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Echinacoside

Cat No.:V29176 Purity: ≥98%
Echinacoside is a naturally occurring polyphenolic compoundand a caffeic acid glycoside with various biological activities including antibiotic, antioxidative, neuroprotective,anti-inflammatory, hepatoprotective, nitric oxide radical-scavenging and vasodilative effects.
Echinacoside
Echinacoside Chemical Structure CAS No.: 82854-37-3
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Echinacoside is a naturally occurring polyphenolic compound and a caffeic acid glycoside with various biological activities including antibiotic, antioxidative, neuroprotective, anti-inflammatory, hepatoprotective, nitric oxide radical-scavenging and vasodilative effects.
Echinacoside (CAS 82854-37-3) is a phenylethanoid glycoside isolated from the stems of Cistanche deserticola. It is a natural polyphenolic compound with various pharmacological activities, including anti-inflammatory, antioxidative, hepatoprotective, neuroprotective, nitric oxide radical-scavenging, and vasodilative effects. Echinacoside effectively inhibits Wnt/β-catenin signaling. It elicits neuroprotection by activating Trk receptors and their downstream signal pathways. It exhibits antioxidant activity by scavenging free radicals and reducing oxidative stress. It also shows anti-inflammatory effects by inhibiting the production of pro-inflammatory cytokines. It has been investigated for its potential neuroprotective effects against neurodegenerative diseases such as Alzheimer's and Parkinson's disease.
Biological Activity I Assay Protocols (From Reference)
Targets
Echinacoside targets multiple pathways. It effectively inhibits Wnt/β-catenin signaling. It activates Trk receptors and their downstream signal pathways, mediating neuroprotection. It targets reactive oxygen species (ROS) and exhibits nitric oxide radical-scavenging activity. Its neuroprotective effects are thought to be mediated via effects on mitogen-activated protein kinase (MAPK), nuclear factor kappa-B (NF-κB), caspases 3 and 8, as well as CHOP pathways. It also shows activity against HSD17B4 at 1995.3 nM. Its anti-osteoporotic activity is mediated through increasing OPG/RANKL ratio.
ln Vitro
In vitro, Echinacoside behaves as an antioxidant and a potent free radical scavenger. It has been shown to rescue SH-SY5Y neuronal cells from TNF-alpha-induced apoptosis. It effectively inhibits Wnt/β-catenin signaling. It activates Trk receptors and their downstream signal pathways. It inhibits amyloid fibrillization of HEWL and protects against Aβ-induced neurotoxicity. It promotes bone regeneration by increasing OPG/RANKL ratio in MC3T3-E1 cells. It inhibits breast cancer cells by suppressing the Wnt/β-catenin signaling pathway. It exhibits anti-inflammatory effects by inhibiting pro-inflammatory cytokine production.
ln Vivo
When taken daily for 12 weeks, the Echinacea series (30-270 mg/kg body weight; face) dramatically reverses weight gain, serum supplemental proline (HOP) levels, wet skin weight, and bone mineral density (BMD) in women who have been castrated (OVX).
In vivo, Echinacoside (30-270 mg/kg body weight; p.o.; daily for 12 weeks) significantly reverses the increases of body weight, serum hydroxyproline (HOP) levels, and the decreases of uterus wet weight and bone mineral density (BMD) in ovariectomized (OVX) rats. It has neuroprotective effects in the mouse MPTP model of Parkinson's disease, improving motor behavior and attenuating the depletion of striatal dopamine, DOPAC, and HVA in MPTP-lesioned mice. It ameliorates D-galactosamine plus lipopolysaccharide-induced acute liver injury in mice via inhibition of apoptosis and inflammation.
Enzyme Assay
For in vitro cell-free assays, Echinacoside's antioxidant activity can be measured using DPPH or ABTS radical scavenging assays. Its nitric oxide radical-scavenging activity can be assessed using the Griess reaction. Wnt/β-catenin signaling inhibition can be studied using reporter gene assays or by measuring β-catenin protein levels. Trk receptor activation can be assessed by measuring receptor phosphorylation using ELISA or Western blot. Its anti-inflammatory activity can be evaluated by measuring inhibition of pro-inflammatory cytokines using ELISA.
Cell Assay
For in vitro cellular assays, neuroprotective effects are assessed in SH-SY5Y neuronal cells. Cells are treated with Echinacoside and exposed to TNF-alpha or other neurotoxic insults. Cell viability is measured using MTT or similar assays. Apoptosis is assessed by flow cytometry or caspase activity assays. Wnt/β-catenin signaling is studied in cancer cell lines by measuring β-catenin levels and target gene expression. Trk receptor activation is assessed in neuronal cells by measuring receptor phosphorylation. Anti-osteoporotic activity is assessed in MC3T3-E1 cells by measuring OPG/RANKL ratio.
Animal Protocol
Animal/Disease Models: 56 6-month-old female SD (SD (Sprague-Dawley)) rats (OVX rat model) [3]
Doses: 30, 90, 270 mg/kg body weight
Route of Administration: po; ) Ratio [3]. one time/day for 12 weeks
Experimental Results: Increases in body weight, serum hydroxyproline (HOP) levels, and decreases in uterine wet weight and bone density were Dramatically reversed.
For in vivo studies, Echinacoside is administered orally to animal models. In ovariectomized rats, it is given at 30-270 mg/kg body weight daily for 12 weeks to assess anti-osteoporotic effects. In the MPTP model of Parkinson's disease, it is administered to assess neuroprotection by measuring motor behavior and striatal dopamine levels. In acute liver injury models, it is given to assess hepatoprotection by measuring liver enzyme levels, apoptosis, and inflammation.
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Animal studies have shown an oral bioavailability of 0.83%. Metabolism/Metabolites Metabolism of echinacoside has been studied in rats, suggesting the involvement of catechol O-methyltransferases, as well as unidentified UDP-glucuronyltransferases and sulfotransferases. A study on the metabolism of echinacoside by human gut microbiota identified 13 metabolites produced independently of human metabolism.
Echinacoside (CAS 82854-37-3) has a molecular formula of C35H46O20 and a molecular weight of 786.73 g/mol. Appearance: typically a powder. Solubility: DMSO and other organic solvents. Storage: store under recommended conditions as per certificate of analysis. Purity: typically >98% for research use. It is a phenylethanoid glycoside and is used as an analytical standard.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a natural polyphenolic compound from Cistanche deserticola, it is generally considered to have low toxicity, but standard toxicological studies would be required for drug development. In vitro cytotoxicity assays in various cell lines are typically performed alongside efficacy studies to confirm that observed effects are not due to a general reduction in cell viability.
References

