| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
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| Targets |
Natural flavonoid
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|---|---|
| ln Vitro |
In worms with limited lifespans, 2,3-dehydrosilybin A (DHS A) may be able to prolong their life expectancy. Human and nematode cells are more resistant when 2,3-dehydrosilybin A (DHS A) is present. In both humans and nematodes, 2,3-dehydrosilybin A decreases the progression of Alzheimer's disease. The way 2,3-dehydrosilybin A affects C. elegans is dependent on the pathways DAF-16 and FGT-1.
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| ln Vivo |
Aging is an unavoidable process characterized by gradual failure of homeostasis that constitutes a critical risk factor for several age-related disorders. It has been unveiled that manipulation of various key pathways may decelerate the aging progression and the triggering of age-related diseases. As a consequence, the identification of compounds, preferably natural-occurring, administered through diet, with lifespan-extending, anti-aggregation and anti-oxidation properties that in parallel exhibit negligible side-effects is the main goal in the battle against aging. Here we analyze the role of 2,3-dehydrosilybin A/B (DHS A/B), a minor component of silymarin used in a plethora of dietary supplements. This flavonolignan is well-known for its anti-oxidative and neuroprotective properties, among others. We demonstrate that DHS A/B confers oxidative stress resistance not only in human primary cells but also in the context of a multi-cellular aging model, namely Caenorhabditis elegans (C. elegans) where it also promotes lifespan extension. We reveal that these DHS A/B outcomes are FGT-1 and DAF-16 dependent. We additionally demonstrate the anti-aggregation properties of DHS A/B in human cells of nervous origin but also in nematode models of Alzheimer's disease (AD), eventually leading to decelerated progression of AD phenotype. Our results identify DHS A/B as the active component of silymarin extract and propose DHS A/B as a candidate anti-aging and anti-aggregation compound. [1]
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| Animal Protocol |
DHS A/B promotes lifespan extension in C. elegans [1]
We initially investigated whether our silymarin preparations promote lifespan extension in wt C. elegans. Significant dose-dependent lifespan extension was scored with the most effective concentration being 50 μΜ (as the sum of flavonolignans; Fig. 1A). We then dissected silymarin into its main constituents to reveal which one is mainly responsible for this lifespan-extending effect. Lifespan assays with silybin A/B, silychristin A/B, silydianin, isosilybin Α and DHS A/B at the same... |
| References | |
| Additional Infomation |
2,3-Dehydrosilybin is a flavonolignan.
2,3-Dehydrosilybin has been reported in Silybum marianum with data available. The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers. See also: 2,3-Dehydrosilybin (annotation moved to). In most of the reported studies, the responsible active compound (if any) of silymarin is not specified while many controversies appear due to the variable compositions of silymarin preparations in the absence of standardization or analysis [19]. Therefore, the positive effects are usually attributed in general to the silymarin extract. In this study, we performed a detailed analysis of almost all components of silymarin with regard to their potential anti-aging properties using C. elegans as a model and we reveal the crucial role of DHS A/B. Given that aging is the main risk factor for age- and aggregation-related diseases, we have also investigated the potential positive effects of DHS A/B on the onset and progression of AD, an aggregation-related disorder. Our results demonstrate the potential use of DHS A/B as a pro-longevity and anti-aggregation nutraceutical.[1] |
| Molecular Formula |
C25H20O10
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|---|---|
| Molecular Weight |
480.42
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| Exact Mass |
480.105
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| CAS # |
25166-14-7
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| Related CAS # |
2,3-Dehydrosilybin B;142796-24-5
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| PubChem CID |
5467200
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
761.0±60.0 °C at 760 mmHg
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| Melting Point |
254 - 255 °C
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| Flash Point |
263.8±26.4 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.712
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| LogP |
2.26
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
35
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| Complexity |
816
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
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| InChi Key |
BVKQRAYKLBRNIK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C25H20O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,24,26-29,31H,10H2,1H3
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| Chemical Name |
3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
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| Synonyms |
2,3-Dehydrosilybin A; DTXSID60858706; Hepatos; 3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)chromen-4-one; 3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one; DTXCID70809446; 2,3 dehydrosilybin; ...; 25166-14-7;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0815 mL | 10.4076 mL | 20.8151 mL | |
| 5 mM | 0.4163 mL | 2.0815 mL | 4.1630 mL | |
| 10 mM | 0.2082 mL | 1.0408 mL | 2.0815 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.
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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