Withanolide A

CAS# 32911-62-9

Withanolide A

Catalog No. BCN8010----Order now to get a substantial discount!

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Quality Control of Withanolide A

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Chemical structure

Withanolide A

3D structure

Chemical Properties of Withanolide A

Cas No. 32911-62-9 SDF Download SDF
PubChem ID 11294368 Appearance White powder
Formula C28H38O6 M.Wt 470.60
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms Withaniol
Solubility Soluble in chloroform; sparingly soluble in methanol; practically insoluble in water
SMILES CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(=O)C=CC6)C)O)C)O)C
Standard InChIKey DXWHOKCXBGLTMQ-SFQAJKIESA-N
Standard InChI InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/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 Withanolide A

1 Withania sp.

Biological Activity of Withanolide A

Description1. Withanolide A extends the lifespan in human EGFR-driven cancerous Caenorhabditis elegans. 2. Withanolide A plays an important role in central muscarinic receptor functional balance and activation of antioxidant system in the cerebral cortex of temporal lobe epileptic condition. 3. Withanolide A shows anticancer activity against the SK-Br-3 cells. 4. Withanolide A may serve as potential neuroprotective agent due to inhibition of MAPK family proteins and activation of PI3K/Akt signaling.
TargetsEGFR | NF-kB | TNF-α | Caspase | ROS | NMDAR | PI3K | Akt | MAPK

Withanolide A Dilution Calculator

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Withanolide A Molarity Calculator

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Preparing Stock Solutions of Withanolide A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1249 mL 10.6247 mL 21.2495 mL 42.4989 mL 53.1237 mL
5 mM 0.425 mL 2.1249 mL 4.2499 mL 8.4998 mL 10.6247 mL
10 mM 0.2125 mL 1.0625 mL 2.1249 mL 4.2499 mL 5.3124 mL
50 mM 0.0425 mL 0.2125 mL 0.425 mL 0.85 mL 1.0625 mL
100 mM 0.0212 mL 0.1062 mL 0.2125 mL 0.425 mL 0.5312 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 Withanolide A

Endophytes of Withania somnifera modulate in planta content and the site of withanolide biosynthesis.[Pubmed:29615668]

Sci Rep. 2018 Apr 3;8(1):5450.

Tissue specific biosynthesis of secondary metabolites is a distinguished feature of medicinal plants. Withania somnifera, source of pharmaceutically important withanolides biosynthesizes withaferin-A in leaves and withanolide-A in roots. To increase the in planta withanolides production, a sustainable approach needs to be explored. Here, we isolated endophytes from different parts of W. somnifera plants and their promising role in in planta withanolide biosynthesis was established in both in-vivo grown as well in in-vitro raised composite W. somnifera plants. Overall, the fungal endophytes improved photosynthesis, plant growth and biomass, and the root-associated bacterial endophytes enhanced the withanolide content in both in-vivo and in-vitro grown plants by modulating the expression of withanolide biosynthesis genes in leaves and roots. Surprisingly, a few indole-3-acetic acid (IAA)-producing and nitrogen-fixing root-associated endophytes could induce the biosynthesis of withaferin-A in roots by inducing in planta IAA-production and upregulating the expression of withanolide biosynthesis genes especially MEP-pathway genes (DXS and DXR) in roots as well. Results indicate the role of endophytes in modulating the synthesis and site of withanolides production and the selected endophytes can be used for enhancing the in planta withanolide production and enriching roots with pharmaceutically important withaferin-A which is generally absent in roots.

Attenuation of Glutamate-Induced Excitotoxicity by Withanolide-A in Neuron-Like Cells: Role for PI3K/Akt/MAPK Signaling Pathway.[Pubmed:28447311]

Mol Neurobiol. 2018 Apr;55(4):2725-2739.

Glutamate-induced excitotoxicity is one of the major underlying mechanisms for neurodegenerative diseases. Efforts are being made to treat such conditions with an array of natural compounds that can modulate the release of glutamate or the underlying mechanisms associated with it. Withania somnifera extract has potent pharmacologic activity similar to that of Korean Ginseng tea and is used to treat several neuronal disorders. However, to date, little efforts have been made to evaluate individual constituents of this plant for neurodegenerative disorders. Present study was carried out to investigate withanolide-A, one of the active constituents of Withania somnifera against glutamate-induced excitotoxicity in retinoic acid differentiated Neuro2a neuroblastoma cells. The results indicated that glutamate treatment for 2 h induced death in cells that was significantly attenuated by pre-treatment with MK-801 (specific NMDA receptor antagonist) and different concentrations of withanolide-A. Withanolide-A abated the glutamate-induced influx of intracellular calcium and excessive ROS production significantly. Further on, glutamate treatment resulted in increased levels of pro-apoptotic and decreased levels of anti-apoptotic proteins, and these protein levels were normalized by various doses of withanolide-A. All of these protective effects were partly due to inhibition of MAPK family proteins and activation of PI3K/Akt signaling. Thus, our results suggest that withanolide-A may serve as potential neuroprotective agent.

