Soyasaponin Bd

CAS# 135272-91-2

Soyasaponin Bd

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Chemical structure

Soyasaponin Bd

3D structure

Chemical Properties of Soyasaponin Bd

Cas No. 135272-91-2 SDF Download SDF
PubChem ID 101672146 Appearance Powder
Formula C48H76O19 M.Wt 957.1
Type of Compound Triterpenoids 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,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-oxo-2,3,4a,5,6,7,8,10,12,12a,14,14a-dodecahydro-1H-picen-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(=O)C1)C)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C
Standard InChIKey JTXVTHCLTOUSSL-VSDZMWCXSA-N
Standard InChI InChI=1S/C48H76O19/c1-43(2)16-22-21-8-9-26-45(4)12-11-28(46(5,20-51)25(45)10-13-48(26,7)47(21,6)15-14-44(22,3)27(52)17-43)64-42-38(34(58)33(57)36(65-42)39(60)61)67-41-37(32(56)30(54)24(19-50)63-41)66-40-35(59)31(55)29(53)23(18-49)62-40/h8,22-26,28-38,40-42,49-51,53-59H,9-20H2,1-7H3,(H,60,61)/t22-,23+,24+,25+,26+,28-,29+,30-,31-,32-,33-,34-,35+,36-,37+,38+,40-,41-,42+,44+,45-,46+,47+,48+/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 Soyasaponin Bd

The seeds of Glycine max

Biological Activity of Soyasaponin Bd

DescriptionCinnamic aldehyde, a COX-2 inhibitor, exhibits cardioprotective, antidepressant-like, anti-leukemia, anti-oxidative and anti-inflammatory properties. Its supplementation can improve glucose and lipid homeostasis in diabetic animals.
TargetsCOX | PGE | TNF-α | IL Receptor | NO | ATPase | SOD
In vitro

Mechanism of cinnamic aldehyde-inducing apoptosis of chronic myeloid leukemic cells in vitro.[Pubmed: 21729535]

Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2011 Jun;19(3):617-20.

The aim of this study was to investigate the apoptosis-inducing effect of Cinnamic aldehyde (CA) on chronic myeloid leukemic (CML) cells and its mechanism.
METHODS AND RESULTS:
K562 cells and primary bone marrow mononuclear cells (MNC) from patients with CML were treated by various concentrations of CA. Flow cytometry was employed to measure the apoptosis of K562 cells and primary CML bone marrow MNC. Western blot was used to determine the expression of C-MYC and the phosphorylation of CrkL in K562 cells, and real-time polymerase chain reaction (real-time PCR) was used to quantify the expression of BCR-ABL mRNA in K562 cells. The results indicated that CA induced the apoptosis of K562 cells in a time- and dose-dependent manner. CA induced apoptosis of CML MNC dose-dependently. CA inhibited the expression of BCR-ABL mRNA and C-MYC, reduced CrkL phosphorylation levels in K562 cells.
CONCLUSIONS:
It is concluded that CA induces apoptosis of CML cells in vitro. Down-regulation of the expression and function of BCR-ABL may be one of its most important anti-leukemia mechanisms.

Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita.[Pubmed: 23379671]

J Agric Food Chem. 2013 Feb 27;61(8):1794-803.


METHODS AND RESULTS:
The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC(50) value of 11 ± 6 mg/L followed by salicylaldehyde (2) and Cinnamic aldehyde (3) with EC(50) values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC(50) at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme.
CONCLUSIONS:
The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action.

In vivo

Cinnamic aldehyde treatment alleviates chronic unexpected stress-induced depressive-like behaviors via targeting cyclooxygenase-2 in mid-aged rats.[Pubmed: 25556926]

J Ethnopharmacol. 2015 Mar 13;162:97-103.

