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Soyasaponin A1

CAS# 78693-94-4

Soyasaponin A1

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Chemical structure

Soyasaponin A1

3D structure

Chemical Properties of Soyasaponin A1

Cas No. 78693-94-4 SDF Download SDF
PubChem ID 441950 Appearance Powder
Formula C59H96O29 M.Wt 1269.4
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9S,10R,12aS,14aR,14bR)-9-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
SMILES CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CCC2(C(C1O)OC6C(C(C(CO6)O)OC7C(C(C(C(O7)CO)O)O)O)O)C)C)C)(C)CO)OC8C(C(C(C(O8)C(=O)O)O)O)OC9C(C(C(C(O9)CO)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C
Standard InChIKey XFXHYKZIZSNVSQ-TZRAUYBZSA-N
Standard InChI InChI=1S/C59H96O29/c1-54(2)16-23-22-8-9-29-56(4)12-11-30(83-53-45(38(72)37(71)43(85-53)48(77)78)87-52-44(36(70)33(67)27(19-62)82-52)86-51-40(74)35(69)32(66)26(18-61)81-51)57(5,21-63)28(56)10-13-59(29,7)58(22,6)15-14-55(23,3)47(46(54)76)88-49-41(75)42(24(64)20-79-49)84-50-39(73)34(68)31(65)25(17-60)80-50/h8,23-47,49-53,60-76H,9-21H2,1-7H3,(H,77,78)/t23-,24-,25+,26+,27+,28+,29+,30-,31+,32+,33-,34-,35-,36-,37-,38-,39+,40+,41+,42-,43-,44+,45+,46-,47+,49-,50-,51-,52-,53+,55+,56-,57+,58+,59+/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.

Soyasaponin A1 Dilution Calculator

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Preparing Stock Solutions of Soyasaponin A1

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.7878 mL 3.9389 mL 7.8777 mL 15.7555 mL 19.6943 mL
5 mM 0.1576 mL 0.7878 mL 1.5755 mL 3.1511 mL 3.9389 mL
10 mM 0.0788 mL 0.3939 mL 0.7878 mL 1.5755 mL 1.9694 mL
50 mM 0.0158 mL 0.0788 mL 0.1576 mL 0.3151 mL 0.3939 mL
100 mM 0.0079 mL 0.0394 mL 0.0788 mL 0.1576 mL 0.1969 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 Soyasaponin A1

Soyasaponins reduce inflammation by downregulating MyD88 expression and suppressing the recruitments of TLR4 and MyD88 into lipid rafts.[Pubmed:32493316]

BMC Complement Med Ther. 2020 Jun 3;20(1):167.

BACKGROUND: Previous studies indicate that soyasaponins may reduce inflammation via modulating toll-like receptor 4 (TLR4)/myeloid differentiation factor 88 (MyD88) signaling. However, its underlying mechanisms are still not fully understood. METHODS: Lipopolysaccharide (LPS)-challenged inflamed male ICR mice were intervened by intragastrical administration with 10 and 20 mumol/kg.BW of Soyasaponin A1, A2 or I for 8 weeks. The serum inflammatory markers were determined by commercial kits and the expression of molecules in TLR4/MyD88 signaling pathway in liver by real-time PCR and western blotting. The recruitments of TLR4 and MyD88 into lipid rafts of live tissue lysates were detected by sucrose gradient ultracentrifugation and western blotting. LPS-stimulated RAW264.7 macrophages were treated with 10, 20 and 40 mumol/L of Soyasaponin A1, A2 or I for 2 h. MyD88-overexpressed HEK293T cells were treated with 20 and 40 mumol/L of soyasaponins (A1, A2 or I) or 20 mumol/L of ST2825 (a MyD88 inhibitor) for 6 h. The expression of molecules in TLR4/MyD88 signaling pathway were determined by western blotting. Data were analyzed by using one way analysis of variance or t-test by SPSS 20.0 statistical software. RESULTS: Soyasaponins A1, A2 or I significantly reduced the levels of tumor necrosis factor alpha (TNFalpha), interleukin (IL)-6 and nitric oxide (NO) in serum (p < 0.05), and decreased the mRNA levels of TNFalpha, IL-6, IL-1beta, cyclooxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS) (p < 0.05), the protein levels of myeloid differentiation protein 2 (MD-2), TLR4, MyD88, toll-interleukin1 receptor domain containing adaptor protein (TIRAP), phosphorylated interleukin-1 receptor-associated kinase 4 (p-IRAK-4), phosphorylated interleukin-1 receptor-associated kinase 1 (p-IRAK-1) and TNF receptor associated factor 6 (TRAF6) (p < 0.05), and the recruitments of TLR4 and MyD88 into lipid rafts in liver (p < 0.05). In LPS-stimulated macrophages, soyasaponins A2 or I significantly decreased MyD88 (p < 0.05), soyasaponins A1, A2 or I reduced p-IRAK-4 and p-IRAK-1 (p < 0.05), and soyasaponin I decreased TRAF6 (p < 0.05). In MyD88-overexpressed HEK293T cells, soyasaponins (A1, A2 or I) and ST2825 significantly decreased MyD88 and TRAF6 (p < 0.05). CONCLUSION: Soyasaponins can reduce inflammation by downregulating MyD88 expression and suppressing the recruitments of TLR4 and MyD88 into lipid rafts. This study provides novel understanding about the anti-inflammatory mechanism of soyasaponins.

