SOYASAPONIN I Chemical Properties

Melting point:

220-222 °C(Solv: methanol (67-56-1))

Boiling point:

1024.2±65.0 °C(Predicted)

Density 

1.41

storage temp. 

2-8°C

solubility 

ethanol: soluble1mg/mL, clear, colorless

pka

2.76±0.70(Predicted)

form 

powder

color 

White

biological source

Glycine max (soybean)

Stability:

Hygroscopic

InChIKey

PTDAHAWQAGSZDD-IOVCITQVSA-N

Safety Information

WGK Germany 

3

HS Code 

29389090

SOYASAPONIN I Usage And Synthesis

Description

Soyasaponin Bb is a triterpenoid saponin that has been found in soy and has enzyme inhibitory, antimetastatic, anti-inflammatory, and neuroprotective biological activities. It selectively inhibits human recombinant and porcine kidney renin (IC₅₀s = 30 and 30 μg/ml, respectively) over bovine trypsin, human urinary kallikrein, and rabbit angiotensin converting enzyme (ACE) when used at a concentration of 100 μg/ml. Soyasaponin Bb inhibits the mouse brain sialyltransferase ST3GAL1 (K_i = 2.1 μM) and decreases levels of α2,3-linked sialic acid on the cell surface and decreases migration of B16/F10 mouse melanoma cells in vitro when used at a concentration of 75 μM. It also dose-dependently increases viability and mRNA expression of heme oxygenase-1 (HO-1) in BRL 3A immortalized rat hepatocytes subjected to alcohol-induced oxidative stress. Soyasaponin Bb (10 mg/kg per day) increases the latency to enter the dark chamber in a passive avoidance test and the percentage of spontaneous alterations in the Y-maze test in a rat model of learning and memory impairment induced by ibotenic acid .

Uses

Soyasaponin I has been used:

• to test its effect on migration and invasion of ovarian cancer cell lines
• as standard for the quantification of saponins from quinoa and fenugreek samples
• as L-15 medium supplement for Zebrafish liver cell lines

Definition

ChEBI: Soyasaponin I is a triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage. It has a role as a sialyltransferase inhibitor. It is a pentacyclic triterpenoid, a triterpenoid saponin, a trisaccharide derivative and a carbohydrate acid derivative. It is functionally related to a soyasapogenol B. It is a conjugate acid of a soyasaponin I(1-).

General Description

Soyasaponin I is an oleanene-type triterpenoid aglycone and is a group B soyasaponin. It is an amphiphilic molecule and is metabolized by intestinal bacteria into sugars and aglycones.

Biochem/physiol Actions

Antioxidant and anti-inflammatory saponin found in soybean. Attenuates TNBS-induced colitis in mice. The structure consists of a glycoside moiety and triterpene derivative. Sialytransferase inhibitor and renin inhibitor.

References

[1] WEI ZHANG D G P. Chemical and biological characterization of oleanane triterpenoids from soy.[J]. Molecules, 2009, 14 8: 2959-2975. DOI: 10.3390/molecules14082959
[2] SAORI TAKAHASHI. Isolation of human renin inhibitor from soybean: soyasaponin I is the novel human renin inhibitor in soybean.[J]. Bioscience, Biotechnology, and Biochemistry, 2008, 72 12: 3232-3236. DOI: 10.1271/bbb.80495
[3] CHI-YUE WU . Soyasaponin I, a Potent and Specific Sialyltransferase Inhibitor[J]. Biochemical and biophysical research communications, 2001, 284 2: Pages 466-469. DOI: 10.1006/bbrc.2001.5002
[4] WEI-WEI CHANG . Soyasaponin I decreases the expression of α2,3-linked sialic acid on the cell surface and suppresses the metastatic potential of B16F10 melanoma cells[J]. Biochemical and biophysical research communications, 2006, 341 2: Pages 614-619. DOI: 10.1016/j.bbrc.2005.12.216
[5] ZHU LIJIE. Soyasaponin Bb Protects Rat Hepatocytes from Alcohol-Induced Oxidative Stress by Inducing Heme Oxygenase-1[J]. Pharmacognosy Magazine, 2016, 46 1: 302-306. DOI: 10.4103/0973-1296.192203
[6] SUNG-WOON HONG. Soyasaponin I improved neuroprotection and regeneration in memory deficient model rats.[J]. PLoS ONE, 2013: e81556. DOI: 10.1371/journal.pone.0081556

SOYASAPONIN I(51330-27-9)Related Product Information

• Daidzein
• 6''-O-ACETYLGLYCITIN
• Daidzin
• Genistin
• Glycitin
• Soyosaponin Ac
• soyosaponin Ab
• Soyasaponin Ba
• SOYASAPOGENOL A(P)
• Soyasaponin Aa
• SOYASAPOGENOL B(P)
• SOYASAPONIN I
• 1,1-Dimethoxy-2-(2-methoxyethoxy)ethane
• 2-[2-(2-METHOXYETHOXY)ETHOXY]ACETIC ACID
• C18E3
• SOYASAPONIN III
• SOYASAPONIN IV
• (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9S,12aR,14aS,14bR)-9-hydro xy-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,5S)-4,5 -dihydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy -oxan-2-yl]oxy-3,4-dihydroxy-oxane-2-carboxylic acid