COX-2 has been considered as a potent molecular target for prevention and therapy of depression. However, a recent study showed that COX-2 inhibitor does not improve depressive symptoms in persons aged 70 and over. Therefore, whether treatments targeting COX-2 have a clinical efficacy in depression, especially elderly individuals, remains unclear. Cinnamic aldehyde is a major constituent of Cinnamomum cassia, which has exhibited excellent anti-inflammatory activities as a COX-2 inhibitor. To investigate the potential antidepressant effect of Cinnamic aldehyde in mid-aged rats.
METHODS AND RESULTS:
The depressive-like behaviors were measured after the rats exposed to chronic unexpected mild stress (CUMS). Cinnamic aldehyde was administrated by oral gavage to stressed rats (22.5, 45, 90 mg/kg, respectively) for 21 days. The mRNA, protein expression and activity of cyclooxygenase-2 (COX-2), as well as prostaglandin E2 (PGE2) levels were measured in the frontal cortex and hippocampus of stressed animals. We found that CUMS procedure not only decreased the sucrose preference, but also elevated the COX-2 activity, mRNA and protein levels, and increased PGE2 concentration in rat brain regions. Treatment with high doses of Cinnamic aldehyde (45, 90 mg/kg) reversed the behavioral abnormalities, and decreased the COX-2 protein and activity (but not COX-2 mRNA expression) and PGE2 concentration in frontal cortex and hippocampus of stressed rats.
CONCLUSIONS:
Cinnamic aldehyde exerted antidepressant-like effects in stressed mid-aged rats, and its mechanism of action appears to decrease COX-2 protein and activity. The current findings suggest that targeting COX-2 system might be benefit to the depression, especially elderly individuals and Cinnamic aldehyde might be a promising medicine to treat the subjects in the depression.

Protocol of Soyasaponin Bd

Animal Research

Protective effects of cinnamic acid and cinnamic aldehyde on isoproterenol-induced acute myocardial ischemia in rats.[Pubmed: 24001892]

J Ethnopharmacol. 2013 Oct 28;150(1):125-30.

Cinnamomum cassia is a well-known traditional Chinese herb that is widely used for the treatment of ischemic heart disease (IHD). It has favorable effects, but its mechanism is not clear. To investigate the effects of Cinnamic aldehyde (CA) and cinnamic acid (CD) isolated from Cinnamomum cassia against myocardial ischemia produced in rats by isoproterenol (ISO).
METHODS AND RESULTS:
Ninety male Sprague-Dawley rats were randomized equally to nine groups: a control group, an untreated model group, Cinnamic aldehyde (22.5, 45, 90 mg/kg) or CD (37.5, 75, 150 mg/kg) treatment, or propranolol (30 mg/kg). Rats were treated for 14 days and then given ISO, 4 mg/kg for 2 consecutive days by subcutaneous injection. ST-segment elevation was measured after the last administration. Serum levels of creatine kinase (CK), lactate dehydrogenase (LDH), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), nitric oxide (NO), and blood rheology were measured after the rats were sacrificed. The hearts were excised for determining heart weight index, microscopic examination, superoxide dismutase (SOD) and malondialdehyde (MDA) measurements.Cinnamic aldehyde and CD decreased the ST elevation induced by acute myocardial ischemia, decreased serum levels of CK-MB, LDH, TNF-α and IL-6, and increased serum NO activity. Cinnamic aldehyde and CD increased SOD activity and decreased MDA content in myocardial tissue.
CONCLUSIONS:
Cinnamic aldehyde and CD were cardioprotective in a rat model of ischemic myocardial injury. The protection was attributable to anti-oxidative and anti-inflammatory properties, as well as increased NO. The results support further study of Cinnamic aldehyde and CD as potential treatments for ischemic heart disease.

Soyasaponin Bd Dilution Calculator

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Preparing Stock Solutions of Soyasaponin Bd

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0448 mL 5.2241 mL 10.4482 mL 20.8965 mL 26.1206 mL
5 mM 0.209 mL 1.0448 mL 2.0896 mL 4.1793 mL 5.2241 mL
10 mM 0.1045 mL 0.5224 mL 1.0448 mL 2.0896 mL 2.6121 mL
50 mM 0.0209 mL 0.1045 mL 0.209 mL 0.4179 mL 0.5224 mL
100 mM 0.0104 mL 0.0522 mL 0.1045 mL 0.209 mL 0.2612 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 Bd

Soyasaponins from Zolfino bean as aldose reductase differential inhibitors.[Pubmed:30734590]

J Enzyme Inhib Med Chem. 2019 Dec;34(1):350-360.

