Astragaloside A (Astramembrannin I; Astragalin A) 83207-58-3_Calcium Channel_Transmembrane_Signaling Pathways_Products

Astragaloside A (also called Astragaloside IV) is the major pure and active form of saponin isolated from Astragalus membranaceus in Traditional Chinese Medicin, and has been widely used for the treatment of cardiovascular diseases (e.g. ischemia) and kidney disease. Astragaloside A exhibits several pharmacological actions, such as anti-hypertension, positive inotropic action, anti-inflammation, and anti-myocardial injury. Astragaloside IV (2-40 μM) dose-dependently decreased TGF-β-induced a-SMA, fibronectin, CTGF, collagen I and III expression, up-regulated Smad7, but decreased p-Smad2 and p-Smad3 expression in NRK-49F cells. Moreover, Astragaloside IV prevented tubular epithelial apoptosis partially through inhibiting MAPK pathway activity, thereby ameliorating renal fibrosis.

Physicochemical Properties

Molecular Formula

C41H68O14

Molecular Weight

784.97

Exact Mass

784.46

CAS #

83207-58-3

Related CAS #

83207-58-3

PubChem CID

13943299

Appearance

Typically exists as solid at room temperature

Density

1.4±0.1 g/cm3

Boiling Point

895.7±65.0 °C at 760 mmHg

Melting Point

284-286ºC

Flash Point

495.5±34.3 °C

Vapour Pressure

0.0±0.6 mmHg at 25°C

Index of Refraction

1.621

LogP

1.96

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

1460

Defined Atom Stereocenter Count

SMILES

C[C@@]12C[C@H](O)[C@H]([C@@]3(CC[C@H](C(O)(C)C)O3)C)[C@@]1(C)CC[C@@]13C[C@]41CC[C@H](O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O)C(C)(C)[C@@H]4[C@H](C[C@@H]23)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1

InChi Key

QMNWISYXSJWHRY-AUJDEUPOSA-N

InChi Code

O[C@H]1[C@H](O)[C@@H](CO)O[C@](O[C@H]2C[C@]([C@@](C[C@H](O)[C@]3([H])[C@@]4(C)O[C@@H](C(C)(O)C)CC4)(C)[C@]3(C)CC5)([H])[C@]56[C@]7(C6)[C@]2([H])C(C)(C)[C@@H](O[C@]8([H])OC[C@@H](O)[C@H](O)[C@H]8O)CC7)([H])[C@@H]1O

Chemical Name

(2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Synonyms

AS-A; AST-A; Astramembrannin I; Astragalin A

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)

Biological Activity

ln Vitro

In vitro activity: Astragaloside IV improves post-ischemic heart function and ameliorated reperfusion arrhythmias accompanied by a significant increase in myocardial antioxidative enzyme superoxide dismutase activity in rat hearts in vitro. While, Astragaloside IVs protective effect on heart function can be partially abrogated by the nitric oxide synthase inhibitor, Nomega-nitro-L-arginine methyl ester.

Kinase Assay: AS-IV treatment also activates JAK2/STAT3 and ERK1/2 signaling pathways, and up-regulates endothelial nitric oxide synthase (eNOS) expression and nitric oxide (NO) production

Cell Assay: Astragaloside IV (2-40 μM) dose-dependently decreased TGF-β-induced a-SMA, fibronectin, CTGF, collagen I and III expression, up-regulated Smad7, but decreased p-Smad2 and p-Smad3 expression in NRK-49F cells [2]. Moreover, Astragaloside IV prevented tubular epithelial apoptosis partially through inhibiting MAPK pathway activity, thereby ameliorating renal fibrosis.

ln Vivo

Astragaloside IV significantly reduces infarct size in dogs subjected to coronary ligation in vivo. Astragaloside IV attenuates isoproterenol-induced subendocardial necrosis, serum lactate dehydrogenase and creatine kinase activation, and lipid oxide product malondialdehyde formation in rats. It also reduces sarcoplasmic reticulum Ca(2+)-uptake ability and Ca(2+)-ATPase (SERCA2a) activity as well as SERCA2a mRNA expression in myocardial injury rats.

Animal Protocol

5 and 10 mg/kg; 3.33, 10, and 33 mg/kg, intraperitoneal injection

Astragaloside IV (5 and 10 mg/kg/day, intraperitoneal injection) reduced serum lactate dehydrogenase and creatine kinase enzyme levels and attenuated this reduction in the Ca2+-ATPase activity in rats. Astragaloside IV (3.33, 10, and 33 mg/kg, intraperitoneal injection) treatment attenuated renal damage and improved renal function through inhibiting TGF-β/Smad signaling pathway in a dose-dependent manner in unilateral ureteral obstruction kidneys.

References

Planta Med.2006 Jan;72(1):4-8;Eur J Pharmacol.2007 Jul 30;568(1-3):203-12.

Additional Infomation

Cyclosiversioside F has been reported in Astragalus basineri, Astragalus mongholicus, and Astragalus membranaceus with data available.

Solubility Data

Solubility (In Vitro)

DMSO:100 mg/mL (127.4 mM)

Water:<1 mg/mL

Ethanol:<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 : 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).
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 : PEG300：Tween 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).
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	1.2739 mL	6.3697 mL	12.7393 mL
	5 mM	0.2548 mL	1.2739 mL	2.5479 mL
	10 mM	0.1274 mL	0.6370 mL	1.2739 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.

PeptideDB

Astragaloside A (Astramembrannin I; Astragalin A) 83207-58-3

CAS No.: 83207-58-3

Physicochemical Properties

Biological Activity

Solubility Data