Soyasapogenol A

CAS# 508-01-0

Soyasapogenol A

2D Structure

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Soyasapogenol A

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Chemical Properties of Soyasapogenol A

Cas No. 508-01-0 SDF Download SDF
PubChem ID 160495 Appearance Powder
Formula C30H50O4 M.Wt 474.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Soyasapogenin A
Solubility Soluble in chloroform and methan
Chemical Name (3R,4S,4aR,6aR,6aS,6bR,9S,10S,12aR,14bR)-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,10-triol
SMILES CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(C(C1O)O)C)C)C)(C)CO)O)C)C
Standard InChIKey CDDWAYFUFNQLRZ-POFPXMCLSA-N
Standard InChI InChI=1S/C30H50O4/c1-25(2)16-19-18-8-9-21-27(4)12-11-22(32)28(5,17-31)20(27)10-13-30(21,7)29(18,6)15-14-26(19,3)24(34)23(25)33/h8,19-24,31-34H,9-17H2,1-7H3/t19-,20?,21-,22+,23+,24-,26-,27+,28-,29-,30-/m1/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 Soyasapogenol A

The seeds of Glycine max

Biological Activity of Soyasapogenol A

Description1. Soyasapogenol A and soyasapogenol B concentrated extracts show a greater ability to inhibit proliferation of cultured Hep-G2 when compared to a total soyasaponin extract that did not contain any soyasapogenols. 2. Soyasapogenol A directly prevents apoptosis of hepatocytes, and secondly, inhibits the elevation of plasma TNF-α, which consequently resulted in the prevention of liver damage in the concanavalin A-induced hepatitis model. 3. Soyasapogenol A shows estrogenic activities.
TargetsTNF-α

Soyasapogenol A Dilution Calculator

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Preparing Stock Solutions of Soyasapogenol A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1066 mL 10.533 mL 21.0659 mL 42.1319 mL 52.6648 mL
5 mM 0.4213 mL 2.1066 mL 4.2132 mL 8.4264 mL 10.533 mL
10 mM 0.2107 mL 1.0533 mL 2.1066 mL 4.2132 mL 5.2665 mL
50 mM 0.0421 mL 0.2107 mL 0.4213 mL 0.8426 mL 1.0533 mL
100 mM 0.0211 mL 0.1053 mL 0.2107 mL 0.4213 mL 0.5266 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 Soyasapogenol A

Effect of soyasapogenol A and soyasapogenol B concentrated extracts on HEP-G2 cell proliferation and apoptosis.[Pubmed:18361499]

J Agric Food Chem. 2008 Apr 23;56(8):2603-8.

The growth inhibition and the induction of apoptosis brought about by soyasaponins extracted from soy flour ( Glycine max (L.)) and concentrated for soyasapogenols A and B formed by hydrolysis were tested for cytoactivity in the human hepatocellular carcinoma cell line Hep-G2. Concentrated Soyasapogenol A (SG-A) and soyasapogenol B (SG-B) extracts contained approximately 69.3% and 46.2% of their respective aglycones (soyasapogenols) assessed by HPLC and ESI-MS, while the soyasaponin extract (TS), derived from crude methanol extraction, did not contain any detectable amounts of SG-A or SG-B. An MTT viability assay showed that all three extracts had an effect on Hep-G2 proliferation in a dose-response manner with 72 h LC50 values of 0.594+/-0.021 mg/mL for TS, 0.052+/-0.011 mg/mL for SG-A, and 0.128+/-0.005 mg/mL for SG-B. Apoptotic cells were determined by flow cytometry cell cycle analysis and confocal laser scanning microscopy (CLSM). Cell cycle analysis indicated a significant ( P< 0.05) greater sub-G1 buildup of apoptotic cells at 24 h (25.63+/-2.1%) and 72 h (47.1+/-3.5%) for the SG-A extract compared to SG-B, whereas the TS extract produced only a minor buildup of sub-G1 cells. CLSM confirmed a morphological change of all treatments after 24 h, at the respective LC50 concentrations. These results show that the samples that contained mainly soyasapogenols A and B showed a greater ability to inhibit proliferation of cultured Hep-G2 when compared to a total soyasaponin extract that did not contain any soyasapogenols.

Protective effects of soyasapogenol A on liver injury mediated by immune response in a concanavalin A-induced hepatitis model.[Pubmed:10720649]

Eur J Pharmacol. 2000 Mar 10;391(1-2):175-81.

The present study was carried out to analyze the effects of Soyasapogenol A on the liver injury mediated by the immune response in concanavalin A-induced hepatitis in mice. Soyasapogenol A reduced the number of infiltrating inflammatory cells in the liver and significantly lowered the elevated level of plasma tumor necrosis factor-alpha (TNF-alpha) 2 h after concanavalin A treatment, and then markedly reduced the elevated plasma alanine aminotransferase activity and decreased the number of apoptotic bodies in the liver parenchymal cells but not in the sinusoidal cells at 24 h. Since the effect of Soyasapogenol A on the elevated plasma TNF-alpha level was not appreciable compared to the preventive effect of Soyasapogenol A on the elevated plasma alanine aminotransferase level, these results suggest that Soyasapogenol A directly prevents apoptosis of hepatocytes, and secondly, inhibits the elevation of plasma TNF-alpha, which consequently resulted in the prevention of liver damage in the concanavalin A-induced hepatitis model.

Estrogenic and antiproliferative properties of soy sapogenols in human breast cancer cells in vitro.[Pubmed:12419690]

Food Chem Toxicol. 2002 Dec;40(12):1767-74.

Two soy sapogenols, Soyasapogenol A (SA) and soyasapogenol B (SB) were tested for their estrogenic activities in estrogen responsive MCF-7 or estrogen-insensitive MDA-MB-231 (MDA) human breast cancer cells. SB and SA had differential actives on cell proliferation with 10 microM SB being growth inhibitory to MDA cells with no significant effect at any concentration on MCF-7 cells. SA also inhibited MDA cell proliferation at 10 micro, but at this same dose stimulated a 2.5-fold increase in MCF-7 proliferation. SA (0.1-10 microM) induced pS2 mRNA levels and the induction was blocked by co-treatment of cells with the anti-estrogen ICI 182,780. SA also induced the formation of an ER-ERE DNA complex measured by electrophoretic mobility shift assay. In summary, these results show that Soyasapogenol A is estrogenic, whereas soyasapogenol B is growth inhibitory.

Description

Soyasapogenol A, a triterpene compound, isolated from the roots of Abrus cantoniensis. Soyasapogenol A directly prevents apoptosis of hepatocytes, and secondly, inhibits the elevation of plasma TNF-α, which consequently results in the prevention of liver damage in the Concanavalin A-induced hepatitis model.

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