Evaluation of soyasaponin, isoflavone, protein, lipid, and free sugar accumulation in developing soybean seeds.[Pubmed:17177534]

J Agric Food Chem. 2006 Dec 27;54(26):10003-10.

A combination of analytical techniques was used to examine and quantify seed compositional components such as protein, lipid, free sugars, isoflavones, and soyasaponins during soybean development and maturation in two Korean soybean cultivars. Protein accumulation was rapid during reproductive stages, while lipid content was only relatively moderately increased. The major carbohydrate saccarides sucrose and stachyose constantly increased during the reproductive stage. Previously published results suggest that the free sugar and lipid content reached their maximal concentrations at a relatively early stage of seed development and remain constant in comparison to other chemical components. The malonylglucosides were the predominant isoflavone form followed by the glucosides, acetyl glucosides, and aglycone forms. As soybean seed matures, total soyasaponin concentration was constantly decreased until the R8 stage. Soyasaponin beta(g) was the major soyasaponin in DDMP-conjugated group B soyasaponins, followed by the non-DDMP counterpart soyasaponin I and Soyasaponin A1. The ratio of total isoflavone to total soyasaponin in the developing soybean increased from 0.06 to 1.31. Protein, lipid, and free sugar contents in the developing soybean seeds showed significant positive correlations with conjugated isoflavones and total isoflavone concentration, while the lipid contents showed a negative correlation with the isoflavone aglycone. Protein, lipid, and free sugar contents showed a negative correlation with total group A and B soyasaponins and total soyasaponins; however, only the soyasaponin A content was significantly negatively correlated with free sugar content. Total soyasaponin content was negatively correlated with isoflavone content (r = -0.828 at p < 0.01).

The isolation of soyasaponins by fractional precipitation, solid phase extraction, and low pressure liquid chromatography.[Pubmed:16503561]

Int J Food Sci Nutr. 2005 Nov;56(7):501-19.

Bioactive soyasaponins are present in soybean (Glycine max). In this study, the isolation of soyasaponins in relatively pure form (>80%) using precipitation, solid phase extraction and reverse phase low pressure liquid chromatography (RP-LPLC) is described. Soy flour soyasaponins were separated from non-saponins by methanol extraction and precipitation with ammonium sulphate. Acetylated group A soyasaponins were isolated first by solid phase extraction followed by RP-LPLC (solvent: ethanol-water). Soyasaponins, from a commercial preparation, were saponified and fractionated into deacetylated group A and group B soyasaponins by solid phase extraction (methanol-water). Partial hydrolysis of group B soyasaponins produced a mixture of soyasaponin III and soyasapogenol B monoglucuronide. RP-LPLC of deacetylated group A soyasaponins separated Soyasaponin A1 and A2 (38% methanol); of group B soyasaponins isolated soyasaponin I (50% ethanol); and of the partial hydrolysate separated soyasaponin III from soyasapogenol B monoglucuronide (50% ethanol). This methodology provides soyasaponin fractions that are suitable for biological evaluation.

