, was evaluated the expectorant, antitussive and anti-inflammatory activities by the mouse models of phenol red secretion, ammonia-induced cough, and xylene-induced ear swelling. Furthermore, the chemical components of the effective fraction were analyzed and identified by an HPLC-Q-TOF/MS method. RESULTS: Treatment with RA-70, Fr-0 and Fr-50 increased the amount of phenol red secretion by 65.3%, 56.5%, and 76.9%, respectively. Fr-50 was chosen for the further investigation and the results showed that Fr-50 at 40, 80 mg/kg significantly enhanced the phenol red secretion of tracheas, increased the latent period and decreased the frequency of cough and inhibited the ear edema in mice. Shionone at 80 mg/kg showed the trend of enhancing sputum secreting, but had no effect on ammonia-induced cough and xylene-induced ear edema. HPLC-Q-TOF/MS analysis indicated that Fr-50 was mainly composed of 12 caffeoylquinic acids (40.8%, in relative peak area), 7 astersaponins (12.0%) and 13 astins/asterinins (pentapeptides, 26.5%). CONCLUSIONS: The root of A. tataricus has significant expectorant, antitussive and anti-inflammatory effects. Caffeoylquinic acids, astersaponins, and aster peptides, rather than Shionone, may be the main constituents responsible for the expectorant and antitussive activities of A. tataricus and act in a synergistic way.

Description

Shionone is the major triterpenoid isolated from Aster tataricus, has anti-tussive, anti-inflammatory activities. Shionone possesses a unique six-membered tetracyclic skeleton and 3-oxo-4-monomethyl structure.

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