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Taraxerone

Cat No.:V34384 Purity: ≥98%
Taraxerone was extracted from P. truncatula.
Taraxerone
Taraxerone Chemical Structure CAS No.: 514-07-8
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Taraxerone was extracted from P. truncatula. Taraxerone enhances alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) activities with EC50s of 512.42 μM and 500.16 μM respectively.
Taraxerone (α-friedoolean-14-en-3-one) is a pentacyclic triterpenoid isolated from the ethyl acetate extract of Sedum sarmentosum with a purity of 96.383%. It has been previously reported to possess cytotoxic activity against cancer cell lines, inhibitory activity on topoisomerase, antimicrobial activity, antiviral activity, antiparasitic activity, and insecticidal activity. However, its effect on alcohol oxidation had not been reported prior to this study. The objective of this research was to evaluate the enhancing effects of Taraxerone on alcohol dehydrogenase (ADH) and acetaldehyde dehydrogenase (ALDH) activities via in vitro and in vivo experiments. [1]
Biological Activity I Assay Protocols (From Reference)
Targets
ADH (EC50 = 512.42 μM); ALDH (EC50 = 500.16 μM)
Taraxerone enhances the activities of alcohol dehydrogenase (ADH) and acetaldehyde dehydrogenase (ALDH). The half maximal efficient concentration (EC50) for ADH activity enhancement is 512.42 ± 3.12 μM. The EC50 for ALDH activity enhancement is 500.16 ± 3.23 μM. [1]
ln Vitro
Taraxerone significantly increased ADH and ALDH activities in a concentration-dependent manner. At concentrations of 1 mM, 3 mM, and 5 mM, ADH activities were increased by 4.87, 5.89, and 6.01 times, respectively, compared to the control group. ALDH activities were elevated by 9.15, 11.46, and 11.51 times at the same concentrations, respectively. At 5 mM, ADH and ALDH activities showed a narrow decrease compared to 3 mM, but the differences were not statistically significant. The enhancing effects of Taraxerone on ADH and ALDH activities were approximately 1.5 and 2 times higher than those of the positive control dihydromyricetin (DHM) at 3 mM and 5 mM treatments, respectively. The dose-response curves yielded EC50 values of 512.42 ± 3.12 μM for ADH and 500.16 ± 3.23 μM for ALDH. [1]
ln Vivo
Mice's plasma concentrations of acetaldehyde and alcohol are markedly lowered by tartacerone. The liver tissue of the dandelion treatment group experienced a sudden rise in ADH and ALDH expression upon ethanol exposure, in comparison to the control group [1]. Catalase, superoxide dismutase, and the reduction in glutathione content brought on by ethanol treatment are all inhibited by dexadelionone [1].
In ethanol-loaded mice, oral administration of Taraxerone (500 μM and 1 mM) along with 40% ethanol significantly lowered plasma alcohol and acetaldehyde concentrations compared to the control group (DMSO-treated). Plasma alcohol levels in the 500 μM Taraxerone group were reduced by 30.1%, 28.5%, and 20% at 1, 2, and 3 hours post-ethanol, respectively. In the 1 mM Taraxerone group, reductions were 32.8%, 58.6%, and 66.7% at the same time points. Plasma acetaldehyde levels in the 500 μM Taraxerone group declined by 6.6%, 23.1%, 38.1%, and 52.2% at 0.5, 1, 2, and 3 hours, respectively; in the 1 mM group, declines were 20.1%, 57.7%, 54.8%, and 56.5%, respectively. Taraxerone treatment also markedly increased ADH and ALDH gene expressions in liver tissues in a concentration-dependent manner. The 1 mM Taraxerone group showed approximately 1.2–2.3 times higher ADH expression and 1.01–4.02 times higher ALDH expression than the 500 μM group. Compared to the DHM-treated positive control group, ADH expressions were 2.24–10.25 times higher and ALDH expressions 2.23–4.36 times higher in Taraxerone-treated groups. Additionally, Taraxerone prevented the ethanol-induced decreases in hepatic antioxidant components (catalase, superoxide dismutase, and reduced glutathione) in a concentration-dependent manner. The 1 mM Taraxerone group exhibited 1.61–1.68 times higher catalase, 1.2–3.12 times higher superoxide dismutase, and 1.1–1.3 times higher glutathione levels compared to the 500 μM group. [1]
Enzyme Assay
The effects of Taraxerone on ADH and ALDH activities were determined using commercial assay kits following the manufacturer's instructions. Taraxerone was dissolved in dimethyl sulfoxide (DMSO). The results were expressed as the ethanol and acetaldehyde concentrations remaining in the reaction mixtures after enzyme reactions; lower concentrations indicated higher enzyme activities. DMSO alone did not affect ADH activity but decreased ALDH activity by 12.56% compared to the saline-treated group; therefore, the DMSO-treated group was used as the control. For the dose-response curve, varying concentrations of Taraxerone were tested, and the EC50 values were calculated from the resulting curves. [1]
Animal Protocol
Male ICR mice weighing 20–25 g were housed under controlled temperature (20±2°C) and a 12-hour light-dark cycle with standard rodent chow and tap water ad libitum for one week. Mice were randomly assigned to five experimental groups (n=4 per group) and fasted overnight. All groups were orally administered 40% ethanol at a volume of 5 mL/kg body weight. Immediately after ethanol administration, Group 1 received 500 μM Taraxerone, Group 2 received 1 mM Taraxerone, Group 3 (positive control) received 3 mM dihydromyricetin (DHM), Group 4 (control) received DMSO, and Group 5 received saline. Taraxerone and DHM were dissolved in DMSO, and all samples were administered orally at 5 mL/kg body weight. Animals were deprived of food and water during the experiment. Blood samples were collected from the caudal vena cava using heparin vacutainers, and liver tissues were collected at 0.5, 1, 2, and 3 hours after ethanol administration. Mice were anesthetized prior to sample collection. [1]
References