Soyasaponins: the relationship between chemical structure and colon anticarcinogenic activity.[Pubmed:14769534]

Nutr Cancer. 2003;47(1):24-33.

Soyasaponins are bioactive compounds found in many legumes. Although crude soyasaponins have been shown to have anti-colon carcinogenic activity, there have been no structure-activity studies. In this study, therefore, purified soyasaponins and soyasapogenins were tested for their ability to suppress the growth of HT-29 colon cancer cells, as determined by the WST-1 assay, over a concentration range of 0-50 ppm. Soyasaponin I and III, soyasapogenol B monoglucuronide, soyasapogenol B, Soyasaponin A1, soyasaponin A2, and soyasapogenol A were evaluated. Also tested were mixtures comprising acetylated group A soyasaponins, deacetylated group A soyasaponins, and group B soyasaponins. The most potent compounds were the aglycones soyasapogenol A and B, which showed almost complete suppression of cell growth. The glycosidic soyasaponins by comparison were largely inactive. Soyasaponin A(1), A(2), and I, group B and deacetylated and acetylated group A fractions had no effect on cell growth. Soyasaponin III and soyasapogenol B monoglucuronide were marginally bioactive. These results suggested that the bioactivity of soyasaponins increased with increased lipophilicity. Results from in vitro fermentation suggested that colonic microflora readily hydrolyzed the soyasaponins to aglycones. These observations suggest that the soyasaponins may be an important dietary chemopreventive agent against colon cancer, after alteration by microflora.

[Comparison of soyasaponin and isoflavone contents between genetically modified (GM) and non-GM soybeans].[Pubmed:12635335]

Shokuhin Eiseigaku Zasshi. 2002 Dec;43(6):339-47.

Soyasaponins and isoflavones are main secondary metabolites in soybeans. In this report we compared the content of secondary metabolites between genetically modified (GM) and non-GM soybeans. Six cultivars/lines of GM and six cultivars/lines of non-GM soybeans were extracted with methanol. Each extract was partitioned with aqueous methanol and hexane and the aqueous methanol fraction was partially purified by HP-20 and LH-20 column chromatography to afford crude soyasaponin and isoflavone fractions. The main A-type soyasaponin, acetylSoyasaponin A1 (AcA1), and the main B-type soyasaponins, soyasaponins I and II (I and II), in the crude fractions were identified by LC/MS analyses with authentic samples. The main isoflavones, daidzin, genistin, daidzein and genistein (DI, GI, DE and GE), in the crude fractions were identified by LC photo-diode array analyses with authentic samples. The contents of AcA1, I and II in the crude soyasaponin fractions and those of DI, GI, DE and GE in the crude isoflavone fractions were analyzed by reversed-phase HPLC. The average contents (mg/100 g) of AcA1, I, II and total of B-type soyasaponins in GM soybeans were 36.4 +/- 24.2, 51.2 +/- 11.8, 26.4 +/- 7.6 and 77.7 +/- 18.5, respectively, and those in non-GM ones were 22.3 +/- 14.7, 46.3 +/- 17.8, 19.8 +/- 9.1 and 65.9 +/- 26.9, respectively. The average contents (mg/100 g) of DI, GI, DE, GE and total isoflavones in GM soybeans were 93.1 +/- 15.5, 121.8 +/- 19.4, 0.073 +/- 0.178, 0.320 +/- 0.082 and 215.3 +/- 33.3, respectively, and those in non-GM ones were 78.8 +/- 34.6, 106.7 +/- 28.3, 2.206 +/- 4.468, 0.822 +/- 0.754 and 188.5 +/- 26.7, respectively. There were no statistically significant differences in soyasaponin and isoflavone contents between GM and non-GM soybeans. Therefore, it was estimated that the GM soybeans are equivalent to the non-GM ones in terms of the composition of the main secondary metabolites.

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