Withanolide A extends the lifespan in human EGFR-driven cancerous Caenorhabditis elegans.[Pubmed:29427754]

Exp Gerontol. 2018 Apr;104:113-117.

The conserved EGFR pathway is linked with multiple cancers in humans including breast, ovarian, and lung carcinoma. Withanolide A, one of the major withanolidal active compounds isolated from the Withania somnifera, extends lifespan and ameliorates stress resistance in wild-type C. elegans by targeting the Insulin/IGF-1 signaling pathway. Up-regulation of IGF1 can transactivate EGFR which inturn reduces longevity and promotes tumor development in an organism. We examined the effects of Withanolide A on the lifespan of a human EGFR-driven C. elegans transgenic model exhibiting the multivulva (Muv) phenotype. The results showed that WA extends the lifespan of both wild human EGFR-driven C. elegans model (human wild-type tyrosine kinase) as well as models bearing single (L858R), and double mutations (T790M-L858R). The lifespan extension observed in these transgenic strains was 20.35, 24.21 and 21.27%, respectively. Moreover, the reduced fat levels were noticed in both wild-type N2 worms and transgenic strains. These observations support the heathspan promoting effect of WA as lipid-rich diet has been reported to promote tumor development. In view of the fact that most of the well known FDA approved drugs such as gefitinib fail to inhibit the EGFR-associated cancers because of these mutations, the present findings show the potential of Withanolide A as a foreseen future nutraceutical to improve the average survival of cancer patients.

Altered muscarinic receptor expression in the cerebral cortex of epileptic rats: restorative role of Withania somnifera.[Pubmed:29216436]

Biochem Cell Biol. 2018 Aug;96(4):433-440.

Temporal lobe epilepsy involves a sequence of events that can lead to neurotransmitter signalling alterations. There are many herbal extracts considered to be alternative therapeutic methods to manage epilepsy. In this study, we investigated the effect of Withania somnifera (WS) root extract and Withanolide A (WA) in the management of temporal lobe epilepsy. Confocal imaging of TOPRO-3-stained cortical sections showed severe damage in the epileptic brain. We also observed a reduced antioxidant potential and increased peroxide levels in the epileptic test group of rats. Oxidative stress resulted in the down-regulation of CREB, NF-kappaB, and TNF-alpha, and with up-regulation of the apoptotic factors caspases 8 and 3 and Bax in the epileptic group. Epileptic condition also resulted in increased muscarinic receptor binding and mRNA expression in the cerebral cortex. Withania somnifera and Withanolide A significantly reversed the altered muscarinic receptor expression and reversed the oxidative stress and resultant derailment in cell signalling. Thus our studies suggest that Withania somnifera and Withanolide A play important roles in central muscarinic receptor functional balance and activation of the antioxidant system in the cerebral cortex in temporal lobe epilepsy. These findings can be of immense therapeutic significance for managing epilepsy.

Molecular docking, QSAR and ADMET studies of withanolide analogs against breast cancer.[Pubmed:28694686]

Drug Des Devel Ther. 2017 Jun 22;11:1859-1870.

Withanolides are a group of pharmacologically active compounds present in most prodigal amounts in roots and leaves of Withania somnifera (Indian ginseng), one of the most important medicinal plants of Indian traditional practice of medicine. Withanolides are steroidal lactones (highly oxygenated C-28 phytochemicals) and have been reported to exhibit immunomodulatory, anticancer and other activities. In the present study, a quantitative structure activity relationship (QSAR) model was developed by a forward stepwise multiple linear regression method to predict the activity of Withanolide Analogs against human breast cancer. The most effective QSAR model for anticancer activity against the SK-Br-3 cell showed the best correlation with activity (r(2)=0.93 and rCV(2) =0.90). Similarly, cross-validation regression coefficient (rCV(2)=0.85) of the best QSAR model against the MCF7/BUS cells showed a high correlation (r(2)=0.91). In particular, compounds CID_73621, CID_435144, CID_301751 and CID_3372729 have a marked antiproliferative activity against the MCF7/BUS cells, while 2,3-dihydrowithaferin A-3-beta-O-sulfate, withanolide 5, Withanolide A, withaferin A, CID_10413139, CID_11294368, CID_53477765, CID_135887, CID_301751 and CID_3372729 have a high activity against the Sk-Br-3 cells compared to standard drugs 5-fluorouracil (5-FU) and camptothecin. Molecular docking was performed to study the binding conformations and different bonding behaviors, in order to reveal the plausible mechanism of action behind higher accumulation of active Withanolide Analogs with beta-tubulin. The results of the present study may help in the designing of lead compound with improved activity.

Description

Withanolide A, isolated from the indian herbal drug Ashwagandha (root of Withania somnifera), could regenerate neurites and reconstruct synapses in severely damaged neurons.

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