Taraxasterol

CAS# 1059-14-9

Taraxasterol

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Quality Control of Taraxasterol

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Chemical structure

Taraxasterol

3D structure

Chemical Properties of Taraxasterol

Cas No. 1059-14-9 SDF Download SDF
PubChem ID 441686 Appearance White powder
Formula C30H50O M.Wt 426.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Isolactucerol; Lactucerol; Saussurol
Solubility Ethanol : 5.5 mg/mL (12.89 mM; ultrasonic and warming and heat to 50°C)
DMSO : 1 mg/mL (2.34 mM; ultrasonic and heat to 80°C)
Chemical Name (3S,4aR,6aR,6aR,6bR,8aR,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol
SMILES CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CCC1=C)C)C)C)(C)C)O)C
Standard InChIKey XWMMEBCFHUKHEX-CWFQSGEHSA-N
Standard InChI InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25+,27-,28+,29-,30-/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 Taraxasterol

1 Cynara sp. 2 Echinops sp. 3 Eupatorium sp. 4 Inula sp. 5 Saussurea sp. 6 Taraxacum sp.

Biological Activity of Taraxasterol

DescriptionTaraxasterol has anti-inflammatory, anti- tumor-promoting , anti-endotoxic shock and anti-allergic asthma activities. It inhibited NO, IFN-γ, PGE(2), TNF-α, IL-1β and IL-6 production.
TargetsNO | PGE | TNF-α | IL Receptor | NF-kB
In vitro

Effects of taraxasterol on inflammatory responses in lipopolysaccharide-induced RAW 264.7 macrophages.[Pubmed: 22366673]

J Ethnopharmacol. 2012 May 7;141(1):206-11.

Taraxasterol, a pentacyclic-triterpene, was isolated from the Chinese medicinal herb Taraxacum officinale. In the present study, we investigated the in vitro anti-inflammatory activity of Taraxasterol in lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophages.
METHODS AND RESULTS:
RAW 264.7 cells were pretreated with 2.5, 5, or 12.5μg/ml of Taraxasterol 1h prior to treatment with 1μg/ml of LPS. Nitric oxide (NO) level in supernatants from cells was examined by Griess reaction, the concentrations of prostaglandin E(2) (PGE(2)), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6) were measured by ELISA. Nuclear factor kappa B (NF-κB) activation was evaluated by immunocytochemical analysis. We found that Taraxasterol inhibited NO, PGE(2), TNF-α, IL-1β and IL-6 production in LPS-induced RAW 264.7 macrophages in a dose-dependent manner. Further studies revealed that Taraxasterol prevented the LPS-induced NF-κB translocation from cytoplasm into nuclear.
CONCLUSIONS:
These results indicate that Taraxasterol has anti-inflammatory effect by blocking NF-κB pathway.

In vivo

Protective effect of taraxasterol against LPS-induced endotoxic shock by modulating inflammatory responses in mice.[Pubmed: 24286370]

Immunopharmacol Immunotoxicol. 2014 Feb;36(1):11-6.

Taraxasterol, a pentacyclic-triterpene, was isolated from the Chinese medicinal herb Taraxacum officinale. In the present study, we investigated the protective effect of Taraxasterol on murine model of endotoxic shock and the mechanism of its action.
METHODS AND RESULTS:
Mice were treated with 2.5, 5 and 10 mg/kg of Taraxasterol prior to a lethal dose of lipopolysaccharide (LPS) challenge. Survival of mice was monitored twice a day for 7 days. To further understand the mechanism, the serum levels of inflammatory cytokine tumor necrosis factor-α (TNF-α), interferon-γ (IFN-γ), interleukin-1β (IL-1β), interleukin-6 (IL-6) and mediator nitric oxide (NO), prostaglandin E₂ (PGE₂) as well as histology of lungs were examined. The results showed that Taraxasterol significantly improved mouse survival and attenuated tissue injury of the lungs in LPS-induced endotoxemic mice. Further studies revealed that Taraxasterol significantly reduced TNF-α, IFN-γ, IL-1β, IL-6, NO and PGE₂ levels in sera from mice with endotoxic shock.
CONCLUSIONS:
These results indicate that Taraxasterol has a protective effect on murine endotoxic shock induced by LPS through modulating inflammatory cytokine and mediator secretion. This finding might provide a new strategy for the treatment of endotoxic shock and associated inflammation.