Seven triterpenoid saponins were identified in methanolic extracts of seeds of the Zolfino bean landrace (Phaseolus vulgaris L.) by HPLC fractionation, revealing their ability to inhibit highly purified human recombinant aldose reductase (hAKR1B1). Six of these compounds were associated by MS analysis with the following saponins already reported in different Phaseolus vulgaris varieties: soyasaponin Ba (V), soyasaponin Bb, Soyasaponin Bd (sandosaponin A), soyasaponin alphag, 3-O-[R-l-rhamnopyranosyl(1 --> 2)-alpha-d-glucopyranosyl(1 --> 2)-alpha-d-glucuronopyranosyl]olean-12-en-22-oxo-3alpha,-24-diol, and soyasaponin betag. The inhibitory activity of the collected fractions containing the above compounds was tested for hAKR1B1-dependent reduction of both l-idose and 4-hydroxynonenal, revealing that some are able to differentially inhibit the enzyme. The present work also highlights the difficulties in the search for aldose reductase differential inhibitors (ARDIs) in mixtures due to the masking effect on ARDIs exerted by the presence of conventional aldose reductase inhibitors. The possibility of differential inhibition generated by a different inhibitory model of action of molecules on different substrates undergoing transformation is also discussed.

Rapid characterisation and comparison of saponin profiles in the seeds of Korean Leguminous species using ultra performance liquid chromatography with photodiode array detector and electrospray ionisation/mass spectrometry (UPLC-PDA-ESI/MS) analysis.[Pubmed:24176342]

Food Chem. 2014 Mar 1;146:270-7.

The present work was reported on investigation of saponin profiles in nine different legume seeds, including soybean, adzuki bean, cowpea, common bean, scarlet runner bean, lentil, chick pea, hyacinth bean, and broad bean using ultra performance liquid chromatography with photodiode array detector and electrospray ionisation/mass spectrometry (UPLC-PDA-ESI/MS) technique. A total of twenty saponins were characterised under rapid and simple conditions within 15min by the 80% methanol extracts of all species. Their chemical structures were elucidated as soyasaponin Ab (1), soyasaponin Ba (2), soyasaponin Bb (3), soyasaponin Bc (4), Soyasaponin Bd (5), soyasaponin alphag (6), soyasaponin betag (7), soyasaponin betaa (8), soyasaponin gammag (9), soyasaponin gammaa (10), azukisaponin VI (11), azukisaponin IV (12), azukisaponin II (13), AzII (14), AzIV (15), lablaboside E (16), lablaboside F (17), lablaboside D (18), chikusetusaponin IVa (19), and lablab saponin I (20). The individual and total saponin compositions exhibited remarkable differences in all legume seeds. In particular, soyasaponin betaa (8) was detected the predominant composition in soybean, cowpea, and lentil with various concentrations. Interestingly, soybean, adzuki bean, common bean, and scarlet runner bean had high saponin contents, while chick pea and broad bean showed low contents.

Metabolomics revealed novel isoflavones and optimal cultivation time of Cordyceps militaris fermentation.[Pubmed:20225861]

J Agric Food Chem. 2010 Apr 14;58(7):4258-67.

Germinated soybean (GS) cultivated with Cordyceps militaris (GSC) might be a promising efficacious source of novel bioactive compounds. In this study, the metabolome changes between GS and GSC were investigated by liquid chromatography-mass spectrometry (LC-MS) and gas chromatography-mass spectrometry (GC-MS) analysis coupled with a multivariate data set. Principal component analysis (PCA) and orthogonal projection to latent structures discriminate analysis (OPLS-DA) of GSC clearly showed higher levels of Soyasaponin Bd, soyasaponin Bc(II), daidzein, genistein, four isoflavones (compounds 1-4), glycerol, proline, glutamine, pentitol, fructose, inositol, octadecanoic acid, and sucrose together with lower levels of pyroglutamic acid, citric acid, histidine, and palmitic acid in GSC than in GS. The structures of compounds 1-4 were analyzed by mass and NMR spectroscopy and were determined to be novel isoflavone methyl-glycosides (daidzein 7-O-beta-d-glucoside 4''-O-methylate (1), glycitein 7-O-beta-d-glucoside 4''-O-methylate (2), genistein 7-O-beta-d-glucoside 4''-O-methylate (3), and genistein 4'-O-beta-d-glucoside 4''-O-methylate (4)). Multivariate statistical models showed that metabolic changes of GSC were maximal within 1 week after the C. militaris inoculation, consistent with the strongest antioxidant activity of GSC cultivated for 1 week. This metabolomics study provides valuable information in regard to optimizing the cultivation process for bioactive compound production and describes an efficient way to screen for novel bioactive compounds from GSC.

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