| Identification | Back Directory | [Name]
SOYASAPONIN I | [CAS]
51330-27-9 | [Synonyms]
SCM 3B
SOYASAPONIN I
SOYASAPONIN I USP/EP/BP
SoyasaponinⅠ(Soyasaponin Bb)
SOYASAPONIN BB; SOYASAPONIN I
2)-O-b-D-galactopyranosyl-(1®
b-D-Glucopyranosiduronic acid, (3b,4b,22b)-22,23-dihydroxyolean-12-en-3-yl O-6-deoxy-a-L-Mannopyranosyl-(1®
β-D-Glucopyranosiduronic acid, (3β,4β,22β)-22,23-dihydroxyolean-12-en-3-yl O-6-deoxy-α-L-Mannopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)- | [Molecular Formula]
C48H78O18 | [MDL Number]
MFCD02752366 | [MOL File]
51330-27-9.mol | [Molecular Weight]
943.12 |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
2.76±0.70(Predicted) | [color ]
White | [biological source]
Glycine max (soybean) | [Stability:]
Hygroscopic | [Major Application]
food and beverages | [InChIKey]
PTDAHAWQAGSZDD-IOVCITQVSA-N |
| Hazard Information | Back Directory | [Description]
Soyasaponin Bb is a triterpenoid saponin that has been found in soy and has enzyme inhibitory, antimetastatic, anti-inflammatory, and neuroprotective biological activities.1,2,3,4,5,6 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.2 Soyasaponin Bb inhibits the mouse brain sialyltransferase ST3GAL1 (Ki = 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.3,4 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.5 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 (Item No. 14584).6 | [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 |
|
|