Inhibitory effect of taraxastane-type triterpenes on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.[Pubmed: 8692541]

Oncology. 1996 Jul-Aug;53(4):341-4.

Two taraxastane-type hydroxy triterpenes, Taraxasterol and faradiol, isolated from the flowers of Compositae plants Cynara scolymus (artichoke) and Chrysanthemum morifilolium (chrysanthemum), respectively, showed strong inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. At 2.0 mumol/mouse, these compounds inhibited markedly the tumor-promoting effect of TPA (1 microgram/mouse) on skin tumor formation following initiation with 7,12-dimethylbenz[alpha]anthracene (50 micrograms/mouse).

Effects of taraxasterol on ovalbumin-induced allergic asthma in mice.[Pubmed: 23727181]

J Ethnopharmacol. 2013 Jul 30;148(3):787-93.

Taraxasterol was isolated from the Chinese medicinal herb Taraxacum officinale which has been frequently used as a remedy for inflammatory diseases. In the present study, we determined the in vivo protective effect of Taraxasterol on allergic asthma induced by ovalbumin (OVA) in mice.
METHODS AND RESULTS:
Mice were sensitized and challenged with OVA, and were orally treated daily with Taraxasterol at 2.5, 5 and 10mg/kg from day 23 to 27 after sensitization. The number of inflammatory cells in bronchoalveolar lavage fluid (BALF) was determined. Th2 cytokine interleukin-4 (IL-4), interleukin-5 (IL-5), interleukin-13 (IL-13) production in BALF and OVA-specific immunoglobulin E (IgE) production in sera were measured using ELISA. Histological changes in lung tissues were examined using hematoxylin and eosin (H&E) and periodic acid-Schiff staining (PAS). Airway hyperresponsiveness (AHR) to inhaled methacholine was assessed. Taraxasterol dramatically decreased the total inflammatory cell and main inflammatory cell counts, reduced the production of Th2 cytokine IL-4, IL-5, IL-13 in BALF and OVA-specific IgE in sera, and suppressed AHR in a dose-dependent manner. Histological studies demonstrated that Taraxasterol substantially suppressed OVA-induced inflammatory cells infiltration into lung tissues and goblet cell hyperplasia in airways.
CONCLUSIONS:
This finding suggests that Taraxasterol protects against OVA-induced allergic asthma in mice.

Protocol of Taraxasterol

Cell Research

Effects of taraxasterol on inflammatory responses in lipopolysaccharide-induced RAW 264.7 macrophages.[Pubmed: 22366673]

J Ethnopharmacol. 2012 May 7;141(1):206-11.

Cell lines: RAW 264.7 cells
Concentrations: 2.5, 5, or 12.5μg/ml
Incubation Time: 1 h
Method: RAW 264.7 cells were pretreated with 2.5, 5, or 12.5μg/ml of Taraxasterol 1h prior to treatment with 1μg/ml of LPS. Nitric oxide (NO) level in supernatants from cells was examined by Griess reaction, the concentrations of prostaglandin E(2) (PGE(2)), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β) and interleukin-6 (IL-6) were measured by ELISA. Nuclear factor kappa B (NF-κB) activation was evaluated by immunocytochemical analysis. We found that Taraxasterol inhibited NO, PGE(2), TNF-α, IL-1β and IL-6 production in LPS-induced RAW 264.7 macrophages in a dose-dependent manner. Further studies revealed that Taraxasterol prevented the LPS-induced NF-κB translocation from cytoplasm into nuclear.

Animal Research

Protective effect of taraxasterol against LPS-induced endotoxic shock by modulating inflammatory responses in mice.[Pubmed: 24286370]

Immunopharmacol Immunotoxicol. 2014 Feb;36(1):11-6.

Animal Models: Mice (24–30 g)
Formulation: A suspension in gumacacia (1% w/v)
Dosages:2.5,5,10mg/kg from day 23 to 27 after sensitization
Administration: p.o.