[1]. Echinacoside ameliorates D-galactosamine plus lipopolysaccharide-induced acute liver injury in mice via inhibition of apoptosis and inflammation. Scand J Gastroenterol. 2014 Aug;49(8):993-1000.

[2]. Echinacoside inhibits breast cancer cells by suppressing the Wnt/β-catenin signaling pathway. Biochem Biophys Res Commun. 2020 Mar 19. pii: S0006-291X(20)30530-1.

[3]. Antiosteoporotic activity of echinacoside in ovariectomized rats. Phytomedicine. 2013 Apr 15;20(6):549-57.

[4]. Echinacoside inhibits amyloid fibrillization of HEWL and protects against Aβ-induced neurotoxicity. Int J Biol Macromol. 2014 Sep 2;72C:243-253.

[5]. Transient exposure to echinacoside is sufficient to activate Trk signaling and protect neuronal cells from rotenone. J Neurochem. 2013 Feb;124(4):571-80.

[6]. Echinacoside promotes bone regeneration by increasing OPG/RANKL ratio in MC3T3-E1 cells. Fitoterapia. 2012 Dec;83(8):1443-50.

Additional Infomation
Echinacoside is an oligosaccharide. It is a phenylethyl glycoside isolated from Echinacea angustifolia in 1950 and is currently being investigated for its applications in Parkinson's disease, Alzheimer's disease, atherosclerosis, osteoporosis, acute colitis, wound healing, and hepatitis treatment. Echinacoside has been shown to inhibit apoptosis in nerve cell lines, demonstrating its potential for treatment of neurological diseases. It has been reported to be present in Jasminum mesnyi, Echinacea angustifolia, and several other organisms with relevant data. Its neuroprotective effect is believed to be achieved by influencing mitogen-activated protein kinase, nuclear factor κB, caspase 3 and 8, and the CHOP pathway.
Echinacoside is a research-grade compound and is not approved for therapeutic use. It serves primarily as a pharmacological tool for studying neuroprotection, Wnt/β-catenin signaling, and oxidative stress. Its mechanism of action involves inhibition of Wnt/β-catenin signaling, activation of Trk receptors, and antioxidant activity. It has been investigated for potential neuroprotective effects against neurodegenerative diseases. No clinical trials have been reported. It is isolated from Cistanche deserticola and has anti-osteoporotic activity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C35H46O20
Molecular Weight
786.73
Exact Mass
786.258
CAS #
82854-37-3
PubChem CID
5281771
Appearance
Off-white to yellow solid powder
Density
1.7±0.1 g/cm3
Boiling Point
1062.7±65.0 °C at 760 mmHg
Flash Point
327.9±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.698
LogP
0.14
Hydrogen Bond Donor Count
12
Hydrogen Bond Acceptor Count
20
Rotatable Bond Count
14
Heavy Atom Count
55
Complexity
1230
Defined Atom Stereocenter Count
15
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
InChi Key
FSBUXLDOLNLABB-ISAKITKMSA-N
InChi Code
InChI=1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1
Chemical Name
[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
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

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)
DMSO : ~50 mg/mL (~63.55 mM)
H2O : ~35.71 mg/mL (~45.39 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.18 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (3.18 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (3.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 100 mg/mL (127.11 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2711 mL 6.3554 mL 12.7108 mL
5 mM 0.2542 mL 1.2711 mL 2.5422 mL
10 mM 0.1271 mL 0.6355 mL 1.2711 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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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