[1]. Taraxerone enhances alcohol oxidation via increases of alcohol dehyderogenase (ADH) and acetaldehyde dehydrogenase (ALDH) activities and gene expressions.Food Chem Toxicol. 2012 Jul;50(7):2508-14.

Additional Infomation
Dandelionone is a carrageenan sesquiterpene compound and a metabolite. It has been reported in Erythrophleum fordii, Cymbidium giganteum, and other organisms with relevant data. See also: root bark (partial) of Myrica cerifera.
Taraxerone was isolated from Sedum sarmentosum (stonecrop, Dolnamul), a perennial herb widely distributed in Asia, Europe, and North America. Approximately 7.5 mg of Taraxerone can be isolated from 1 kg of dried sedum stems and leaves using a simple solvent extraction method. Fresh sedum stems and leaves are consumed as an ingredient in salads, and sedum juice is used in gelatin jelly. The study suggests that intake of sedum may help prevent adverse effects of alcohol consumption. Taraxerone is a triterpenoid (C30) synthesized from squalene precursor. The study also notes that DMSO (the solvent used) slightly inhibited ALDH activity and reduced ADH/ALDH gene expressions and hepatic catalase content; however, Taraxerone overcame these inhibitory effects. The authors propose that Taraxerone could be developed as a new anti-alcohol intoxication agent, though further studies on chronic ethanol consumption and ethanol-induced liver injury are needed. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H48O
Molecular Weight
424.7015
Exact Mass
424.37
CAS #
514-07-8
PubChem CID
92785
Appearance
White to off-white solid
Density
1.0±0.1 g/cm3
Boiling Point
488.3±44.0 °C at 760 mmHg
Flash Point
202.8±23.4 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.534
LogP
10.48
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Heavy Atom Count
31
Complexity
831
Defined Atom Stereocenter Count
7
SMILES
O=C1C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]([H])(C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1(C([H])([H])[H])C3=C([H])C([H])([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@@]4([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H]
InChi Key
DBCAVZSSFGIHQZ-YLAYQGCQSA-N
InChi Code
InChI=1S/C30H48O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-23H,10-19H2,1-8H3/t20-,22+,23+,27-,28-,29-,30+/m0/s1
Chemical Name
(4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-2,4a,5,6,8,9,10,12,12a,13,14,14a-dodecahydro-1H-picen-3-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
THF : 10 mg/mL (~23.55 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3546 mL 11.7730 mL 23.5460 mL
5 mM 0.4709 mL 2.3546 mL 4.7092 mL
10 mM 0.2355 mL 1.1773 mL 2.3546 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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