Taraxasterol Dilution Calculator

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Preparing Stock Solutions of Taraxasterol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3436 mL 11.7178 mL 23.4357 mL 46.8713 mL 58.5892 mL
5 mM 0.4687 mL 2.3436 mL 4.6871 mL 9.3743 mL 11.7178 mL
10 mM 0.2344 mL 1.1718 mL 2.3436 mL 4.6871 mL 5.8589 mL
50 mM 0.0469 mL 0.2344 mL 0.4687 mL 0.9374 mL 1.1718 mL
100 mM 0.0234 mL 0.1172 mL 0.2344 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 Taraxasterol

Effects of taraxasterol on inflammatory responses in lipopolysaccharide-induced RAW 264.7 macrophages.[Pubmed:22366673]

J Ethnopharmacol. 2012 May 7;141(1):206-11.

AIM OF THE STUDY: Taraxasterol, a pentacyclic-triterpene, was isolated from the Chinese medicinal herb Taraxacum officinale. In the present study, we investigated the in vitro anti-inflammatory activity of Taraxasterol in lipopolysaccharide (LPS)-induced RAW 264.7 murine macrophages. MATERIALS AND METHODS: RAW 264.7 cells were pretreated with 2.5, 5, or 12.5mug/ml of Taraxasterol 1h prior to treatment with 1mug/ml of LPS. Nitric oxide (NO) level in supernatants from cells was examined by Griess reaction, the concentrations of prostaglandin E(2) (PGE(2)), tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta) and interleukin-6 (IL-6) were measured by ELISA. Nuclear factor kappa B (NF-kappaB) activation was evaluated by immunocytochemical analysis. RESULTS: We found that Taraxasterol inhibited NO, PGE(2), TNF-alpha, IL-1beta and IL-6 production in LPS-induced RAW 264.7 macrophages in a dose-dependent manner. Further studies revealed that Taraxasterol prevented the LPS-induced NF-kappaB translocation from cytoplasm into nuclear. CONCLUSIONS: These results indicate that Taraxasterol has anti-inflammatory effect by blocking NF-kappaB pathway.

Inhibitory effect of taraxastane-type triterpenes on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.[Pubmed:8692541]

Oncology. 1996 Jul-Aug;53(4):341-4.

Two taraxastane-type hydroxy triterpenes, Taraxasterol and faradiol, isolated from the flowers of Compositae plants Cynara scolymus (artichoke) and Chrysanthemum morifilolium (chrysanthemum), respectively, showed strong inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. At 2.0 mumol/mouse, these compounds inhibited markedly the tumor-promoting effect of TPA (1 microgram/mouse) on skin tumor formation following initiation with 7,12-dimethylbenz[alpha]anthracene (50 micrograms/mouse).

Protective effect of taraxasterol against LPS-induced endotoxic shock by modulating inflammatory responses in mice.[Pubmed:24286370]

Immunopharmacol Immunotoxicol. 2014 Feb;36(1):11-6.

Taraxasterol, a pentacyclic-triterpene, was isolated from the Chinese medicinal herb Taraxacum officinale. In the present study, we investigated the protective effect of Taraxasterol on murine model of endotoxic shock and the mechanism of its action. Mice were treated with 2.5, 5 and 10 mg/kg of Taraxasterol prior to a lethal dose of lipopolysaccharide (LPS) challenge. Survival of mice was monitored twice a day for 7 days. To further understand the mechanism, the serum levels of inflammatory cytokine tumor necrosis factor-alpha (TNF-alpha), interferon-gamma (IFN-gamma), interleukin-1beta (IL-1beta), interleukin-6 (IL-6) and mediator nitric oxide (NO), prostaglandin E(2) (PGE(2)) as well as histology of lungs were examined. The results showed that Taraxasterol significantly improved mouse survival and attenuated tissue injury of the lungs in LPS-induced endotoxemic mice. Further studies revealed that Taraxasterol significantly reduced TNF-alpha, IFN-gamma, IL-1beta, IL-6, NO and PGE(2) levels in sera from mice with endotoxic shock. These results indicate that Taraxasterol has a protective effect on murine endotoxic shock induced by LPS through modulating inflammatory cytokine and mediator secretion. This finding might provide a new strategy for the treatment of endotoxic shock and associated inflammation.

Description

Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum officinale. Taraxasterol has a role as a metabolite and an anti-inflammatory agent.

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